3/3/2014

DrugBank: Erythromycin (DB00199)

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Pharmacology

ADMET

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Show Drugs with Similar Structures targets (3) (/drugs/DB00199#targets) enzymes (5) (/drugs/DB00199#enzymes) transporters (4) (/drugs/DB00199#transporters) Biointeractions (15) (/drugs/DB00199/biointeractions)

Identification Name Accession Number Type Groups Description Erythromycin DB00199 (APRD00953) small molecule approved Erythromycin is a macrolide antibiotic produced by Streptomyces erythreus. It inhibits bacterial protein synthesis by binding to bacterial 50S ribosomal subunits; binding inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins. Erythromycin may be bacteriostatic or bactericidal depending on the organism and drug concentration.

Structure

(http://structures.wishartlab.com/molecules/DB00199/image.png)

MOL (/drugs/DB00199.mol) SDF (/drugs/DB00199.sdf) PDB (/drugs/DB00199.pdb) SMILES (/drugs/DB00199.smiles) InChI (/drugs/DB00199.inchi) View 2D Structure (/drugs/DB00199/structure) View 3D Structure (/drugs/DB00199/structure?dim=3d)

Synonyms

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Language Not Available Not Available Not Available Not Available Code Not Available Not Available Not Available Not Available Previous 1 Next

3''-O-demethylerythromycin Abomacetin Erythromycin A Erythromycin C

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Salts Brand names

Not Available
10 Name Akne-Mycin Eryc Erygel
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Company Not Available Not Available Not Available

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Ilosone Staticin T-stat
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DrugBank: Erythromycin (DB00199)

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Brand mixtures

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Ingredients Alcohol Anhydrous + Erythromycin Alcohol Anhydrous + Erythromycin + Laureth 4 Erythromycin + Tretinoin Erythromycin + Tretinoin Alcohol Anhydrous + Erythromycin Alcohol Anhydrous + Erythromycin Previous 1 Next

Sans-Acne Solution Staticin Lot Stievamycin Forte Gel Stievamycin Gel T-Stat Lot T-Stat Pad-Lot
Show ing 1 to 6 of 6 entries

Categories

Gastrointestinal Agents (/mesh/gastrointestinal-agents) Anti-Bacterial Agents (/mesh/anti-bacterial-agents) Protein Synthesis Inhibitors (/mesh/protein-synthesis-inhibitors) 114-07-8 Average: 733.9268 Monoisotopic: 733.461241235 C37H67NO13 InChIKey=ULGZDMOVFRHVEP-RWJQBGPGSA-N InChI=1S/C37H67NO13/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)1519(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-26,28-32,34,40-42,44-45H,1417H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1
Plain Text (/drugs/DB00199.inchi)

CAS number Weight

Chemical Formula InChI Key InChI

IUPAC Name

(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl1-oxacyclotetradecane-2,10-dione CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H] (O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O

Plain Text (/drugs/DB00199.smiles)

SMILES

Mass Spec Taxonomy Kingdom Superclass Class Subclass Direct parent Alternative parents

Not Available

Organic Compounds Phenylpropanoids and Polyketides Macrolides and Analogues Not Available Macrolides and Analogues Dihexoses; O-glycosyl Compounds; Amino Sugars; Oxanes; Tertiary Alcohols; Tertiary Amines; Ketones; 1,2-Diols; Secondary Alcohols; Carboxylic Acid Esters; Polyamines; Acetals disaccharide; amino sugar; oxane; saccharide; tertiary alcohol; tertiary amine; 1,2-diol; secondary alcohol; carboxylic acid ester; ketone; polyol; acetal; ether; polyamine; carboxylic acid derivative; carbonyl group; amine; alcohol; organonitrogen compound This compound belongs to the macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Substituents

Classification description Pharmacology

For use in the treatment of infections caused by susceptible strains of microorganisms in the following diseases: respiratory tract infections (upper and lower) of mild to moderate degree, pertussis (whooping cough), as adjunct to antitoxin in infections due to Corynebacterium diphtheriae, in the treatment of infections due to Corynebacterium minutissimum, intestinal amebiasis caused by Entamoeba histolytica, acute pelvic inflammatory disease caused by Neisseria gonorrhoeae, skin and soft tissue infections of mild to moderate severity caused by Streptococcus pyogenes and Staphylococcus aureus, primary syphilis caused by Treponema pallidum, infections caused by Chlamydia http://www.drugbank.ca/drugs/DB00199 2/18

Indication

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DrugBank: Erythromycin (DB00199) and Staphylococcus aureus, primary syphilis caused by Treponema pallidum, infections caused by Chlamydia trachomatis, nongonococcal urethritis caused by Ureaplasma urealyticum, and Legionnaires' disease caused by Legionella pneumophila.
Erythromycin is produced by a strain of Streptomyces erythraeus and belongs to the macrolide group of antibiotics. After absorption, erythromycin diffuses readily into most body fluids. In the absence of meningeal inflammation, low concentrations are normally achieved in the spinal fluid, but the passage of the drug across the blood-brain barrier increases in meningitis. Erythromycin is excreted in breast milk. The drug crosses the placental barrier with fetal serum drug levels reaching 5 - 20% of maternal serum concentrations. Erythromycin is not removed by peritoneal dialysis or hemodialysis. Erythromycin acts by penetrating the bacterial cell membrane and reversibly binding to the 50 S subunit of bacterial ribosomes or near the P or donor site so that binding of tRNA (transfer RNA) to the donor site is blocked. Translocation of peptides from the A or acceptor site to the P or donor site is prevented, and subsequent protein synthesis is inhibited. Erythromycin is effective only against actively dividing organisms. The exact mechanism by which erythmromycin reduces lesions of acne vulgaris is not fully known: however, the effect appears to be due in part to the antibacterial activity of the drug. Orally administered erythromycin base and its salts are readily absorbed in the microbiologically active form. Topical application of the ophthalmic ointment to the eye may result in absorption into the cornea and aqueous humor.

Pharmacodynamics

Mechanism of action

Absorption

Volume of distribution Not Available Protein binding Metabolism Erythromycin is largely bound to plasma proteins, ranging from 75 - 95% binding depending on the form. Hepatic. Extensively metabolized - after oral administration, less than 5% of the administered dose can be recovered in the active form in the urine. Erythromycin is partially metabolized by CYP3A4 resulting in numerous drug interactions. Substrate Erythromycin Enzymes
Cytochrome P450 3A4 (/bio_entities/BE0002638)

norerythromycin (/metabolites/DBMET00365)

Details (/reactions/367)

Route of elimination Half life Clearance Toxicity Affected organisms Pathways

Not Available 0.8 - 3 hours Not Available Symptoms of overdose include diarrhea, nausea, stomach cramps, and vomiting. Enteric bacteria and other eubacteria Pathway Erythromycin Action Pathway Category Drug action SMPDB ID
SMP00250 (http://www.smpdb.ca/view/SMP00250?reset=true&highlight[DB00199]=true)

SNP Mediated Effects SNP Mediated Adverse Drug Reactions ADMET Predicted ADMET features

Not Available Not Available

Property Human Intestinal Absorption Blood Brain Barrier Caco-2 permeable P-glycoprotein substrate P-glycoprotein inhibitor I P-glycoprotein inhibitor II Renal organic cation transporter CYP450 2C9 substrate CYP450 2D6 substrate CYP450 3A4 substrate CYP450 1A2 substrate

Value + Substrate Inhibitor Non-inhibitor Non-inhibitor Non-substrate Non-substrate Substrate Non-inhibitor

Probability 0.5114 0.9889 0.8957 0.8098 0.8564 0.5963 0.9222 0.7898 0.9225 0.6528 0.9045

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CYP450 2C9 substrate CYP450 2D6 substrate CYP450 2C19 substrate CYP450 3A4 substrate CYP450 inhibitory promiscuity Ames test Carcinogenicity Biodegradation Rat acute toxicity hERG inhibition (predictor I) hERG inhibition (predictor II) Pharmacoeconomics Manufacturers

DrugBank: Erythromycin (DB00199)

Non-inhibitor Non-inhibitor Non-inhibitor Non-inhibitor Low CYP Inhibitory Promiscuity Non AMES toxic Non-carcinogens Not ready biodegradable 2.2296 LD50, mol/kg Weak inhibitor Non-inhibitor 0.907 0.923 0.9074 0.5744 0.9391 0.9133 0.9335 1.0 Not applicable 0.9902 0.8956

Hospira inc Parke davis div warner lambert co Warner chilcott inc Abbott laboratories pharmaceutical products div Barr laboratories inc Stiefel laboratories inc Altana inc Merz pharmaceuticals llc Perrigo co Syosset laboratories inc Akorn inc Bausch and lomb pharmaceuticals inc E fougera div altana inc Pharmaderm div altana inc Pharmafair inc Dista products co div eli lilly and co Dow pharmaceutical sciences inc Paddock laboratories inc Taro pharmaceuticals north america inc Bioglan pharma inc Alpharma us pharmaceuticals division Eli lilly and co Perrigo new york inc Wockhardt eu operations (swiss) ag Hi tech pharmacal co inc Westwood squibb pharmaceuticals inc Ivax pharmaceuticals inc sub teva pharmaceuticals usa Orthoneutrogena Versapharm inc Ah robins co Solvay pharmaceuticals Watson laboratories inc Life laboratories inc Lilly research laboratories div eli lilly and co Ross laboratories div abbott laboratories inc Pharmacia and upjohn co Naska pharmacal co inc div rugby darby group cosmetics Wyeth ayerst laboratories Abbott laboratories chemical and agricultural products div Mylan pharmaceuticals inc Elkins sinn div ah robins co inc Abraxis pharmaceutical products Baxter healthcare corp anesthesia and critical care Teva parenteral medicines inc Bristol laboratories inc div bristol myers co Warner chilcott div warner lambert co Lederle laboratories div american cyanamid co Purepac pharmaceutical co Bristol myers squibb co Pfizer laboratories div pfizer inc

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Packagers

DrugBank: Erythromycin (DB00199)

Abbott Laboratories Ltd. (http://www.abbott.com) Advanced Pharmaceutical Services Inc. Akorn Inc. (http://www.akorn.com) Amerisource Health Services Corp. (http://www.amerisourcebergen.com) Apotheca Inc. A-S Medication Solutions LLC (http://orders.a-smeds.com) Atlantic Biologicals Corporation (http://www.atlanticbiologicals.com) Barr Pharmaceuticals Bausch & Lomb Inc. (http://www.bausch.com) Bryant Ranch Prepack (http://bryantranchprepack.com) Cardinal Health (http://www.cardinal.com) Carlisle Laboratories Inc. Casa De Amigos Pharmacy Central Texas Community Health Centers (http://www.chcsct.com) Community Action Inc. Community Health Services Comprehensive Consultant Services Inc. Contract Pharm (http://www.contractpharma.com) Core Pharmaceuticals (http://www.corepharma.com) Coria Laboratories (http://www.corialabs.com) Darby Dental Supply Co. Inc. (http://www.darbydental.com) Dept Health Central Pharmacy Dermik Labs Direct Dispensing Inc. Dispensing Solutions (http://www.drxdispensing.com) Diversified Healthcare Services Inc. (http://www.dhscorp.com) DPT Laboratories Ltd. (http://www.dptlabs.com) DRX Pharmaceuticals E. Fougera and Co. (http://www.fougera.com) Eli Lilly & Co. (http://www.lilly.com) Eye Care and Cure Corp. (http://www.eyecareandcure.com) Eye Supply Usa Inc. (http://www.eyesupplyusa.com) Fera Pharmaceuticals (http://www.ferapharma.com) H.J. Harkins Co. Inc. (http://hjharkinscompanyinc.com) Hospira Inc. (http://www.hospira.com) Inyx Usa Ltd. Ivax Pharmaceuticals Kaiser Foundation Hospital Lake Erie Medical and Surgical Supply Liberty Pharmaceuticals Major Pharmaceuticals (http://www.majorpharmaceuticals.com) Mayne Pharma International Pty Ltd. (http://www.maynepharma.com) Medical Ophthalmics Medicis Pharmaceutical Co. (http://www.medicis.com) Medisca Inc. (http://www.medisca.com) Medvantx Inc. (http://www.medvantx.com) Merz Pharmaceuticals LLC (http://www.merz.com) Mississippi State Dept Health (http://www.msdh.state.ms.us) Murfreesboro Pharmaceutical Nursing Supply (http://www.unitdosesupply.com) MWI Veterinary Supply Co. (http://www.mwivet.com) Mylan (http://www.mylan.com) Nucare Pharmaceuticals Inc. (http://www.nucarerx.com) Nycomed Inc. (http://www.nycomed.com) Ocusoft (http://www.ocusoft.com) Ortho Mcneil Janssen Pharmaceutical Inc. (http://www.ortho-mcneil.com) Paddock Labs (http://www.paddocklabs.com) Palmetto Pharmaceuticals Inc. (http://www.palmettopharm.com) Patient First Corp. (http://www.patientfirst.com) PCA LLC PD-Rx Pharmaceuticals Inc. (http://www.pdrx.com) Perrigo Co. (http://www.perrigo.com) Pharmaceutical Corporation of America Pharmaceutical Utilization Management Program VA Inc. Pharmacia Inc. (http://www.pharmaciaupjohn.com) Pharmaderm (http://www.pharmaderm.com) Pharmedix (http://www.pharmedixrx.com) Pharmpak Inc. (http://www.pharmpakinc.com) Physicians Total Care Inc. (http://www.physicianstotalcare.com) Polfa (http://www.polfa.pl) Preferred Pharmaceuticals Inc. (http://www.preferredpharmaceuticals.com) Prepackage Specialists http://www.drugbank.ca/drugs/DB00199

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DrugBank: Erythromycin (DB00199) Prepackage Specialists Prepak Systems Inc. (http://www.prepaksys.com) Prescription Dispensing Service Inc. Proter SPA Qualitest (http://www.worldoftest.com) Rebel Distributors Corp. (http://www.rebelrx.com) Redpharm Drug Remedy Repack (http://www.remedyrepack.com) Resource Optimization and Innovation LLC Sandhills Packaging Inc. (http://www.sandhillspackaging.com) Sandoz (http://www.sandoz.ca) Sanofi-Aventis Inc. (http://www.sanofi-aventis.com) Seneca Pharmaceuticals Inc. Southwood Pharmaceuticals (http://www.southwoodhealthcare.com) St Mary's Medical Park Pharmacy Stat Rx Usa (http://statrxusa.exporterus.com) Tolmar Inc. (http://www.tolmar.com) Tya Pharmaceuticals Valeant Ltd. (http://www.valeant.com) Veratex Corp. Wa Butler Co. Wilson Ophthalmic Corp. (http://www.hilco.com) Wockhardt Ltd. (http://www.wockhardtin.com) X-Gen Pharmaceuticals (http://www.x-gen.us)
10 Form Capsule, coated Liquid Liquid Ointment Powder Powder Powder, for solution Powder, for solution Powder, for suspension Suspension
Show ing 1 to 10 of 11 entries records per page

Dosage forms

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Route Oral Dental Oral Ophthalmic Intravenous Oral Intravenous Oral Oral Oral Previous 1 2 Next Strength

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Cost 3.96USD 0.19USD 0.41USD 0.45USD 0.35USD 0.22USD 0.57USD 236.63USD 4.95USD 142.45USD Previous Unit g tablet capsule capsule tablet tablet tablet jar g packet

Unit description Akne-mycin 2% ointment Apo-Erythro Base 250 mg Tablet Apo-Erythro E-C 250 mg Capsule (Enteric-Coated Pellet) Apo-Erythro E-C 333 mg Capsule (Enteric-Coated Pellet) Apo-Erythro-Es 600 mg Tablet Apo-Erythro-S 250 mg Tablet Apo-Erythro-S 500 mg Tablet Benzamycin 5-3% Gel 46.6 gm Jar Benzamycin gel BenzamycinPak 60 5-3% Packets (2 Box Contains 60 Packets)
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DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents Properties

Not Available

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State Experimental Properties solid Property melting point water solubility logP Caco2 permeability pKa Predicted Properties Property water solubility logP logP

DrugBank: Erythromycin (DB00199)

Value 191 C 2000mg/L at 28C 3.06 -5.43 8.88 (at 25 C) Value 4.59e-01 g/l 2.37 2.6 Source

Source PhysProp European Pharmacopeia MCFARLAND,JW ET AL. (1997) ADME Research, USCD MCFARLAND,JW ET AL. (1997)

ALOGPS (http://www.vcclab.org/lab/alogps/) ALOGPS (http://www.vcclab.org/lab/alogps/) ChemAxon (http://www.chemaxon.com/products/calculatorplugins/property-predictors/#logp_logd) ALOGPS (http://www.vcclab.org/lab/alogps/) ChemAxon (http://www.chemaxon.com/products/calculatorplugins/property-predictors/#pka) ChemAxon (http://www.chemaxon.com/products/calculatorplugins/property-predictors/#pka) ChemAxon (http://www.chemaxon.com/products/calculatorplugins/property-predictors/#pka) ChemAxon (http://www.chemaxon.com/products/calculatorplugins/property-calculations/#h_bond) ChemAxon (http://www.chemaxon.com/products/calculatorplugins/property-calculations/#h_bond) ChemAxon (http://www.chemaxon.com/products/calculatorplugins/propertycalculations/#topolgical_surface) ChemAxon (http://www.chemaxon.com/products/calculatorplugins/propertycalculations/#topology_analysis) ChemAxon (http://www.chemaxon.com/products/calculatorplugins/property-calculations/#refractivity) ChemAxon (http://www.chemaxon.com/products/calculatorplugins/molecular-modelling/#polarization) ChemAxon (http://www.chemaxon.com/products/calculatorplugins/propertycalculations/#topology_analysis) ChemAxon (http://www.chemaxon.com/products/calculatorplugins/molecular-modelling/#polarization) ChemAxon (http://www.chemaxon.com/products/calculatorplugins/molecular-modelling/#polarization) ChemAxon (http://www.chemaxon.com/products/calculatorplugins/molecular-modelling/#polarization)

logS pKa (strongest acidic)

-3.2 12.44

pKa (strongest basic)

8.38

physiological charge

hydrogen acceptor count

13

hydrogen donor count

polar surface area

193.91

rotatable bond count

refractivity

186.04

polarizability

78.21

number of rings

bioavailability

rule of five

No

Ghose filter

No

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Veber's rule No

DrugBank: Erythromycin (DB00199)

plugins/molecular-modelling/#polarization) ChemAxon (http://www.chemaxon.com/products/calculatorplugins/molecular-modelling/#polarization) ChemAxon (http://www.chemaxon.com/products/calculatorplugins/molecular-modelling/#polarization)

MDDR-like rule

Yes

Spectra Spectra References Synthesis Reference Takehiro Amano, Masami Goi, Kazuto Sekiuchi, Tomomichi Yoshida, Masahiro Hasegawa, Process for preparing erythromycin A oxime or a salt thereof. U.S. Patent US5274085, issued October, 1966. US5274085 General Reference (https://www.google.com/?tbm=pts#q=5274085&tbm=pts) Not Available

1. Kanazawa S, Ohkubo T, Sugawara K: The effects of grapefruit juice on the pharmacokinetics of erythromycin. Eur J Clin Pharmacol. 2001 Jan-Feb;56(11):799-803. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/11294369) 2. Ogwal S, Xide TU: Bioavailability and stability of erythromycin delayed release tablets. Afr Health Sci. 2001 Dec;1(2):90-6. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/12789122) 3. Okudaira T, Kotegawa T, Imai H, Tsutsumi K, Nakano S, Ohashi K: Effect of the treatment period with erythromycin on cytochrome P450 3A activity in humans. J Clin Pharmacol. 2007 Jul;47(7):871-6. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/17585116) Resource KEGG Drug KEGG Compound PubChem Compound PubChem Substance ChemSpider ChEBI ChEMBL Therapeutic Targets Database PharmGKB HET Link D00140 C01912 12560 (http://www.genome.jp/dbget-bin/www_bget?drug:D00140) (http://www.genome.jp/dbget-bin/www_bget?cpd:C01912) (http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=12560)

External Links

46508487

(http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508487)

12041 48923

(http://www.chemspider.com/Chemical-Structure.12041.html) (http://www.ebi.ac.uk/chebi/searchId.do?chebiId=48923) (http://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL532) (http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000111)

CHEMBL532 DAP000111

PA449493

(http://www.pharmgkb.org/drug/PA449493)

ERY (http://www.ebi.ac.uk/msd-srv/chempdb/cgi-bin/cgi.pl? FUNCTION=getByCode&CODE=ERY) 2237041 (http://205.193.93.51/dpdonline/searchRequest.do?din=2237041)

Drug Product Database RxList Drugs.com

http://www.rxlist.com/cgi/generic/erithrom.htm

(http://www.rxlist.com/cgi/generic/erithrom.htm) (http://www.drugs.com/cdi/erythromycin-

http://www.drugs.com/cdi/erythromycin-ointment.html ointment.html)

PDRhealth

http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ery1163.shtml (http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ery1163.shtml) Erythromycin (http://en.wikipedia.org/wiki/Erythromycin)

Wikipedia ATC Codes

D10AF02 D DERMATOLOGICALS (/atc/D) D10 ANTI-ACNE PREPARATIONS (/atc/D10) D10A ANTI-ACNE PREPARATIONS FOR TOPICAL USE (/atc/D10A) D10AF Antiinfectives for treatment of acne (/atc/D10AF) J01FA01 J ANTIINFECTIVES FOR SYSTEMIC USE (/atc/J) J01 ANTIBACTERIALS FOR SYSTEMIC USE (/atc/J01) J01F MACROLIDES, LINCOSAMIDES AND STREPTOGRAMINS (/atc/J01F) J01FA Macrolides (/atc/J01FA)

S01AA17 S SENSORY ORGANS (/atc/S) http://www.drugbank.ca/drugs/DB00199

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DrugBank: Erythromycin (DB00199) S SENSORY ORGANS (/atc/S) S01 OPHTHALMOLOGICALS (/atc/S01) S01A ANTIINFECTIVES (/atc/S01A) S01AA Antibiotics (/atc/S01AA)
34:00.00 08:12.12.04 52:04.04 Not Available show (/system/fda_labels/DB00199.pdf?1265922812)(149 KB) show (/system/msds/DB00199.pdf?1265922748)(73 KB)

AHFS Codes

PDB Entries FDA label MSDS Interactions Drug Interactions

Drug Acenocoumarol (/drugs/DB01418) The macrolide, erythromycin, may increase the anticoagulant effect of acenocoumarol.

Alfentanil (/drugs/DB00802) The macrolide, erythromycin, may increase the effect and toxicity of alfentanil. Alprazolam (/drugs/DB00404) Aminophylline (/drugs/DB01223) Amiodarone (/drugs/DB01118) Anisindione (/drugs/DB01125) Aprepitant (/drugs/DB00673) Artemether (/drugs/DB06697) Astemizole (/drugs/DB00637) Atorvastatin (/drugs/DB01076) Avanafil (/drugs/DB06237) The macrolide, erythromycin, may increase the effect of the benzodiazepine, alprazolam. The macrolide, erythromycin, may increase the effect and toxicity of the theophylline derivative, aminophylline. Increased risk of cardiotoxicity and arrhythmias

The macrolide, erythromycin, may increase the anticoagulant effect of anisindione.

Erythromycin, a moderate CYP3A4 inhibitor, may increase the effect and toxicity of aprepitant. Additive QTc-prolongation may occur. Concomitant therapy should be avoided.

Increased risk of cardiotoxicity and arrhythmias

The macrolide, erythromycin, may increase the toxicity of the statin, atorvastatin.

Co-administration with the moderate CYP3A4 inhibitor erythromycin resulted in an approximate 3.6-fold increase in AUC0-inf and 2.0-fold increase in Cmax of avanafil. Decreases metabolism, thus decreasing the effects of bendamustine.

Bendamustine (/drugs/DB06769)

Bretylium (/drugs/DB01158) Increased risk of cardiotoxicity and arryhthmias Bromazepam (/drugs/DB01558) Erythromcyin may increase the serum concentration of bromazepam by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of bromazepam if erythromycin is initiated, discontinued or dose changed. Dosage adjustments may be required. Erythromycin increases serum levels of bromocriptine

Bromocriptine (/drugs/DB01200) Buspirone (/drugs/DB00490) Cabergoline (/drugs/DB00248) Carbamazepine (/drugs/DB00564) Cerivastatin (/drugs/DB00439)

The macrolide, erythromycin, may increase the effect and toxicity of buspirone.

Erythromycin increases serum levels and toxicity of cabergoline

The macrolide, erythromycin, may increase the effect of carbamazepine.

The macrolide, erythromycin, may increase the toxicity of the statin, cerivastatin.

Cilostazol (/drugs/DB01166) Erythromycin increases the effect of cilostazol Cinacalcet (/drugs/DB01012) The macrolide, erythromycin, may increase the serum concentration and toxicity of cinacalcet.

Cisapride (/drugs/DB00604) Increased risk of cardiotoxicity and arrhythmias

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Citalopram (/drugs/DB00215) Clozapine (/drugs/DB00363) Colchicine (/drugs/DB01394) Cyclosporine (/drugs/DB00091) Diazepam (/drugs/DB00829) Dicoumarol (/drugs/DB00266) Digoxin (/drugs/DB00390) Dihydroergotamine (/drugs/DB00320) Disopyramide (/drugs/DB00280) Docetaxel (/drugs/DB01248)

DrugBank: Erythromycin (DB00199)

Possible serotoninergic syndrome with this combination

Erythromycin increases the effect of clozapine

Severe colchicine toxicity can occur

The macrolide, erythromycin, may increase the effect of cyclosporine.

The macrolide, erythromycin, may increase the effect of the benzodiazepine, diazepam.

The macrolide, erythromycin, may increase the anticoagulant effect of dicumarol..

The macrolide, erythromycin, may increase the effect of digoxin in 10% of patients. Possible ergotism and severe ischemia with this combination

Increased risk of cardiotoxicity and arrhythmias

Erythromycin may increase the serum levels and toxicity of docetaxel.

Dofetilide (/drugs/DB00204) Increased risk of cardiotoxicity and arrhythmias Dyphylline (/drugs/DB00651) The macrolide, erythromycin, may increase the effect and toxicity of the theophylline derivative, dyphylline.

Eletriptan (/drugs/DB00216) The macrolide, erythromycin, may increase the effect and toxicity of eletriptan. Eltrombopag (/drugs/DB06210) Eplerenone (/drugs/DB00700) Ergonovine (/drugs/DB01253) Ergotamine (/drugs/DB00696) Erlotinib (/drugs/DB00530) Everolimus (/drugs/DB01590) Felodipine (/drugs/DB01023) Fluoxetine (/drugs/DB00472) Gefitinib (/drugs/DB00317) Grepafloxacin (/drugs/DB00365) Imatinib (/drugs/DB00619) Indacaterol (/drugs/DB05039) Itraconazole (/drugs/DB01167) Ivacaftor (/drugs/DB08820) Levofloxacin (/drugs/DB01137) Lincomycin (/drugs/DB01627) Lovastatin (/drugs/DB00227) Affects hepatic CYP1A2 metabolism, increases Eltrombopag level or affect.

This CYP3A4 inhibitor increases the effect and toxicity of eplerenone

Possible ergotism and severe ischemia with this combination

Possible ergotism and severe ischemia with this combination

This CYP3A4 inhibitor increases levels/toxicity of erlotinib The macrolide, erythromycin, may increase the serum concentration and toxicity of everolimus. Erythromycin increases the effect of felodipine

Possible serotoninergic syndrome with this combination

This CYP3A4 inhibitor increases levels/toxicity of gefitinib Increased risk of cardiotoxicity and arrhythmias

The macrolide, erythromycin, may increase the serum concentration of imatinib. Strong inhibitors of CYP3A4 may increase levels of indacaterol. Monitor closely for adverse events. The macrolide, erythromycin, may increase the effect and toxicity of itraconazole.

Moderate CYP3A4 inhibitors may increase levels of ivacaftor. Consider dose reduction. Increased risk of cardiotoxicity and arrhythmias

Possible antagonism of action with this combination.

The macrolide, erythromycin, may increase the toxicity of the statin, lovastatin.

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Lumefantrine (/drugs/DB06708) Mesoridazine (/drugs/DB00933) Methylergometrine (/drugs/DB00353) Methylprednisolone (/drugs/DB00959) Methysergide (/drugs/DB00247) Midazolam (/drugs/DB00683) Moxifloxacin (/drugs/DB00218) Oxtriphylline (/drugs/DB01303) Pazopanib (/drugs/DB06589) Pimozide (/drugs/DB01100) Pitavastatin (/drugs/DB08860) Quetiapine (/drugs/DB01224)

DrugBank: Erythromycin (DB00199)

Additive QTc-prolongation may occur. Concomitant therapy should be avoided.

Increased risk of cardiotoxicity and arrhythmias

Possible ergotism and severe ischemia with this combination

The macrolide, erythromycin, may increase the effect of corticosteroid, methylprednisolone. Possible ergotism and severe ischemia with this combination

The macrolide, erythromycin, may increase the effect of the benzodiazepine, midazolam. Increased risk of cardiotoxicity and arrhythmias

The macrolide, erythromycin, may increase the effect and toxicity of the theophylline derivative, oxtriphylline. Affects CYP3A4 metabolism therefore will decrease levels or effect of pazopanib. Consider alternate therapy. Increased risk of cardiotoxicity and arrhythmias Erythromycin decreases metabolism of pitavastatin. Do not exceed 1 mg per day of pitavastatin or use alternative therapy. The macrolide, erythromycin, may increase the effect and toxicity of quetiapine.

Quinidine (/drugs/DB00908) Increased risk of cardiotoxicity and arrhythmias Quinidine barbiturate (/drugs/DB01346) Quinupristin (/drugs/DB01369) Ranolazine (/drugs/DB00243) Repaglinide (/drugs/DB00912) Rifabutin (/drugs/DB00615) Rifampicin (/drugs/DB01045) Ritonavir (/drugs/DB00503) Roflumilast (/drugs/DB01656) Saxagliptin (/drugs/DB06335) Sertraline (/drugs/DB01104) Sibutramine (/drugs/DB01105) Sildenafil (/drugs/DB00203) Silodosin (/drugs/DB06207) Increased risk of cardiotoxicity and arrhythmias

This combination presents an increased risk of toxicity

Increased levels of ranolazine - risk of toxicity

The macrolide, erythromycin, may increase the effect of repaglinide.

The rifamycin, rifabutin, may decrease the effect of the macrolide, erythromycin. The rifamycin, rifampin, may decrease the effect of the macrolide, erythromycin.

Increased toxicity of both agents Increases roflumilast levels.

Erythromycin is an inhibitor of CYP3A4 which increases exposure of saxagliptin. Decrease dose of saxagliptin to 2.5 mg per day. Possible serotoninergic syndrome with this combination

Erythromycin increases the effect and toxicity of sibutramine

The macrolide, erythromycin, may increase the effect and toxicity of sildenafil. Erythromycin is a moderate inhibitor of CYP3A4 and inhibits P-glycoprotein thus increasing the potential for adverse effects The macrolide, erythromycin, may increase the toxicity of the statin, simvastatin.

Simvastatin (/drugs/DB00641) Sirolimus (/drugs/DB00877) Sotalol (/drugs/DB00489) Sparfloxacin (/drugs/DB01208) Tacrolimus http://www.drugbank.ca/drugs/DB00199

The macrolide, erythromycin, may increase the serum concentration of sirolimus. Increased risk of cardiotoxicity and arrhythmias Increased risk of cardiotoxicity and arrhythmias

Additive QTc-prolongation may occur increasing the risk of serious ventricular

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Tacrolimus (/drugs/DB00864)

DrugBank: Erythromycin (DB00199)

Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution. The macrolide antibiotic, erythromycin, may also increase the blood concentration of tacrolimus. Erythromycin, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Erythromycin is initiated, discontinued, or dose changed. Telithromycin may reduce clearance of Erythromycin. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Erythromycin if Telithromycin is initiated, discontinued or dose changed. Increased risk of cardiotoxicity and arrhythmias

Tamsulosin (/drugs/DB00706)

Telithromycin (/drugs/DB00976)

Terfenadine (/drugs/DB00342) Theophylline (/drugs/DB00277) Thioridazine (/drugs/DB00679) Thiothixene (/drugs/DB01623)

The macrolide, erythromycin, may increase the effect and toxicity of theophylline.

Increased risk of cardiotoxicity and arrhythmias

May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to coadministration. Erythromycin is a moderate inhibitor of CYP3A4 and will considerably increase tolvaptan serum concentrations The p-glycoprotein inhibitor, Erythromycin, may increase the bioavailability of oral Topotecan. A clinically significant effect is also expected with IV Topotecan. Concomitant therapy should be avoided. Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration.

Tolvaptan (/drugs/DB06212) Topotecan (/drugs/DB01030)

Toremifene (/drugs/DB00539)

Tramadol (/drugs/DB00193) Erythromycin may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance. Trazodone (/drugs/DB00656) The CYP3A4 inhibitor, Erythromycin , may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Erythromycin is initiated, discontinued or dose changed. The macrolide, erythromycin, may increase the effect of the benzodiazepine, triazolam.

Triazolam (/drugs/DB00897) Trimipramine (/drugs/DB00726) Valproic Acid (/drugs/DB00313)

Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution. The macrolide antibiotic, Erythromycin, may increase the serum concentratin of Valproic acid. Consider alternate therapy or monitor for changes in Valproic acid therapeutic and adverse effects if Erythromycin is initiated, discontinued or dose changed. Erythromycin, a moderate CYP3A4 inhibitor, may reduce the metabolism and clearance of vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of vardenafil if erythromycin is initiated, discontinued or dose changed. Erythromycin, a moderate CYP3A4 inhibitor, may increase the serum concentration of veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Monitor for changes in the therapeutic/adverse effects of verapamil if erythromycin is initiated, discontinued or dose changed. Erythromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the vinblastine serum concentration and distribution in certain cells. Consider alternate therapy to avoid vinblastine toxicity. Monitor for changes in the therapeutic/adverse effects of vinblastine if erythromycin is initiated, discontinued or dose changed. Erythromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the Vincristine serum concentration and distribution in certain cells. Consider alternate therapy to avoid Vincristine toxicity. Monitor for changes in the therapeutic and adverse effects of Vincristine if Erythromycin is initiated, discontinued or dose changed. Erythromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the Vinorelbine serum concentration and distribution in certain cells. Consider alternate therapy to avoid Vinorelbine toxicity. Monitor for changes in the therapeutic and adverse effects of Vinorelbine if Erythromycin is initiated, discontinued or dose changed. P-glycoprotein inhibitors may increase the chance of adverse drug reactions.

Vardenafil (/drugs/DB00862)

Verapamil (/drugs/DB00661)

Vinblastine (/drugs/DB00570)

Vincristine (/drugs/DB00541)

Vinorelbine (/drugs/DB00361)

Vismodegib (/drugs/DB08828)

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Voriconazole (/drugs/DB00582)

DrugBank: Erythromycin (DB00199)

Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of erythromycin by decreasing its metabolism. Erythromycin may increase the serum concentration of voriconazole by decreasing its metabolism. Additive QTc prolongation may also occur. Consider alternate therapy or monitor for QTc prolongation and changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or dose changed. Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP). The macrolide, erythromycin, may increase the anticoagulant effect of warfarin. Erythromycin may decrease the serum concentration and effect of zafirlukast.

Vorinostat (/drugs/DB02546) Warfarin (/drugs/DB00682) Zafirlukast (/drugs/DB00549) Ziprasidone (/drugs/DB00246) Zopiclone (/drugs/DB01198)

Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy is contraindicated. The macrolide antibiotic, erythromycin, may increase the serum concentration of zopiclone. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zopiclone if erythromycin is initiated, discontinued or dose changed. Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP). Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP). Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).

Zuclopenthixol (/drugs/DB01624) Zuclopenthixol acetate (/drugs/DB08919) Zuclopenthixol decanoate (/drugs/DB08920) Food Interactions

Avoid alcohol. Take on empty stomach: 1 hour before or 2 hours after meals. Take with a full glass of water Avoid taking with grapefruit juice.

1. 23S rRNA (/bio_entities/BE0004800)

Kind: nucleotide Organism: Enteric bacteria and other eubacteria Pharmacological action: yes Actions: inhibitor

Components
Name UniProt ID Details

References:
1. Moazed D, Noller HF: Chloramphenicol, erythromycin, carbomycin and vernamycin B protect overlapping sites in the peptidyl transferase region of 23S ribosomal RNA. Biochimie. 1987 Aug;69(8):879-84. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/3122849) 2. Schlunzen F, Zarivach R, Harms J, Bashan A, Tocilj A, Albrecht R, Yonath A, Franceschi F: Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria. Nature. 2001 Oct 25;413(6858):814-21. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/11677599) 3. Garza-Ramos G, Xiong L, Zhong P, Mankin A: Binding site of macrolide antibiotics on the ribosome: new resistance mutation identifies a specific interaction of ketolides with rRNA. J Bacteriol. 2001 Dec;183(23):6898-907. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/11698379)

2. 50S ribosomal protein L22 (/bio_entities/BE0002464)

Kind: protein Organism: Escherichia coli O157:H7 Pharmacological action: yes Actions: inhibitor

Components
Name 50S ribosomal protein L22 UniProt ID P61177 (http://www.uniprot.org/uniprot/P61177) Details
Details (/polypeptides/P61177)

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DrugBank: Erythromycin (DB00199) (http://www.uniprot.org/uniprot/P61177)

References:
1. Halling SM, Jensen AE: Intrinsic and selected resistance to antibiotics binding the ribosome: analyses of Brucella 23S rrn, L4, L22, EF-Tu1, EF-Tu2, efflux and phylogenetic implications. BMC Microbiol. 2006 Oct 2;6:84. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/17014718) 2. Tu D, Blaha G, Moore PB, Steitz TA: Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance. Cell. 2005 Apr 22;121(2):257-70. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/15851032) 3. Rolain JM, Raoult D: Prediction of resistance to erythromycin in the genus Rickettsia by mutations in L22 ribosomal protein. J Antimicrob Chemother. 2005 Aug;56(2):396-8. Epub 2005 Jul 4. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/15996971) 4. Cagliero C, Mouline C, Cloeckaert A, Payot S: Synergy between efflux pump CmeABC and modifications in ribosomal proteins L4 and L22 in conferring macrolide resistance in Campylobacter jejuni and Campylobacter coli. Antimicrob Agents Chemother. 2006 Nov;50(11):3893-6. Epub 2006 Aug 28. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/16940070) 5. Schlunzen F, Harms JM, Franceschi F, Hansen HA, Bartels H, Zarivach R, Yonath A: Structural basis for the antibiotic activity of ketolides and azalides. Structure. 2003 Mar;11(3):329-38. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/12623020) 6. Davydova N, Streltsov V, Wilce M, Liljas A, Garber M: L22 ribosomal protein and effect of its mutation on ribosome resistance to erythromycin. J Mol Biol. 2002 Sep 20;322(3):635-44. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/12225755)

3. 50S ribosomal protein L4 (/bio_entities/BE0002465)

Kind: protein Organism: Escherichia coli O157:H7 Pharmacological action: yes Actions: inhibitor

Components
Name 50S ribosomal protein L4 UniProt ID P60725 (http://www.uniprot.org/uniprot/P60725) Details
Details (/polypeptides/P60725)

References:
1. Halling SM, Jensen AE: Intrinsic and selected resistance to antibiotics binding the ribosome: analyses of Brucella 23S rrn, L4, L22, EF-Tu1, EF-Tu2, efflux and phylogenetic implications. BMC Microbiol. 2006 Oct 2;6:84. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/17014718) 2. Tu D, Blaha G, Moore PB, Steitz TA: Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance. Cell. 2005 Apr 22;121(2):257-70. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/15851032) 3. OConnor M, Gregory ST, Dahlberg AE: Multiple defects in translation associated with altered ribosomal protein L4. Nucleic Acids Res. 2004 Oct 27;32(19):5750-6. Print 2004. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/15509870) 4. Schlunzen F, Harms JM, Franceschi F, Hansen HA, Bartels H, Zarivach R, Yonath A: Structural basis for the antibiotic activity of ketolides and azalides. Structure. 2003 Mar;11(3):329-38. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/12623020)

1. Cytochrome P450 3A4 (/bio_entities/BE0002638)

Kind: protein Organism: Human Pharmacological action: unknown Actions: substrate
inhibitor

Components
Name Cytochrome P450 3A4 UniProt ID P08684 (http://www.uniprot.org/uniprot/P08684) Details
Details (/polypeptides/P08684)

References:
1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table (http://medicine.iupui.edu/clinpharm/ddis/table.asp). Indiana University School of Medicine (2007). Accessed May 28, 2010. 2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D23743. Epub 2009 Nov 24. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/19934256) 3. Ekins S, Bravi G, Wikel JH, Wrighton SA: Three-dimensional-quantitative structure activity relationship analysis of cytochrome P-450 3A4 substrates. J Pharmacol Exp Ther. 1999 Oct;291(1):424-33. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/10490933) 4. Lexicomp

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DrugBank: Erythromycin (DB00199)

2. Cytochrome P450 3A7 (/bio_entities/BE0003612)

Kind: protein Organism: Human Pharmacological action: unknown Actions: substrate
inhibitor

Components
Name Cytochrome P450 3A7 UniProt ID P24462 (http://www.uniprot.org/uniprot/P24462) Details
Details (/polypeptides/P24462)

References:
1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table (http://medicine.iupui.edu/clinpharm/ddis/table.asp). Indiana University School of Medicine (2007). Accessed May 28, 2010.

3. Cytochrome P450 3A5 (/bio_entities/BE0002362)

Kind: protein Organism: Human Pharmacological action: unknown Actions: inhibitor

Components
Name Cytochrome P450 3A5 UniProt ID P20815 (http://www.uniprot.org/uniprot/P20815) Details
Details (/polypeptides/P20815)

References:
1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table (http://medicine.iupui.edu/clinpharm/ddis/table.asp). Indiana University School of Medicine (2007). Accessed May 28, 2010.

4. Cytochrome P450 1A2 (/bio_entities/BE0002433)

Kind: protein Organism: Human Pharmacological action: unknown Actions: inhibitor

Components
Name Cytochrome P450 1A2 UniProt ID P05177 (http://www.uniprot.org/uniprot/P05177) Details
Details (/polypeptides/P05177)

References:
1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D23743. Epub 2009 Nov 24. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/19934256)

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DrugBank: Erythromycin (DB00199)

5. Cytochrome P450 2B6 (/bio_entities/BE0003549)

Kind: protein Organism: Human Pharmacological action: unknown Actions: substrate

Components
Name Cytochrome P450 2B6 UniProt ID P20813 (http://www.uniprot.org/uniprot/P20813) Details
Details (/polypeptides/P20813)

References:
1. Lexicomp

1. Multidrug resistance protein 1 (/bio_entities/BE0001032)

Kind: protein Organism: Human Pharmacological action: unknown Actions: substrate
inhibitor inducer

Components
Name Multidrug resistance protein 1 UniProt ID P08183 (http://www.uniprot.org/uniprot/P08183) Details
Details (/polypeptides/P08183)

References:
1. Schuetz EG, Beck WT, Schuetz JD: Modulators and substrates of P-glycoprotein and cytochrome P4503A coordinately up-regulate these proteins in human colon carcinoma cells. Mol Pharmacol. 1996 Feb;49(2):311-8. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/8632764) 2. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/11602674) 3. Ekins S, Kim RB, Leake BF, Dantzig AH, Schuetz EG, Lan LB, Yasuda K, Shepard RL, Winter MA, Schuetz JD, Wikel JH, Wrighton SA: Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein. Mol Pharmacol. 2002 May;61(5):964-73. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/11961113) 4. Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/12699389) 5. Takano M, Hasegawa R, Fukuda T, Yumoto R, Nagai J, Murakami T: Interaction with P-glycoprotein and transport of erythromycin, midazolam and ketoconazole in Caco-2 cells. Eur J Pharmacol. 1998 Oct 9;358(3):289-94. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/9822896) 6. Kim RB, Wandel C, Leake B, Cvetkovic M, Fromm MF, Dempsey PJ, Roden MM, Belas F, Chaudhary AK, Roden DM, Wood AJ, Wilkinson GR: Interrelationship between substrates and inhibitors of human CYP3A and P-glycoprotein. Pharm Res. 1999 Mar;16(3):408-14. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/10213372) 7. Asakura E, Nakayama H, Sugie M, Zhao YL, Nadai M, Kitaichi K, Shimizu A, Miyoshi M, Takagi K, Takagi K, Hasegawa T: Azithromycin reverses anticancer drug resistance and modifies hepatobiliary excretion of doxorubicin in rats. Eur J Pharmacol. 2004 Jan 26;484(2-3):333-9. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/14744620) 8. Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG: Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. J Pharmacol Exp Ther. 2002 Oct;303(1):323-32. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/12235267) 9. Dahan A, Sabit H, Amidon GL: The H2 receptor antagonist nizatidine is a P-glycoprotein substrate: characterization of its intestinal epithelial cell efflux transport. AAPS J. 2009 Jun;11(2):205-13. Epub 2009 Mar 25. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/19319690) 10. Sun H, Huang Y, Frassetto L, Benet LZ: Effects of uremic toxins on hepatic uptake and metabolism of erythromycin. Drug Metab Dispos. 2004 Nov;32(11):1239-46. Epub 2004 Jul 30. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/15286055)

2. Multidrug resistance-associated protein 1 (/bio_entities/BE0000785)

Kind: protein Organism: Human Pharmacological action: unknown Actions: inhibitor

Components
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Name Multidrug resistance-associated protein 1

DrugBank: Erythromycin (DB00199)

UniProt ID P33527 (http://www.uniprot.org/uniprot/P33527) Details
Details (/polypeptides/P33527)

References:
1. Terashi K, Oka M, Soda H, Fukuda M, Kawabata S, Nakatomi K, Shiozawa K, Nakamura T, Tsukamoto K, Noguchi Y, Suenaga M, Tei C, Kohno S: Interactions of ofloxacin and erythromycin with the multidrug resistance protein (MRP) in MRP-overexpressing human leukemia cells. Antimicrob Agents Chemother. 2000 Jun;44(6):1697-700. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/10817732)

3. Solute carrier organic anion transporter family member 1A2 (/bio_entities/BE0003642)

Kind: protein Organism: Human Pharmacological action: unknown Actions: inhibitor

Components
Name Solute carrier organic anion transporter family member 1A2 UniProt ID P46721 (http://www.uniprot.org/uniprot/P46721) Details
Details (/polypeptides/P46721)

References:
1. Cvetkovic M, Leake B, Fromm MF, Wilkinson GR, Kim RB: OATP and P-glycoprotein transporters mediate the cellular uptake and excretion of fexofenadine. Drug Metab Dispos. 1999 Aug;27(8):866-71. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/10421612)

4. Solute carrier family 22 member 7 (/bio_entities/BE0003646)

Kind: protein Organism: Human Pharmacological action: unknown Actions: inhibitor

Components
Name Solute carrier family 22 member 7 UniProt ID Q9Y694 (http://www.uniprot.org/uniprot/Q9Y694) Details
Details (/polypeptides/Q9Y694)

References:
1. Kobayashi Y, Sakai R, Ohshiro N, Ohbayashi M, Kohyama N, Yamamoto T: Possible involvement of organic anion transporter 2 on the interaction of theophylline with erythromycin in the human liver. Drug Metab Dispos. 2005 May;33(5):619-22. Epub 2005 Feb 11. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/15708966) 2. Kobayashi Y, Ohshiro N, Shibusawa A, Sasaki T, Tokuyama S, Sekine T, Endou H, Yamamoto T: Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice. Mol Pharmacol. 2002 Jul;62(1):7-14. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/12065749)

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08

This project is supported by The Metabolomics Innovation Centre (TMIC)

(http://genomealberta.ca)

(http://www.metabolomicscentre.ca)

(http://genomebc.ca)

(http://genomecanada.ca)

(http://www.metabolomicscentre.ca/), a nationally-funded research and core facility that supports a wide range of cutting-edge metabolomic studies. TMIC is funded by Genome Alberta (http://www.genomealberta.ca), Genome British Columbia (http://www.genomebc.ca/), and Genome Canada (http://www.genomecanada.ca), a not-for-profit organization that is leading Canada's national genomics strategy with $900 million in funding from the federal government.
DrugBank Version 4.0 Contact Us (/contact)

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