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1431753130778.

373

DrugBank:Azithromycin(DB00207)

Identification

Taxonomy

Pharmacology

ADMET

Pharmacoeconomics

Properties

Spectra

References

Interactions

2Comments

ShowDrugswithSimilarStructures

targets(3) enzymes(3) transporters(1) Biointeractions(8)(/drugs/DB00207/biointeractions)

Identification
Name

Azithromycin

AccessionNumber

DB00207(APRD00397)

Type

SmallMolecule

Groups

Approved

Description

Azithromycinisasemisyntheticmacrolideantibioticoftheazalideclass.Likeothermacrolideantibiotics,azithromycininhibitsbacterialprotein
synthesisbybindingtothe50Sribosomalsubunitofthebacterial70Sribosome.Bindinginhibitspeptidyltransferaseactivityandinterfereswith
aminoacidtranslocationduringtheprocessoftranslation.Itseffectsmaybebacteriostaticorbactericidaldependingoftheorganismandthedrug
concentration.Itslonghalflife,whichenablesoncedailydosingandshorteradministrationdurations,isapropertydistinctfromothermacrolides.

Structure

(http://moldb.wishartlab.com/molecules/DB00207/image.png)
MOL(/structures/structures/small_molecule_drugs/DB00207.mol) SDF(/structures/structures/small_molecule_drugs/DB00207.sdf)
PDB(/structures/structures/small_molecule_drugs/DB00207.pdb) SMILES(/structures/structures/small_molecule_drugs/DB00207.smiles)
InChI(/structures/structures/small_molecule_drugs/DB00207.inchi) ViewStructure(/structures/structures/small_molecule_drugs/DB00207)

Synonyms

Show

Search

10

entries
Synonym

Language

Code

(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)13((2,6Dideoxy3Cmethyl3OmethylalphaLribohexopyranosyl)oxy)2ethyl3,4,10
trihydroxy3,5,6,8,10,12,14heptamethyl11((3,4,6trideoxy3(dimethylamino)betaDxylohexopyranosyl)oxy)1oxa6
azacyclopentadecan15one

Not
Available

Not
Available

Azenil

Not
Available

Not
Available

Azifast

Not
Available

Not
Available

Azigram

Not
Available

Not
Available

Azimakrol

Not
Available

Not
Available

Azithromycine

French

INN

Azithromycinum

Latin

INN

Azitromicina

Spanish

Not
Available

Azitromin

Not
Available

Not
Available

Hemomycin

Not
Available

Not
Available

Previous

Showing1to10of12entries
Prescription
Products

Show

Next

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10

entries

Name

Dosage

Strength

Route

Labeller

Marketing
Start

Marketing
End

Azasite

solution/drops

10mg/mL

ophthalmic

Akorn,Inc.

20140514

NotAvailable

Azasite

solution

10mg/mL

ophthalmic

InspirePharmaceuticals,Inc.

20070716

NotAvailable

Azithromycin

injection,powder,lyophilized, 100mg/mL
forsolution

intravenous

BaxterHealthcareCorporation

19970101

NotAvailable

Azithromycin

tablet,filmcoated

500mg

oral

LakeErieMedicalDBAQualityCare
ProductsLLC

20020524

NotAvailable

Azithromycin

tablet,filmcoated

500mg

oral

REMEDYREPACKINC.

20130305

NotAvailable

http://www.drugbank.ca/drugs/DB00207

1/12

1431753130866.963

DrugBank:Azithromycin(DB00207)
Azithromycin

tablet,filmcoated

600mg

oral

REMEDYREPACKINC.

20130305

NotAvailable

Azithromycin

tablet,filmcoated

250mg

oral

REMEDYREPACKINC.

20130924

NotAvailable

Azithromycin

powder,forsuspension

1g

oral

PhysiciansTotalCare,Inc.

20080908

NotAvailable

Azithromycin

tablet,filmcoated

250mg

oral

CardinalHealth

19960718

NotAvailable

Azithromycin

powder,forsuspension

1g

oral

GreenstoneLLC

19990212

NotAvailable

Previous

Showing1to10of37entries
Generic
Prescription
Products

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10

entries

Name

Dosage

Strength

Route

Labeller

Marketing
Start

Marketing
End

Azithromycin

powder,forsuspension

200
mg/5mL

oral

TevaPharmaceuticalsUSAInc

20101217

NotAvailable

Azithromycin

powder,forsuspension

100
mg/5mL

oral

TevaPharmaceuticalsUSAInc

20101228

NotAvailable

Azithromycin

tablet,filmcoated

250mg

oral

TevaPharmaceuticalsUSAInc

20051116

NotAvailable

Azithromycin

tablet,filmcoated

600mg

oral

TevaPharmaceuticalsUSAInc

20051116

NotAvailable

Azithromycin

powder,forsuspension

100
mg/5mL

oral

TevaPharmaceuticalsUSAInc

20080922

NotAvailable

Azithromycin

powder,forsuspension

200
mg/5mL

oral

TevaPharmaceuticalsUSAInc

20080922

NotAvailable

Azithromycin

tablet,filmcoated

500mg

oral

TevaPharmaceuticalsUSAInc

20051116

NotAvailable

Azithromycin

tablet,filmcoated

600mg

oral

KAISERFOUNDATIONHOSPITALS

20090901

NotAvailable

Azithromycin

injection,powder,
lyophilized,forsolution

2mg/mL

intravenous Hospira,Inc.

20090626

NotAvailable

Azithromycin

injection,powder,
lyophilized,forsolution

100mg/mL

intravenous Hospira,Inc.

20090626

NotAvailable

Previous

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OvertheCounter
Products

NotAvailable

International
Brands

Show

14

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10

entries
Name

Company

Azenil

NotAvailable

Azibiot

NotAvailable

Azin

NotAvailable

Azithrocin

NotAvailable

Azitromax

NotAvailable

Aztrin

NotAvailable

Hemomycin

NotAvailable

Misultina

NotAvailable

Penalox

NotAvailable

Sumamed

NotAvailable
Previous

Showing1to10of14entries
Brandmixtures
Salts

NotAvailable
Name/CAS
Azithromycin
dihydrate
(/salts/DBSALT000882)

http://www.drugbank.ca/drugs/DB00207

Structure

Properties
Not
applicable

DBSALT000882(/salts/DBSALT000882)

2/12

1431753130903.501

DrugBank:Azithromycin(DB00207)

(http://moldb.wishartlab.com/molecules/DBSALT000882/image.png)

Categories

AntiBacterialAgents(/mesh/antibacterialagents)
Macrolides(/mesh/macrolides)

CASnumber

83905015

Weight

Average:748.9845
Monoisotopic:748.508525778

ChemicalFormula

C38H72N2O12

InChIKey

MQTOSJVFKKJCRPBICOPXKESAN

InChI

InChI=1S/C38H72N2O12/c1152738(10,46)31(42)24(6)40(13)1920(2)1736(8,45)33(523529(41)26(39(11)12)1621(3)48
35)22(4)30(23(5)34(44)5027)51281837(9,4714)32(43)25(7)4928/h2033,35,4143,4546H,1519H2,114H3/t20,21,22+,23,24,25+,26+,27
,28+,29,30+,31,32+,33,35+,36,37,38/m1/s1

IUPACName

(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)11{[(2S,3R,4S,6R)4(dimethylamino)3hydroxy6methyloxan2yl]oxy}2ethyl3,4,10trihydroxy13
{[(2R,4R,5S,6S)5hydroxy4methoxy4,6dimethyloxan2yl]oxy}3,5,6,8,10,12,14heptamethyl1oxa6azacyclopentadecan15one

SMILES

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)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O

Taxonomy
Description

Thiscompoundbelongstotheclassoforganiccompoundsknownasmacrolidesandanalogues.Theseareorganiccompoundscontaininga
lactoneringofatleasttwelvemembers.

Kingdom

Organiccompounds(http://classyfire.wishartlab.com/tax_nodes/C0000000)

SuperClass

Phenylpropanoidsandpolyketides(http://classyfire.wishartlab.com/tax_nodes/C0000261)

Class

Macrolidesandanalogues(http://classyfire.wishartlab.com/tax_nodes/C0000147)

SubClass

NotAvailable

DirectParent

Macrolidesandanalogues(http://classyfire.wishartlab.com/tax_nodes/C0000147)

AlternativeParents

Aminosugars(http://classyfire.wishartlab.com/tax_nodes/C0001148)
Oxanes(http://classyfire.wishartlab.com/tax_nodes/C0002012)
Monosaccharides(http://classyfire.wishartlab.com/tax_nodes/C0001540)
Tertiaryalcohols(http://classyfire.wishartlab.com/tax_nodes/C0001670)
Trialkylamines(http://classyfire.wishartlab.com/tax_nodes/C0002239)
Secondaryalcohols(http://classyfire.wishartlab.com/tax_nodes/C0001661)
Lactones(http://classyfire.wishartlab.com/tax_nodes/C0000050)
Carboxylicacidesters(http://classyfire.wishartlab.com/tax_nodes/C0001238)
1,2diols(http://classyfire.wishartlab.com/tax_nodes/C0002467)
1,2aminoalcohols(http://classyfire.wishartlab.com/tax_nodes/C0001897)
Oxacycliccompounds(http://classyfire.wishartlab.com/tax_nodes/C0004140)
Monocarboxylicacidsandderivatives(http://classyfire.wishartlab.com/tax_nodes/C0001137)
Dialkylethers(http://classyfire.wishartlab.com/tax_nodes/C0001167)
Azacycliccompounds(http://classyfire.wishartlab.com/tax_nodes/C0004139)
Acetals(http://classyfire.wishartlab.com/tax_nodes/C0001656)
Hydrocarbonderivatives(http://classyfire.wishartlab.com/tax_nodes/C0004150)
Carbonylcompounds(http://classyfire.wishartlab.com/tax_nodes/C0001831)

Substituents

Macrolide
Aminosugar
Desosamine
Aminosaccharide
Oxane
Monosaccharide
Saccharide
Tertiaryalcohol
Tertiaryaliphaticamine
Tertiaryamine
Secondaryalcohol
Polyol
Lactone

http://www.drugbank.ca/drugs/DB00207

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1431753130949.864

DrugBank:Azithromycin(DB00207)
Carboxylicacidester
1,2diol
1,2aminoalcohol
Oxacycle
Azacycle
Organoheterocycliccompound
Monocarboxylicacidorderivatives
Ether
Dialkylether
Carboxylicacidderivative
Acetal
Hydrocarbonderivative
Organooxygencompound
Organonitrogencompound
Carbonylgroup
Amine
Alcohol
Aliphaticheteromonocycliccompound

Molecular
Framework
External
Descriptors

Aliphaticheteromonocycliccompounds
macrolideantibiotic(CHEBI:2955(http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2955))

Pharmacology
Indication

Forthetreatmentofpatientswithmildtomoderateinfectionscausedbysusceptiblestrainsofthedesignatedmicroorganismsinthespecific
conditions:H.influenzae,M.catarrhalis,S.pneumoniae,C.pneumoniae,M.pneumoniae,S.pyogenes,S.aureus,S.agal

Pharmacodynamics Azithromycin,asemisyntheticantibioticbelongingtothemacrolidesubgroupofazalides,isusedtotreatSTDsduetochlamydiaandgonorrhea,
communityacquiredpneumonia,pelvicinflammatorydisease,pediatricotitismediaandpharyngitis,andMycobacteriumaviumcomplex(MAC)in
patientswithadvancedHIVdisease.Similarinstructuretoerythromycin.azithromycinreacheshigherintracellularconcentrationsthan
erythromycin,increasingitsefficacyanddurationofaction.
Mechanismof
action

Azithromycinbindstothe50Ssubunitofthe70Sbacterialribosomes,andthereforeinhibitsRNAdependentproteinsynthesisinbacterialcells.

Absorption

Bioavailabilityis37%followingoraladministration.Absorptionisnotaffectedbyfood.Azithromycinisextensivelydistributedintissueswithtissue
concentrationsreachingupto50timesgreaterthanplasmaconcentrations.Drugbecomesconcentratedwithinmacrophagesand
polymorphonucleocytesgivingitgoodactivityagainstChlamydiatrachomatis.

Volumeof
distribution

31.1L/kg

Proteinbinding

Serumproteinbindingisvariableintheconcentrationrangeapproximatinghumanexposure,decreasingfrom51%at0.02g/mLto7%at2
g/mL.

Metabolism

Hepatic.Invitroandinvivostudiestoassessthemetabolismofazithromycinhavenotbeenperformed.

Routeof
elimination

Biliaryexcretionofazithromycin,predominantlyasunchangeddrug,isamajorrouteofelimination.

Halflife

68hours

Clearance
Toxicity
Affectedorganisms
Pathways

apparentplasmacl=630mL/min[followingsingle500mgoralandi.v.doses]
Potentiallyserioussideeffectsofangioedemaandcholestaticjaundicewerereported
Entericbacteriaandothereubacteria
Pathway

Category

AzithromycinActionPathway

Drugaction

SNPMediated
Effects

NotAvailable

SNPMediated
AdverseDrug
Reactions

NotAvailable

SMPDBID
SMP00247(http://smpdb.ca/view/SMP00247?highlight[compounds][]=DB00207&highlight[proteins][]=DB00207)

ADMET
PredictedADMET
features

Property

Value

Probability

HumanIntestinalAbsorption

0.5518

BloodBrainBarrier

0.9739

Caco2permeable

0.7578

http://www.drugbank.ca/drugs/DB00207

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1431753131115.435

DrugBank:Azithromycin(DB00207)
Pglycoproteinsubstrate

Substrate

0.8765

PglycoproteininhibitorI

Inhibitor

0.8513

PglycoproteininhibitorII

Noninhibitor

0.8893

Renalorganiccationtransporter

Noninhibitor

0.8753

CYP4502C9substrate

Nonsubstrate

0.8373

CYP4502D6substrate

Nonsubstrate

0.9116

CYP4503A4substrate

Substrate

0.6403

CYP4501A2substrate

Noninhibitor

0.9295

CYP4502C9substrate

Noninhibitor

0.9021

CYP4502D6substrate

Noninhibitor

0.8904

CYP4502C19substrate

Noninhibitor

0.9023

CYP4503A4substrate

Noninhibitor

0.9533

CYP450inhibitorypromiscuity

LowCYPInhibitoryPromiscuity

0.9751

Amestest

NonAMEStoxic

0.9133

Carcinogenicity

Noncarcinogens

0.9397

Biodegradation

Notreadybiodegradable

0.9673

Ratacutetoxicity

2.5423LD50,mol/kg

Notapplicable

hERGinhibition(predictorI)

Weakinhibitor

0.9929

hERGinhibition(predictorII)

Noninhibitor

0.8555

Pharmacoeconomics
Manufacturers

Pfizerchemicalsdivpfizerinc
Pfizerglobalresearchdevelopment
Plivainc
Sandozinc
Tevapharmaceuticalsusa
Pfizercentralresearch
Apppharmaceuticalsllc
Glandpharmaltd
Hospirainc
Plivahrvatskadoo
Sagentstridesllc
Tevaparenteralmedicinesinc
Pfizerinc(http://www.pfizer.com/)
Inspirepharmaceuticalsinc
Mylanpharmaceuticalsinc
Tevapharmaceuticalsusainc
Wockhardtltd

Packagers

AdvancedPharmaceuticalServicesInc.
AidarexPharmacuticalsLLC(http://www.aidarex.com)
AmerisourceHealthServicesCorp.(http://www.amerisourcebergen.com)
ApothecaInc.
APPPharmaceuticals(http://www.apppharma.com)
AQPharmaceuticalsInc.(http://www.aqpharmaceuticals.com)
ASMedicationSolutionsLLC(http://orders.asmeds.com)
BaxterInternationalInc.(http://www.baxter.com)
CardinalHealth(http://www.cardinal.com)
CatalentPharmaSolutions(http://www.catalent.com)
ComprehensiveConsultantServicesInc.
DeptHealthCentralPharmacy
DirectDispensingInc.
DispensingSolutions(http://www.drxdispensing.com)
DiversifiedHealthcareServicesInc.(http://www.dhscorp.com)
EonLabs
GreenstoneLLC(http://www.greenstonellc.com)
H.J.HarkinsCo.Inc.(http://hjharkinscompanyinc.com)
HospiraInc.(http://www.hospira.com)
InnoviantPharmacyInc.(http://www.innoviantpharmacy.com)
InspirePharmaceuticals(http://www.inspirepharm.com)
KaiserFoundationHospital
LakeErieMedicalandSurgicalSupply
LibertyPharmaceuticals

http://www.drugbank.ca/drugs/DB00207

5/12

1431753131173.804

DrugBank:Azithromycin(DB00207)
MajorPharmaceuticals(http://www.majorpharmaceuticals.com)
MediscaInc.(http://www.medisca.com)
MurfreesboroPharmaceuticalNursingSupply(http://www.unitdosesupply.com)
Mylan(http://www.mylan.com)
NucarePharmaceuticalsInc.(http://www.nucarerx.com)
PalmettoPharmaceuticalsInc.(http://www.palmettopharm.com)
PatheonInc.(http://www.patheon.com)
PDRxPharmaceuticalsInc.(http://www.pdrx.com)
PfizerInc.(http://www.pfizer.com)
PharmaceuticalUtilizationManagementProgramVAInc.
PharmpakInc.(http://www.pharmpakinc.com)
PhysiciansTotalCareInc.(http://www.physicianstotalcare.com)
PlivaInc.(http://www.pliva.com)
PreferredPharmaceuticalsInc.(http://www.preferredpharmaceuticals.com)
PrepackageSpecialists
PrepakSystemsInc.(http://www.prepaksys.com)
PublicHealthDepartmentSeattleandKingCounty(http://www.kingcounty.gov/healthservices/health.aspx)
RebelDistributorsCorp.(http://www.rebelrx.com)
RedpharmDrug
RemedyRepack(http://www.remedyrepack.com)
SagentPharmaceuticals(http://www.sagentpharma.com)
Sandoz(http://www.sandoz.ca)
SicorPharmaceuticals
SouthwoodPharmaceuticals(http://www.southwoodhealthcare.com)
StatRxUsa(http://statrxusa.exporterus.com)
StatScriptsLLC(http://www.statscripts.com)
StridesArcolabLimited(http://www.stridesarco.com)
TevaPharmaceuticalIndustriesLtd.(http://www.tevapharm.com)
TyaPharmaceuticals
UDLLaboratories(http://www.udllabs.com)
USPharmaceuticalGroup
WarnerChilcottCo.Inc.(http://ir.wcrx.com)
WockhardtLtd.(http://www.wockhardtin.com)

Dosageforms

Show

Search

10

entries
Form

Route

Strength

Injection

intravenous

500mg/10mL

Injection,powder,lyophilized,forsolution

intravenous

100mg/mL

Injection,powder,lyophilized,forsolution

intravenous

2mg/mL

Injection,powder,lyophilized,forsolution

intravenous

500mg/5mL

Powderforsuspension

oral

100mg

Powderforsuspension

oral

200mg

Powder,forsuspension

oral

1g

Powder,forsuspension

oral

100mg/5mL

Powder,forsuspension

oral

1200mg/30mL

Powder,forsuspension

oral

2g/60mL
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Prices

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10

entries
Unitdescription

Cost

Unit

ApoAzithromycin250mgTablet

3.11USD

tablet

Azasite1%eyedrops

42.85USD

ml

Azithromycin2.5gmbulkvial

75.6USD

each

Azithromycin200mg/5mlSuspension15mlBottle

34.25USD

bottle

Azithromycin250mgtablet

6.33USD

tablet

Azithromycin3500mgtabletDispPack

48.52USD

disp

Azithromycin500mgtablet

15.87USD

tablet

http://www.drugbank.ca/drugs/DB00207

6/12

1431753131233.812

DrugBank:Azithromycin(DB00207)
Azithromycin6250mgtabletDispPack

48.52USD

disp

Azithromycin600mgtablet

19.04USD

tablet

Azithromycini.v.500mgvial

11.09USD

each

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DrugBankdoesnotsellnorbuydrugs.Pricinginformationissuppliedforinformationalpurposesonly.
Patents

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Search

10

entries
Country

PatentNumber

Approved

Expires(estimated)

Canada

2148071

20001017

20150427

Canada

2467611

20100330

20240518

UnitedStates

5192535

19930309

20100309

UnitedStates

6984403

20040214

20240214

Showing1to4of4entries
Properties
State
Experimental
Properties

Predicted
Properties

Solid
Property

Value

Source

meltingpoint

114C

PhysProp

watersolubility

slight

NotAvailable

logP

4.02

MCFARLAND,JWETAL.(1997)

pKa

8.74(at25C)

MCFARLAND,JWETAL.(1997)

Property

Value

Source

WaterSolubility

0.514mg/mL

ALOGPS(http://www.vcclab.org/lab/alogps/)

logP

3.03

ALOGPS(http://www.vcclab.org/lab/alogps/)

logP

2.44

ChemAxon(http://www.chemaxon.com/products/calculatorplugins/propertypredictors/#logp_logd)

logS

3.2

ALOGPS(http://www.vcclab.org/lab/alogps/)

pKa(StrongestAcidic)

12.43

ChemAxon(http://www.chemaxon.com/products/calculatorplugins/propertypredictors/#pka)

pKa(StrongestBasic)

9.57

ChemAxon(http://www.chemaxon.com/products/calculatorplugins/propertypredictors/#pka)

PhysiologicalCharge

ChemAxon(http://www.chemaxon.com/products/calculatorplugins/propertypredictors/#pka)

HydrogenAcceptorCount

13

ChemAxon(http://www.chemaxon.com/products/calculatorplugins/propertycalculations/#h_bond)

HydrogenDonorCount

PolarSurfaceArea

180.08

RotatableBondCount

ChemAxon(http://www.chemaxon.com/products/calculatorplugins/propertycalculations/#h_bond)
2

ChemAxon(http://www.chemaxon.com/products/calculatorplugins/propertycalculations/#topolgical_surface)
ChemAxon(http://www.chemaxon.com/products/calculatorplugins/propertycalculations/#topology_analysis)

Refractivity

194.11m mol

Polarizability

83.113

ChemAxon(http://www.chemaxon.com/products/calculatorplugins/propertycalculations/#refractivity)
ChemAxon(http://www.chemaxon.com/products/calculatorplugins/molecularmodelling/#polarization)

NumberofRings

ChemAxon(http://www.chemaxon.com/products/calculatorplugins/propertycalculations/#topology_analysis)

Bioavailability

ChemAxon(http://www.chemaxon.com/products/calculatorplugins/molecularmodelling/#polarization)

RuleofFive

Yes

ChemAxon(http://www.chemaxon.com/products/calculatorplugins/molecularmodelling/#polarization)

GhoseFilter

Yes

ChemAxon(http://www.chemaxon.com/products/calculatorplugins/molecularmodelling/#polarization)

Veber'sRule

Yes

ChemAxon(http://www.chemaxon.com/products/calculatorplugins/molecularmodelling/#polarization)

MDDRlikeRule

Yes

ChemAxon(http://www.chemaxon.com/products/calculatorplugins/molecularmodelling/#polarization)

Spectra
MassSpec(NIST)

NotAvailable

Spectra

NotAvailable

References

Synthesis
Reference

WilliamHeggie,ZitaMariaDeMouroVazAzevedoMendes,Processforthepreparationofazithromycin.U.S.PatentUS6013778,issued
November,1994.

http://www.drugbank.ca/drugs/DB00207

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DrugBank:Azithromycin(DB00207)
US6013778(https://www.google.com/?tbm=pts#q=6013778&tbm=pts)

GeneralReference

ExternalLinks

ATCCodes

1. NoedlH,KrudsoodS,ChalermratanaK,SilachamroonU,LeowattanaW,TangpukdeeN,LooareesuwanS,MillerRS,FukudaM,Jongsakul
K,SriwichaiS,RowanJ,BhattacharyyaH,OhrtC,KnirschC:Azithromycincombinationtherapywithartesunateorquinineforthetreatment
ofuncomplicatedPlasmodiumfalciparummalariainadults:arandomized,phase2clinicaltrialinThailand.ClinInfectDis.2006Nov
1543(10):126471.Epub2006Oct12.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/17051490)
Resource

Link

KEGGCompound

C06838(http://www.genome.jp/dbgetbin/www_bget?cpd:C06838)

BindingDB

50197040(http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50197040)

ChEBI

2955(http://www.ebi.ac.uk/chebi/searchId.do?chebiId=2955)

ChEMBL

CHEMBL529(http://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL529)

TherapeuticTargetsDatabase

DNC001539(http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DNC001539)

PharmGKB

PA448519(http://www.pharmgkb.org/drug/PA448519)

HET

ZIT(http://www.ebi.ac.uk/msdsrv/chempdb/cgibin/cgi.pl?FUNCTION=getByCode&CODE=ZIT)

RxList

http://www.rxlist.com/cgi/generic/zithromax.htm(http://www.rxlist.com/cgi/generic/zithromax.htm)

Drugs.com

http://www.drugs.com/cdi/azithromycindrops.html(http://www.drugs.com/cdi/azithromycindrops.html)

Wikipedia

Azithromycin(http://en.wikipedia.org/wiki/Azithromycin)

J01FA10
JANTIINFECTIVESFORSYSTEMICUSE(/atc/J#J)
J01ANTIBACTERIALSFORSYSTEMICUSE(/atc/J01#J01)
J01FMACROLIDES,LINCOSAMIDESANDSTREPTOGRAMINS(/atc/J01F#J01F)
J01FAMacrolides(/atc/J01FA#J01FA)
S01AA26
SSENSORYORGANS(/atc/S#S)
S01OPHTHALMOLOGICALS(/atc/S01#S01)
S01AANTIINFECTIVES(/atc/S01A#S01A)
S01AAAntibiotics(/atc/S01AA#S01AA)

AHFSCodes

08:12.12.92

PDBEntries

NotAvailable

FDAlabel

Download(/system/fda_labels/DB00207.pdf?1265922797)(76.3KB)

MSDS

Download(/system/msds/DB00207.pdf?1265922737)(73.9KB)

Interactions
DrugInteractions

Drug
Acenocoumarol
(/drugs/DB01418)

Azithromycinmayincreasetheanticoagulanteffectofacenocoumarolbyincreasingitsserumconcentration.

Anisindione(/drugs/DB01125)

Azithromycinmayincreasetheanticoagulanteffectofanisindionebyincreasingitsserumconcentration.

Artemether(/drugs/DB06697)

AdditiveQTcprolongationmayoccur.Concomitanttherapyshouldbeavoided.

Cyclosporine
(/drugs/DB00091)

Themacrolide,azithromycin,mayincreasetheeffectofcyclosporine.

Dicoumarol(/drugs/DB00266)

Azithromycinmayincreasetheanticoagulanteffectofdicumarolbyincreasingitsserumconcentration.

Disopyramide
(/drugs/DB00280)

Themacrolide,azithromycin,mayincreasetheeffectofdisopyramide.

Lovastatin(/drugs/DB00227)

Themacrolideantibiotic,azithromycin,mayincreasetheserumconcentrationoflovastatinbydecreasingitsmetabolism.
Monitorforchangesinthetherapeuticandadverseeffectsoflovastatinifazithromycinisinitiated,discontinuedordose
changed.

Lumefantrine
(/drugs/DB06708)

AdditiveQTcprolongationmayoccur.Concomitanttherapyshouldbeavoided.

Vismodegib(/drugs/DB08828) Pglycoproteininhibitorsmayincreasethechanceofadversedrugreactions.

FoodInteractions

Vorinostat(/drugs/DB02546)

AdditiveQTcprolongationmayoccur.ConsideralternatetherapyormonitorforQTcprolongationasthiscanleadtoTorsade
dePointes(TdP).

Warfarin(/drugs/DB00682)

Azithromycinmayincreasetheanticoagulanteffectofwarfarinbyincreasingitsserumconcentration.

Ziprasidone(/drugs/DB00246)

AdditiveQTcprolongingeffectsmayincreasetheriskofseverearrhythmias.Concomitanttherapyiscontraindicated.

Zuclopenthixol
(/drugs/DB01624)

AdditiveQTcprolongationmayoccur.ConsideralternatetherapyorusecautionandmonitorforQTcprolongationasthiscan
leadtoTorsadedePointes(TdP).

DonottakeAluminumormagnesiumantacidsorsupplementswhileonthismedication.

http://www.drugbank.ca/drugs/DB00207

8/12

1431753131298.898

DrugBank:Azithromycin(DB00207)
Takeonemptystomach:1hourbeforeor2hoursaftermeals.

Targets

1.23SrRNA(/biodb/bio_entities/BE0004800)
Kind:nucleotide
Organism:Entericbacteriaandothereubacteria
Pharmacologicalaction:

yes

Actions: inhibitor

Components
Name

UniProtID

Details

References:
1. NgLK,MartinI,LiuG,BrydenL:Mutationin23SrRNAassociatedwithmacrolideresistanceinNeisseriagonorrhoeae.AntimicrobAgentsChemother.2002Sep46(9):30205.
Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/12183262)
2. JalavaJ,VaaraM,HuovinenP:Mutationattheposition2058ofthe23SrRNAasacauseofmacrolideresistanceinStreptococcuspyogenes.AnnClinMicrobiolAntimicrob.
2004May63:5.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/15128458)
3. PereyreS,RenaudinH,CharronA,BebearC,BebearCM:Emergenceofa23SrRNAmutationinMycoplasmahominisassociatedwithalossoftheintrinsicresistanceto
erythromycinandazithromycin.JAntimicrobChemother.2006Apr57(4):7536.Epub2006Feb7.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/16464889)

2.50SribosomalproteinL4(/biodb/bio_entities/BE0002465)
Kind:protein
Organism:EscherichiacoliO157:H7
Pharmacologicalaction:

yes

Actions: inhibitor

Components
Name

UniProtID

50SribosomalproteinL4

P60725(http://www.uniprot.org/uniprot/P60725)

Details
Details(/biodb/polypeptides/P60725)

References:
1. HallingSM,JensenAE:Intrinsicandselectedresistancetoantibioticsbindingtheribosome:analysesofBrucella23Srrn,L4,L22,EFTu1,EFTu2,effluxandphylogenetic
implications.BMCMicrobiol.2006Oct26:84.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/17014718)
2. TuD,BlahaG,MoorePB,SteitzTA:StructuresofMLSBKantibioticsboundtomutatedlargeribosomalsubunitsprovideastructuralexplanationforresistance.Cell.2005Apr
22121(2):25770.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/15851032)
3. SchlunzenF,HarmsJM,FranceschiF,HansenHA,BartelsH,ZarivachR,YonathA:Structuralbasisfortheantibioticactivityofketolidesandazalides.Structure.2003
Mar11(3):32938.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/12623020)
4. PetropoulosAD,KouvelaEC,StarostaAL,WilsonDN,DinosGP,KalpaxisDL:TimeresolvedbindingofazithromycintoEscherichiacoliribosomes.JMolBiol.2009Jan
30385(4):117992.Epub2008Nov27.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/19071138)
5. ChampneyWS,MillerM:Inhibitionof50SribosomalsubunitassemblyinHaemophilusinfluenzaecellsbyazithromycinanderythromycin.CurrMicrobiol.2002Jun44(6):418
24.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/12000992)

3.50SribosomalproteinL22(/biodb/bio_entities/BE0002464)
Kind:protein
Organism:EscherichiacoliO157:H7
Pharmacologicalaction:

yes

Actions: inhibitor

Components
Name

UniProtID

50SribosomalproteinL22

P61177(http://www.uniprot.org/uniprot/P61177)

Details
Details(/biodb/polypeptides/P61177)

References:
1. HallingSM,JensenAE:Intrinsicandselectedresistancetoantibioticsbindingtheribosome:analysesofBrucella23Srrn,L4,L22,EFTu1,EFTu2,effluxandphylogenetic
implications.BMCMicrobiol.2006Oct26:84.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/17014718)

http://www.drugbank.ca/drugs/DB00207

9/12

1431753131328.023

DrugBank:Azithromycin(DB00207)

2. TuD,BlahaG,MoorePB,SteitzTA:StructuresofMLSBKantibioticsboundtomutatedlargeribosomalsubunitsprovideastructuralexplanationforresistance.Cell.2005Apr
22121(2):25770.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/15851032)
3. SchlunzenF,HarmsJM,FranceschiF,HansenHA,BartelsH,ZarivachR,YonathA:Structuralbasisfortheantibioticactivityofketolidesandazalides.Structure.2003
Mar11(3):32938.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/12623020)
4. PetropoulosAD,KouvelaEC,StarostaAL,WilsonDN,DinosGP,KalpaxisDL:TimeresolvedbindingofazithromycintoEscherichiacoliribosomes.JMolBiol.2009Jan
30385(4):117992.Epub2008Nov27.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/19071138)
5. ChampneyWS,MillerM:Inhibitionof50SribosomalsubunitassemblyinHaemophilusinfluenzaecellsbyazithromycinanderythromycin.CurrMicrobiol.2002Jun44(6):418
24.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/12000992)

Enzymes

1.CytochromeP4502A6(/biodb/bio_entities/BE0003336)
Kind:protein
Organism:Human
Pharmacologicalaction:

unknown

Actions: inhibitor

Components
Name

UniProtID

CytochromeP4502A6

P11509(http://www.uniprot.org/uniprot/P11509)

Details
Details(/biodb/polypeptides/P11509)

References:
1. PreissnerS,KrollK,DunkelM,SengerC,GoldsobelG,KuzmanD,GuentherS,WinnenburgR,SchroederM,PreissnerR:SuperCYP:acomprehensivedatabaseon
CytochromeP450enzymesincludingatoolforanalysisofCYPdruginteractions.NucleicAcidsRes.2010Jan38(Databaseissue):D23743.Epub2009Nov24.Pubmed
(http://www.ncbi.nlm.nih.gov/pubmed/19934256)

2.CytochromeP4503A4(/biodb/bio_entities/BE0002638)
Kind:protein
Organism:Human
Pharmacologicalaction:

unknown

Actions: substrate inhibitor

Components
Name

UniProtID

CytochromeP4503A4

P08684(http://www.uniprot.org/uniprot/P08684)

Details
Details(/biodb/polypeptides/P08684)

References:
1. PreissnerS,KrollK,DunkelM,SengerC,GoldsobelG,KuzmanD,GuentherS,WinnenburgR,SchroederM,PreissnerR:SuperCYP:acomprehensivedatabaseon
CytochromeP450enzymesincludingatoolforanalysisofCYPdruginteractions.NucleicAcidsRes.2010Jan38(Databaseissue):D23743.Epub2009Nov24.Pubmed
(http://www.ncbi.nlm.nih.gov/pubmed/19934256)

3.CytochromeP4501A2(/biodb/bio_entities/BE0002433)
Kind:protein
Organism:Human
Pharmacologicalaction:

unknown

Actions: inhibitor

Components
Name

UniProtID

CytochromeP4501A2

P05177(http://www.uniprot.org/uniprot/P05177)

Details
Details(/biodb/polypeptides/P05177)

References:
1. Lexicomp

http://www.drugbank.ca/drugs/DB00207

10/12

1431753131353.312

DrugBank:Azithromycin(DB00207)

Transporters

1.Multidrugresistanceprotein1(/biodb/bio_entities/BE0001032)
Kind:protein
Organism:Human
Pharmacologicalaction:

unknown

Actions: inhibitor

Components
Name

UniProtID

Details

Multidrugresistanceprotein1

P08183(http://www.uniprot.org/uniprot/P08183)

Details(/biodb/polypeptides/P08183)

References:
1. WangE,LewK,BareckiM,CascianoCN,ClementRP,JohnsonWW:QuantitativedistinctionsofactivesitemolecularrecognitionbyPglycoproteinandcytochromeP4503A4.
ChemResToxicol.2001Dec14(12):1596603.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/11743742)
2. AsakuraE,NakayamaH,SugieM,ZhaoYL,NadaiM,KitaichiK,ShimizuA,MiyoshiM,TakagiK,TakagiK,HasegawaT:Azithromycinreversesanticancerdrugresistanceand
modifieshepatobiliaryexcretionofdoxorubicininrats.EurJPharmacol.2004Jan26484(23):3339.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/14744620)

Comments

2Comments

DrugBank

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Jointhediscussion
Bmorale2 3yearsago

IthinktheSpanishversionofthisshouldbetranslatedto"Azitromicina"notasitshowsas"Aritromicina".

Reply Share

CraigKnox

Mod >Bmorale2 3yearsago

Hi,thanksforthetip,lookslikeitwasaspellingerror.I'vecorrectedit.
1

Reply Share

WHAT'STHIS?

ALSOONDRUGBANK

Abiraterone(DB05812)

Denosumab(DB06643)

4comments2yearsago

1comment2yearsago

AdamMaciejewskiHiPangPangGunThanksforyourquestion.

GlennPilkingtonTsequencesyouhavelistedaredifferenttothe

Currently,wedon'thavethisfeature,butpleaselookatourcurrent
'pharmacoeconomics'sectionforinformationregardingprices,
manufacturers,packagers,anddosages.Thankyou,Adam

patent(WO2013181575A2)sequencesandtheheavychainsequence
isforahIgG1nothIgG2.

LYM2(DB05788)

FTY720(DB05286)

2commentsayearago

2commentsayearago

AdamMaciejewskiHiNieLun,thankyouforlettingusknowaboutthis.

AdamMaciejewskiHelloDanielHimmelstein,thankyouforpointing

IhavecreatedabiotechentryforLYM2,andhavemergedthetwo
drugs.PleaseseeDB09025.Thankyou!

thisout.Indeed,FTY720isthesamedrugasthelaterapproved
Fingolimod.IwillmergethetwoentriesintoDB08868.Ifyouhaveany
furtherquestionsorcomments,pleasedon'thesitateto

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DrugcreatedonJune13,200507:24/UpdatedonSeptember16,201317:08

(http://www.cihrirsc.gc.ca)

http://www.drugbank.ca/drugs/DB00207

(http://www.metabolomicscentre.ca)

11/12

1431753133823.464

DrugBank:Azithromycin(DB00207)
(http://www.aihealthsolutions.ca)

(http://genomealberta.ca)

(http://genomebc.ca)

(http://genomecanada.ca)
ThisprojectissupportedbytheCanadianInstitutesofHealthResearch(http://www.cihrirsc.gc.ca)(award#111062),AlbertaInnovatesHealthSolutions
(http://www.aihealthsolutions.ca),andbyTheMetabolomicsInnovationCentre(TMIC)(http://www.metabolomicscentre.ca/),anationallyfundedresearchandcore
facilitythatsupportsawiderangeofcuttingedgemetabolomicstudies.TMICisfundedbyGenomeAlberta(http://www.genomealberta.ca),GenomeBritishColumbia
(http://www.genomebc.ca/),andGenomeCanada(http://www.genomecanada.ca),anotforprofitorganizationthatisleadingCanada'snationalgenomicsstrategywith
$900millioninfundingfromthefederalgovernment.
DrugBankVersion4.2ContactUs(http://drugbank/w/contact)

http://www.drugbank.ca/drugs/DB00207

12/12