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Nitrofurantoin

From Wikipedia, the free encyclopedia


Nitrofurantoin

Systematic (IUPAC) name


)-1-[(5-nitro-2-furyl)methylideneamino]imidazolidine-2,4-dione

Trade names

Clinical data
Macrobid, Macrodantin and others

AHFS/Drugs.com monograph
MedlinePlus

Pregnancy
category

a682291

AU:A

US:B

(No risk in nonhuman studies)

Routes of
by mouth
administration
Legal status

Legal status

AU:S4

CA:

UK:POM

(Prescription only)

-only
(Prescription

only)

US:-only

Pharmacokinetic data
Bioavailability 40%
Metabolism liver (75%)

Biological half-life 20 minutes


urine and bile
Excretion
Identifiers
CAS Number 67-20-9
ATC code

J01XE01 (WHO)

PubChem

CID 6604200

DrugBank

DB00698

ChemSpider

5036498

UNII

927AH8112L

KEGG

D00439

ChEBI

CHEBI:71415

ChEMBL

CHEMBL572
Chemical data
C8H6N4O5
238.16

Formula
Molar mass
SMILES[show]
InChI[show]

Physical data
270 to 272 C (518 to 522 F)
Melting point
(decomp.)
(what is this?) (verify)
Nitrofurantoin, sold under the trade name Macrobid among others, is an antibiotic used to
treat bladder infections.[1] It is not effective for kidney infections. It is taken by mouth.[1]
Common side effects include nausea, loss of appetite, diarrhea, and headaches. Rarely
numbness, lung problems, or liver problems may occur. It should not be used in people with
kidney problems.[1] While it looks like it is generally safe during pregnancy it should not be
used near delivery.[1][2] It works by slowing growth rather than killing bacteria.[1]
Nitrofurantoin was first sold in 1953.[3] It is on the World Health Organization's List of
Essential Medicines, the most important medications needed in a basic health system.[4] It is
available as a generic medication.[1] The wholesale cost is 0.005 and 0.46 USD a dose.[5] In
the United States it is about 60 USD for 10 days of treatment.[1]

Contents

1 Medical uses
o 1.1 Antibacterial activity
o 1.2 Pregnancy

2 Adverse effects

o 2.1 Pulmonary toxicity


o 2.2 Hepatotoxicity
o 2.3 Neuropathy
o 2.4 Contraindications

3 Pharmacology

4 Mechanism of action

5 History

6 Animal feed

7 Society and culture


o 7.1 Cost
o 7.2 Trade names

8 References

9 External links

Medical uses
Current uses include the treatment of uncomplicated urinary tract infections (UTIs) and
prophylaxis against UTIs in people prone to recurrent UTIs.[6]
Increasing bacterial antibiotic resistance to other commonly used agents, such as
fluoroquinolones and trimethoprim/sulfamethoxazole, has led to increased interest in using
nitrofurantoin.[7][8] Several trials comparing nitrofurantoin to other commonly used agents
have shown this drug results in similar cure rates for uncomplicated UTIs.[9][10][11][12] The
efficacy of nitrofurantoin in treating UTIs combined with a low rate of bacterial resistance to
this agent makes it one of the first-line agents for treating uncomplicated UTIs as
recommended by the Infectious Diseases Society of America and the European Society for
Microbiology and Infectious Diseases.[13]
Nitrofurantoin is not recommended for the treatment of pyelonephritis,[13]prostatitis[14] and
intra-abdominal abscess,[15] because of extremely poor tissue penetration and low blood
levels.

Antibacterial activity
Nitrofurantoin has been shown to have good activity against:

E. coli

Staphylococcus saprophyticus

Coagulase negative staphylococci

Enterococcus faecalis

Staphylococcus aureus

Streptococcus agalactiae

Citrobacter species

Klebsiella species

It is used in the treatment of infections caused by these organisms.[16]


Many or all strains of the following genera are resistant to nitrofurantoin:[16]

Enterobacter

Klebsiella

Proteus

Pseudomonas

Antibiotic susceptibility testing should always be performed to further elucidate the


resistance profile of the particular strain of bacteria causing infection.

Pregnancy
Nitrofurantoin is pregnancy category B.[6] It is one of the few drugs commonly used in
pregnancy to treat UTIs.[17] Other drugs used for UTIs in pregnancy include cephalexin,
amoxicillin, and pivmecillinam. The drug should not be given to women in late pregnancy
due to the potential risk of hemolytic anemia in the newborn, as the newborn has not yet
developed the enzymatic pathways necessary for glutathione metabolism and the drug may
cause oxidative damage to the red blood cells. Newborns of women given this drug late in
pregnancy had a higher risk of developing neonatal jaundice.[18]
Several trials on the safety and teratogenicity of nitrofurantoin in pregnancy have shown
mixed results. A retrospective study in 2009 claimed that several birth defects, such as
hypoplastic left heart syndrome, ophthalmic malformations, cleft lip and cleft palate, and
atrial septal defect, were more common in neonates exposed to nitrofurantoin during
pregnancy.[19] A meta analysis of four out of twenty-two available studies on the safety of
nitrofurantoin found no increased risk.[20] A case-control study in 1998 found an increased
risk of craniosynostosis after exposure to "nitrosatable" drugs.[21] A more recent 2013

population-based cohort study which used women registered in the Norwegian Prescription
Database and linked the subjects to a birth outcomes database, however, found no increased
risk of major malformations in neonates born to women who took nitrofurantoin in early
pregnancy.[18] Many of the studies showing increased risk of nitrofurantoin had limitations
and relied on patients' recall of the antibiotics they took during pregnancy rather than
objective data, which may have led to recall bias. Nevertheless, in light of these conflicting
data, the American College of Obstetrics and Gynecology (ACOG) recommends using
antibiotics only for appropriate indications and for the shortest effective duration.[22]

Adverse effects
The most common side effects with nitrofurantoin are nausea, headache, and flatulence. Less
common adverse events (occurring in less than 1% of those taking the drug) include:[6]

Gastrointestinal: diarrhea, dyspepsia, abdominal pain, constipation, emesis

Neurologic: dizziness, drowsiness, amblyopia

Respiratory: acute pulmonary hypersensitivity reaction

Allergic: pruritus, urticaria

Dermatologic: hair loss

Miscellaneous: fever, chills, malaise

Patients should be informed that nitrofurantoin colours urine brown; this is completely
harmless.[6]
Some of the more serious but rare side effects of nitrofurantoin have been a cause of concern.
These include pulmonary reactions, hepatotoxicity, and neuropathy.

Pulmonary toxicity
The pulmonary toxicity caused by nitrofurantoin can be categorized into acute, subacute, and
chronic pulmonary reactions. The acute and subacute reactions are thought to be due to a
hypersensitivity reaction and often resolve when the drug is discontinued. Acute reactions
have been estimated to occur in about one in 5000 women who take the drug.[23][24] These
reactions usually develop 38 days after the first dose of nitrofurantoin, but may occur from a
few hours to a few weeks after starting the drug. Symptoms include fever, dyspnea, chills,
cough, pleuritic chest pain, headache, back pain, and epigastric pain. Chest radiograph will
often show unilateral or bilateral infiltrates similar to pulmonary edema. Treatment includes
discontinuation of the nitrofurantoin, which should result in symptom improvement within 24
hours.[25]
Chronic pulmonary reactions caused by nitrofurantoin include diffuse interstitial
pneumonitis, pulmonary fibrosis, or both.[6] This uncommon reaction may occur 1 month to 6
years after starting the drug and is usually related to its total lifetime dose. This reaction

manifests with progressive shortness of breath.[26] It is important to recognize nitrofurantoin


as possible cause of symptoms and discontinue the drug when the suspicion of pulmonary
side effects arises as it can be reversible if the drug is stopped early.[24]

Hepatotoxicity
Hepatic reactions, including hepatitis, cholestatic jaundice, chronic active hepatitis, and
hepatic necrosis, occur rarely. The onset of chronic active hepatitis may be insidious, and
patients should be monitored periodically for changes in biochemical tests that would indicate
liver injury.[6] These reactions usually occur after exposure to the drug for more than 6 weeks.
If signs of liver failure are observed in a patient taking nitrofurantoin, the drug should be
discontinued. Re-challenge with the drug at a later date is not recommended, as the reaction
may have a hypersensitivity component and recur when the drug is resumed.[27]

Neuropathy
Neuropathy is a rare side effect of taking nitrofurantoin. Patients may experience numbness
and tingling in a stocking-glove pattern, which may or may not improve upon discontinuation
of the drug.[28]

Contraindications
Nitrofurantoin is contraindicated in patients with decreased renal function (CrCl < 60 ml/min)
due to systemic accumulation and subtherapeutic levels reached in the urinary tract.[6]
However, a retrospective chart review suggests the data for this cutoff are slim and a cutoff of
CrCl < 40 ml/min would be more appropriate.[29] Many of the severe side effects of this drug
are more common in the elderly and those with renal impairment, as this causes the drug to
be retained in the body and reach higher systemic levels. Thus, the drug is not recommended
for the elderly population according to 2012 AGS Beers criteria.[30]
Nitrofurantoin is also contraindicated in babies up to the age of one month, as they have
immature enzyme systems in their red blood cells (glutathione instability), so nitrofurantoin
must not be used because it can cause haemolytic anaemia. For the same reason,
nitrofurantoin should not be given to pregnant women after 38 weeks of pregnancy.
Nitrofurantoin is contraindicated in patients with glucose-6-phosphate dehydrogenase
deficiency because of risk of intravascularhemolysis resulting in anemia.[6]

Pharmacology
Organisms are said to be susceptible to nitrofurantoin if their minimum inhibitory
concentration is 32 g/ml or less. The peak blood concentration of nitrofurantoin following
an oral dose of nitrofurantoin 100 mg, is less than 1 g/ml and may be undetectable. Its
bioavailability is about 90% and the urinary excretion is 40%[31][full citation needed] tissue
penetration is negligible; the drug is well concentrated in the urine: 75% of the dose is rapidly
metabolised by the liver, but 25% of the dose is excreted in the urine unchanged, reliably
achieving levels of 200 g/ml or more. In studies of dogs, the majority of urinary excretion is
through glomerular filtration with some tubular secretion.[32] There is also tubular absorption
which is increased with urine acidification.[32] However the activity of nitrofurantoin is also

pH depenent and mean inhibitory concentration rises sharply with increased pH above 6.[32]
Nitrofurantoin cannot be used to treat infections other than simple cystitis.
At the concentrations achieved in urine (>100 g/ml), nitrofurantoin is a bactericide. It is
bacteriostatic against most susceptible organisms at concentrations less than 32 g/ml.[6]
Nitrofurantoin and the quinolone antibiotics are mutually antagonistic in vitro. It is not
known whether this is of clinical significance, but the combination should be avoided.[6]
Resistance to nitrofurantoin may be chromosomal or plasmid-mediated and involves
inhibition of nitrofuran reductase.[33] Acquired resistance in E. coli continues to be rare.
Nitrofurantoin and its metabolites are excreted mainly by the kidneys. In renal impairment,
the concentration achieved in urine may be subtherapeutic. Nitrofurantoin should not be used
in patients with a creatinine clearance of 60 ml/min or less. However, a retrospective chart
review may suggest nitrofurantoin is not contraindicated in this population.[34]

Mechanism of action
It is concentrated in the urine, leading to higher and more effective levels in the urinary tract
than in other tissues or compartments.[24] With a 100 mg oral dose, plasma levels are typically
less than 1g/ml while in the urine it reaches 200 g/ml.[35]
The mechanism of action of nitrofurantoin is unique and complex. The drug works by
damaging bacterial DNA, since its reduced form is highly reactive.[6] This is made possible by
the rapid reduction of nitrofurantoin inside the bacterial cell by flavoproteins (nitrofuran
reductase) to multiple reactive intermediates that attack ribosomal proteins, DNA,[36]
respiration, pyruvate metabolism and other macromolecules within the cell. Nitrofurantoin
exerts greater effects on bacterial cells than mammalian cells because bacterial cells activate
the drug more rapidly. It is not known which of the actions of nitrofurantoin is primarily
responsible for its bactericidal activity. The broad mechanism of action for this drug likely is
responsible for the low development of resistance to its effects, as the drug affects many
different processes important to the bacterial cell.[6]

History
Nitrofurantoin has been available for the treatment of lower urinary tract infections (UTIs)
since 1953.[3]

Animal feed
Residues from the breakdown of nitrofuran veterinary antibiotics, including nitrofurantoin,
have been found in chicken in Vietnam, China, Brazil, and Thailand.[37] The European Union
banned the use of nitrofurans in food producing animals by classifying it in ANNEX IV (list
of pharmacologically active substances for which no maximum residue limits can be fixed) of
the Council Regulation 2377/90. The Food and Drug Administration (FDA) of the United
States has prohibited furaltadone since February 1985 and withdrew the approval for the
other nitrofuran drugs (except some topical uses) in January 1992. The topical use of

furazolidone and nitrofurazone was prohibited in 2002. Australia prohibited the use of
nitrofurans in food production in 1992. Japan did not allocate MRLs for nitrofurans leading
to the implementation of a "zero tolerance or no residue standard". In Thailand, the Ministry
of Health issued in 2001 Proclamation No. 231 MRL of veterinary drug in food which did not
allocate MRL for nitrofurans. The Ministry of Agriculture and Cooperatives had already
prohibited importation and use of furazolidone and nitrofurazone in animal feed in 1999
which was extended to all nitrofurans in 2002. Several metabolites of nitrofurans, such as
furazolidone, furaltadone and nitrofurazone cause cancer or genetic damage in rats.[37]

Society and culture


Cost
It is available as a generic medication.[1] The wholesale cost is 0.005 and 0.46 USD a dose.[5]
In the United States 60 USD for 10 days of treatment.[1]

Trade names
Nitrofurantoin is marketed under many names in countries worldwide.[38]

References
1.
"Nitrofurantoin". The American Society of Health-System Pharmacists. Retrieved Aug 1,
2015.
"Prescribing medicines in pregnancy database". Australian Government. 3 March 2014.
Retrieved 22 April 2014.
Blass, Benjamin (2015). Basic Principles of Drug Discovery and Development. Elsevier.
p. 511. ISBN 9780124115255.
"WHO Model List of EssentialMedicines"(PDF). World Health Organization. October
2013. Retrieved 22 April 2014.
"Nitrofurantoin". International Drug Price Indicator Guide. Retrieved 31 August 2015.
"Macrobid Drug Label"(PDF). FDA. Retrieved 21 April 2014.
Garau J (January 2008). "Other antimicrobials of interest in the era of extendedspectrum beta-lactamases: fosfomycin, nitrofurantoin and tigecycline". Clin. Microbiol.
Infect. 14 Suppl 1: 198202. doi:10.1111/j.1469-0691.2007.01852.x. PMID 18154548.
McKinnell, JA; Stollenwerk, NS; Jung, CW; Miller, LG (Jun 2011). "Nitrofurantoin
compares favorably to recommended agents as empirical treatment of uncomplicated urinary
tract infections in a decision and cost analysis.". Mayo Clinic Proceedings 86 (6): 4808.
doi:10.4065/mcp.2010.0800. PMC 3104907. PMID 21576512.
Christiaens TC, De Meyere M, Verschraegen G, Peersman W, Heytens S, De Maeseneer
JM (Sep 2002). "Randomised controlled trial of nitrofurantoin versus placebo in the
treatment of uncomplicated urinary tract infection in adult women.". The British journal of
general practice: the journal of the Royal College of General Practitioners 52 (482): 729
34. PMC 1314413. PMID 12236276.
Gupta, K; Hooton, TM; Roberts, PL; Stamm, WE (Nov 12, 2007). "Short-course
nitrofurantoin for the treatment of acute uncomplicated cystitis in women.". Archives of
Internal Medicine 167 (20): 220712. doi:10.1001/archinte.167.20.2207. PMID 17998493.

Iravani, A; Klimberg, I; Briefer, C; Munera, C; Kowalsky, SF; Echols, RM (Mar 1999).


"A trial comparing low-dose, short-course ciprofloxacin and standard 7-day therapy with cotrimoxazole or nitrofurantoin in the treatment of uncomplicated urinary tract infection.". The
Journal of antimicrobial chemotherapy. 43 Suppl A: 6775. doi:10.1093/jac/43.suppl_1.67.
PMID 10225575.
Stein, GE (Nov 1999). "Comparison of single-dose fosfomycin and a 7-day course of
nitrofurantoin in female patients with uncomplicated urinary tract infection.". Clinical
therapeutics 21 (11): 186472. doi:10.1016/S0149-2918(00)86734-X. PMID 10890258.
Gupta, K.; Hooton, T. M.; Naber, K. G.; Wullt, B.; Colgan, R.; Miller, L. G.; Moran, G.
J.; Nicolle, L. E.; Raz, R.; Schaeffer, A. J.; Soper, D. E. (2011). "International Clinical
Practice Guidelines for the Treatment of Acute Uncomplicated Cystitis and Pyelonephritis in
Women: A 2010 Update by the Infectious Diseases Society of America and the European
Society for Microbiology and Infectious Diseases". Clinical Infectious Diseases 52 (5):
e103e120. doi:10.1093/cid/ciq257. PMID 21292654.
Lipsky, Benjamin A.; Byren, Ivor; Hoey, Christopher T. "Treatment of Bacterial
Prostatitis". Clinical Infectious Diseases 50 (12): 16411652. doi:10.1086/652861.
Solomkin JS, Mazuski JE, Bradley JS, Rodvold KA, Goldstein EJ, Baron EJ, O'Neill PJ,
Chow AW, Dellinger EP, Eachempati SR, Gorbach S, Hilfiker M, May AK, Nathens AB,
Sawyer RG, Bartlett JG (January 2010). "Diagnosis and Management of Complicated Intra
abdominal Infection in Adults and Children: Guidelines by the Surgical Infection Society and
the Infectious Diseases Society of America". Clinical Infectious Diseases 50 (2): 133164.
doi:10.1086/649554. PMID 20034345.
Gupta, K; Scholes, D; Stamm, WE (Feb 24, 1999). "Increasing prevalence of
antimicrobial resistance among uropathogens causing acute uncomplicated cystitis in
women.". JAMA: the Journal of the American Medical Association 281 (8): 7368.
doi:10.1001/jama.281.8.736. PMID 10052444.
Lee M, Bozzo P, Einarson A, Koren G (June 2008). "Urinary tract infections in
pregnancy". Can Fam Physician 54 (6): 8534. PMC 2426978. PMID 18556490.
Nordeng, H; Lupattelli, A; Romren, M; Koren, G (Feb 2013). "Neonatal outcomes
after gestational exposure to nitrofurantoin.". Obstetrics and gynecology 121 (2 Pt 1): 306
13. doi:10.1097/AOG.0b013e31827c5f88. PMID 23344280.
Crider, KS; Cleves, MA; Reefhuis, J; Berry, RJ; Hobbs, CA; Hu, DJ (Nov 2009).
"Antibacterial medication use during pregnancy and risk of birth defects: National Birth
Defects Prevention Study.". Archives of pediatrics & adolescent medicine 163 (11): 97885.
doi:10.1001/archpediatrics.2009.188. PMID 19884587.
Ben David S, Einarson T, Ben David Y, Nulman I, Pastuszak A, Koren G (1995). "The
safety of nitrofurantoin during the first trimester of pregnancy: meta-analysis.". Fundamental
& clinical pharmacology 9 (5): 5037. doi:10.1111/j.1472-8206.1995.tb00525.x.
PMID 8617414.
Gardner, JS; Guyard-Boileau, B; Alderman, BW; Fernbach, SK; Greene, C; Mangione,
EJ (Feb 1998). "Maternal exposure to prescription and non-prescription pharmaceuticals or
drugs of abuse and risk of craniosynostosis.". International Journal of Epidemiology 27 (1):
647. doi:10.1093/ije/27.1.64. PMID 9563695.
American College of Obstetricians and Gynecologists Committee on Obstetric Practice
(Jun 2011). "ACOG Committee Opinion No. 494: Sulfonamides, nitrofurantoin, and risk of
birth defects.". Obstetrics and gynecology 117 (6): 14845.
doi:10.1097/AOG.0b013e3182238c57. PMID 21606771.
Jick, S S; Jick, H; Walker, A M; Hunter, J R (1989-09-01). "Hospitalizations for
pulmonary reactions following nitrofurantoin use.". Chest 96 (3): 512515.
doi:10.1378/chest.96.3.512. ISSN 0012-3692.

Huttner, Angela; Verhaegh, Els M.; Harbarth, Stephan; Muller, Anouk E.;
Theuretzbacher, Ursula; Mouton, Johan W. (2015-09-01). "Nitrofurantoin revisited: a
systematic review and meta-analysis of controlled trials". Journal of Antimicrobial
Chemotherapy 70 (9): 24562464. doi:10.1093/jac/dkv147. ISSN 0305-7453.
PMID 26066581.
Williams, EM; Triller, DM (May 2006). "Recurrent acute nitrofurantoin-induced
pulmonary toxicity.". Pharmacotherapy 26 (5): 7138. doi:10.1592/phco.26.5.713.
PMID 16718946.
Goemaere NN, Grijm K, van Hal PT, den Bakker MA (2008). "Nitrofurantoin-induced
pulmonary fibrosis: a case report". Journal of Medical Case Reports 2 (1): 169.
doi:10.1186/1752-1947-2-169. PMC 2408600. PMID 18495029. Retrieved 21 April 2014.
Amit, G; Cohen, P; Ackerman, Z (Mar 2002). "Nitrofurantoin-induced chronic active
hepatitis.". The Israel Medical Association journal : IMAJ 4 (3): 1846. PMID 11908259.
Tan, IL; Polydefkis, MJ; Ebenezer, GJ; Hauer, P; McArthur, JC (February 2012).
"Peripheral nerve toxic effects of nitrofurantoin". Archives of neurology 69 (2): 2658.
doi:10.1001/archneurol.2011.1120. PMID 22332195.
Oplinger, M; Andrews, CO (Jan 2013). "Nitrofurantoin contraindication in patients with
a creatinine clearance below 60 mL/min: looking for the evidence". The Annals of
pharmacotherapy 47 (1): 10611. doi:10.1345/aph.1R352. PMID 23341159.
American Geriatrics Society 2012 Beers Criteria Update Expert Panel (Apr 2012).
"American Geriatrics Society updated Beers Criteria for potentially inappropriate
medication use in older adults.". Journal of the American Geriatrics Society 60 (4): 61631.
doi:10.1111/j.1532-5415.2012.03923.x. PMC 3571677. PMID 22376048. Retrieved 21 April
2014.
Antibiot. Chemother. 1978, 25, 233252
Shah (1989). "Reappraisal of the risk/benefit of nitrofurantoin: review of toxicity and
efficacy". Adverse Drug Reactions and Acute Poisoning Reviews 8: 183201.
PMID 2694823.
McCalla DR, Kaiser C, Green MH (1978). "Genetics of nitrofurazone resistance in
Escherichia coli". J Bacteriol 133: 1016.
Bains A, Buna D, Hoag NA (2009). "A retrospective review assessing the efficacy and
safety of nitrofurantoin in renal impairment". Canadian Pharmacists Journal 142 (5): 248
252. doi:10.3821/1913-701X-142.5.248.
Blass, Benjamin. Basic Principles of Drug Discovery and Development. p. 513.
ISBN 9780124115255.
Tu Y, McCalla DR (1975). "Effect of activated nitrofurans on DNA,". Biochem Biophys
Acta 402: 14249.
FAO: Nitrofuran study
1

drugs.com, Nitrofurantoin listings, page accessed May 2, 2015

External links

drugs.com for Macrodantin

RxList for Macrobid (Nitrofurantoin)


[hide]

Antibacterials: nucleic acid inhibitors (J01E, J01M)

2,4-Diaminopyrimidine
o Trimethoprim#

DHFR
inhibitor

o Brodimoprim
o Tetroxoprim
o Iclaprim

Antifolates
(inhibits
purine
metabolism,
thereby
inhibiting
DNA and RNA
synthesis)

Shortacting
Sulfonamides
(DHPS
inhibitor)

Sulfaisodimidine

Sulfamethizole

Sulfadimidine

Sulfapyridine

Sulfafurazole

Sulfanilamide
o Prontosil

Intermediateacting

Sulfathiazole

Sulfathiourea

Sulfamethoxazole

Sulfadiazine#

Sulfamoxole

Longacting

Other/ungrouped

Combinations

Sulfadimethoxine

Sulfadoxine

Sulfalene

Sulfametomidine

Sulfametoxydiazine

Sulfamethoxypyridazine

Sulfaperin

Sulfamerazine

Sulfaphenazole

Sulfamazone

Sulfacetamide

Sulfadicramide

Sulfametrole

Trimethoprim/sulfamethoxazole#

1st g.

Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA
replication)

Cinoxacin

Flumequine

Nalidixic acid

Oxolinic acid

Pipemidic acid

Piromidic acid

2nd
g.

Fluoroquinolones

3rd
g.

4th
g.

Rosoxacin

Ciprofloxacin#

Ofloxacin

Enoxacin

Fleroxacin

Lomefloxacin

Nadifloxacin

Norfloxacin

Pefloxacin

Rufloxacin

Levofloxacin

Balofloxacin

Grepafloxacin

Pazufloxacin

Sparfloxacin

Temafloxacin

Tosufloxacin

Besifloxacin

Gatifloxacin

Finafloxacin

Gemifloxacin

Moxifloxacin

Clinafloxacin

Garenoxacin

Prulifloxacin

Sitafloxacin

Trovafloxacin/Alatrofloxacin

Danofloxacin

Difloxacin

Enrofloxacin

Ibafloxacin

Marbofloxacin

Orbifloxacin

Pradofloxacin

Sarafloxacin

Vet.

Anaerobic
DNA
inhibitors

Newer nonfluorinated

Nemonoxacin

Related
(DG)

Aminocoumarins: Novobiocin

Metronidazole#

Tinidazole

Ornidazole

Nitroimidazole
derivatives

Nitrofuran
derivatives

RNA synthesis

Nitrofurantoin#

Furazolidone

Nifurtoinol

Rifamycins/
RNA
polymerase

Clinical trials:

Rifampicin#

Rifabutin

Rifapentine

Rifaximin

Rifalazil

WHO-EM
Withdrawn from market

Phase III
Never to phase III

Categories:

Antibiotics

Hydantoins

World Health Organization essential medicines

Nitrofurans

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