NAV

Grepafloxacin

Identification

Summary

Grepafloxacin is a fluoroquinolone antibiotic used to treat various gram positive and gram negative bacterial infections.

Generic Name
Grepafloxacin
DrugBank Accession Number
DB00365
Background

Grepafloxacin is an oral broad-spectrum quinoline antibacterial agent used to treat bacterial infections. Due to the QTc-prolonging potential, as indicated by the changes in the QT interval on the electrocardiogram, and the risk for cardiovascular adverse events, grepafloxacin was withdrawn in the United States.

Type
Small Molecule
Groups
Approved, Investigational, Withdrawn
Structure
3D
Similar Structures
Weight
Average: 359.3947
Monoisotopic: 359.16451979
Chemical Formula
C19H22FN3O3
Synonyms
  • Grepafloxacin
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Pharmacology

Indication

For treatment of adults with mild to moderate infections caused by susceptible strains of Haemophilus influenzae, Streptococcus pneumoniae, or Moraxella catarrhalis.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Grepafloxacin has in vitro activity against a wide range of gram-positive and gram-negative aerobic microorganisms, as well as some atypical microorganisms.

Mechanism of action

Grepafloxacin exerts its antibacterial activity by inhibiting bacterial topoisomerase II (DNA gyrase) and topoisomerase IV, essential enzymes for duplication, transcription, and repair of bacterial DNA.

TargetActionsOrganism
ADNA gyrase subunit A
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
ADNA topoisomerase 4 subunit A
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Absorption

Rapidly and extensively absorbed following oral administration. The absolute bioavailability is approximately 70%.

Volume of distribution

Not Available

Protein binding

50%

Metabolism

Primarily hepatic via CYP1A2 and CYP3A4. The major metabolite is a glucuronide conjugate; minor metabolites include sulfate conjugates and oxidative metabolites. The oxidative metabolites are formed mainly by the cytochrome P450 enzyme CYP1A2, while the cytochrome P450 enzyme CYP3A4 plays a minor role. The nonconjugated metabolites have little antimicrobial activity compared with the parent drug, and the conjugated metabolites have no antimicrobial activity

Route of elimination

Not Available

Half-life

15 ± 3 hours

Clearance

Not Available

Adverse Effects
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Toxicity

Withdrawn from the US market in 1999 due to associations with QTc prolongation and adverse cardiovascular events.

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AbametapirThe serum concentration of Grepafloxacin can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Grepafloxacin can be increased when combined with Abatacept.
AbirateroneThe serum concentration of Grepafloxacin can be increased when it is combined with Abiraterone.
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Grepafloxacin.
AceclofenacAceclofenac may increase the neuroexcitatory activities of Grepafloxacin.
Food Interactions
  • Avoid caffeine.
  • Drink plenty of fluids.
  • Take with or without food. The absorption is unaffected by food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Grepafloxacin hydrochlorideA4ER1Z8N9N161967-81-3IEPMBYOIQGCVHO-UHFFFAOYSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
RaxarTablet200 mg / tabOralOtsuka Pharma Gmbh1998-07-011999-10-27Canada flag

Categories

ATC Codes
J01MA11 — Grepafloxacin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Quinoline carboxylic acids
Direct Parent
Quinoline carboxylic acids
Alternative Parents
Fluoroquinolones / N-arylpiperazines / Haloquinolines / Hydroquinolones / Aminoquinolines and derivatives / Hydroquinolines / Pyridinecarboxylic acids / Dialkylarylamines / Benzenoids / Aryl fluorides
show 12 more
Substituents
1,4-diazinane / Amine / Amino acid / Amino acid or derivatives / Aminoquinoline / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
quinolines, quinolone antibiotic, fluoroquinolone antibiotic (CHEBI:5543)
Affected organisms
  • Enteric bacteria and other eubacteria
  • Streptococcus pneumoniae

Chemical Identifiers

UNII
L1M1U2HC31
CAS number
119914-60-2
InChI Key
AIJTTZAVMXIJGM-UHFFFAOYSA-N
InChI
InChI=1S/C19H22FN3O3/c1-10-8-22(6-5-21-10)15-7-14-16(11(2)17(15)20)18(24)13(19(25)26)9-23(14)12-3-4-12/h7,9-10,12,21H,3-6,8H2,1-2H3,(H,25,26)
IUPAC Name
1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
SMILES
CC1CN(CCN1)C1=C(F)C(C)=C2C(=O)C(=CN(C3CC3)C2=C1)C(O)=O

References

Synthesis Reference
US4920120
General References
Not Available
Human Metabolome Database
HMDB0014509
KEGG Compound
C11368
PubChem Compound
72474
PubChem Substance
46507253
ChemSpider
65391
BindingDB
50117924
RxNav
83719
ChEBI
5543
ChEMBL
CHEMBL583
Therapeutic Targets Database
DAP001005
PharmGKB
PA449812
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Grepafloxacin
MSDS
Download (115 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
0TerminatedTreatmentOsteomyelitis1

Pharmacoeconomics

Manufacturers
  • Otsuka pharmaceutical co ltd
Packagers
  • GlaxoSmithKline Inc.
Dosage Forms
FormRouteStrength
TabletOral200 mg / tab
TabletOral
Tablet, film coated
Tablet, coated
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5563138No1996-10-082013-10-08US flag
CA1340492No1999-04-132016-04-13Canada flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP2.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.632 mg/mLALOGPS
logP-0.12ALOGPS
logP0.068Chemaxon
logS-2.8ALOGPS
pKa (Strongest Acidic)5.68Chemaxon
pKa (Strongest Basic)8.86Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area72.88 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity97.4 m3·mol-1Chemaxon
Polarizability37.86 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9886
Blood Brain Barrier-0.9855
Caco-2 permeable+0.5
P-glycoprotein substrateSubstrate0.8825
P-glycoprotein inhibitor INon-inhibitor0.9062
P-glycoprotein inhibitor IINon-inhibitor0.9228
Renal organic cation transporterNon-inhibitor0.7877
CYP450 2C9 substrateNon-substrate0.8299
CYP450 2D6 substrateNon-substrate0.9127
CYP450 3A4 substrateNon-substrate0.7079
CYP450 1A2 substrateNon-inhibitor0.8516
CYP450 2C9 inhibitorNon-inhibitor0.9197
CYP450 2D6 inhibitorNon-inhibitor0.9365
CYP450 2C19 inhibitorNon-inhibitor0.9064
CYP450 3A4 inhibitorNon-inhibitor0.8116
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.763
Ames testAMES toxic0.7309
CarcinogenicityNon-carcinogens0.8042
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.0923 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9009
hERG inhibition (predictor II)Non-inhibitor0.7785
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0fr6-1029000000-706de57181850354ad84
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0009000000-376c67217d8b170a8bcf
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-0019000000-845fabb93a598fb7e570
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-76a17d505d08ec6e8d1c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-066r-1029000000-7f247c637377b8f2fee5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uxr-2049000000-fc7a36011fe64cb25c51
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00n0-0095000000-20ee4d80271f0cc93024
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-199.5416249
predicted
DarkChem Lite v0.1.0
[M-H]-189.27893
predicted
DeepCCS 1.0 (2019)
[M+H]+200.5100249
predicted
DarkChem Lite v0.1.0
[M+H]+191.63692
predicted
DeepCCS 1.0 (2019)
[M+Na]+199.0830249
predicted
DarkChem Lite v0.1.0
[M+Na]+198.8531
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details1. DNA gyrase subunit A
Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function
DNA gyrase negatively supercoils closed circular double-stranded DNA in an ATP-dependent manner and also catalyzes the interconversion of other topological isomers of double-stranded DNA rings, inc...
Gene Name
gyrA
Uniprot ID
P43700
Uniprot Name
DNA gyrase subunit A
Molecular Weight
97817.145 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Stewart BA, Johnson AP, Woodford N: Relationship between mutations in parC and gyrA of clinical isolates of Streptococcus pneumoniae and resistance to ciprofloxacin and grepafloxacin. J Med Microbiol. 1999 Dec;48(12):1103-6. [Article]
  4. Jorgensen JH, Weigel LM, Ferraro MJ, Swenson JM, Tenover FC: Activities of newer fluoroquinolones against Streptococcus pneumoniae clinical isolates including those with mutations in the gyrA, parC, and parE loci. Antimicrob Agents Chemother. 1999 Feb;43(2):329-34. [Article]
  5. Griggs DJ, Marona H, Piddock LJ: Selection of moxifloxacin-resistant Staphylococcus aureus compared with five other fluoroquinolones. J Antimicrob Chemother. 2003 Jun;51(6):1403-7. Epub 2003 Apr 25. [Article]
Details2. DNA topoisomerase 4 subunit A
Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function
Topoisomerase IV is essential for chromosome segregation. It relaxes supercoiled DNA. Performs the decatenation events required during the replication of a circular DNA molecule.
Gene Name
parC
Uniprot ID
P43702
Uniprot Name
DNA topoisomerase 4 subunit A
Molecular Weight
83366.24 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Ernst EJ, Klepser ME, Petzold CR, Doern GV: Evaluation of survival and pharmacodynamic relationships for five fluoroquinolones in a neutropenic murine model of pneumococcal lung infection. Pharmacotherapy. 2002 Apr;22(4):463-70. [Article]
  4. Morris JE, Pan XS, Fisher LM: Grepafloxacin, a dimethyl derivative of ciprofloxacin, acts preferentially through gyrase in Streptococcus pneumoniae: role of the C-5 group in target specificity. Antimicrob Agents Chemother. 2002 Feb;46(2):582-5. [Article]
  5. Kawamura-Sato K, Hasegawa T, Torii K, Ito H, Ohta M: Prevalence of Ile-460-Val/ParE substitution in clinical Streptococcus pneumoniae isolates that were less susceptible to fluoroquinolones. Curr Microbiol. 2005 Jul;51(1):27-30. Epub 2005 May 31. [Article]

Enzymes

Details1. Cytochrome P450 1A2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Rodighiero V: Effects of liver disease on pharmacokinetics. An update. Clin Pharmacokinet. 1999 Nov;37(5):399-431. [Article]
  2. Bril F, Gonzalez CD, Di Girolamo G: Antimicrobial agents-associated with QT interval prolongation. Curr Drug Saf. 2010 Jan;5(1):85-92. [Article]
  3. Gabriel L, Tod M, Goutelle S: Quantitative Prediction of Drug Interactions Caused by CYP1A2 Inhibitors and Inducers. Clin Pharmacokinet. 2016 Aug;55(8):977-90. doi: 10.1007/s40262-016-0371-x. [Article]
  4. Efthymiopoulos C, Bramer SL, Maroli A, Blum B: Theophylline and warfarin interaction studies with grepafloxacin. Clin Pharmacokinet. 1997;33 Suppl 1:39-46. [Article]
  5. Liu L, Miao MX, Zhong ZY, Xu P, Chen Y, Liu XD: Chronic administration of caderofloxacin, a new fluoroquinolone, increases hepatic CYP2E1 expression and activity in rats. Acta Pharmacol Sin. 2016 Apr;37(4):561-70. doi: 10.1038/aps.2015.160. Epub 2016 Feb 1. [Article]
Details2. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Pal D, Mitra AK: MDR- and CYP3A4-mediated drug-drug interactions. J Neuroimmune Pharmacol. 2006 Sep;1(3):323-39. Epub 2006 Aug 2. [Article]
  2. Owens RC Jr: QT prolongation with antimicrobial agents: understanding the significance. Drugs. 2004;64(10):1091-124. [Article]

Transporters

Details1. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Yamaguchi H, Yano I, Hashimoto Y, Inui KI: Secretory mechanisms of grepafloxacin and levofloxacin in the human intestinal cell line caco-2. J Pharmacol Exp Ther. 2000 Oct;295(1):360-6. [Article]
  2. Naruhashi K, Tamai I, Inoue N, Muraoka H, Sai Y, Suzuki N, Tsuji A: Active intestinal secretion of new quinolone antimicrobials and the partial contribution of P-glycoprotein. J Pharm Pharmacol. 2001 May;53(5):699-709. [Article]
  3. Yamaguchi H, Yano I, Saito H, Inui K: Effect of cisplatin-induced acute renal failure on bioavailability and intestinal secretion of quinolone antibacterial drugs in rats. Pharm Res. 2004 Feb;21(2):330-8. [Article]
Details2. Multidrug resistance-associated protein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Tamai I, Yamashita J, Kido Y, Ohnari A, Sai Y, Shima Y, Naruhashi K, Koizumi S, Tsuji A: Limited distribution of new quinolone antibacterial agents into brain caused by multiple efflux transporters at the blood-brain barrier. J Pharmacol Exp Ther. 2000 Oct;295(1):146-52. [Article]
Details3. Solute carrier family 22 member 6
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Uwai Y, Okuda M, Takami K, Hashimoto Y, Inui K: Functional characterization of the rat multispecific organic anion transporter OAT1 mediating basolateral uptake of anionic drugs in the kidney. FEBS Lett. 1998 Nov 6;438(3):321-4. [Article]
Details4. Solute carrier family 22 member 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. [Article]
Details5. Solute carrier family 22 member 5
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
Molecular Weight
62751.08 Da
References
  1. Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [Article]
Details6. Canalicular multispecific organic anion transporter 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Sasabe H, Tsuji A, Sugiyama Y: Carrier-mediated mechanism for the biliary excretion of the quinolone antibiotic grepafloxacin and its glucuronide in rats. J Pharmacol Exp Ther. 1998 Mar;284(3):1033-9. [Article]

Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:59