Grepafloxacin

HCID 72474

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Basic information

CAS: 119914-60-2
Standard SMILES: Cc1c(F)c(N2CCNC(C)C2)cc2c1c(=O)c(C(=O)O)cn2C1CC1
InChIKey: AIJTTZAVMXIJGM-UHFFFAOYSA-N
Molecular formula: C19H22FN3O3
Average molar mass: 359.4 g/mol
Monoisotopic mass: 359.16451978

Overview

Grepafloxacin is a member of quinolines, a quinolone antibiotic and a fluoroquinolone antibiotic.

Names & identifiers

Preferred name: Grepafloxacin
IUPAC: 1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
English name: Grepafloxacin
Molecular formula: C19H22FN3O3
Molecular weight: 359.39

Names & synonyms

Grepafloxacin119914-60-21-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acidGrepafloxacineGrepafloxacino1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acidL1M1U2HC313-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-OPC-17116DTXSID2048321grepafloxacinumRefChem:922501

Show more names

dl-GrepafloxacinGrepafloxacin USP/EP/BPGrepafloxacin/OPC-17116/dl-Grepafloxacin1-Cyclopropyl-6-fluoro-7-(3-methyl-1-piperazinyl)-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

DTXCID0028296J01MA11(+--)-1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid(RS)-1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic acid631-454-3Raxar146863-02-7dl-Grepafloxacin Hydrochloride

Database identifiers

CAS: 119914-60-2
PubChem CID: 72474
DTXSID: DTXSID2048321
ChEMBL: CHEMBL583
ChEBI: CHEBI:5543
UNII: L1M1U2HC31
EC Number: 631-454-3
Nikkaji: J384.494C

Properties

Computed structural properties

XLogP: -0.2
Topological polar surface area: 72.9 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 7
Rotatable bonds: 3
Heavy atoms: 26
Formal charge: 0
Complexity: 636

Experimental & physicochemical properties

Drugs · 2 items

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Anti infectives for systemic use -> Antibacterials for systemic use

LogP2.9

Solubility6.32e-01 g/L

Human DrugsPharmaceuticals

Physical DescriptionSolid

Physicochemical properties

Melting point: 189 · 189-192 ºC
Boiling point: 610 · 610.0±55.0 °C(Predicted)
Density: 1.366 · 1.366
storage temp.: 2 · under inert gas (nitrogen or Argon) at 2–8 °C
solubility: DMSO (Slightly), Methanol (Slightly)
form: Solid
pka: 6.44 · 6.44±0.50(Predicted)
color: Pale Beige to Pale Yellow
Stability: Hygroscopic
CAS DataBase Reference: 119914 · 119914-60-2(CAS DataBase Reference)
FDA UNII: 1 M1U2HC31 · L1M1U2HC31
ATC code: 1 MA11 · J01MA11
Symbol(GHS): 6 · GHS06
Signal word: Danger
Hazard statements: 301 · H301
Precautionary statements: 301 · P301+P310

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Safety data

Signal word: Danger
Symbol(GHS): GHS06
Hazard statements: H301
Precautionary statements: P301+P310

Chemistry & industry

Pharmacology

ATC Code · 2 items

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Protein Binding50%

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

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

Biological Half-Life15 ± 3 hours

Metabolism/Metabolites · 1 item

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