1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

• ChemBase ID: 249
• Molecular Formular: C19H22FN3O3
• Molecular Mass: 359.3946832
• Monoisotopic Mass: 359.1645198
• SMILES: Fc1c(N2CC(NCC2)C)cc2n(C3CC3)cc(c(=O)c2c1C)C(=O)O
• Canonical SMILES: CC1NCCN(C1)c1cc2c(c(c1F)C)c(=O)c(cn2C1CC1)C(=O)O
• 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)
• InChIKey: AIJTTZAVMXIJGM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: grepafloxacin hydrochloride
• Brand Name: Raxar
• Synonyms: Grepafloxacin

Database IDs

• CAS Number: 119914-60-2
• PubChem SID: 160963712; 46507253
• PubChem CID: 72474

CALCULATED PROPERTIES

JChem

• Acid pKa: 5.876593
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.26560268
• LogD (pH = 7.4): 0.12430624
• Log P: 0.118112005
• Molar Refractivity: 97.3994 cm^3
• Polarizability: 35.853886 Å^3
• Polar Surface Area: 72.88 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.12
• LOG S: -2.76
• Solubility (Water): 6.32e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 2.9

DETAILS

DrugBank - DB00365

• Drug Groups: approved; withdrawn
• Description: Grepafloxacin hydrochloride (Raxar®, Glaxo Wellcome) is an oral broad-spectrum quinoline antibacterial agent used to treat bacterial infections. Grepafloxacin was withdrawn in the United States due to its side effect of lengthening the QT interval on the electrocardiogram, leading to cardiac events and sudden death. [Wikipedia]
• Indication: For treatment of adults with mild to moderate infections caused by susceptible strains of Haemophilus influenzae, Streptococcus pneumoniae, or Moraxella catarrhalis.
• Pharmacology: Grepafloxacin has in vitro activity against a wide range of gram-positive and gram-negative aerobic microorganisms, as well as some atypical microorganisms.
• Toxicity: Withdrawn from the US market in 1999 due to associations with QTc prolongation and adverse cardiovascular events.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: 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
• Absorption: Rapidly and extensively absorbed following oral administration. The absolute bioavailability is approximately 70%.
• Half Life: 15 ± 3 hours
• Protein Binding: 50%
• External Links: Wikipedia; RxList; Drugs.com