1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

• ChemBase ID: 916
• Molecular Formular: C19H22FN3O4
• Molecular Mass: 375.3940832
• Monoisotopic Mass: 375.15943442
• SMILES: Fc1c(N2CC(NCC2)C)c(OC)c2n(C3CC3)cc(c(=O)c2c1)C(=O)O
• Canonical SMILES: COc1c(N2CCNC(C2)C)c(F)cc2c1n(cc(c2=O)C(=O)O)C1CC1
• InChI: InChI=1S/C19H22FN3O4/c1-10-8-22(6-5-21-10)16-14(20)7-12-15(18(16)27-2)23(11-3-4-11)9-13(17(12)24)19(25)26/h7,9-11,21H,3-6,8H2,1-2H3,(H,25,26)
• InChIKey: XUBOMFCQGDBHNK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: gatifloxacin; 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• Brand Name: Tequin; Zymar
• Synonyms: 1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid; Tequin; Zymar; gatifloxacin; Gatifloxacin; Gatiflo; Tequin and Zymar; 1-Cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; Gatifloxacin

Database IDs

• CAS Number: 112811-59-3; 160738-57-8
• MDL Number: MFCD00895399
• PubChem SID: 46506159; 160964379
• PubChem CID: 5379

CALCULATED PROPERTIES

JChem

• Acid pKa: 5.685334
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.87816894
• LogD (pH = 7.4): -0.580783
• Log P: -0.58031964
• Molar Refractivity: 98.8214 cm^3
• Polarizability: 36.64735 Å^3
• Polar Surface Area: 82.11 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.23
• LOG S: -2.77
• Solubility (Water): 6.31e-01 g/l

PROPERTIES

Physical Property

• Solubility: 60 mg/mL (at pH 4); Chloroform; H2O; Methanol (Sparingly)
• Apperance: Off-White Solid
• Melting Point: 185-187°C (dec.)
• Hydrophobicity(logP): 2.6

Safety Information

• Storage Condition: -20°C; -20°C Freezer

Pharmacology Properties

• Mechanism of Action: Inhibits the bacterial enzymes DNA gyrase and topoisomerase IV

Product Information

• Salt Data: Free Base
• Application(s): Antibacterial; Antibiotic

DETAILS

DrugBank - DB01044

• Drug Groups: approved; investigational
• Description: Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial enzymes DNA gyrase and topoisomerase IV. Bristol-Myers Squibb introduced Gatifloxacin in 1999 under the proprietary name Tequin? for the treatment of respiratory tract infections, having licensed the medication from Kyorin Pharmaceutical Company of Japan. Allergan produces an eye-drop formulation called Zymar?. Gatifloxacin is available as tablets and in various aqueous solutions for intravenous therapy. [Wikipedia]
• Indication: For the treatment of bronchitis, sinusitis, community-acquired pneumonia, and skin infections (abscesses, wounds) caused by S. pneumoniae, H. influenzae, S. aureus, M. pneumoniae, C. pneumoniae, L. pneumophila, S. pyogenes
• Pharmacology: Gatifloxacin is a synthetic broad-spectrum 8-methoxyfluoroquinolone antibacterial agent for oral or intravenous administration. is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase, which allows the untwisting required to replicate one DNA double helix into two. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian. Gatifloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. It should be used only to treat or prevent infections that are proven or strongly suspected to be caused by bacteria.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Gatifloxacin undergoes limited biotransformation in humans with less than 1% of the dose excreted in the urine as ethylenediamine and methylethylenediamine metabolites
• Absorption: Well absorbed from the gastrointestinal tract after oral administration with absolute bioavailability of gatifloxacin is 96%
• Half Life: 7-14 hours
• Protein Binding: 20%
• References: Park-Wyllie LY, Juurlink DN, Kopp A, Shah BR, Stukel TA, Stumpo C, Dresser L, Low DE, Mamdani MM: Outpatient gatifloxacin therapy and dysglycemia in older adults. N Engl J Med. 2006 Mar 30;354(13):1352-61. Epub 2006 Mar 1. [Pubmed] ; Gurwitz JH: Serious adverse drug effects--seeing the trees through the forest. N Engl J Med. 2006 Mar 30;354(13):1413-5. Epub 2006 Mar 1. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1340

Research Area: Infection
Biological Activity:
Gatifloxacin (Gatiflo, Tequin and Zymar), is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial enzymes DNA gyrase and topoisomerase IV. [1]

Toronto Research Chemicals - G250000

An antibacterial.

REFERENCES

• Park-Wyllie LY, Juurlink DN, Kopp A, Shah BR, Stukel TA, Stumpo C, Dresser L, Low DE, Mamdani MM: Outpatient gatifloxacin therapy and dysglycemia in older adults. N Engl J Med. 2006 Mar 30;354(13):1352-61. Epub 2006 Mar 1. Pubmed
• Gurwitz JH: Serious adverse drug effects--seeing the trees through the forest. N Engl J Med. 2006 Mar 30;354(13):1413-5. Epub 2006 Mar 1. Pubmed
• http://en.wikipedia.org/wiki/Gatifloxacin
• Bauernfeind, A.: J. Antimicro. Chemother., 40, 639 (1997)
• Fukuda, H., et al.: Antimicrob. Ag. Chemother., 42, 1917 (1997)
• Eur. Pat., 1987, Sankyo, 241 206; CA, 110, 135095, (synth, activity)
• Hosaka, M. et al., Antimicrob. Agents Chemother., 1992, 36, 2108; 1996, 40, 2756, (activity, pharmacol)
• Casta~ner, J. et al., Drugs of the Future, 1993, 18, 203
• Wakabayashi, E. et al., Antimicrob. Agents Chemother., 1994, 38, 594, (activity)
• Perry, C.M. et al., Drugs, 1999, 58, 683, (rev)
• Dalhoff, A., Expert Opin. Invest. Drugs, 1999, 8, 123