CAS 112811-59-3 Gatifloxacin (HCID 5379)

Overview

Gatifloxacin is a monocarboxylic acid that is 4-oxo-1,4-dihydroquinoline-3-carboxylic acid which is substituted on the nitrogen by a cyclopropyl group and at positions 6, 7, and 8 by fluoro, 3-methylpiperazin-1-yl, and methoxy groups, respectively. Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial topoisomerase type-II enzymes. It has a role as an antimicrobial agent, an antiinfective agent and an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor. It is a quinolone, a quinolinemonocarboxylic acid, an organofluorine compound, a N-arylpiperazine and a quinolone antibiotic.

Names & identifiers

Preferred name: Gatifloxacin
IUPAC: 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid

Names & synonyms

Gatifloxacin112811-59-3TequinGatifloZymarAM-1155GatifloxacineZymaxidZymergatifloxacin anhydrousAM 11553-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-

Show more names

gatifloxacinoDTXSID50457041-Cyclopropyl-1,4-dihydro-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acidgatifloxacinumPD-1354321-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acidNSC-758701CHEBI:5280

Database identifiers

CAS: 112811-59-3
PubChem CID: 5379
DTXSID: DTXSID5045704
ChEMBL: CHEMBL31
ChEBI: CHEBI:5280
UNII: 81485Y3A9A
EC Number: 664-293-2
Nikkaji: J523.172H

Properties

Computed structural propertiesFilling in

XLogP: -0.7
Topological polar surface area: 82.1 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 8
Rotatable bonds: 4
Heavy atoms: 27
Formal charge: 0
Complexity: 653

Experimental & physicochemical properties

Drugs · 2 items

Pharmaceuticals -> Antibiotics

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

LogP2.6

Solubility6.31e-01 g/L

Human Drugs · 3 items

Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Quinolones; Fluoroquinolones

FDA approved drugs -> Active ingredient

Melting Point · 2 items

182-185 °C

182 - 185 °C

Physical DescriptionSolid

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (97.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (97.5%)

Toxicology

Treatment · 1 item

In the event of acute oral overdose, the stomach should be emptied by inducing vomiting or by gastric lavage. The patient should be carefully observed (including ECG monitoring) and given symptomatic and supportive treatment. Adequate hydration should be maintained. (L1712)

Health EffectsAntibiotic resistance

Exposure RoutesOphthalmic. Well absorbed from the gastrointestinal tract after oral administration with absolute bioavailability of gatifloxacin is 96%

Toxicity SummaryThe bactericidal action of Gatifloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination.

Signs and SymptomsThe most common side effects from antibiotics are diarrhea, nausea, vomiting. Fungal infections of the mouth, digestive tract and vagina can also occur with antibiotics

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Chemistry & industry

Pharmacology

ATC Code · 4 items

S - Sensory organs

J - Antiinfectives for systemic use

QS - Sensory organs

QJ - Antiinfectives for systemic use

Protein Binding20%

Pharmacodynamics · 1 item

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.

Mechanism of ActionThe bactericidal action of Gatifloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination.

Biological Half-Life7-14 hours

Metabolism/Metabolites · 2 items

Gatifloxacin undergoes limited biotransformation in humans with less than 1% of the dose excreted in the urine as ethylenediamine and methylethylenediamine metabolites

Gatifloxacin undergoes limited biotransformation in humans with less than 1% of the dose excreted in the urine as ethylenediamine and methylethylenediamine metabolites Half Life: 7-14 hours

Uses & manufacturing

Uses · 2 items

Use (kg) in USA (2002): 7250

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