1-Cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-4-ium-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate
Basic information
- CAS
112811-59-3- Standard SMILES
COc1c(N2CC[NH2+]C(C)C2)c(F)cc2c(=O)c(C(=O)[O-])cn(C3CC3)c12- InChIKey
XUBOMFCQGDBHNK-UHFFFAOYSA-N- Molecular formula
- C19H22FN3O4
- Average molar mass
- 375.4 g/mol
- Monoisotopic mass
- 375.15943435
Overview
Gatifloxacin is an antibiotic agent and a member of the fourth-generation fluoroquinolone family. It works by inhibiting the bacterial enzymes DNA gyrase and topoisomerase IV. It was first introduced by Bristol-Myers Squibb in 1999 under the brand name Tequin® for the treatment of respiratory tract infections. Gatifloxacin is available as tablets and in various aqueous solutions for intravenous therapy. It is also available as eye drops under the brand name Zymar® marketed by Allergan. The FDA withdrew its approval for the use of non-ophthalmic drug products containing gatifloxacin due to the high prevalence of gatifloxacin-associated dysglycemia adverse event reports and the high incidence of hyperglycemic and hypoglycemic episodes in patients taking gatifloxacin compared to those on macrolide antibiotics.
Names & identifiers
- Preferred name
- 1-Cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-4-ium-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate
- IUPAC
- 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-4-ium-1-yl)-4-oxoquinoline-3-carboxylate
- English name
- Gatifloxacin
- Molecular formula
- C19H22FN3O4
- Molecular weight
- 375.39
Names & synonyms
Spectrum3_000999Spectrum5_001468SCHEMBL22591HMS3259P06RKL10068AKOS016340697CS-1841NC00702160738-57-8STL048947AKOS0057022861-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-ium-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate
Show more names
ZymarTEQUINCG5501S)-AHPCGatiquinPD135432PD 135432PD-135432)BMS-206584GASTRODINUM
1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-4-ium-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate
Database identifiers
- CAS
112811-59-3- PubChem CID
- 4872633
Properties
Computed structural properties
- XLogP
- -0.6
- Topological polar surface area
- 89.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 3
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 647
Experimental & physicochemical properties
DrugsPharmaceuticals
LogP2.6
Solubility6.31e-01 g/L
Melting Point
182-185 °C
182 - 185 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 162 °C · 162°C
- Boiling point
- 607.8 · 607.8±55.0 °C(Predicted)
- Density
- 1.386 · 1.386±0.06 g/cm3(Predicted)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- Chloroform (Slightly, Heated), Methanol (Slightly, Heated)
- pka
- 6.43 · 6.43±0.50(Predicted)
- form
- White to yellow crystalline powder.
- color
- White to Off-White
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 1
- hs_code
- 29335990
- risk_code
- 20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36/37
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral
- Precautionary statements
- P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362+P364-P403+P233-P501c
Chemistry & industry
Pharmacology
Protein Binding20%
Pharmacodynamics
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/MetabolitesGatifloxacin undergoes limited biotransformation in humans with less than 1% of the dose excreted in the urine as ethylenediamine and methylethylenediamine metabolites
Absorption, Distribution and ExcretionWell absorbed from the gastrointestinal tract after oral administration with absolute bioavailability of gatifloxacin is 96%
Cellular LocationsCytoplasm
Applications
DescriptionGatifloxacin belongs to a class of drugs known as quinolone antibiotics and is used to treat acute sinus, lung, or urinary tract infections and sexually transmitted bacterial infection.This drug may be taken orally, in tablet form, or by injection.Common side effects associated with gatifloxacin include nausea, vaginitis(irritation or inflammation of the vagina)，diarrhea, headache, dizziness, and irregular heart beats. In general, gatifloxacin is used in people who are unresponsive to other AOM therapies.In one study, gatifloxacin was compared with amoxicillin/clavulanate in the treatment of recurrent otitis media (OM) and AOM in treatment failures in children.Three hundred fifty-four infants and children with recurrent OM or AOM failure received gatifloxacin or amoxicillin/clavulanate.Results showed that both drugs were well tolerated; the most common side effect was diarrhea.Researchers concluded that treatment with gatifloxacin once daily was as effective as amoxicillin/clavulanate twice daily.In other medical literature, gatifloxacin has been noted as a third-line treatment option in AOM.
Related reactions
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Compound notes
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