Chemistry:Gatifloxacin

Short description: Chemical compound

Gatifloxacin

Clinical data
Trade names	Gatiflo, Tequin, Zymar, others
AHFS/Drugs.com	Monograph
MedlinePlus	a605012
Routes of administration	Oral (discontinued), Intravenous (discontinued) ophthalmic
ATC code	J01MA16 (WHO) S01AE06 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding	20%
Elimination half-life	7 to 14 hours
Identifiers
IUPAC name 1-Cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic acid
CAS Number	112811-59-3 Y
PubChem CID	5379
DrugBank	DB01044 Y
ChemSpider	5186 Y
UNII	81485Y3A9A
KEGG	D08011 Y
ChEBI	CHEBI:5280 Y
ChEMBL	ChEMBL31 Y
NIAID ChemDB	044913
Chemical and physical data
Formula	C19H22FN3O4
Molar mass	375.400 g·mol−1
3D model (JSmol)	Interactive image
SMILES Fc1c(c(OC)c2c(c1)C(=O)C(\C(=O)O)=C/N2C3CC3)N4CC(NCC4)C
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) Y Key:XUBOMFCQGDBHNK-UHFFFAOYSA-N Y
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Gatifloxacin (brand names 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.

It was patented in 1986 and approved for medical use in 1999.

Side effects

A Canada study published in the New England Journal of Medicine in March 2006, claimed that Tequin can have significant side effects including dysglycemia. An editorial by Jerry Gurwitz in the same issue called for the Food and Drug Administration (FDA) to consider giving Tequin a black box warning. This editorial followed distribution of a letter dated February 15 by Bristol-Myers Squibb to health care providers indicating action taken with the FDA to strengthen warnings for the medication. Subsequently, Bristol-Myers Squibb reported it would stop manufacture of Tequin, end sales of the drug after existing stockpiles were exhausted, and return all rights to Kyorin.

By contrast, ophthalmic gatifloxacin is generally well tolerated. The observed systemic concentration of the drug following oral administration of 400 mg (0.01 ounces) gatifloxacin is approximately 800 times higher than that of the 0.5% gatifloxacin eye drop. Given as an eye drop, gatifloxacin has very low systemic exposure. Therefore, the systemic exposures resulting from the gatifloxacin ophthalmic solution are not likely to pose any risk for systemic toxicities.

Contraindications

Hypersensitivity

Society and culture

Availability

Gatifloxacin is currently available in the US and Canada only as an ophthalmic solution.

In 2011, the Union Health and Family Welfare Ministry of India banned the manufacture, sale, and distribution of gatifloxacin because of its adverse side effects.

In China, gatifloxacin is sold in tablet as well as in eye drop formulations.

Brand names

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 it in eye-drop formulation under the names Zymar, Zymaxid and Zylopred. In many countries, gatifloxacin is also available as tablets and in various aqueous solutions for intravenous therapy.