Gatifloxacin

Gatifloxacin

File:Gatifloxacin.svg
File:Gatifloxacin ball-and-stick.png
Systematic (IUPAC) name
1-cyclopropyl-6-fluoro- 8-methoxy-7-(3-methylpiperazin-1-yl)- 4-oxo-quinoline-3-carboxylic acid
Clinical data
Trade names	Zymar
AHFS/Drugs.com	monograph
MedlinePlus	a605012
Legal status	℞ (Prescription only)
Routes of administration	Oral (discontinued), Intravenous (discontinued) ophthalmic
Pharmacokinetic data
Protein binding	20%
Biological half-life	7 to 14 hours
Identifiers
CAS Number	112811-59-3 Y
ATC code	J01MA16 (WHO) S01AE06
PubChem	CID: 5379
DrugBank	DB01044 Y
ChemSpider	5186 Y
UNII	81485Y3A9A Y
KEGG	D08011 Y
ChEBI	CHEBI:5280 Y
ChEMBL	CHEMBL31 Y
NIAID ChemDB	044913
Chemical data
Formula	C19H22FN3O4
Molecular mass	375.394 g/mol
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 sold under the 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. 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 and Zymaxid. In many countries, gatifloxacin is also available as tablets and in various aqueous solutions for intravenous therapy.

Side-effects and removal from the market

A Canadian study published in the New England Journal of Medicine in March 2006 claims Tequin can have significant side effects including dysglycemia. An editorial by Dr. 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 it was reported on May 1, 2006 that Bristol-Myers Squibb would stop manufacture of Tequin, end sales of the drug after existing stockpiles were exhausted, and return all rights to Kyorin.

Union Health and Family Welfare Ministry of India on 18 March 2011 banned the manufacture, sale and distribution of Gatifloxacin as it caused certain adverse side effects

Contraindications

Diabetes

Availability

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

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

Ophthalmic anti-infectives are generally well tolerated. The concentration of the drug observed following oral administration of 400 mg gatifloxacin systemically is approximately 800 times higher than that of the 0.5% Gatifloxacin eye drop. Given as an eye drop, Gatifloxacin Ophthalmic Solution 0.3% & 0.5% cause very low systemic exposures. Therefore, the systemic exposures resulting from the gatifloxacin ophthalmic solution are not likely to pose any risk for systemic toxicities.