Gatifloxacin
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|---|---|
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| 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 | Rx only |
| Routes | Oral (discontinued), Intravenous (discontinued) ophthalmic |
| Pharmacokinetic data | |
| Protein binding | 20% |
| Half-life | 7 to 14 hours |
| Identifiers | |
| CAS number | 112811-59-3  |
| ATC code | J01MA16 S01AE06 |
| PubChem | CID 5379 |
| DrugBank | DB01044 |
| ChemSpider | 5186 |
| UNII | 81485Y3A9A |
| KEGG | D08011 |
| ChEBI | CHEBI:5280 |
| ChEMBL | CHEMBL31 |
| NIAID ChemDB | 044913 |
| Chemical data | |
| Formula | C19H22FN3O4 |
| Mol. mass | 375.394 g/mol |
| SMILES
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Gatifloxacin sold under the brand names Gatiflo, Tequin and Zymar, is an antibiotic of the fourth-generation fluoroquinolone family,[1] 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.[2] 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.[3] 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.[4] 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.[5]
Other serious side effects reported with gatifloxacin include hallucinations,[6] liver damage[7] and purpura.[8] 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[9]
Contraindications
Diabetes[10]
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.
Gatifloxacin was banned in India on the 18 March 2011 for systemic use.[11] A statement from the health ministry said: 'The use of the following drugs is likely to involve certain risks to human beings, whereas safer alternatives to the said drugs are available.' The move comes after international studies revealed that gatifloxacin posed 17 times higher risk of developing serious hyperglycemia (high blood sugar) than other antibiotics in elderly patients.[12]
The Ministry of Health and Family Welfare, Govt of India in the Gazette notification dated on 16 March 2011, has prohibited the manufacture, sale and distribution of two drugs; gatifloxacin for systemic use and Tegaserod. The prohibitory order on gatifloxacin is applicable only for its systemic use as mentioned in the Gazette notification and does not apply to any topical formulations of gatifloxacin.
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.
References
- ↑ Burka JM, Bower KS, Vanroekel RC, Stutzman RD, Kuzmowych CP, Howard RS (July 2005). "The effect of fourth-generation fluoroquinolones gatifloxacin and moxifloxacin on epithelial healing following photorefractive keratectomy". Am. J. Ophthalmol. 140 (1): 83–7. doi:10.1016/j.ajo.2005.02.037. PMID 15953577.
- ↑ Park-Wyllie, Laura Y.; David N. Juurlink, Alexander Kopp, Baiju R. Shah, Therese A. Stukel, Carmine Stumpo, Linda Dresser, Donald E. Low, Muhammad M. Mamdani (March 2006). "Outpatient Gatifloxacin Therapy and Dysglycemia in Older Adults". The New England Journal of Medicine 354 (13): 1352–1361. doi:10.1056/NEJMoa055191. PMID 16510739. Retrieved 2006-05-01. Note: publication date 30 March; available on-line 1 March
- ↑ Gurwitz, Jerry H. (March 2006). "Serious Adverse Drug Effects — Seeing the Trees through the Forest". The New England Journal of Medicine 354 (13): 1413–1415. doi:10.1056/NEJMe068051. PMID 16510740. Retrieved 2006-05-01.
- ↑ Lewis-Hall, Freda (February 15, 2006). "Dear Healthcare Provider:" (PDF). Bristol-Myers Squibb. Retrieved May 1, 2006.
- ↑ Schmid, Randolph E. (May 1, 2006). "Drug Company Taking Tequin Off Market". Associated Press. Archived from the original on November 25, 2007. Retrieved 2006-05-01.
- ↑ Adams M, Tavakoli H (2006). "Gatifloxacin-induced hallucinations in a 19-year-old man". Psychosomatics 47 (4): 360. doi:10.1176/appi.psy.47.4.360. PMID 16844899.
- ↑ Coleman CI, Spencer JV, Chung JO, Reddy P (2002). "Possible gatifloxacin-induced fulminant hepatic failure". Ann Pharmacother 36 (7–8): 1162–7. doi:10.1345/aph.1A414. PMID 12086547.
- ↑ I Masood, R Bhargava, Z Ahmad, DK Sharma, SZ Rahman, SS Amin. Gatifloxacin-Induced Purpura – An Unusual Adverse Drug Reaction. J Ind Acad Clinical Med 2005; 6 (3): 239–240
- ↑ "Two drugs banned". The Hindu (Chennai, India). 19 March 2011.
- ↑ Peggy Peck (2 May 2006). "Bristol-Myers Squibb Hangs No Sale Sign on Tequin". Med Page Today. Retrieved 24 February 2009.
- ↑ "Drugs banned in India". Central Drugs Standard Control Organization, Dte.GHS, Ministry of Health and Family Welfare, Government of India. Retrieved 2013-09-17.
- ↑ http://www.sify.com/news/india-bans-two-drugs-news-health-ldsukjaiaie.html?title=india-bans-two-drugs
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