Gatifloxacin

Last updated
Gatifloxacin
Gatifloxacin.svg
Gatifloxacin ball-and-stick.png
Clinical data
Trade names Gatiflo, Tequin, Zymar, others
AHFS/Drugs.com Monograph
MedlinePlus a605012
Routes of
administration
Oral (discontinued),
Intravenous (discontinued)
ophthalmic
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding 20%
Elimination half-life 7 to 14 hours
Identifiers
  • 1-Cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard 100.190.526 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C19H22FN3O4
Molar mass 375.400 g·mol−1
3D model (JSmol)
  • Fc1c(c(OC)c2c(c1)C(=O)C(\C(=O)O)=C/N2C3CC3)N4CC(NCC4)C
  • 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) Yes check.svgY
  • Key:XUBOMFCQGDBHNK-UHFFFAOYSA-N Yes check.svgY
   (verify)

Gatifloxacin (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.

Contents

It was patented in 1986 and approved for medical use in 1999. [2]

Side effects

A Canadian study published in the New England Journal of Medicine in March 2006, claimed that Tequin can have significant side effects including dysglycemia. [3] 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. [4] 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. [5] 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. [6]

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.[ citation needed ]

Contraindications

Hypersensitivity [7] [ failed verification ]

Society and culture

Availability

Gatifloxacin is currently available in the US and Canada only as an ophthalmic solution.[ citation needed ]

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. [8]

In China, gatifloxacin is sold in tablet as well as in eye drop formulations.[ citation needed ]

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.[ citation needed ]

Related Research Articles

<span class="mw-page-title-main">Ciprofloxacin</span> Fluoroquinolone antibiotic

Ciprofloxacin is a fluoroquinolone antibiotic used to treat a number of bacterial infections. This includes bone and joint infections, intra-abdominal infections, certain types of infectious diarrhea, respiratory tract infections, skin infections, typhoid fever, and urinary tract infections, among others. For some infections it is used in addition to other antibiotics. It can be taken by mouth, as eye drops, as ear drops, or intravenously.

<span class="mw-page-title-main">Levofloxacin</span> Antibiotic

Levofloxacin, sold under the brand name Levaquin among others, is an antibiotic medication. It is used to treat a number of bacterial infections including acute bacterial sinusitis, pneumonia, H. pylori, urinary tract infections, chronic prostatitis, and some types of gastroenteritis. Along with other antibiotics it may be used to treat tuberculosis, meningitis, or pelvic inflammatory disease. Use is generally recommended only when other options are not available. It is available by mouth, intravenously, and in eye drop form.

<span class="mw-page-title-main">Captopril</span> Antihypertensive drug of the ACE inhibitor class

Captopril, sold under the brand name Capoten among others, is an angiotensin-converting enzyme (ACE) inhibitor used for the treatment of hypertension and some types of congestive heart failure. Captopril was the first oral ACE inhibitor found for the treatment of hypertension. It does not cause fatigue as associated with beta-blockers. Due to the adverse drug event of causing hyperkalemia, as seen with most ACE Inhibitors, the medication is usually paired with a diuretic.

<span class="mw-page-title-main">Clopidogrel</span> Antiplatelet medication

Clopidogrel—sold under the brand names Plavix and Deplat, among others—is an antiplatelet medication used to reduce the risk of heart disease and stroke in those at high risk. It is also used together with aspirin in heart attacks and following the placement of a coronary artery stent. It is taken by mouth. Its effect starts about two hours after intake and lasts for five days.

<span class="mw-page-title-main">Irbesartan</span> Chemical compound

Irbesartan, sold under the brand name Avapro among others, is a medication used to treat high blood pressure, heart failure, and diabetic kidney disease. It is a reasonable initial treatment for high blood pressure. It is taken by mouth. Versions are available as the combination irbesartan/hydrochlorothiazide.

<span class="mw-page-title-main">Didanosine</span> Chemical compound

Didanosine, sold under the brand name Videx, is a medication used to treat HIV/AIDS. It is used in combination with other medications as part of highly active antiretroviral therapy (HAART). It is of the reverse-transcriptase inhibitor class.

<span class="mw-page-title-main">Ofloxacin</span> Antibiotic to treat bacterial infections

Ofloxacin is a quinolone antibiotic useful for the treatment of a number of bacterial infections. When taken by mouth or injection into a vein, these include pneumonia, cellulitis, urinary tract infections, prostatitis, plague, and certain types of infectious diarrhea. Other uses, along with other medications, include treating multidrug resistant tuberculosis. An eye drop may be used for a superficial bacterial infection of the eye and an ear drop may be used for otitis media when a hole in the ear drum is present.

<span class="mw-page-title-main">Ketorolac</span> Nonsteroidal anti-inflammatory drug (NSAID; analgesic)

Ketorolac, sold under the brand names Toradol, and Biorolac among others, is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain. Specifically it is recommended for moderate to severe pain. Recommended duration of treatment is less than six days, and in Switzerland not more than two days. It is used by mouth, by nose, by injection into a vein or muscle, and as eye drops. Effects begin within an hour and last for up to eight hours.

<span class="mw-page-title-main">Norfloxacin</span> Chemical compound, antibiotic

Norfloxacin, sold under the brand name Noroxin among others, is an antibiotic that belongs to the class of fluoroquinolone antibiotics. It is used to treat urinary tract infections, gynecological infections, inflammation of the prostate gland, gonorrhea and bladder infection. Eye drops were approved for use in children older than one year of age.

Dorzolamide/timolol, sold under the brand name Cosopt among others, is a medication used to treat high pressure inside the eye including glaucoma. It is a combination of dorzolamide hydrochloride and timolol maleate. It may be used when a beta blocker, like timolol, is not sufficient alone. It is used as an eye drop.

<span class="mw-page-title-main">Dasatinib</span> Chemical compound

Dasatinib, sold under the brand name Sprycel among others, is a targeted therapy medication used to treat certain cases of chronic myelogenous leukemia (CML) and acute lymphoblastic leukemia (ALL). Specifically it is used to treat cases that are Philadelphia chromosome-positive (Ph+). It is taken by mouth.

<span class="mw-page-title-main">Saxagliptin</span> Chemical compound

Saxagliptin, sold under the brand name Onglyza, is an oral hypoglycemic of the dipeptidyl peptidase-4 (DPP-4) inhibitor class. Early development was solely by Bristol-Myers Squibb; in 2007 AstraZeneca joined with Bristol-Myers Squibb to co-develop the final compound and collaborate on the marketing of the drug.

Abatacept, sold under the brand name Orencia, is a medication used to treat autoimmune diseases like rheumatoid arthritis, by interfering with the immune activity of T cells. It is a modified antibody.

<span class="mw-page-title-main">Enrofloxacin</span> Chemical compound

Enrofloxacin, sold under the brand name Baytril, among others, is a fluoroquinolone antibiotic used for the treatment of animals. It is a bactericidal agent.

<span class="mw-page-title-main">Bromfenac</span> Chemical compound

Bromfenac is a nonsteroidal anti-inflammatory drug (NSAID) marketed in the US as an ophthalmic solution by ISTA Pharmaceuticals for short-term, local use. Prolensa and Bromday are the once-daily formulation of bromfenac, while Xibrom was approved for twice-daily administration. In the European Union, the brand name is Yellox. Bromfenac is indicated for the treatment of ocular inflammation and pain after cataract surgery.

Dysglycemia is a general definition for any abnormalities in blood glucose levels. They include hyperglycemia, hypoglycemia, impaired glucose tolerance test, impaired fasting glucose, among others.

<span class="mw-page-title-main">Apixaban</span> Anticoagulant medication

Apixaban, sold under the brand name Eliquis, is an anticoagulant medication used to treat and prevent blood clots and to prevent stroke in people with nonvalvular atrial fibrillation through directly inhibiting factor Xa. Specifically, it is used to prevent blood clots following hip or knee replacement and in those with a history of prior clots. It is used as an alternative to warfarin and does not require monitoring by blood tests or dietary restrictions. It is taken by mouth.

<span class="mw-page-title-main">Daclatasvir</span> Chemical compound

Daclatasvir, sold under the brand name Daklinza, is an antiviral medication used in combination with other medications to treat hepatitis C (HCV). The other medications used in combination include sofosbuvir, ribavirin, and interferon, vary depending on the virus type and whether the person has cirrhosis. It is taken by mouth.

Nivolumab/relatlimab, sold under the brand name Opdualag, is a fixed-dose combination medication use to treat melanoma. It contains nivolumab, a programmed death receptor-1 (PD-1) blocking antibody, and relatlimab, a lymphocyte activation gene-3 (LAG-3) blocking antibody. It is given by intravenous infusion.

<span class="mw-page-title-main">Deucravacitinib</span> Chemical compound

Deucravacitinib, sold under the brand name Sotyktu, is medication used for the treatment of moderate-to-severe plaque psoriasis. It is a tyrosine kinase 2 (TYK2) inhibitor and it is taken by mouth. It was developed by Bristol Myers Squibb.

References

  1. 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". American Journal of Ophthalmology. 140 (1): 83–87. doi:10.1016/j.ajo.2005.02.037. PMID   15953577.
  2. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 501. ISBN   9783527607495.
  3. Park-Wyllie LY, Juurlink DN, Kopp A, Shah BR, Stukel TA, Stumpo C, et al. (March 2006). "Outpatient gatifloxacin therapy and dysglycemia in older adults". The New England Journal of Medicine. 354 (13): 1352–1361. doi:10.1056/NEJMoa055191. hdl: 1807/16915 . PMID   16510739.Note: publication date 30 March; available on-line 1 March
  4. Gurwitz JH (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.
  5. Lewis-Hall F (February 15, 2006). "Dear Healthcare Provider" (PDF). Bristol-Myers Squibb. Retrieved May 1, 2006.
  6. Schmid RE (May 1, 2006). "Drug Company Taking Tequin Off Market". Associated Press. Archived from the original on November 25, 2007. Retrieved 2006-05-01.
  7. Peggy Peck (2 May 2006). "Bristol-Myers Squibb Hangs No Sale Sign on Tequin". Med Page Today. Retrieved 24 February 2009.
  8. "Two drugs banned". The Hindu. Chennai, India. 19 March 2011. Archived from the original on 6 March 2012.