Trovan

Trovafloxacin

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a605016
Routes of administration	Oral, intravenous
ATC code	J01MA13 (WHO)
Legal status
Legal status	Withdrawn from market
Identifiers
IUPAC name 7-(6-Amino-3-azabicyclo[3.1.0]hex-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-[1,8] naphthyridine-3-carboxylic acid
CAS Number	147059-72-1 Y
PubChem CID	62959
DrugBank	DB00685 Y
ChemSpider	16736478 Y
UNII	9F388J00UK
KEGG	D08654 Y
ChEBI	CHEBI:9763 N
ChEMBL	CHEMBL428 Y
Chemical and physical data
Formula	C20H15F3N4O3
Molar mass	416.353 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(O)C2=CN(c1nc(c(F)cc1C2=O)N3C[C@H]4[C@H](N)[C@H]4C3)c5ccc(F)cc5F
InChI InChI=1S/C20H15F3N4O3/c21-8-1-2-15(13(22)3-8)27-7-12(20(29)30)17(28)9-4-14(23)19(25-18(9)27)26-5-10-11(6-26)16(10)24/h1-4,7,10-11,16H,5-6,24H2,(H,29,30)/t10-,11+,16+ Y Key:WVPSKSLAZQPAKQ-CDMJZVDBSA-N Y
NY (what is this?)

Trovafloxacin (sold as Trovan by Pfizer and Turvel by Laboratorios Almirall) was a broad spectrum antibiotic that inhibits the uncoiling of supercoiled DNA in various bacteria by blocking the activity of DNA gyrase and topoisomerase IV. It was withdrawn from the market due to the risk of hepatotoxicity. It had better gram-positive bacterial coverage and less gram-negative coverage than the previous fluoroquinolones.

Trovafloxacin use is significantly restricted due to its high potential for inducing serious, sometimes fatal liver damage.

In 1996, during a meningitis epidemic in Kano, Nigeria, the drug was administered to approximately 200 infected children. Eleven children died in the trial: five after taking Trovan and six after taking an older antibiotic used for comparison in the clinical trial. Others suffered blindness, deafness and brain damage, common sequalae of meningitis that have not been seen in patients treated with trovafloxacin for other infection types. An investigation by the Washington Post concluded that Pfizer had administered the drug as part of an illegal clinical trial without authorization from the Nigerian government or consent from the children's parents. The case came to light in December 2000 as the result of an investigation by The Washington Post, and sparked significant public outcry. The most serious error was the falsification and backdating of an ethics approval letter by the lead investigator of the trial, Dr. Abdulhamid Isa Dutse. Dr. Dutse is now the chief medical officer of Aminu Kano Teaching Hospital. The result of the trial was that children treated with oral trovafloxacin had a 5% (5/100) mortality rate compared to a 6% (6/100) mortality rate with intramuscular ceftriaxone.