Alatrofloxacin

Alatrofloxacin

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a605016
Routes of administration	Intravenous
ATC code	none
Legal status
Legal status	Withdrawn
Pharmacokinetic data
Bioavailability	N/A
Protein binding	76% (trovafloxacin)
Metabolism	Quickly hydrolyzed to trovafloxacin
Elimination half-life	9 to 12 hours (trovafloxacin)
Excretion	Fecal and renal (trovafloxacin)
Identifiers
IUPAC name 7-[(1R,5S)-6-{[(2S)-1-{[(2S)-2-Aminopropanoyl]amino}-1-oxopropan-2-yl]amino}-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid
CAS Number	146961-76-4^N
ChemSpider	21243647^N
UNII	7QVV6I50DT
ChEMBL	ChEMBL1201197^N
Chemical and physical data
Formula	C26H25F3N6O5
Molar mass	558.518 g·mol^−1
3D model (JSmol)	Interactive image
SMILES C[C@@H](C(=O)N[C@@H](C)C(=O)N[C@H]1[C@H]2[C@@H]1CN(C2)C3=C(C=C4C(=O)C(=CN(C4=N3)C5=C(C=C(C=C5)F)F)C(=O)O)F)N
InChI InChI=1S/C26H25F3N6O5/c1-10(30)24(37)31-11(2)25(38)32-20-14-7-34(8-15(14)20)23-18(29)6-13-21(36)16(26(39)40)9-35(22(13)33-23)19-4-3-12(27)5-17(19)28/h3-6,9-11,14-15,20H,7-8,30H2,1-2H3,(H,31,37)(H,32,38)(H,39,40)/t10-,11-,14-,15+,20+/m0/s1^N Key:UUZPPAMZDFLUHD-VUJLHGSVSA-N^N
^NY (what is this?)  (verify)

Alatrofloxacin (Trovan IV) is a fluoroquinolone antibiotic developed by Pfizer, delivered as a mesylate salt.^[1]

Trovafloxacin and alatrofloxacin were both withdrawn from the U.S. market in June 2006 due to hepatotoxicity leading to liver transplant or death.^[2][3]

See also

• Fluoroquinolones

References

1. "Center for Drug Evaluation and Research – Application Number: 020759/020760 – Chemistry Review(s)" (PDF). Food and Drug Administration. Retrieved 29 August 2014.
2. Qureshi ZP, Seoane-Vazquez E, Rodriguez-Monguio R, Stevenson KB, Szeinbach SL (July 2011). "Market withdrawal of new molecular entities approved in the United States from 1980 to 2009". Pharmacoepidemiology and Drug Safety. 20 (7): 772–777. doi:10.1002/pds.2155. PMID 21574210. S2CID 23821961.
3. "TROVAN® Tablets(trovafloxacin mesylate)TROVAN® I.V.(alatrofloxacin mesylate injection)For Intravenous Infusion". DailyMed. Retrieved 2024-08-03.