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Legal status	Withdrawn;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 ;
ChemSpider	21243647 ;
UNII	7QVV6I50DT;
ChEMBL	ChEMBL1201197 ;
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 ; Key:UUZPPAMZDFLUHD-VUJLHGSVSA-N ;
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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Trovafloxacin and alatrofloxacin were both withdrawn from the U.S. market in June 2006 due to hepatotoxicity leading to liver transplant or death.[2]

References

"Center for Drug Evaluation and Research – Application Number: 020759/020760 – Chemistry Review(s)" (PDF). Food and Drug Administration. Retrieved 29 August 2014.
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.

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