Alatrofloxacin

Alatrofloxacin

Systematic (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
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a605016
Pregnancy cat.	C(US)
Legal status	Withdrawn
Routes	Intravenous
Pharmacokinetic data
Bioavailability	N/A
Protein binding	76% (trovafloxacin)
Metabolism	Quickly hydrolyzed to trovafloxacin
Half-life	9 to 12 hours (trovafloxacin)
Excretion	Fecal and renal (trovafloxacin)
Identifiers
CAS number	157182-32-6 N 157605-25-9
ATC code	None
PubChem	CID 5489474
ChemSpider	21106252 Y
UNII	7QVV6I50DT Y
ChEMBL	CHEMBL1201197 N
Chemical data
Formula	C26H25F3N6O5
Mol. mass	558.509 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C26H25F3N6O5/c1-10(30)24(37)33-25(38)11(2)31-20-14-7-34(8-15(14)20)23-18(29)6-13-21(36)16(26(39)40)9-35(22(13)32-23)19-4-3-12(27)5-17(19)28/h3-6,9-11,14-15,20,31H,7-8,30H2,1-2H3,(H,39,40)(H,33,37,38)/t10?,11?,14-,15+,20? Y Key:GAJLLIJXQAMBHW-HVOYUNNHSA-N Y
N(what is this?)  (verify)

Alatrofloxacin (Trovan IV) is a fluoroquinolone antibiotic developed by Pfizer, delivered as a mesylate salt.^[1] It is the parental prodrug of trovafloxacin (Trovan) meant for intravenous administration. Trovafloxacin is a broad-spectrum antibiotic introduced in 1998 that encountered criticism for its Nigerian trials and adverse clinical reactions.^[2][3]

Trovafloxacin and alatrofloxacin were both withdrawn from the U.S. market in 2001.

See also

• Fluoroquinolone toxicity
• Fluoroquinolone

References

1. ^ "PubChem CID 5489474". http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5489474. 
2. ^ Hall IH, Schwab UE, Ward ES, Ives TJ (2003). "Effects of alatrofloxacin, the parental prodrug of trovafloxacin, on phagocytic, anti-inflammatory and immunomodulation events of human THP-1 monocytes". Biomed. Pharmacother. 57 (8): 359–65. doi:10.1016/S0753-3322(03)00054-4. PMID 14568230. 
3. ^ Lenzer J (2006). "Secret report surfaces showing that Pfizer was at fault in Nigerian drug tests". BMJ 332 (7552): 1233. doi:10.1136/bmj.332.7552.1233-a. PMC 1471980. PMID 16735322. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1471980. 

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