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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
Identifiers
CAS number	157182-32-6 157605-25-9 (mesylate)
ATC code	?
PubChem	5489474
Chemical data
Formula	C₂₆H₂₅F₃N₆O₅
Mol. mass	558.509 g/mol
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)
Therapeutic considerations
Pregnancy cat.	C(US)
Legal status	Withdrawn
Routes	Intravenous

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 which encountered criticism for its Nigerian trials and adverse clinical reactions.^[2]^[3]

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Trovafloxacin and alatrofloxacin were both withdrawn from the U.S. market in 2001.

References

^ PubChem CID 5489474.
^ 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. PMID 14568230.
^ 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. PMID 16735322.