Alatrofloxacin

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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Withdrawn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

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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]

Trovafloxacin and alatrofloxacin were both withdrawn from the U.S. market in 2001.

References

  1. PubChem 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. 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. PMID 16735322.

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