Alatrofloxacin

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Alatrofloxacin
	File:Alatrofloxacin.svg
Clinical data
Pregnancy; category	US: C (Risk not ruled out) ; ;
Routes of; administration	Intravenous
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Legal status	Withdrawn;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	157182-32-6 157605-25-9 (mesylate);
PubChem CID	5489474;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C26H25F3N6O5
Molar mass	558.509 g/mol

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Trovafloxacin and alatrofloxacin were both withdrawn from the U.S. market in 2001.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

↑ "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.

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[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.

[1]

[2]

[3]

Clinical data
File:Alatrofloxacin.svg
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Intravenous
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	157182-32-6 157605-25-9 (mesylate)
PubChem CID	5489474
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₂₆H₂₅F₃N₆O₅
Molar mass	558.509 g/mol

Alatrofloxacin

References

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