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Alatrofloxacin: Difference between revisions

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m Adding category Category:1,8 Naphthyridines (using HotCat)
Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChemSpiderID InChI1 SMILES1 InChIKey1.
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| image = Alatrofloxacin.svg
| image = Alatrofloxacin.svg
| width = 250
| width = 250
| ChemSpiderID = 2343243
| ChemSpiderID = 21106252
| InChI = 1/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
| InChI = 1/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
| smiles = Fc1ccc(c(F)c1)N/3c2nc(c(F)cc2C(=O)C(\C(=O)O)=C\3)N5C[C@@H]4C(NC(=O)[C@@H](NC(=O)[C@@H](N)C)C)[C@@H]4C5
| smiles = Fc1ccc(c(F)c1)N/3c2nc(c(F)cc2C(=O)C(\C(=O)O)=C\3)N5C[C@@H]4C(NC(=O)[C@@H](NC(=O)[C@@H](N)C)C)[C@@H]4C5
| InChIKey = UUZPPAMZDFLUHD-LZGARRQBBY
| InChIKey = UUZPPAMZDFLUHD-LZGARRQBBY
| InChI1 = 1/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?
| smiles1 = CC(N)C(=O)NC(=O)C(C)NC1[C@H]2CN(C[C@@H]12)c3nc4c(cc3F)C(=O)C(=C/N4c5ccc(F)cc5F)\C(O)=O
| InChIKey1 = GAJLLIJXQAMBHW-HVOYUNNHBA
| CAS_number = 157182-32-6
| CAS_number = 157182-32-6
| CAS_supplemental = {{CAS|157605-25-9}} ([[mesylate]])
| CAS_supplemental = {{CAS|157605-25-9}} ([[mesylate]])

Revision as of 20:05, 15 October 2010

Alatrofloxacin
Clinical data
Routes of
administration		Intravenous
ATC code
  • none
Legal status
Legal status
  • Withdrawn
Pharmacokinetic data
BioavailabilityN/A
Protein binding76% (trovafloxacin)
MetabolismQuickly hydrolyzed to trovafloxacin
Elimination half-life9 to 12 hours (trovafloxacin)
ExcretionFecal and renal (trovafloxacin)
Identifiers
  • 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
PubChem CID
ChemSpider
Chemical and physical data
FormulaC26H25F3N6O5
Molar mass558.509 g/mol g·mol−1
3D model (JSmol)
  • Fc1ccc(c(F)c1)N/3c2nc(c(F)cc2C(=O)C(\C(=O)O)=C\3)N5C[C@@H]4C(NC(=O)[C@@H](NC(=O)[C@@H](N)C)C)[C@@H]4C5

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.

See also

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. doi:10.1016/S0753-3322(03)00054-4. PMID 14568230.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.
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