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<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename =
| Drugs.com = {{drugs.com|CONS|alatrofloxacin}}
| Drugs.com = {{drugs.com|CONS|alatrofloxacin}}
| MedlinePlus = a605016
| MedlinePlus = a605016
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = C
| pregnancy_US = C
| pregnancy_category =
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
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| CAS_number = 146961-76-4
| CAS_number = 146961-76-4
| ATC_prefix = none
| ATC_prefix = none
| ATC_suffix =
| ATC_suffix =
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 21243647
| ChemSpiderID = 21243647
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<!--Chemical data-->
<!--Chemical data-->
| C=26 | H=25 | F=3 | N=6 | O=5
| C=26 | H=25 | F=3 | N=6 | O=5


| smiles = C[C@@H](C(=O)N[C@@H](C)C(=O)N[C@H]1[C@H]2[C@@H]1CN(C2)C3=C(C=C4C(=O)C(=CN(C4=N3)C5=C(C=C(C=C5)F)F)C(=O)O)F)N
| smiles = C[C@@H](C(=O)N[C@@H](C)C(=O)N[C@H]1[C@H]2[C@@H]1CN(C2)C3=C(C=C4C(=O)C(=CN(C4=N3)C5=C(C=C(C=C5)F)F)C(=O)O)F)N

Latest revision as of 01:55, 31 December 2022

Alatrofloxacin
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa605016
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  • Withdrawn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
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC26H25F3N6O5
Molar mass558.518 g·mol−1
3D model (JSmol)
  • C[C@@H](C(=O)N[C@@H](C)C(=O)N[C@H]1[C@H]2[C@@H]1CN(C2)C3=C(C=C4C(=O)C(=CN(C4=N3)C5=C(C=C(C=C5)F)F)C(=O)O)F)N
  • InChI=1S/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 ☒N
  • Key:UUZPPAMZDFLUHD-VUJLHGSVSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Alatrofloxacin (Trovan IV) is a fluoroquinolone antibiotic developed by Pfizer, delivered as a mesylate salt.[1]

Trovafloxacin and alatrofloxacin were both withdrawn from the U.S. market in June 2006 due to hepatotoxicity leading to liver transplant or death.[2]

See also[edit]

References[edit]

  1. ^ "Center for Drug Evaluation and Research – Application Number: 020759/020760 – Chemistry Review(s)" (PDF). Food and Drug Administration. Retrieved 29 August 2014.
  2. ^ Qureshi ZP, Seoane-Vazquez E, Rodriguez-Monguio R, Stevenson KB, Szeinbach SL (July 2011). "Market withdrawal of new molecular entities approved in the United States from 1980 to 2009". Pharmacoepidemiology and Drug Safety. 20 (7): 772–777. doi:10.1002/pds.2155. PMID 21574210. S2CID 23821961.
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