Alatrofloxacin
Chemical compound
- none
- Withdrawn
- 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
- 146961-76-4 N
- 21243647 N
- 7QVV6I50DT
- ChEMBL1201197 N
- Interactive image
- 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
- 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
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Trovafloxacin and alatrofloxacin were both withdrawn from the U.S. market in June 2006 due to hepatotoxicity leading to liver transplant or death.[2][3]
See also
References
- ^ "Center for Drug Evaluation and Research – Application Number: 020759/020760 – Chemistry Review(s)" (PDF). Food and Drug Administration. Retrieved 29 August 2014.
- ^ 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.
- ^ "TROVAN® Tablets(trovafloxacin mesylate)TROVAN® I.V.(alatrofloxacin mesylate injection)For Intravenous Infusion". DailyMed. Retrieved 2024-08-03.
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(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)
DHFR inhibitor | |||||||||
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Sulfonamides (DHPS inhibitor) |
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Combinations |
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Other DHPS inhibitors |
(inhibit bacterial
topoisomerase
and/or DNA gyrase,
thereby inhibiting
DNA replication)
1st generation | |||||||||
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Fluoroquinolones |
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Newer non-fluorinated | |||||||||
Related (DG) |
inhibitors
Nitroimidazole derivatives |
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Rifamycins/ RNA polymerase | |
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Lipiarmycins |
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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