TR6

Trovafloxacin


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Chemical Component Summary

NameTrovafloxacin
Synonyms7-[(1R,5S,6s)-6-amino-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
Identifiers7-[(1S,5R)-6-azanyl-3-azabicyclo[3.1.0]hexan-3-yl]-1-[2,4-bis(fluoranyl)phenyl]-6-fluoranyl-4-oxidanylidene-1,8-naphthyridine-3-carboxylic acid
FormulaC20 H15 F3 N4 O3
Molecular Weight416.353
TypeNON-POLYMER
Isomeric SMILESc1cc(c(cc1F)F)N2C=C(C(=O)c3c2nc(c(c3)F)N4C[C@@H]5[C@H](C4)C5N)C(=O)O
InChIInChI=1S/C20H15F3N4O3/c21-8-1-2-15(13(22)3-8)27-7-12(20(29)30)17(28)9-4-14(23)19(25-18(9)27)26-5-10-11(6-26)16(10)24/h1-4,7,10-11,16H,5-6,24H2,(H,29,30)/t10-,11+,16+
InChIKeyWVPSKSLAZQPAKQ-CDMJZVDBSA-N

Chemical Details

Formal Charge0
Atom Count45
Chiral Atom Count3
Bond Count49
Aromatic Bond Count12

Drug Info: DrugBank

DrugBank IDDB00685 
NameTrovafloxacin
Groups
  • approved
  • withdrawn
  • investigational
DescriptionTrovafloxacin is a broad spectrum antibiotic that has been commonly marketed under the brand name Trovan by Pfizer. It exerts its antibacterial activity by inhibiting the uncoiling of supercoiled DNA in various bacteria by blocking the activity of DNA gyrase and topoisomerase IV. It was shown to be more effective against Gram-positive bacteria than Gram-negative bacteria when compared to previous fluoroquinolones. Due to its hepatotoxic potential, trovafloxacin was withdrawn from the market.
Synonyms
  • trovafloxacino
  • Trovafloxacin mesylate
  • Trovafloxacin
  • Trovafloxacin hydrochloride
Brand Names
  • Trovan
  • Trovan Tablets 200mg
  • Trovan Tablets 100mg
IndicationFor treatment of infections caused by susceptible strains of the designated microorganisms in uncomplicated urethral gonorrhea in males and endocervical and rectal gonorrhea in females caused by <i>Neisseria gonorrhoeae</i> as well as non gonoccocal urethritis and cervicitis due to <i>Chlamydia trachomatis</i>.
Categories
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
  • Antiinfectives for Systemic Use
  • Cytochrome P-450 CYP1A2 Inhibitors
ATC-CodeJ01MA13
CAS number147059-72-1

Drug Targets

NameTarget SequencePharmacological ActionActions
DNA gyrase subunit AMTDSIQSSITPVNIEEELKSSYLDYAMSVIVGRALPDVRDGLKPVHRRVL...unknowninhibitor
DNA topoisomerase 4 subunit AMTNINYEGIEQMPLRTFTEKAYLNYSMYVIMDRALPFIGDGLKPVQRRIV...unknowninhibitor
DNA topoisomerase 2-alphaMEVSPLQPVNENMQVNKIKKNEDAKKRLSVERIYQKKTQLEHILLRPDTY...unknowninhibitor
Cytochrome P450 1A2MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...unknowninhibitor
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682