Enoxacin

Title: Enoxacin
CAS Registry Number: 74011-58-8
CAS Name: 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid
Manufacturers' Codes: AT-2266; CI-919; PD-107779
Trademarks: Comprecin (Parke-Davis); Flumark (Dainippon)
Molecular Formula: C15H17FN4O3
Molecular Weight: 320.32
Percent Composition: C 56.24%, H 5.35%, F 5.93%, N 17.49%, O 14.98%
Literature References: Fluorinated quinolone antibacterial; nalidixic acid analog. Prepn and antibacterial activity: J. Matsumoto et al., EP 9425; eidem, US 4352803; eidem, US 4359578 (1980, 1982, 1982 all to Dainippon and Roger Bellon); J. Matsumoto et al., J. Med. Chem. 27, 292 (1984). HPLC determn in plasma, urine: T. B. Vree et al., J. Chromatogr. 343, 449 (1985). In vitro comparison with other quinolones and azaquinolones: S. Selwyn, M. Bakhtiar, Drugs Exp. Clin. Res. 10, 653 (1984). Pharmacokinetics, therapeutic efficacy: K. G. Naber et al., Infection 13, 219 (1985). Efficacy in treatment of urinary tract infections: R. R. Bailey, B. A. Peddie, N. Z. Med. J. 98, 286 (1985). Toxicology studies: H. Senda et al., Chemotherapy (Tokyo) 32, Suppl. 3, 192 (1984). Series of articles on activity, pharmacology, metabolism, early clinical studies: ibid. 1-1093; J. Antimicrob. Chemother. 14, Suppl. C, 1-96 (1984); on activity, pharmacokinetics, clinical safety and efficacy: Infection 14, Suppl. 3, S183-S220 (1986).
Properties: Crystals from ethanol/methylene chloride, mp 220-224°. LD50 in male, female mice, male, female rats (mg/kg): 327, 391, 236, 294 i.v.; 1237, 1320, >2000, >2000 s.c.; all >5000 orally (Senda).
Melting point: mp 220-224°
Toxicity data: LD50 in male, female mice, male, female rats (mg/kg): 327, 391, 236, 294 i.v.; 1237, 1320, >2000, >2000 s.c.; all >5000 orally (Senda)
Derivative Type: Sesquihydrate
CAS Registry Number: 84294-96-2
Trademarks: Bactidan (Fabre); Enoxen (Dainippon); Enoxor (Fabre); Gyramid (Warner-Lambert)
Molecular Formula: C15H17FN4O3.1½H2O
Molecular Weight: 329.33
Percent Composition: C 54.71%, H 5.51%, F 5.77%, N 17.01%, O 17.00%
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Synthetic); Quinolones and Analogs.
Enoxaparin Enoximone Enoxolone Enprostil Enrofloxacin

Enoxacin
Enoxacin.svg
Systematic (IUPAC) name
1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a601013
Legal status  ?
Routes Oral
Identifiers
CAS number 74011-58-8 YesY
ATC code J01MA04
PubChem CID 3229
DrugBank DB00467
ChemSpider 3116 YesY
UNII 325OGW249P YesY
KEGG D00310 YesY
ChEBI CHEBI:157175 YesY
ChEMBL CHEMBL826 YesY
Chemical data
Formula C15H17FN4O3 
Mol. mass 320.319 g/mol
 YesY (what is this?)  (verify)

Enoxacin (sold under the following trade names Almitil, Bactidan, Bactidron, Comprecin, Enoksetin, Enoxen, Enroxil, Enoxin, Enoxor, Flumark, Penetrex, Gyramid, Vinone) is an oral broad-spectrum fluoroquinolone antibacterial agent used in the treatment of urinary tract infections and gonorrhea. Insomnia is a common adverse effect.[1][2] It is no longer available in the United States.

It has been shown recently that it may have cancer inhibiting effect.[3]