Cefmenoxime

Title: Cefmenoxime
CAS Registry Number: 65085-01-0
CAS Name: (6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Additional Names: (6R,7R)-7-[2-(2-amino-4-thiazolyl)glyoxylamido]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 72-(Z)-(O-methyloxime)
Manufacturers' Codes: SCE-1365
Molecular Formula: C16H17N9O5S3
Molecular Weight: 511.56
Percent Composition: C 37.57%, H 3.35%, N 24.64%, O 15.64%, S 18.80%
Literature References: Third generation cephalosporin antibiotic; related structurally to cefotaxime and ceftizoxime, q.q.v. The name cefmenoxime applies to the isomer having a syn-methoxyimino group. Prepn (unspecified stereochemistry): M. Ochiai et al., DE 2556736; eidem, US 4098888 (1976, 1978 both to Takeda); syn-isomer: R. Heymes, A. Lutz, DE 2713272; eidem, US 4476122 (1983, 1984 both to Roussel-Uclaf). Series of articles on antibacterial activity, absorption, excretion, metabolism, mechanism of action, clinical studies: Chemotherapy (Tokyo) 29, Suppl. 1, 1-998 (1979). In vitro and in vivo study: K. Tsuchiya et al., Antimicrob. Agents Chemother. 19, 56 (1981). b-Lactamase stability: K. Okonogi et al., ibid. 20, 171 (1981). Clinical pharmacokinetics study: D. Höffler, P. Koeppe, Arzneim.-Forsch. 33, 269 (1983). Symposium: Am. J. Med. 77(6A), 1-59 (1984).
Derivative Type: Hydrochloride (syn-isomer)
CAS Registry Number: 75738-58-8
Manufacturers' Codes: Abbott 50192
Trademarks: Bestcall (Takeda); Cefmax (TAP); Cemix (Takeda); Tacef (Grenthal)
Molecular Formula: (C16H17N9O5S3)2.HCl
Molecular Weight: 1059.58
Percent Composition: C 36.27%, H 3.33%, N 23.79%, O 15.10%, S 18.16%, Cl 3.35%
Derivative Type: Sodium salt (syn-isomer)
CAS Registry Number: 65085-02-1
Molecular Formula: C16H16N9NaO5S3
Molecular Weight: 533.54
Percent Composition: C 36.02%, H 3.02%, N 23.63%, Na 4.31%, O 14.99%, S 18.03%
Properties: [a]D20 -13.5 ±1° (c = 1 in water).
Optical Rotation: [a]D20 -13.5 ±1° (c = 1 in water)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.
Cefmetazole Cefminox Cefodizime Cefonicid Cefoperazone

Cefmenoxime
Cefmenoxime.svg
Systematic (IUPAC) name
(6R,7R)-7-{[(2E)-2-(2-amino-1,3-thiazol-4-yl)-
2-methoxyimino-acetyl]amino}-3-[(1-methyltetrazol-
5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]
oct-2-ene-2-carboxylic acid
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Routes Intramuscular, intravenous
Pharmacokinetic data
Bioavailability 100% (given IM)
Protein binding 50% to 70%
Metabolism Negligible
Half-life 1 hour
Excretion Renal, unchanged
Identifiers
CAS number 65085-01-0 YesY
ATC code J01DD05
PubChem CID 9570757
DrugBank DB00267
ChemSpider 7845223 YesY
UNII KBZ4844CXN YesY
KEGG D07641 YesY
ChEBI CHEBI:55490 YesY
ChEMBL CHEMBL1201224 N
Chemical data
Formula C16H17N9O5S3 
Mol. mass 511.562 g/mol
 N (what is this?)  (verify)

Cefmenoxime is a third-generation cephalosporin antibiotic.