Cefmenoxime

Cefmenoxime is a third-generation cephalosporin antibiotic.

Cefmenoxime
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Intramuscular, intravenous
ATC code
Pharmacokinetic data
Bioavailability100% (given IM)
Protein binding50% to 70%
MetabolismNegligible
Elimination half-life1 hour
ExcretionKidney, unchanged
Identifiers
  • (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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H17N9O5S3
Molar mass511.55 g·mol−1
3D model (JSmol)
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)/c3nc(sc3)N)CSc4nnnn4C)C(=O)O
  • InChI=1S/C16H17N9O5S3/c1-24-16(20-22-23-24)33-4-6-3-31-13-9(12(27)25(13)10(6)14(28)29)19-11(26)8(21-30-2)7-5-32-15(17)18-7/h5,9,13H,3-4H2,1-2H3,(H2,17,18)(H,19,26)(H,28,29)/b21-8-/t9-,13-/m1/s1 Y
  • Key:HJJDBAOLQAWBMH-YCRCPZNHSA-N Y
 NY (what is this?)  (verify)

Synthesis

The alkylation of ethyl 2-hydroxyimino-3-oxobutanoate [5408-04-8][66508-93-8] (1) with dimethylsulfate gives Ethyl (2Z)-2-methoxyimino-3-oxo-butanoate [60846-14-2] (2). Halogenation with molecular bromine leads to ethyl 4-bromo-2-methoxyimino-3-oxobutanoate [60845-87-6] (3). Treatment with thiourea led to Ethyl (Z)-2-(2-amino-4-thiazolyl)-2-methoxyiminoacetate [64485-88-7] [60846-15-3] (4). Amide formation with chloroacetyl chloride gave PC6372031 (5). Saponification with potassium hydroxide gave PC5371531 (6). Halogenation with phosphorus pentachloride gave PC12884126 (7). Amide formation with PC15573427 (8) gave PC53669018 (9). Removal of the protecting group with Benzyltriethylammonium bromide [5197-95-5] furnished PC54254231 (10). The tert-butyl ester was deprotected with trifluoroacetic acid giving PC53850835 (11). Lastly, thioether formation with 5-Mercapto-1-methyltetrazole [13183-79-4] (12) completed the synthesis of Cefmenoxime (13).

References
  1. Serradell, M.N.; Castaer, J.; Blancafort, P.; SCE-1365. Drugs Fut 1980, 5, 3, 146.
  2. Ochiai M, Aki O, Morimoto A, Okada T, Matsushita Y. New cephalosporin derivatives with high antibacterial activities. Chem Pharm Bull (Tokyo). 1977 Nov;25(11):3115-7. doi: 10.1248/cpb.25.3115. PMID: 603968.
  3. Ochiai M, Morimoto A, Miyawaki T, Matsushita Y, Okada T, Natsugari H, Kida M. Synthesis and structure-activity relationships of 7 beta-[2-(2-aminothiazol-4-yl)acetamido]cephalosporin derivatives. V. Synthesis and antibacterial activity of 7 beta-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-cephalosporin derivates and related compounds. J Antibiot (Tokyo). 1981 Feb;34(2):171-85. doi: 10.7164/antibiotics.34.171. PMID: 6271716.
  4. Ochiai M, Morimoto A, Miyawaki T. Synthesis and structure-activity relationships of 7 beta-[2-(2-aminothiazol-4-yl)acetamido]cephalosporin derivatives. VI. Alternative syntheses of 7 beta-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]cephalosporin derivatives. J Antibiot (Tokyo). 1981 Feb;34(2):186-92. doi: 10.7164/antibiotics.34.186. PMID: 6271717.
  5. Michihiko Ochiai, et al. U.S. patent 4,098,888 (1978 to Takeda Pharmaceutical Co Ltd).
  6. Japan. Pat., 80 38 349, (1980); CA, 93, 204670
  • Diseases Database (DDB): 30892
  • Yokota N, Koguchi M, Suzuki Y, Fukayama S, Ishihara R, Deguchi K, Oda S, Tanaka S, Nakane Y, Fukumoto T (1995). "Antibacterial activities of cefmenoxime against recent fresh clinical isolates from patients in sinusitis". Jpn J Antibiot. 48 (5): 602–9. PMID 7637194.
  • Paladino J, Fell R (1994). "Pharmacoeconomic analysis of cefmenoxime dual individualization in the treatment of nosocomial pneumonia". Ann Pharmacother. 28 (3): 384–9. doi:10.1177/106002809402800316. PMID 8193431. S2CID 29444681.
  • Duncker G, Reich U, Krausse R (1994). "Cefmenoxime in corneal organ culture". Ophthalmologica. 208 (5): 262–6. doi:10.1159/000310505. PMID 7816419.


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