Cefmenoxime

Cefmenoxime
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Intramuscular, intravenous
ATC code	J01DD05 (WHO) S01AA31 (WHO), S02AA18 (WHO);
Pharmacokinetic data
Bioavailability	100% (given IM)
Protein binding	50% to 70%
Metabolism	Negligible
Elimination half-life	1 hour
Excretion	Kidney, unchanged
Identifiers
	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;
CAS Number	65085-01-0 ;
PubChem CID	9570757;
DrugBank	DB00267 ;
ChemSpider	7845223 ;
UNII	KBZ4844CXN;
KEGG	D07641 ;
ChEBI	CHEBI:55490 ;
ChEMBL	ChEMBL1201224 ;
CompTox Dashboard (EPA)	DTXSID2022755 ;
Chemical and physical data
Formula	C16H17N9O5S3
Molar mass	511.55 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)/c3nc(sc3)N)CSc4nnnn4C)C(=O)O;
	InChI 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 ; Key:HJJDBAOLQAWBMH-YCRCPZNHSA-N ;
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Cefmenoxime is a third-generation cephalosporin antibiotic.^[1]

Synthesis

The alkylation of ethyl 2-hydroxyimino-3-oxobutanoate (1) with dimethylsulfate gives ethyl (2Z)-2-methoxyimino-3-oxo-butanoate (2). Halogenation with molecular bromine leads to ethyl 4-bromo-2-methoxyimino-3-oxobutanoate (3). Treatment with thiourea gives ethyl (Z)-2-(2-amino-4-thiazolyl)-2-methoxyiminoacetate (4) which is reacted with chloroacetyl chloride to give the amide (5). Saponification with potassium hydroxide gives (6) which is halogenated with phosphorus pentachloride to (7). Amide formation with the cephalosporin intermediate (8) then gives (9). Removal of the protecting group with benzyltriethylammonium bromide yields (10). The tert-butyl ester was deprotected with trifluoroacetic acid to give (11). Lastly, thioether formation with 5-mercapto-1-methyltetrazole (12) completes the synthesis of cefmenoxime.^[2]^[3]^[4]^[5]

^ Campoli-Richards DM, Todd PA (August 1987). "Cefmenoxime. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use". Drugs. 34 (2): 188–221. doi:10.2165/00003495-198734020-00002. PMID 3304966.
^ US 4098888, Ochiai M, Okada T, Aki O, Morimoto A, Kawakita K, Matsushita Y, "Thiazolylacetamido cephalosporin type compounds", issued 7 April 1978, assigned to Takeda Pharmaceutical Co Ltd.
^ Ochiai M, Aki O, Morimoto A, Okada T, Matsushita Y (November 1977). "New cephalosporin derivatives with high antibacterial activities". Chemical & Pharmaceutical Bulletin. 25 (11): 3115–3117. doi:10.1248/cpb.25.3115. PMID 603968.
^ Ochiai M, Morimoto A, Miyawaki T, Matsushita Y, Okada T, Natsugari H, et al. (February 1981). "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". The Journal of Antibiotics. 34 (2): 171–185. doi:10.7164/antibiotics.34.171. PMID 6271716.
^ Ochiai M, Morimoto A, Miyawaki T (February 1981). "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". The Journal of Antibiotics. 34 (2): 186–192. doi:10.7164/antibiotics.34.186. PMID 6271717.

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