Cefmenoxime

Last updated

Cefmenoxime
Cefmenoxime.svg
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration 		Intramuscular, intravenous
ATC code
Pharmacokinetic data
Bioavailability 100% (given IM)
Protein binding 50% to 70%
Metabolism Negligible
Elimination half-life 1 hour
Excretion Kidney, 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
Formula C16H17N9O5S3
Molar mass 511.55 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 Yes check.svgY
  • Key:HJJDBAOLQAWBMH-YCRCPZNHSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Cefmenoxime is a third-generation cephalosporin antibiotic. [1]

Contents

Synthesis

Cefmenoxime synthesis.svg

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]

References

  1. ↑ 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.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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.

Further reading

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