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Cefmenoxime

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Chemical compound

Pharmaceutical compound

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% (givenIM)
Protein binding	50% to 70%
Metabolism	Negligible
Eliminationhalf-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^Y
PubChemCID	9570757
DrugBank	DB00267^Y
ChemSpider	7845223^Y
UNII	KBZ4844CXN
KEGG	D07641^Y
ChEBI	CHEBI:55490^Y
ChEMBL	ChEMBL1201224^N
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^Y Key:HJJDBAOLQAWBMH-YCRCPZNHSA-N^Y
^NY (what is this?) (verify)

Cefmenoxime is a third-generationcephalosporin antibiotic.^[1]

Thealkylation of ethyl 2-hydroxyimino-3-oxobutanoate (1) withdimethylsulfate gives ethyl (2Z)-2-methoxyimino-3-oxo-butanoate (2).Halogenation with molecular bromine leads to ethyl 4-bromo-2-methoxyimino-3-oxobutanoate (3). Treatment withthiourea gives ethyl (Z)-2-(2-amino-4-thiazolyl)-2-methoxyiminoacetate (4) which is reacted withchloroacetyl chloride to give theamide (5).Saponification with potassium hydroxide gives (6) which is halogenated withphosphorus pentachloride to (7). Amide formation with thecephalosporin intermediate (8) then gives (9). Removal of theprotecting group withbenzyltriethylammonium bromide yields (10). The tert-butylester was deprotected withtrifluoroacetic 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.

β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)

β-lactamase sensitive (1st generation)	Benzylpenicillin (G)^# Benzathine benzylpenicillin^# Procaine benzylpenicillin^# Phenoxymethylpenicillin (V)^# Propicillin^‡ Pheneticillin^‡ Azidocillin^‡ Clometocillin^‡ Penamecillin^‡
β-lactamase resistant (2nd generation)	Cloxacillin^# (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin^‡

Aminopenicillins (3rd generation)	Amoxicillin^# Ampicillin^# (Pivampicillin Hetacillin^‡ Bacampicillin^‡ Lenampicillin Metampicillin^‡ Talampicillin^‡) Epicillin^‡
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin^‡ /Carindacillin^‡ Temocillin^‡
Ureidopenicillins (4th generation)	Piperacillin Azlocillin^‡ Mezlocillin^‡
Other	Mecillinam (Pivmecillinam) Sulbenicillin^‡

1st generation	Cefazolin^# Cefalexin^# Cefadroxil Cefapirin Cefazedone^‡ Cefazaflur^‡ Cefradine^‡ Cefroxadine^‡ Ceftezole^‡ Cefaloglycin^‡ Cefacetrile^‡ Cefalonium^‡ Cefaloridine^‡ Cefalotin Cefatrizine^‡
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole^‡ Cefonicid^‡ Ceforanide^‡ Cefuzonam^‡ Cephamycin (Cefoxitin Cefotetan Cefminox^‡ Cefbuperazone^‡ Cefmetazole^‡) Carbacephem (Loracarbef^‡)
3rd generation	Cefixime^# Ceftriaxone^# Cefotaxime^# Antipseudomonal (Ceftazidime^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam^‡ Cefetamet^‡ Cefodizime^‡ Cefpimizole^‡ Cefsulodin^‡ Cefteram^‡ Ceftiolene^‡ Oxacephem (Flomoxef Latamoxef^‡)
4th generation	Cefepime Cefozopran^‡ Cefpirome Cefquinome^‡
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol^#
Veterinary	Ceftiofur Cefquinome Cefovecin

Combinations

Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization:Daptomycin Surfactin
Other	Inhibits PG elongation and crosslinking:Ramoplanin^§

Intracellular