Cefminox

Chemical compound

J01DC12 (WHO)

Legal statusLegal status

In general: ℞ (Prescription only)

Identifiers

IUPAC name

(6R,7S)-7-(((((2S)-2-amino-2-carboxyethyl)thio)acetyl)amino)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid

CAS Number

84305-41-9^Y

PubChem CID

71141

ChemSpider

64286^N

UNII

PW08Y13465

KEGG

D07642^Y

ChEBI

CHEBI:135817

ChEMBL

ChEMBL1276342^N

Chemical and physical dataFormulaC₁₆H₂₁N₇O₇S₃Molar mass519.57 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

O=C2N1/C(=C(\CS[C@@H]1[C@]2(OC)NC(=O)CSC[C@H](C(=O)O)N)CSc3nnnn3C)C(=O)O

InChI

InChI=1S/C16H21N7O7S3/c1-22-15(19-20-21-22)33-4-7-3-32-14-16(30-2,13(29)23(14)10(7)12(27)28)18-9(24)6-31-5-8(17)11(25)26/h8,14H,3-6,17H2,1-2H3,(H,18,24)(H,25,26)(H,27,28)/t8-,14-,16+/m1/s1^N
Key:JSDXOWVAHXDYCU-VXSYNFHWSA-N^N

^NY (what is this?) (verify)

Cefminox (INN) is a second-generation cephalosporin antibiotic.^[1]^[2]

Spectrum

Cefminox is a broad-spectrum, bactericidal cephalosporin antibiotic. It is especially effective against Gram-negative and anaerobic bacteria. ^{[citation needed]}The following represents MIC data for a few medically significant microorganisms.

Clostridium difficile: 2 - 4 μg/ml
Escherichia coli: 0.125 - 16 μg/ml
Pseudomonas aeruginosa: 256 μg/ml^[3]

References

^ Torres AJ, Valladares LD, Jover JM, Sánchez-Pernaute A, Frías J, Carcas AJ, et al. (September 2000). "Cefminox versus metronidazole plus gentamicin intra-abdominal infections: a prospective randomized controlled clinical trial". Infection. 28 (5): 318–22. doi:10.1007/s150100070027. PMID 11073141. S2CID 41555982.
^ US 8497086, "Reaction Medium For Methicillin-Resistant Staphylococcus Aureus (MRSA) Bacteria", issued 20 July 2013, assigned to Biomereux
^ "Cefminox sodium Susceptibility and Minimum Inhibitory Concentration (MIC) Data" (PDF). www.toku-e.com.

Antibacterials active on the cell wall and envelope (J01C-J01D)

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

Penicillins (Penams)

Narrow
spectrum

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^‡

Extended
spectrum

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^‡

Carbapenems / Penems

Cephems
Cephalosporins
Cephamycins
Carbacephems

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

Monobactams

β-lactamase inhibitors

Combinations

Polypeptides

Glycopeptides Lipoglycopeptides	Inhibit PG chain elongation: Vancomycin^# (Oritavancin Telavancin) Teicoplanin (Dalbavancin) Ristocetin^‡ Avoparcin Inhibit autolysin: Corbomycin (not approved)
Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization: Daptomycin Surfactin
Polymyxins	Bind to LPS in the outer bacterial membrane, acting in detergent-like fashion: Colistin Polymyxin B
Other	Inhibits PG elongation and crosslinking: Ramoplanin^§