cefmenoxime
Trade name: cefmax
Approved
Dec 30, 1987
Cefmenoxime is a semisynthetic beta-lactam cephalosporin antibiotic with activity similar to that of cefotaxime. Like other 'third-generation' cephalosporins it is active in vitro against most common Gram-positive and Gram-negative pathogens, is a potent inhibitor of Enterobacteriaceae (including beta-lactamase-producing strains), and is resistant to hydrolysis by beta-lactamases. Cefmenoxime has a high rate of clinical efficacy in many types of infection and is at least equal in clinical and bacteriological efficacy to several other cephalosporins in urinary tract infections, respiratory tract infections, postoperative infections and gonorrhoea. The bactericidal activity of cefmenoxime results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Cefmenoxime is stable in the presence of a variety of b-lactamases, including penicillinases and some cephalosporinases. Cefmenoxime is marketed in Japan under the brand name Bestron, indicated for the treatment of otitis externa, otitis media, and sinusitis. Cefmenoxime hydrochloride was approved by the U.S. Food and Drug Administration (FDA) on Dec 30, 1987. It was developed and marketed as Cefmax®, but it has being discontinued. — NCATS
Clinical trial activity
0 trials · 0 clinical orgs · 1 marketing orgs
Timeline
1980s
- Dec 30, 1987
TAP Pharmaceuticals — Earliest FDA Approval
- Dec 30, 1987
TAP Pharmaceuticals — NDA Organization
Indications
Mechanism of action
- Bacterial penicillin-binding proteinINHIBITOR
Bacterial penicillin-binding protein inhibitor
- D-alanyl-D-alanine carboxypeptidase DacB (dacB) ↗
- Peptidoglycan D,D-transpeptidase FtsI (ftsI) ↗
- Penicillin-binding protein 1A (mrcA) ↗
- Penicillin-binding protein 1B (mrcB) ↗
- D-alanyl-D-alanine carboxypeptidase DacA (dacA) ↗
- Peptidoglycan D,D-transpeptidase MrdA (mrdA) ↗
- D-alanyl-D-alanine carboxypeptidase DacC (dacC) ↗
Approval history
- approvedDec 30, 1987
Chemistry & pharmacology
SMILES
CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CSc3nnnn3C)CS[C@H]12)c1csc(N)n1- Mol. weight
- 511.57 g/mol
- Lipinski Ro5
- 2 violation(s)
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Parenteral
- Availability
- Discontinued
Oral
No
Parenteral
Yes
Topical
No
Sources
- ChEMBLCHEMBL1201224 ↗
- WikipediaCefmenoxime ↗
- NCATSKBZ4844CXN ↗
- ChEMBLCHEMBL3183193 ↗
Also known as
- (6r,7r)-7-[[(2e)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (iupac)
- (6r,7r)-7-[[(2e)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (iupac)
- (6r,7r)-7-((z)-2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido)-3-((1-methyl-1h-5-tetraazolylthio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure
- (6r,7r)-7-((z)-2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido)-3-((1-methyl-1h-5-tetraazolylthio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure
- abbott-50192
- abbott-50192
- cefmax
- cefmax
- cefmax
- cefmenoxima
- cefmenoxima
- cefmenoxime
- cefmenoxime
- cefmenoxime
- cefmenoxime
- cefmenoxime
- cefmenoxime
- cefmenoxime
- cefmenoxime hcl
- cefmenoxime hcl
- cefmenoxime hcl
- cefmenoxime hydrochloride
- cefmenoxime hydrochloride
- cefmenoxime hydrochloride
- cefmenoxime hydrochloride
- cefmenoxime hydrochloride
- cefmenoxime hydrochloride
- cefmenoxime hydrochloride
- cefmenoximum
- cefmenoximum
- sce-1365
- sce-1365
- tacef
- tacef
Organizations
Marketing (2)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| TAP Pharmaceuticals | For profit | NDA | Dec 30, 1987 |
| TAP Pharmaceuticals | For profit | SYN | Dec 30, 1987 |