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targets (2)
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Identification
Name Cefmenoxime
Accession Number DB00267 (APRD00851)
Type small molecule
Groups approved
Description

Cefmenoxime is a third-generation cephalosporin antibiotic. [Wikipedia]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Cefmenoxima [INN-Spanish]
Cefmenoxime hydrochloride
Cefmenoximum [INN-Latin]
Salts Not Available
Brand names
Name Company
Bestcall
Cefmax
Tacef
Brand mixtures Not Available
Categories
  • Anti-Bacterial Agents
  • Cephalosporins
CAS number 65085-01-0
Weight Average: 511.558
Monoisotopic: 511.051476769
Chemical Formula C16H17N9O5S3
InChI Key InChIKey=HJJDBAOLQAWBMH-YCRCPZNHSA-N
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
Plain Text
IUPAC Name
(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C1=CSC(N)=N1)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication Used to treat female gynecologic and obstetric infections caused by susceptible aerobic (including the gonococcus) and anaerobic bacteria.
Pharmacodynamics Cefmenoxime is a semisynthetic beta-lactam cephalosporin antibiotic with activity similar to that of cefotaxime. It has broad spectrum activity against Gram positive and Gram negative bacteria.
Mechanism of action 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.
Absorption Bioavailability is approximately 100% following intramuscular injection.
Volume of distribution Not Available
Protein binding 50-70%
Metabolism Not appreciably metabolized.
Route of elimination Not Available
Half life 1 hour
Clearance Not Available
Toxicity Information on cefmenoxime overdosage in humans is not available. However, with other b-lactam antibiotics, adverse effects following overdosage have included nausea, vomiting, epigastric distress, diarrhea, and convulsions.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Tap pharmaceutical products inc
Packagers Not Available
Dosage forms
Form Route Strength
Powder, for solution Intramuscular
Powder, for solution Intravenous
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
logP -1.3 Not Available
Predicted Properties
Property Value Source
water solubility 4.46e-01 g/l ALOGPS
logP -0.13 ALOGPS
logP -0.83 ChemAxon
logS -3.1 ALOGPS
pKa (strongest acidic) 3.04 ChemAxon
pKa (strongest basic) 4.14 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 11 ChemAxon
hydrogen donor count 3 ChemAxon
polar surface area 190.81 ChemAxon
rotatable bond count 8 ChemAxon
refractivity 133.51 ChemAxon
polarizability 47.04 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Yokota N, Koguchi M, Suzuki Y, Fukayama S, Ishihara R, Deguchi K, Oda S, Tanaka S, Nakane Y, Fukumoto T: [Antibacterial activities of cefmenoxime against recent fresh clinical isolates from patients in sinusitis] Jpn J Antibiot. 1995 May;48(5):602-9. Pubmed
  2. Paladino JA, Fell RE: Pharmacoeconomic analysis of cefmenoxime dual individualization in the treatment of nosocomial pneumonia. Ann Pharmacother. 1994 Mar;28(3):384-9. Pubmed
  3. Duncker GI, Reich U, Krausse R: Cefmenoxime in corneal organ culture. Ophthalmologica. 1994;208(5):262-6. Pubmed
  4. Tsuchiya K, Kondo M, Kida M, Nakao M, Iwahi T, Nishi T, Noji Y, Takeuchi M, Nozaki Y: Cefmenoxime (SCE-1365), a novel broad-spectrum cephalosporin: in vitro and in vivo antibacterial activities. Antimicrob Agents Chemother. 1981 Jan;19(1):56-65. Pubmed
External Links
Resource Link
KEGG Drug D01739 Link_out
ChEBI 55490 Link_out
ChEMBL 55490 Link_out
Therapeutic Targets Database DAP001178 Link_out
PharmGKB PA164750569 Link_out
Wikipedia http://en.wikipedia.org/wiki/Cefmenoxime Link_out
ATC Codes
  • J01DD05
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Penicillin-binding proteins 1A/1B

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: Q8XJ01 Link_out
Gene: pbpA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Tsuchiya K, Kondo M, Kida M, Nakao M, Iwahi T, Nishi T, Noji Y, Takeuchi M, Nozaki Y: Cefmenoxime (SCE-1365), a novel broad-spectrum cephalosporin: in vitro and in vivo antibacterial activities. Antimicrob Agents Chemother. 1981 Jan;19(1):56-65. Pubmed

2. Peptidoglycan synthetase ftsI

Pharmacological action: yes
Actions: inhibitor

Cell wall formation. Essential for the formation of a septum of the murein sacculus. Synthesis of cross-linked peptidoglycan from the lipid intermediates

Organism class: bacterial
UniProt ID: P0AD68 Link_out
Gene: ftsI
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Tsuchiya K, Kondo M, Kida M, Nakao M, Iwahi T, Nishi T, Noji Y, Takeuchi M, Nozaki Y: Cefmenoxime (SCE-1365), a novel broad-spectrum cephalosporin: in vitro and in vivo antibacterial activities. Antimicrob Agents Chemother. 1981 Jan;19(1):56-65. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19