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Identification
NameCefmenoxime
Accession NumberDB00267  (APRD00851)
Typesmall molecule
Groupsapproved
Description

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

Structure
Thumb
Synonyms
SynonymLanguageCode
CefmenoximaSpanishINN
CefmenoximumLatinINN
Salts
Name/CAS Structure Properties
Cefmenoxime hydrochloride
Thumb
  • InChI Key: HZYJYGJIOCXOTH-FAIYLGIWSA-N
  • Monoisotopic Mass: 547.028154508
  • Average Mass: 548.019
DBSALT000801
Brand names
NameCompany
BestcallTakeda
CefmaxNot Available
TacefTakeda
Brand mixturesNot Available
Categories
CAS number65085-01-0
WeightAverage: 511.558
Monoisotopic: 511.051476769
Chemical FormulaC16H17N9O5S3
InChI KeyInChIKey=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
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassLactams
SubclassBeta Lactams
Direct parentCephalosporins
Alternative parentsN-acyl-alpha Amino Acids and Derivatives; Alpha Amino Acid Amides; 2,4-disubstituted Thiazoles; 1,3-Thiazines; Primary Aromatic Amines; Aminothiazoles; Tertiary Carboxylic Acid Amides; Tetrazoles; Secondary Carboxylic Acid Amides; Oxime Ethers; Hemiaminals; Tertiary Amines; Azetidines; Thioethers; Enamines; Enolates; Aminals; Carboxylic Acids; Polyamines; Imines
Substituentsn-acyl-alpha amino acid or derivative; alpha-amino acid amide; alpha-amino acid or derivative; 2,4-disubstituted 1,3-thiazole; 1,3-thiazolamine; primary aromatic amine; meta-thiazine; azole; thiazole; tertiary carboxylic acid amide; tetrazole; oxime ether; carboxamide group; tertiary amine; azetidine; secondary carboxylic acid amide; hemiaminal; thioether; enolate; aminal; polyamine; enamine; carboxylic acid derivative; carboxylic acid; primary amine; amine; organonitrogen compound; imine
Classification descriptionThis compound belongs to the cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moeity or a derivative thereof.
Pharmacology
IndicationUsed to treat female gynecologic and obstetric infections caused by susceptible aerobic (including the gonococcus) and anaerobic bacteria.
PharmacodynamicsCefmenoxime 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 actionThe 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.
AbsorptionBioavailability is approximately 100% following intramuscular injection.
Volume of distributionNot Available
Protein binding50-70%
Metabolism

Not appreciably metabolized.

Route of eliminationNot Available
Half life1 hour
ClearanceNot Available
ToxicityInformation 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption - 0.8906
Blood Brain Barrier - 0.9756
Caco-2 permeable - 0.8215
P-glycoprotein substrate Substrate 0.7149
P-glycoprotein inhibitor I Non-inhibitor 0.9087
P-glycoprotein inhibitor II Inhibitor 0.5588
Renal organic cation transporter Non-inhibitor 0.8324
CYP450 2C9 substrate Non-substrate 0.8348
CYP450 2D6 substrate Non-substrate 0.818
CYP450 3A4 substrate Non-substrate 0.5135
CYP450 1A2 substrate Non-inhibitor 0.7839
CYP450 2C9 substrate Non-inhibitor 0.7802
CYP450 2D6 substrate Non-inhibitor 0.8903
CYP450 2C19 substrate Non-inhibitor 0.7598
CYP450 3A4 substrate Inhibitor 0.6053
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6981
Ames test Non AMES toxic 0.7685
Carcinogenicity Non-carcinogens 0.8748
Biodegradation Not ready biodegradable 0.9608
Rat acute toxicity 2.0641 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.98
hERG inhibition (predictor II) Non-inhibitor 0.7924
Pharmacoeconomics
Manufacturers
  • Tap pharmaceutical products inc
PackagersNot Available
Dosage forms
FormRouteStrength
Powder, for solutionIntramuscular
Powder, for solutionIntravenous
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
logP-1.3Not Available
Predicted Properties
PropertyValueSource
water solubility4.46e-01 g/lALOGPS
logP-0.13ALOGPS
logP-0.83ChemAxon
logS-3.1ALOGPS
pKa (strongest acidic)3.04ChemAxon
pKa (strongest basic)4.14ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count11ChemAxon
hydrogen donor count3ChemAxon
polar surface area190.81ChemAxon
rotatable bond count8ChemAxon
refractivity133.51ChemAxon
polarizability47.04ChemAxon
number of rings4ChemAxon
bioavailability0ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Yasushi Morita, “Method for preventing coloration of aqueous preparations of cefmenoxime.” U.S. Patent US4808577, issued November, 1985.

US4808577
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
ResourceLink
KEGG DrugD01739
ChEBI55490
ChEMBL
Therapeutic Targets DatabaseDAP001178
PharmGKBPA164750569
WikipediaCefmenoxime
ATC CodesJ01DD05
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Penicillin-binding protein 1A

Kind: protein

Organism: Clostridium perfringens (strain 13 / Type A)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 1A Q8XJ01 Details

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 synthase FtsI

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Peptidoglycan synthase FtsI P0AD68 Details

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 September 16, 2013 17:09