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Identification
NameCefmenoxime
Accession NumberDB00267  (APRD00851)
TypeSmall Molecule
GroupsApproved
Description

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

Structure
Thumb
Synonyms
(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-[[(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)
Cefmenoxima
Cefmenoximum
External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
BestcallTakeda
CefmaxNot Available
TacefTakeda
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Cefmenoxime hydrochloride
Thumb
  • InChI Key: HZYJYGJIOCXOTH-FAIYLGIWSA-N
  • Monoisotopic Mass: 547.028154508
  • Average Mass: 548.019
DBSALT000801
Categories
UNIIKBZ4844CXN
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)[[email protected]]2NC(=O)C(=N/OC)\C1=CSC(N)=N1)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 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 moiety or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporins
Alternative Parents
Substituents
  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Alkylarylthioether
  • 2,4-disubstituted 1,3-thiazole
  • Primary aromatic amine
  • Meta-thiazine
  • Heteroaromatic compound
  • Thiazole
  • Tetrazole
  • Tertiary carboxylic acid amide
  • Azole
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Oxime ether
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Sulfenyl compound
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Enamine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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.
Related Articles
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
PropertyValueProbability
Human Intestinal Absorption-0.8906
Blood Brain Barrier-0.9756
Caco-2 permeable-0.8215
P-glycoprotein substrateSubstrate0.7149
P-glycoprotein inhibitor INon-inhibitor0.9087
P-glycoprotein inhibitor IIInhibitor0.5588
Renal organic cation transporterNon-inhibitor0.8324
CYP450 2C9 substrateNon-substrate0.8348
CYP450 2D6 substrateNon-substrate0.818
CYP450 3A4 substrateNon-substrate0.5135
CYP450 1A2 substrateNon-inhibitor0.7839
CYP450 2C9 inhibitorNon-inhibitor0.7802
CYP450 2D6 inhibitorNon-inhibitor0.8903
CYP450 2C19 inhibitorNon-inhibitor0.7598
CYP450 3A4 inhibitorInhibitor0.6053
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6981
Ames testNon AMES toxic0.7685
CarcinogenicityNon-carcinogens0.8748
BiodegradationNot ready biodegradable0.9608
Rat acute toxicity2.0641 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.98
hERG inhibition (predictor II)Non-inhibitor0.7924
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Tap pharmaceutical products inc
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP-1.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.446 mg/mLALOGPS
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 Area190.81 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity133.51 m3·mol-1ChemAxon
Polarizability47.04 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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 References
  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:7637194 ]
  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:8193431 ]
  3. Duncker GI, Reich U, Krausse R: Cefmenoxime in corneal organ culture. Ophthalmologica. 1994;208(5):262-6. [PubMed:7816419 ]
  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:6941742 ]
External Links
ATC CodesJ01DD05
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcenocoumarolCefmenoxime may increase the anticoagulant activities of Acenocoumarol.
AmikacinCefmenoxime may increase the nephrotoxic activities of Amikacin.
GentamicinCefmenoxime may increase the nephrotoxic activities of Gentamicin.
KanamycinCefmenoxime may increase the nephrotoxic activities of Kanamycin.
NeomycinCefmenoxime may increase the nephrotoxic activities of Neomycin.
ProbenecidThe serum concentration of Cefmenoxime can be increased when it is combined with Probenecid.
StreptomycinCefmenoxime may increase the nephrotoxic activities of Streptomycin.
TobramycinCefmenoxime may increase the nephrotoxic activities of Tobramycin.
WarfarinCefmenoxime may increase the anticoagulant activities of Warfarin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Clostridium perfringens (strain 13 / Type A)
Pharmacological action
yes
Actions
inhibitor
General Function:
Transferase activity, transferring glycosyl groups
Specific Function:
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits) (By similarity).
Gene Name:
pbpA
Uniprot ID:
Q8XJ01
Molecular Weight:
75176.35 Da
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:17139284 ]
  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:17016423 ]
  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:6941742 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Peptidoglycan glycosyltransferase activity
Specific Function:
Essential cell division protein that is required for the synthesis of peptidoglycan at the division septum (PubMed:1103132, PubMed:9614966). Catalyzes the synthesis of cross-linked peptidoglycan from the lipid-linked precursors (PubMed:7030331). Required for localization of FtsN (PubMed:9282742).
Gene Name:
ftsI
Uniprot ID:
P0AD68
Molecular Weight:
63876.925 Da
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:6941742 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:09