Identification

Name
Cefmenoxime
Accession Number
DB00267  (APRD00851)
Type
Small Molecule
Groups
Approved
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 IDs
SCE-1365
Product Ingredients
IngredientUNIICASInChI Key
Cefmenoxime hydrochlorideNON736D32W75738-58-8HZYJYGJIOCXOTH-FAIYLGIWSA-N
International/Other Brands
Bestcall (Takeda) / Cefmax / Tacef (Takeda)
Categories
UNII
KBZ4844CXN
CAS number
65085-01-0
Weight
Average: 511.558
Monoisotopic: 511.051476769
Chemical Formula
C16H17N9O5S3
InChI Key
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

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.

TargetActionsOrganism
APenicillin-binding protein 1A
inhibitor
Clostridium perfringens (strain 13 / Type A)
APeptidoglycan synthase FtsI
inhibitor
Escherichia coli (strain K12)
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcenocoumarolCefmenoxime may increase the anticoagulant activities of Acenocoumarol.
AcetaminophenCefmenoxime may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
Acetylsalicylic acidThe risk or severity of nephrotoxicity can be increased when Cefmenoxime is combined with Acetylsalicylic acid.
AcyclovirCefmenoxime may decrease the excretion rate of Acyclovir which could result in a higher serum level.
Adefovir DipivoxilThe risk or severity of nephrotoxicity can be increased when Cefmenoxime is combined with Adefovir Dipivoxil.
Alendronic acidThe risk or severity of nephrotoxicity and hypocalcemia can be increased when Cefmenoxime is combined with Alendronic acid.
AlmotriptanCefmenoxime may decrease the excretion rate of Almotriptan which could result in a higher serum level.
AlprazolamCefmenoxime may decrease the excretion rate of Alprazolam which could result in a higher serum level.
AmantadineCefmenoxime may decrease the excretion rate of Amantadine which could result in a higher serum level.
AmikacinThe risk or severity of nephrotoxicity can be increased when Cefmenoxime is combined with Amikacin.
Food Interactions
Not 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
Human Metabolome Database
HMDB0014412
KEGG Drug
D01739
PubChem Compound
9570757
PubChem Substance
46506246
ChemSpider
7845223
ChEBI
55490
ChEMBL
CHEMBL1201224
Therapeutic Targets Database
DAP001178
PharmGKB
PA164750569
Wikipedia
Cefmenoxime
ATC Codes
J01DD05 — Cefmenoxime

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Tap pharmaceutical products inc
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Lactams
Sub Class
Beta lactams
Direct Parent
Cephalosporins
Alternative Parents
N-acyl-alpha amino acids and derivatives / Alkylarylthioethers / 2,4-disubstituted thiazoles / 1,3-thiazines / 2-amino-1,3-thiazoles / Heteroaromatic compounds / Tetrazoles / Tertiary carboxylic acid amides / Azetidines / Amino acids
show 12 more
Substituents
Cephalosporin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / Aryl thioether / 2,4-disubstituted 1,3-thiazole / Alkylarylthioether / Meta-thiazine / 1,3-thiazol-2-amine / Azole / Heteroaromatic compound
show 28 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
cephalosporin (CHEBI:55490)

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 str...
Gene Name
pbpA
Uniprot ID
Q8XJ01
Uniprot Name
Penicillin-binding protein 1A
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 fr...
Gene Name
ftsI
Uniprot ID
P0AD68
Uniprot Name
Peptidoglycan synthase FtsI
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]

Drug created on June 13, 2005 07:24 / Updated on October 01, 2018 16:28