Identification
- Generic Name
- Cefmenoxime
- DrugBank Accession Number
- DB00267
- Background
Cefmenoxime is a novel broad-spectrum and third-generation cephalosporin antibiotic that is typically used in the treatment of female gynecologic and obstetric infections. It is reported to exhibit high activity against a wide variety of gram-positive and gram-negative bacteria.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Cefmenoxime (DB00267)
- Weight
- Average: 511.558
Monoisotopic: 511.051476769 - Chemical Formula
- C16H17N9O5S3
- 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
- Cefmenoxima
- Cefmenoxime
- Cefmenoximum
- CMX
- External IDs
- SCE-1365
Pharmacology
- Indication
Used to treat female gynecologic and obstetric infections caused by susceptible aerobic (including the gonococcus) and anaerobic bacteria.
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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.
Target Actions Organism APeptidoglycan synthase FtsI inhibitorEscherichia coli (strain K12) APenicillin-binding protein 1A inhibitorClostridium perfringens (strain 13 / Type A) - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Cefmenoxime may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with Cefmenoxime. Aceclofenac The risk or severity of nephrotoxicity can be increased when Cefmenoxime is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Cefmenoxime is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Cefmenoxime is combined with Acenocoumarol. Acetaminophen Cefmenoxime may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetylsalicylic acid The risk or severity of nephrotoxicity can be increased when Cefmenoxime is combined with Acetylsalicylic acid. Aclidinium Cefmenoxime may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine Cefmenoxime may decrease the excretion rate of Acrivastine which could result in a higher serum level. Acyclovir The risk or severity of nephrotoxicity can be increased when Cefmenoxime is combined with Acyclovir. 
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- Not Available
Products
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Ingredient UNII CAS InChI Key Cefmenoxime hydrochloride NON736D32W 75738-58-8 HZYJYGJIOCXOTH-FAIYLGIWSA-N - International/Other Brands
- Bestcall (Takeda) / Cefmax / Tacef (Takeda)
Categories
- ATC Codes
- S02AA18 — CefmenoximeJ01DD05 — Cefmenoxime
- J01DD — Third-generation cephalosporins
- J01D — OTHER BETA-LACTAM ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Amides
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- beta-Lactams
- Cephacetrile
- Cephalosporins
- Heterocyclic Compounds, Fused-Ring
- Lactams
- Nephrotoxic agents
- Ophthalmologicals
- Otologicals
- Sensory Organs
- Sulfur Compounds
- Thiazines
- Third-Generation Cephalosporins
- Chemical TaxonomyProvided by Classyfire
- 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
- 1,3-thiazol-2-amine / 2,4-disubstituted 1,3-thiazole / Alkylarylthioether / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle show 28 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cephalosporin (CHEBI:55490)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- KBZ4844CXN
- CAS number
- 65085-01-0
- 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
References
- Synthesis Reference
Yasushi Morita, "Method for preventing coloration of aqueous preparations of cefmenoxime." U.S. Patent US4808577, issued November, 1985.
US4808577- General References
- 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. [Article]
- Paladino JA, Fell RE: Pharmacoeconomic analysis of cefmenoxime dual individualization in the treatment of nosocomial pneumonia. Ann Pharmacother. 1994 Mar;28(3):384-9. [Article]
- Duncker GI, Reich U, Krausse R: Cefmenoxime in corneal organ culture. Ophthalmologica. 1994;208(5):262-6. [Article]
- 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0014412
- KEGG Drug
- D01739
- PubChem Compound
- 9570757
- PubChem Substance
- 46506246
- ChemSpider
- 7845223
- ChEBI
- 55490
- ChEMBL
- CHEMBL1201224
- ZINC
- ZINC000003830413
- Therapeutic Targets Database
- DAP001178
- PharmGKB
- PA164750569
- Wikipedia
- Cefmenoxime
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Tap pharmaceutical products inc
- Packagers
- Not Available
- Dosage Forms
- Not Available
- 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 0.446 mg/mL ALOGPS logP -0.13 ALOGPS logP -0.93 Chemaxon logS -3.1 ALOGPS pKa (Strongest Acidic) 2.62 Chemaxon pKa (Strongest Basic) 3.53 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 11 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 190.81 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 133.51 m3·mol-1 Chemaxon Polarizability 47.05 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - 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 inhibitor Non-inhibitor 0.7802 CYP450 2D6 inhibitor Non-inhibitor 0.8903 CYP450 2C19 inhibitor Non-inhibitor 0.7598 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- 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. [Article]
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 02, 2023 22:06