Cefmetazole
Explore a selection of our essential drug information below, or:
Identification
- Summary
Cefmetazole is a cephalosporin antibiotic used to treat a variety of bacterial infections.
- Generic Name
- Cefmetazole
- DrugBank Accession Number
- DB00274
- Background
A semisynthetic cephamycin antibiotic with a broad spectrum of activity against both gram-positive and gram-negative microorganisms. It has a high rate of efficacy in many types of infection and to date no severe side effects have been noted.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
- Weight
- Average: 471.534
Monoisotopic: 471.045328759 - Chemical Formula
- C15H17N7O5S3
- Synonyms
- (6R,7S)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- Cefmetazole
- Cefmetazolo
- Cefmetazolum
- External IDs
- U-72791
Pharmacology
- Indication
For the treatment of infections caused by susceptible organisms.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Susceptible bacterial infections •••••••••••• ••••••••• - Contraindications & Blackbox Warnings
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- Pharmacodynamics
Cefmetazole is a second-generation cephalosporin. The cephalosporins are bactericidal drugs with both gram-positive and gram-negative activity. They inhibit bacterial cell wall synthesis in a way similar to the penicillins. Cefmetazole is more active than 1st-generation cephalosporins against indole-positive Proteus, Serratia, anaerobic gram-negative bacilli (including B. fragilis), and some E. coli, Klebsiella, and P. mirabilis, but is less active than cefoxitin or cefotetan against most gram-negative bacilli.
- Mechanism of action
The bactericidal activity of cefmetazole results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
Target Actions Organism APenicillin binding protein 2a inhibitorStaphylococcus aureus APenicillin-binding protein 1A inhibitorEscherichia coli (strain K12) APenicillin-binding protein 1B inhibitorEscherichia coli (strain K12) APeptidoglycan synthase FtsI inhibitorEscherichia coli (strain K12) AD-alanyl-D-alanine carboxypeptidase DacA inhibitorEscherichia coli (strain K12) AD-alanyl-D-alanine carboxypeptidase DacC inhibitorEscherichia coli (strain K12) - Absorption
Bioavailability is approximately 100% following intramuscular injection.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
No appreciable metabolism.
- Route of elimination
Not Available
- Half-life
1.50 ±0.14 hours
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Oral LD50 in rats is 3,204 mg/kg. 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 Cefmetazole 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 Cefmetazole. Aceclofenac The risk or severity of nephrotoxicity can be increased when Cefmetazole is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Cefmetazole is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Cefmetazole is combined with Acenocoumarol. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Cefmetazole sodium 37Y9VR4W7A 56796-39-5 BITQGIOJQWZUPL-UHFFFAOYSA-M - International/Other Brands
- Zefazone
Categories
- ATC Codes
- J01DC09 — Cefmetazole
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- N-acyl-alpha amino acids and derivatives
- Alternative Parents
- Cephems / Alkylarylthioethers / 1,3-thiazines / Tetrazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Azetidines / Thiohemiaminal derivatives / Sulfenyl compounds / Azacyclic compounds show 10 more
- Substituents
- Alkylarylthioether / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Azetidine / Azole / Beta-lactam / Carbonitrile / Carbonyl group / Carboxamide group show 27 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cephalosporin (CHEBI:3489)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- 3J962UJT8H
- CAS number
- 56796-20-4
- InChI Key
- SNBUBQHDYVFSQF-HIFRSBDPSA-N
- InChI
- InChI=1S/C15H17N7O5S3/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25)/t13-,15+/m1/s1
- IUPAC Name
- (6R,7S)-7-{2-[(cyanomethyl)sulfanyl]acetamido}-7-methoxy-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@]2(NC(=O)CSCC#N)OC)C(O)=O
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014419
- KEGG Drug
- D00910
- KEGG Compound
- C08103
- PubChem Compound
- 42008
- PubChem Substance
- 46504461
- ChemSpider
- 38311
- BindingDB
- 50350471
- 2182
- ChEBI
- 3489
- ChEMBL
- CHEMBL1201195
- ZINC
- ZINC000003830417
- Therapeutic Targets Database
- DAP001179
- PharmGKB
- PA164746819
- PDBe Ligand
- 4KO
- Wikipedia
- Cefmetazole
- PDB Entries
- 4kos
- MSDS
- Download (52.2 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data3 Completed Prevention Colorectal Neoplasms 1 somestatus stop reason just information to hide 3 Completed Treatment Surgery, Colorectal 1 somestatus stop reason just information to hide 0 Terminated Treatment Osteomyelitis 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Pharmacia and upjohn co
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, powder, for solution Intramuscular 0.5 g Injection, powder, for solution Intramuscular 0.5 g/2mL Injection, powder, for solution Intramuscular 1 g Injection, powder, for solution Intramuscular; Parenteral 1 g/100ml Injection, powder, for solution Intravenous 1 g/10mL Injection, powder, for solution Intravenous 2 g Injection, powder, for solution Intramuscular Injection, powder, for solution Intravenous - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility 94.2 mg/L Not Available logP -0.60 SANGSTER (1993) - Predicted Properties
Property Value Source Water Solubility 2.16 mg/mL ALOGPS logP -0.38 ALOGPS logP -0.65 Chemaxon logS -2.3 ALOGPS pKa (Strongest Acidic) 3.18 Chemaxon pKa (Strongest Basic) -1.7 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 163.33 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 124.57 m3·mol-1 Chemaxon Polarizability 44.5 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.8407 Blood Brain Barrier - 0.9932 Caco-2 permeable - 0.8957 P-glycoprotein substrate Substrate 0.8283 P-glycoprotein inhibitor I Non-inhibitor 0.8047 P-glycoprotein inhibitor II Non-inhibitor 0.8382 Renal organic cation transporter Non-inhibitor 0.8723 CYP450 2C9 substrate Non-substrate 0.8274 CYP450 2D6 substrate Non-substrate 0.8182 CYP450 3A4 substrate Substrate 0.5951 CYP450 1A2 substrate Non-inhibitor 0.8575 CYP450 2C9 inhibitor Non-inhibitor 0.82 CYP450 2D6 inhibitor Non-inhibitor 0.895 CYP450 2C19 inhibitor Non-inhibitor 0.8093 CYP450 3A4 inhibitor Non-inhibitor 0.8551 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6417 Ames test Non AMES toxic 0.8271 Carcinogenicity Non-carcinogens 0.9182 Biodegradation Not ready biodegradable 0.9062 Rat acute toxicity 2.2638 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9715 hERG inhibition (predictor II) Non-inhibitor 0.7599
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0006-9252300000-3b897b33c8f75fb7d195 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-05fr-0006900000-ac0c99bfc037753764fd Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0901400000-72490fff74e105674829 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00du-7324900000-27eb0691d3257522be73 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-6900200000-942140486d4b5e9a9f55 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-05fr-9411100000-0e9ff270341126c70a02 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0w93-6638900000-e1af8c1e4ca376c94fee Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 208.8391411 predictedDarkChem Lite v0.1.0 [M-H]- 192.08528 predictedDeepCCS 1.0 (2019) [M+H]+ 208.9456411 predictedDarkChem Lite v0.1.0 [M+H]+ 194.44328 predictedDeepCCS 1.0 (2019) [M+Na]+ 208.7253411 predictedDarkChem Lite v0.1.0 [M+Na]+ 200.81837 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Staphylococcus aureus
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Not Available
- Specific Function
- penicillin binding
- Gene Name
- mecA
- Uniprot ID
- C1KC03
- Uniprot Name
- Penicillin binding protein 2a
- Molecular Weight
- 54918.915 Da
References
- Yokota T, Yoshida R, Utsui Y, Tajima M: Cefmetazole: a broad spectrum cephem antibiotic effective on methicillin- and cephem-resistant Staphylococcus aureus. Drugs Exp Clin Res. 1985;11(1):29-38. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General 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).
- Specific Function
- penicillin binding
- Gene Name
- mrcA
- Uniprot ID
- P02918
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 93635.545 Da
References
- de la Rosa EJ, de Pedro MA, Vazquez D: Penicillin binding proteins: role in initiation of murein synthesis in Escherichia coli. Proc Natl Acad Sci U S A. 1985 Sep;82(17):5632-5. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General 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).
- Specific Function
- penicillin binding
- Gene Name
- mrcB
- Uniprot ID
- P02919
- Uniprot Name
- Penicillin-binding protein 1B
- Molecular Weight
- 94291.875 Da
References
- de la Rosa EJ, de Pedro MA, Vazquez D: Penicillin binding proteins: role in initiation of murein synthesis in Escherichia coli. Proc Natl Acad Sci U S A. 1985 Sep;82(17):5632-5. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Essential cell division protein that catalyzes cross-linking of the peptidoglycan cell wall at the division septum (PubMed:1103132, PubMed:3531167, PubMed:6450748, PubMed:7030331, PubMed:9614966). Required for localization of FtsN (PubMed:9282742).
- Specific Function
- penicillin binding
- Gene Name
- ftsI
- Uniprot ID
- P0AD68
- Uniprot Name
- Peptidoglycan synthase FtsI
- Molecular Weight
- 63876.925 Da
References
- de la Rosa EJ, de Pedro MA, Vazquez D: Penicillin binding proteins: role in initiation of murein synthesis in Escherichia coli. Proc Natl Acad Sci U S A. 1985 Sep;82(17):5632-5. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
- Specific Function
- beta-lactamase activity
- Gene Name
- dacA
- Uniprot ID
- P0AEB2
- Uniprot Name
- D-alanyl-D-alanine carboxypeptidase DacA
- Molecular Weight
- 44443.62 Da
References
- de la Rosa EJ, de Pedro MA, Vazquez D: Penicillin binding proteins: role in initiation of murein synthesis in Escherichia coli. Proc Natl Acad Sci U S A. 1985 Sep;82(17):5632-5. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
- Specific Function
- carboxypeptidase activity
- Gene Name
- dacC
- Uniprot ID
- P08506
- Uniprot Name
- D-alanyl-D-alanine carboxypeptidase DacC
- Molecular Weight
- 43608.595 Da
References
- de la Rosa EJ, de Pedro MA, Vazquez D: Penicillin binding proteins: role in initiation of murein synthesis in Escherichia coli. Proc Natl Acad Sci U S A. 1985 Sep;82(17):5632-5. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- Robertson A, Fink S, Karp W: Effect of cephalosporins on bilirubin-albumin binding. J Pediatr. 1988 Feb;112(2):291-4. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Electrogenic proton-coupled amino-acid transporter that transports oligopeptides of 2 to 4 amino acids with a preference for dipeptides. Transports neutral and monovalently charged peptides with a proton to peptide stoichiometry of 1:1 or 2:1 (By similarity) (PubMed:15521010, PubMed:18367661, PubMed:19685173, PubMed:26320580, PubMed:7896779, PubMed:8914574, PubMed:9835627). Primarily responsible for the absorption of dietary di- and tripeptides from the small intestinal lumen (By similarity). Mediates transepithelial transport of muramyl and N-formylated bacterial dipeptides contributing to recognition of pathogenic bacteria by the mucosal immune system (PubMed:15521010, PubMed:9835627)
- Specific Function
- dipeptide transmembrane transporter activity
- Gene Name
- SLC15A1
- Uniprot ID
- P46059
- Uniprot Name
- Solute carrier family 15 member 1
- Molecular Weight
- 78805.265 Da
References
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Proton-coupled amino-acid transporter that transports oligopeptides of 2 to 4 amino acids with a preference for dipeptides (PubMed:16434549, PubMed:18367661, PubMed:7756356). Transports neutral and anionic dipeptides with a proton to peptide stoichiometry of 2:1 or 3:1 (By similarity). In kidney, involved in the absorption of circulating di- and tripeptides from the glomerular filtrate (PubMed:7756356). Can also transport beta-lactam antibiotics, such as the aminocephalosporin cefadroxil, and other antiviral and anticancer drugs (PubMed:16434549). Transports the dipeptide-like aminopeptidase inhibitor bestatin (By similarity). Also able to transport carnosine (PubMed:31073693). Involved in innate immunity by promoting the detection of microbial pathogens by NOD-like receptors (NLRs) (By similarity). Mediates transport of bacterial peptidoglycans across the plasma membrane or, in macrophages, the phagosome membrane: catalyzes the transport of certain bacterial peptidoglycans, such as muramyl dipeptide (MDP), the NOD2 ligand (PubMed:20406817)
- Specific Function
- dipeptide transmembrane transporter activity
- Gene Name
- SLC15A2
- Uniprot ID
- Q16348
- Uniprot Name
- Solute carrier family 15 member 2
- Molecular Weight
- 81782.77 Da
References
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 29, 2024 18:17