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Identification
- Summary
Cefotetan is an antibiotic medication used for the prophylaxis and treatment of various bacterial infections, including urinary tract infections, bone and joint infection, and lower respiratory tract infections.
- Brand Names
- Cefotan
- Generic Name
- Cefotetan
- DrugBank Accession Number
- DB01330
- Background
A semisynthetic cephamycin antibiotic that is administered intravenously or intramuscularly. The drug is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative microorganisms.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Cefotetan (DB01330)
- Weight
- Average: 575.619
Monoisotopic: 575.002143315 - Chemical Formula
- C17H17N7O8S4
- Synonyms
- (6R,7S)-7-(4-(carbamoylcarboxymethylene)-1,3-dithiethane-2-carboxamido)-7-methoxy-3-(((1-methyl-1H-tetrazol-5- yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2- carboxylic acid
- Cefotetan
- Cefotetanum
Pharmacology
- Indication
For prophylaxis and treatment of bacterial infections.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Bacterial infections •••••••••••• Treatment of Bacterial urinary tract infections •••••••••••• Treatment of Bone and joint infections •••••••••••• Treatment of Intra-abdominal infections •••••••••••• Treatment of Lower respiratory tract infection bacterial •••••••••••• - Associated Therapies
- Contraindications & Blackbox Warnings
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Cefotetan is a semisynthetic cephamycin antibiotic that is administered intravenously or intramuscularly. The drug is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative microorganisms.
- Mechanism of action
The bactericidal action of cefotetan results from inhibition of cell wall synthesis by binding and inhibiting the bacterial penicillin binding proteins which help in the cell wall biosynthesis.
Target Actions Organism APenicillin-binding protein 3 inhibitorStreptococcus pneumoniae - Absorption
Not Available
- Volume of distribution
- 10.4 L [elderly patients (greater than 65 years) with normal renal function]
- 10.3 L [healthy volunteers (aged 25 to 28 years)]
- Protein binding
Cefotetan is 88% plasma protein bound.
- Metabolism
No active metabolites of cefotetan have been detected; however, small amounts (less than 7%) of cefotetan in plasma and urine may be converted to its tautomer, which has antimicrobial activity similar to the parent drug.
- Route of elimination
No active metabolites of cefotetan have been detected; however, small amounts (less than 7%) of cefotetan in plasma and urine may be converted to its tautomer, which has antimicrobial activity similar to the parent drug. In normal patients, from 51% to 81% of an administered dose of Cefotetan is excreted unchanged by the kidneys over a 24 hour period, which results in high and prolonged urinary concentrations.
- Half-life
In volunteers with reduced renal function, the plasma half-life of cefotetan is prolonged
- Clearance
- 1.8 +/- 0.1 L/h [elderly patients with normal renal function (.65 years)]
- 1.8 +/- 0.3 L/h [healthy volunteers (aged 25 to 28 years)]
- Adverse Effects
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Not Available
- 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 Cefotetan 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 Cefotetan. Aceclofenac The risk or severity of nephrotoxicity can be increased when Cefotetan is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Cefotetan is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Cefotetan is combined with Acenocoumarol. - Food Interactions
- Avoid alcohol. Alcohol can cause a disulfiram effect.
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 Cefotetan disodium 0GXP746VXB 74356-00-6 ZQQALMSFFARWPK-GLHLDKNHSA-L - International/Other Brands
- Yamatetan
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cefotan Injection, powder, for solution 1 g/10mL Intramuscular; Intravenous Teligent Pharma, Inc. 2015-10-01 Not applicable US 
Cefotan Injection 10 g/1 Intramuscular; Intravenous Astrazeneca Ab 1985-12-27 2007-07-07 US Cefotan Injection 2 g/1mL Intramuscular; Intravenous Physicians Total Care, Inc. 1996-09-12 2004-12-31 US Cefotan Injection, powder, for solution 2 g/20mL Intramuscular; Intravenous PAI Holdings, LLC dba PAI Pharma 2024-04-08 Not applicable US Cefotan Injection 2 g/50mL Intramuscular; Intravenous Astrazeneca Ab 1993-07-30 2007-12-07 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cefotetan Injection, powder, for solution 10 g/1 Intravenous Fresenius Kabi Italia S.R.L. 2009-12-03 2018-09-30 US Cefotetan Injection, powder, for solution 2 g/20mL Intramuscular; Intravenous Fresenius Kabi Italia S.R.L. 2009-11-18 Not applicable US Cefotetan Injection, powder, for solution 2 g/1 Intramuscular; Intravenous Hikma Pharmaceuticals USA Inc. 2011-10-26 Not applicable US Cefotetan Injection, powder, for solution 1 g/10mL Intramuscular; Intravenous Fresenius Kabi Italia S.R.L. 2009-11-18 Not applicable US Cefotetan Injection, powder, for solution 1 g/1 Intramuscular; Intravenous Hikma Pharmaceuticals USA Inc. 2011-10-26 Not applicable US
Categories
- ATC Codes
- J01DC05 — Cefotetan
- Drug Categories
- Amides
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- beta-Lactams
- Cephalosporins
- Cephamycins
- Drugs that are Mainly Renally Excreted
- Heterocyclic Compounds, Fused-Ring
- Lactams
- Nephrotoxic agents
- Second-Generation Cephalosporins
- Sulfur Compounds
- Tetrazoles
- Thiazines
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as cephamycins. These are compounds containing a the cephalosporin (oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid) nucleus, with an alkyloxy group attached to the C6 carbon atom.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Lactams
- Sub Class
- Beta lactams
- Direct Parent
- Cephamycins
- Alternative Parents
- N-acyl-alpha amino acids and derivatives / Alkylarylthioethers / Vinylogous thioesters / 1,3-thiazines / Dicarboxylic acids and derivatives / Tetrazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Azetidines / Secondary carboxylic acid amides show 13 more
- Substituents
- Alkylarylthioether / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Azetidine / Azole / Carbonyl group / Carboxamide group / Carboxylic acid show 25 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cephalosporin (CHEBI:3499)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- 48SPP0PA9Q
- CAS number
- 69712-56-7
- InChI Key
- SRZNHPXWXCNNDU-IXOPCIAXSA-N
- InChI
- InChI=1S/C17H17N7O8S4/c1-23-16(20-21-22-23)34-4-5-3-33-15-17(32-2,14(31)24(15)7(5)11(29)30)19-9(26)13-35-12(36-13)6(8(18)25)10(27)28/h13,15H,3-4H2,1-2H3,(H2,18,25)(H,19,26)(H,27,28)(H,29,30)/b12-6-/t13?,15-,17+/m1/s1
- IUPAC Name
- (6R,7S)-7-{4-[carbamoyl(carboxy)methylidene]-1,3-dithietane-2-amido}-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)C1SC(S1)=C(C(N)=O)C(O)=O)OC)C(O)=O
References
- Synthesis Reference
Maurizio Zenoni, "Process for obtaining compounds usable in the production of Cefotetan, and new compounds obtained thereby." U.S. Patent US20020169327, issued November 14, 2002.
US20020169327- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015425
- KEGG Drug
- D00260
- KEGG Compound
- C06886
- PubChem Compound
- 53025
- PubChem Substance
- 46506572
- ChemSpider
- 47904
- BindingDB
- 80643
- 2187
- ChEBI
- 3499
- ChEMBL
- CHEMBL474579
- Therapeutic Targets Database
- DAP000451
- PharmGKB
- PA164784033
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Cefotetan
- FDA label
- Download (275 KB)
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- APP Pharmaceuticals
- B. Braun Melsungen AG
- Baxter International Inc.
- Cardinal Health
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Injection, powder, for solution Intramuscular Powder, for solution Intramuscular; Intravenous Injection Intramuscular; Intravenous 1 g/50mL Injection Intramuscular; Intravenous 1 g/1mL Injection Intramuscular; Intravenous 1 g/1 Injection Intramuscular; Intravenous 10 g/1 Injection Intramuscular; Intravenous 2 g/1mL Injection Intramuscular; Intravenous 2 g/1 Injection Intramuscular; Intravenous 2 g/50mL Injection, powder, for solution Intramuscular; Intravenous 1 g/10mL Injection, powder, for solution Intramuscular; Intravenous 2 g/20mL Powder, for solution Intramuscular; Intravenous 2 g / vial Powder, for solution Intramuscular; Intravenous 1 g / vial Injection, powder, for solution Intramuscular; Intravenous 1 g/1 Injection, powder, for solution Intramuscular; Intravenous 2 g/1 Injection, powder, for solution Intravenous 10 g/1 Injection, solution Intravenous 1 g/50mL Injection, solution Intravenous 2 g/50mL - Prices
Unit description Cost Unit Cefotetan 2 gm vial 27.31USD vial Cefotetan-dextr 2 g duplex bag 25.14USD each Cefotetan-dextr 1 g duplex bag 17.58USD each Cefotetan 1 gm vial 13.66USD vial DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.521 mg/mL ALOGPS logP -0.65 ALOGPS logP -0.38 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 3.03 Chemaxon pKa (Strongest Basic) -1.5 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 11 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 219.93 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 153.55 m3·mol-1 Chemaxon Polarizability 52.62 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 - 0.9451 Blood Brain Barrier - 0.9903 Caco-2 permeable - 0.799 P-glycoprotein substrate Substrate 0.7418 P-glycoprotein inhibitor I Non-inhibitor 0.8992 P-glycoprotein inhibitor II Non-inhibitor 0.7207 Renal organic cation transporter Non-inhibitor 0.9032 CYP450 2C9 substrate Non-substrate 0.8489 CYP450 2D6 substrate Non-substrate 0.8219 CYP450 3A4 substrate Non-substrate 0.5 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8308 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6374 Ames test Non AMES toxic 0.7712 Carcinogenicity Non-carcinogens 0.9274 Biodegradation Not ready biodegradable 0.9081 Rat acute toxicity 1.7915 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9933 hERG inhibition (predictor II) Non-inhibitor 0.7103
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 244.2099839 predictedDarkChem Lite v0.1.0 [M-H]- 233.7074839 predictedDarkChem Lite v0.1.0 [M-H]- 203.59224 predictedDeepCCS 1.0 (2019) [M+H]+ 245.1509839 predictedDarkChem Lite v0.1.0 [M+H]+ 233.7725839 predictedDarkChem Lite v0.1.0 [M+H]+ 205.98781 predictedDeepCCS 1.0 (2019) [M+Na]+ 244.2527839 predictedDarkChem Lite v0.1.0 [M+Na]+ 234.1979839 predictedDarkChem Lite v0.1.0 [M+Na]+ 211.90031 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Streptococcus pneumoniae
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
- Specific Function
- serine-type D-Ala-D-Ala carboxypeptidase activity
- Gene Name
- pbp3
- Uniprot ID
- Q75Y35
- Uniprot Name
- Penicillin-binding protein 3
- Molecular Weight
- 45209.84 Da
References
- Nolan RD, Jude DA: The interactions of [14C]cefotetan with penicillin binding proteins of a wide variety of Gram-positive and gram-negative species. J Antimicrob Chemother. 1983 Jan;11 Suppl:169-77. [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
- Gulian JM, Dalmasso C, Gonard V: Interaction of beta-lactam antibiotics on bilirubin-albumin complex: comparison by three methods, total bilirubin, unbound bilirubin and erythrocyte-bound bilirubin. Chemotherapy. 1990;36(2):91-7. [Article]
- Robertson A, Fink S, Karp W: Effect of cephalosporins on bilirubin-albumin binding. J Pediatr. 1988 Feb;112(2):291-4. [Article]
Drug created at June 30, 2007 17:52 / Updated at October 13, 2024 04:02