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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyCefotetan
Identification
- Name
- Cefotetan
- Accession Number
- DB01330
- Type
- Small Molecule
- Groups
- Approved
- Description
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.
- Structure
Structure for Cefotetan (DB01330)
- 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
- Product Ingredients
Ingredient UNII CAS InChI Key Cefotetan disodium 0GXP746VXB 74356-00-6 ZQQALMSFFARWPK-GLHLDKNHSA-L - Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Cefotan Injection 1 g/50mL Intramuscular; Intravenous Astra Zeneca Lp 1993-07-30 2008-01-24 US 
Cefotan Injection 10 g/1 Intramuscular; Intravenous Astra Zeneca Lp 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 Teligent Pharma, Inc. 2015-10-01 Not applicable US Cefotan Injection 2 g/1 Intramuscular; Intravenous Astra Zeneca Lp 1986-04-21 2008-05-09 US Cefotan Injection 1 g/1mL Intramuscular; Intravenous Physicians Total Care, Inc. 1996-08-20 2004-12-31 US Cefotan Injection 1 g/1 Intramuscular; Intravenous Astra Zeneca Lp 1985-12-27 2008-05-09 US Cefotan Injection 2 g/50mL Intramuscular; Intravenous Astra Zeneca Lp 1993-07-30 2007-12-07 US Cefotan Injection, powder, for solution 1 g/10mL Intramuscular; Intravenous Teligent Pharma, Inc. 2015-10-01 Not applicable US Cefotan Inj 2gm/vial Powder, for solution 2 g Intramuscular; Intravenous Ayerst Laboratories 1990-12-31 1996-09-10 Canada 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Cefotetan Injection, powder, for solution 10 g/1 Intravenous Fresenius Kabi 2009-12-03 Not applicable US Cefotetan Injection, powder, for solution 2 g/20mL Intramuscular; Intravenous Fresenius Kabi 2009-11-18 Not applicable US Cefotetan Injection, powder, for solution 2 g/1 Intramuscular; Intravenous West-Ward Pharmaceuticals Corp 2017-09-17 Not applicable US Cefotetan Injection, powder, for solution 1 g/10mL Intramuscular; Intravenous Fresenius Kabi 2009-11-18 Not applicable US Cefotetan Injection, powder, for solution 1 g/1 Intramuscular; Intravenous West-Ward Pharmaceuticals Corp 2017-09-17 Not applicable US - International/Other Brands
- Yamatetan
- Categories
- Amides
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Aza Compounds
- Azabicyclo Compounds
- beta-Lactams
- Cephalosporins
- Cephamycins
- Drugs that are Mainly Renally Excreted
- Lactams
- Nephrotoxic agents
- Second-Generation Cephalosporins
- Sulfur Compounds
- Tetrazoles
- Thiazines
- UNII
- 48SPP0PA9Q
- CAS number
- 69712-56-7
- Weight
- Average: 575.619
Monoisotopic: 575.002143315 - Chemical Formula
- C17H17N7O8S4
- 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
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Pharmacology
- Indication
For prophylaxis and treatment of bacterial infections.
- Associated Conditions
- Associated Therapies
- Pharmacodynamics
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)]
- Toxicity
- Not Available
- Affected organisms
- Enteric bacteria and other eubacteria
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction (R)-warfarin The risk or severity of bleeding can be increased when Cefotetan is combined with (R)-warfarin. (S)-Warfarin The risk or severity of bleeding can be increased when Cefotetan is combined with (S)-Warfarin. 4-hydroxycoumarin The risk or severity of bleeding can be increased when Cefotetan is combined with 4-hydroxycoumarin. Abacavir 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. Acarbose Cefotetan may decrease the excretion rate of Acarbose which could result in a higher serum level. Aceclofenac Cefotetan may decrease the excretion rate of Aceclofenac which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Cefotetan which could result in a higher serum level. Acenocoumarol The risk or severity of bleeding can be increased when Cefotetan is combined with Acenocoumarol. Acetaminophen Cefotetan may decrease the excretion rate of Acetaminophen which could result in a higher serum level. - Food Interactions
- Avoid alcohol as it can cause a disulfiram effect.
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
- ChEBI
- 3499
- ChEMBL
- CHEMBL474579
- Therapeutic Targets Database
- DAP000451
- PharmGKB
- PA164784033
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Cefotetan
- ATC Codes
- J01DC05 — Cefotetan
- FDA label
- Download (275 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 0 Recruiting Treatment Osteomyelitis 1 2 Completed Treatment Surgery, Colorectal 1 3 Completed Prevention Surgery, Colorectal 1
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 Intramuscular; Intravenous 1 g/1mL Injection Intramuscular; Intravenous 1 g/50mL Injection Intramuscular; Intravenous 1 g/1 Injection Intramuscular; Intravenous 10 g/1 Injection Intramuscular; Intravenous 2 g/1 Injection Intramuscular; Intravenous 2 g/1mL Injection Intramuscular; Intravenous 2 g/50mL Powder, for solution Intramuscular; Intravenous 2 g Powder, for solution Intramuscular; Intravenous 1 g Injection, powder, for solution Intramuscular; Intravenous 1 g/10mL Injection, powder, for solution Intramuscular; Intravenous 1 g/1 Injection, powder, for solution Intramuscular; Intravenous 2 g/1 Injection, powder, for solution Intramuscular; Intravenous 2 g/20mL 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) 3.23 ChemAxon pKa (Strongest Basic) -1.3 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 51.81 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
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 LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available
Taxonomy
- 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
- Cephamycin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / Aryl thioether / Alkylarylthioether / Meta-thiazine / Dicarboxylic acid or derivatives / Vinylogous thioester / Azole / Heteroaromatic compound show 25 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cephalosporin (CHEBI:3499)
Targets
- Kind
- Protein
- Organism
- Streptococcus pneumoniae
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serine-type d-ala-d-ala carboxypeptidase activity
- Specific Function
- Not Available
- 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. [PubMed:6573313]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum 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. [PubMed:2311445]
- Robertson A, Fink S, Karp W: Effect of cephalosporins on bilirubin-albumin binding. J Pediatr. 1988 Feb;112(2):291-4. [PubMed:3339510]
Drug created on June 30, 2007 11:52 / Updated on April 10, 2019 13:51