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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. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Cefotetanum [inn-latin]
Brand names
  • Cefotan
  • Yamatetan
Brand name mixtures Not Available
Categories
  • Anti-Bacterial Agents
  • Cephalosporins
CAS number 69712-56-7
Weight Average: 575.619
Monoisotopic: 575.002143315
Chemical Formula C17H17N7O8S4
InChI Key InChIKey=SRZNHPXWXCNNDU-PWIJFWJWSA-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-/m0/s1
Plain Text
IUPAC Name
(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
CO[C@]1(NC(=O)C2SC(S2)=C(C(N)=O)C(O)=O)C2SCC(CSC3=NN=NN3C)=C(N2C1=O)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Keto-Acids
  • Cephalosporins
Substructures
  • Ethers
  • Hydroxy Compounds
  • Acetates
  • Keto-Acids
  • Amino Ketones
  • Carboxylic Acids and Derivatives
  • Aliphatic and Aryl Amines
  • Aminals and Derivatives
  • Beta Lactams
  • Carbamates and Derivatives
  • Enamines
  • Tetrazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Ketenes and Derivatives
  • Cephalosporins
  • Lactams
  • Azetidines
  • Acetals and Derivatives
  • Cyanamides
Pharmacology
Indication For prophylaxis and treatment of bacterial infections.
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.
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
Pharmacoeconomics
Manufacturers
  • Astrazeneca pharmaceuticals lp
  • App pharmaceuticals llc
  • B braun medical inc
Packagers
Dosage forms
Form Route Strength
Injection, solution Intramuscular
Injection, solution Intravenous
Prices
Unit description Cost Unit
Cefotetan 2 gm vial 27.31 USD vial
Cefotetan-dextr 2 g duplex bag 25.14 USD each
Cefotetan-dextr 1 g duplex bag 17.58 USD each
Cefotetan 1 gm vial 13.66 USD vial
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 5.21e-01 g/l ALOGPS
logP -0.65 ALOGPS
logP -0.38 ChemAxon Molconvert
logS -3.04 ALOGPS
pKa 4.06 ChemAxon Molconvert
hydrogen acceptor count 11 ChemAxon Molconvert
hydrogen donor count 4 ChemAxon Molconvert
polar surface area 219.93 ChemAxon Molconvert
rotatable bond count 9 ChemAxon Molconvert
refractivity 153.55 ChemAxon Molconvert
polarizability 52.63 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00260 Link_out
KEGG Compound C06886 Link_out
PubChem Compound 50614 Link_out
PubChem Substance 46506572 Link_out
ChemSpider 45877 Link_out
ChEBI 3499 Link_out
ChEMBL 3499 Link_out
Therapeutic Targets Database DAP000451 Link_out
PharmGKB PA448854 Link_out
Drug Product Database 0 Link_out
RxList http://www.rxlist.com/cgi/generic/cefotet.htm Link_out
Drugs.com http://www.drugs.com/cdi/cefotetan.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Cefotetan Link_out
ATC Codes
  • J01DC05
AHFS Codes Not Available
PDB Entries Not Available
FDA label show (275.2 KB)
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions
  • Avoid alcohol as it can cause a disulfiram effect.
Targets

1. Penicillin-binding protein 3

Pharmacological action: yes
Actions: inhibitor
UniProt ID: Q75Y35 Link_out
Gene: pbp3
SNPs: SNPJam Report Link_out

References:
  1. 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
Carriers

1. Serum albumin

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 colloidal osmotic pressure of blood

UniProt ID: P02768 Link_out
Gene: ALB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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
  2. Robertson A, Fink S, Karp W: Effect of cephalosporins on bilirubin-albumin binding. J Pediatr. 1988 Feb;112(2):291-4. Pubmed
Comments
Drug created on June 30, 2007 11:52 / Updated on April 19, 2011 15:09

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.