You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameCefotetan
Accession NumberDB01330
TypeSmall Molecule
GroupsApproved
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
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
Cefotetanum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cefotaninjection, powder, for solution2 g/20mLintramuscular; intravenousTeligent Pharma, Inc.2015-10-01Not applicableUs
Cefotaninjection, powder, for solution1 g/10mLintramuscular; intravenousTeligent Pharma, Inc.2015-10-01Not applicableUs
Cefotan Inj 2gm/vialpowder for solution2 gintramuscular; intravenousAyerst Laboratories1990-12-311996-09-10Canada
Cefotan Injection - 1gpowder for solution1 gintramuscular; intravenousWyeth Canada1994-12-312006-08-04Canada
Cefotan Injection - 2 Gpowder for solution2 gintramuscular; intravenousWyeth Canada1994-12-312006-08-04Canada
Cefotetan and Dextroseinjection, solution1 g/50mLintravenousB. Braun Medical Inc.2010-08-20Not applicableUs
Cefotetan and Dextroseinjection, solution2 g/50mLintravenousB. Braun Medical Inc.2010-08-20Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cefotetaninjection, powder, for solution1 g/10mLintramuscular; intravenousFresenius Kabi USA, LLC2009-11-18Not applicableUs
Cefotetaninjection, powder, for solution10 g/1intravenousFresenius Kabi USA, LLC2009-12-03Not applicableUs
Cefotetaninjection, powder, for solution2 g/20mLintramuscular; intravenousFresenius Kabi USA, LLC2009-11-18Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CefotanNot Available
YamatetanNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Cefotetan disodium
ThumbNot applicableDBSALT001161
Categories
UNII48SPP0PA9Q
CAS number69712-56-7
WeightAverage: 575.619
Monoisotopic: 575.002143315
Chemical FormulaC17H17N7O8S4
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporins
Alternative Parents
Substituents
  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Alkylarylthioether
  • Vinylogous thioester
  • Dicarboxylic acid or derivatives
  • Meta-thiazine
  • Heteroaromatic compound
  • Tetrazole
  • Tertiary carboxylic acid amide
  • Azole
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Ketene acetal or derivatives
  • Dithietane
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Sulfenyl compound
  • Hemithioaminal
  • Thioether
  • Enamine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor prophylaxis and treatment of bacterial infections.
PharmacodynamicsCefotetan 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 actionThe 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.
Related Articles
AbsorptionNot 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 bindingCefotetan 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 eliminationNo 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 lifeIn 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)]
ToxicityNot Available
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9451
Blood Brain Barrier-0.9903
Caco-2 permeable-0.799
P-glycoprotein substrateSubstrate0.7418
P-glycoprotein inhibitor INon-inhibitor0.8992
P-glycoprotein inhibitor IINon-inhibitor0.7207
Renal organic cation transporterNon-inhibitor0.9032
CYP450 2C9 substrateNon-substrate0.8489
CYP450 2D6 substrateNon-substrate0.8219
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6374
Ames testNon AMES toxic0.7712
CarcinogenicityNon-carcinogens0.9274
BiodegradationNot ready biodegradable0.9081
Rat acute toxicity1.7915 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9933
hERG inhibition (predictor II)Non-inhibitor0.7103
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Powder for solutionintramuscular; intravenous2 g
Powder for solutionintramuscular; intravenous1 g
Injection, powder, for solutionintramuscular; intravenous1 g/10mL
Injection, powder, for solutionintramuscular; intravenous2 g/20mL
Injection, powder, for solutionintravenous10 g/1
Injection, solutionintravenous1 g/50mL
Injection, solutionintravenous2 g/50mL
Prices
Unit descriptionCostUnit
Cefotetan 2 gm vial27.31USD vial
Cefotetan-dextr 2 g duplex bag25.14USD each
Cefotetan-dextr 1 g duplex bag17.58USD each
Cefotetan 1 gm vial13.66USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.521 mg/mLALOGPS
logP-0.65ALOGPS
logP-0.38ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.23ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area219.93 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity153.55 m3·mol-1ChemAxon
Polarizability51.81 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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 ReferencesNot Available
External Links
ATC CodesJ01DC05
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (275 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AcenocoumarolCefotetan may increase the anticoagulant activities of Acenocoumarol.
AmikacinCefotetan may increase the nephrotoxic activities of Amikacin.
ArbekacinCefotetan may increase the nephrotoxic activities of Arbekacin.
CarbocisteineThe risk or severity of adverse effects can be increased when Cefotetan is combined with Carbocisteine.
DicoumarolCefotetan may increase the anticoagulant activities of Dicoumarol.
EthanolThe risk or severity of adverse effects can be increased when Cefotetan is combined with Ethanol.
FramycetinCefotetan may increase the nephrotoxic activities of Framycetin.
GentamicinCefotetan may increase the nephrotoxic activities of Gentamicin.
KanamycinCefotetan may increase the nephrotoxic activities of Kanamycin.
NeomycinCefotetan may increase the nephrotoxic activities of Neomycin.
NetilmicinCefotetan may increase the nephrotoxic activities of Netilmicin.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Cefotetan.
ProbenecidThe serum concentration of Cefotetan can be increased when it is combined with Probenecid.
RibostamycinCefotetan may increase the nephrotoxic activities of Ribostamycin.
SpectinomycinCefotetan may increase the nephrotoxic activities of Spectinomycin.
StreptomycinCefotetan may increase the nephrotoxic activities of Streptomycin.
TobramycinCefotetan may increase the nephrotoxic activities of Tobramycin.
WarfarinCefotetan may increase the anticoagulant activities of Warfarin.
Food Interactions
  • Avoid alcohol as it can cause a disulfiram effect.

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
Molecular Weight:
45209.84 Da
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:6573313 ]

Carriers

Kind
Protein
Organism
Human
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 colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
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:2311445 ]
  2. Robertson A, Fink S, Karp W: Effect of cephalosporins on bilirubin-albumin binding. J Pediatr. 1988 Feb;112(2):291-4. [PubMed:3339510 ]
Comments
comments powered by Disqus
Drug created on June 30, 2007 11:52 / Updated on August 17, 2016 12:23