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
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
Product Ingredients
IngredientUNIICASInChI Key
Cefotetan disodium0GXP746VXB74356-00-6ZQQALMSFFARWPK-GLHLDKNHSA-L
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CefotanInjection, powder, for solution1 g/10mLIntramuscular; IntravenousTeligent Pharma, Inc.2015-10-01Not applicableUs
CefotanInjection, powder, for solution2 g/20mLIntramuscular; 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 Ltd.1994-12-312006-08-04Canada
Cefotan Injection - 2 GPowder, for solution2 gIntramuscular; IntravenousWyeth Ltd.1994-12-312006-08-04Canada
Cefotetan and DextroseInjection, solution2 g/50mLIntravenousB. Braun Medical Inc.2010-08-20Not applicableUs
Cefotetan and DextroseInjection, solution1 g/50mLIntravenousB. Braun Medical Inc.2010-08-20Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CefotetanInjection, powder, for solution10 g/1IntravenousFresenius Kabi2009-12-03Not applicableUs
CefotetanInjection, powder, for solution1 g/1Intramuscular; IntravenousWest Ward Pharmaceutical2017-09-17Not applicableUs
CefotetanInjection, powder, for solution1 g/10mLIntramuscular; IntravenousFresenius Kabi2009-11-18Not applicableUs
CefotetanInjection, powder, for solution2 g/1Intramuscular; IntravenousWest Ward Pharmaceutical2017-09-17Not applicableUs
CefotetanInjection, powder, for solution2 g/20mLIntramuscular; IntravenousFresenius Kabi2009-11-18Not applicableUs
International/Other Brands
Cefotan / Yamatetan
Categories
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][[email protected]]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[[email protected]]2(NC(=O)C1SC(S1)=C(C(N)=O)C(O)=O)OC)C(O)=O

Pharmacology

Indication

For prophylaxis and treatment of bacterial infections.

Structured Indications
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.

TargetActionsOrganism
APenicillin-binding protein 3
inhibitor
Streptococcus 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
DrugInteractionDrug group
AcenocoumarolCefotetan may increase the anticoagulant activities of Acenocoumarol.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Cefotetan.Investigational
CarbocisteineThe risk or severity of adverse effects can be increased when Cefotetan is combined with Carbocisteine.Approved, Investigational
ClorindioneCefotetan may increase the anticoagulant activities of Clorindione.Experimental
DicoumarolCefotetan may increase the anticoagulant activities of Dicoumarol.Approved
DiphenadioneCefotetan may increase the anticoagulant activities of Diphenadione.Experimental
EthanolThe risk or severity of adverse effects can be increased when Cefotetan is combined with Ethanol.Approved
Ethyl biscoumacetateCefotetan may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FluindioneCefotetan may increase the anticoagulant activities of Fluindione.Investigational
PhenindioneCefotetan may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenprocoumonCefotetan may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Cefotetan.Approved
ProbenecidThe serum concentration of Cefotetan can be increased when it is combined with Probenecid.Approved
TioclomarolCefotetan may increase the anticoagulant activities of Tioclomarol.Experimental
WarfarinCefotetan may increase the anticoagulant activities of Warfarin.Approved
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
HMDB15425
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
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
2CompletedTreatmentSurgery, Colorectal1
3CompletedPreventionSurgery, Colorectal1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
Injection, powder, for solutionIntramuscular; Intravenous1 g/10mL
Injection, powder, for solutionIntramuscular; Intravenous2 g/20mL
Powder, for solutionIntramuscular; Intravenous2 g
Powder, for solutionIntramuscular; Intravenous1 g
Injection, powder, for solutionIntramuscular; Intravenous1 g/1
Injection, powder, for solutionIntramuscular; Intravenous2 g/1
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot 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
  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 colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
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]

Drug created on June 30, 2007 11:52 / Updated on November 09, 2017 02:58