Cefotetan

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
Thumb
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.

Pharmacology
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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
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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)]
Adverse Effects
Adverseeffects
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Toxicity

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.
DrugInteraction
AbacavirCefotetan may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Cefotetan.
AceclofenacThe risk or severity of nephrotoxicity can be increased when Cefotetan is combined with Aceclofenac.
AcemetacinThe risk or severity of nephrotoxicity can be increased when Cefotetan is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Cefotetan is combined with Acenocoumarol.
AcetaminophenCefotetan may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Cefotetan which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidThe risk or severity of nephrotoxicity can be increased when Acetylsalicylic acid is combined with Cefotetan.
AclidiniumCefotetan may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineCefotetan may decrease the excretion rate of Acrivastine which could result in a higher serum level.
Interactions
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Food Interactions
  • Avoid alcohol. Alcohol can cause a disulfiram effect.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Cefotetan disodium0GXP746VXB74356-00-6ZQQALMSFFARWPK-GLHLDKNHSA-L
International/Other Brands
Yamatetan
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CefotanInjection1 g/1mLIntramuscular; IntravenousPhysicians Total Care, Inc.1996-08-202004-12-31US flag
CefotanInjection, powder, for solution2 g/20mLIntramuscular; IntravenousTeligent Pharma, Inc.2015-10-01Not applicableUS flag
CefotanInjection1 g/50mLIntramuscular; IntravenousAstra Zeneca Lp1993-07-302008-01-24US flag
CefotanInjection1 g/1Intramuscular; IntravenousAstra Zeneca Lp1985-12-272008-05-09US flag
CefotanInjection, powder, for solution1 g/10mLIntramuscular; IntravenousTeligent Pharma, Inc.2015-10-01Not applicableUS flag
CefotanInjection10 g/1Intramuscular; IntravenousAstra Zeneca Lp1985-12-272007-07-07US flag
CefotanInjection2 g/1mLIntramuscular; IntravenousPhysicians Total Care, Inc.1996-09-122004-12-31US flag
CefotanInjection2 g/50mLIntramuscular; IntravenousAstra Zeneca Lp1993-07-302007-12-07US flag
CefotanInjection2 g/1Intramuscular; IntravenousAstra Zeneca Lp1986-04-212008-05-09US flag
Cefotan Inj 2gm/vialPowder, for solution2 g / vialIntramuscular; IntravenousAyerst Laboratories1990-12-311996-09-10Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CefotetanInjection, powder, for solution1 g/10mLIntramuscular; IntravenousFresenius Kabi USA, LLC2009-11-18Not applicableUS flag
CefotetanInjection, powder, for solution1 g/1Intramuscular; IntravenousHikma Pharmaceuticals USA Inc.2011-10-26Not applicableUS flag
CefotetanInjection, powder, for solution10 g/1IntravenousFresenius Kabi USA, LLC2009-12-032018-09-30US flag
CefotetanInjection, powder, for solution2 g/20mLIntramuscular; IntravenousFresenius Kabi USA, LLC2009-11-18Not applicableUS flag
CefotetanInjection, powder, for solution2 g/1Intramuscular; IntravenousHikma Pharmaceuticals USA Inc.2011-10-26Not applicableUS flag

Categories

ATC Codes
J01DC05 — Cefotetan
Drug Categories
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
Human Metabolome Database
HMDB0015425
KEGG Drug
D00260
KEGG Compound
C06886
PubChem Compound
53025
PubChem Substance
46506572
ChemSpider
47904
BindingDB
80643
RxNav
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
PhaseStatusPurposeConditionsCount
3CompletedPreventionSurgery, Colorectal1
2CompletedTreatmentSurgery, Colorectal1
1CompletedPreventionGallbladder Inflammation1
0TerminatedTreatmentOsteomyelitis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • APP Pharmaceuticals
  • B. Braun Melsungen AG
  • Baxter International Inc.
  • Cardinal Health
  • Physicians Total Care Inc.
Dosage Forms
FormRouteStrength
Injection, powder, for solutionIntramuscular
Powder, for solutionIntramuscular; Intravenous
InjectionIntramuscular; Intravenous1 g/1
InjectionIntramuscular; Intravenous1 g/50mL
InjectionIntramuscular; Intravenous1 g/1mL
InjectionIntramuscular; Intravenous10 g/1
InjectionIntramuscular; Intravenous2 g/1
InjectionIntramuscular; Intravenous2 g/50mL
InjectionIntramuscular; Intravenous2 g/1mL
Injection, powder, for solutionIntramuscular; Intravenous1 g/10mL
Injection, powder, for solutionIntramuscular; Intravenous2 g/20mL
Powder, for solutionIntramuscular; Intravenous2 g / vial
Powder, for solutionIntramuscular; Intravenous1 g / vial
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

Targets

Drugtargets2
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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. [Article]

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
  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. [Article]
  2. Robertson A, Fink S, Karp W: Effect of cephalosporins on bilirubin-albumin binding. J Pediatr. 1988 Feb;112(2):291-4. [Article]

Drug created on June 30, 2007 17:52 / Updated on May 07, 2021 21:35