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Cefotetan

July 24, 2017
Common Name

Cefotetan Description

Cefotetan is only found in individuals that have used or taken this drug. It is a semisynthetic cephamycin antibiotic that is administered intravenously or intramuscliarly. 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]The bactericidal action of cefotetan reslits from inhibition of cell wall synthesis by binding and inhibiting the bacterial penicillin binding proteins which help in the cell wall biosynthesis. Structure

MOLSDFPDBSMILESInChI

Synonyms

Value Source (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 acidChEBI CefotetanumChEBI (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- carboxylateGenerator

Chemical Formlia

C17H17N7O8S4 Average Molecliar Weight

575.619 Monoisotopic Molecliar Weight

575.002143315 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)slifanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Traditional Name

cefotetan CAS Registry Number

69712-56-7 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

InChI Identifier

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

InChI Key

SRZNHPXWXCNNDU-IXOPCIAXSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities 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

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

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
  • Dithietanes
  • Primary carboxylic acid amides
  • Ketene acetals
  • Thiohemiaminal derivatives
  • Azacyclic compounds
  • Slifenyl compounds
  • Dialkylthioethers
  • Carboxylic acids
  • Hydrocarbon derivatives
  • Carbonyl compounds
  • Organopnictogen compounds
  • Organic oxides
  • Organonitrogen compounds

    • 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
  • Tertiary carboxylic acid amide
  • Tetrazole
  • Azetidine
  • Carboxamide group
  • Dithietane
  • Ketene acetal or derivatives
  • Primary carboxylic acid amide
  • Secondary carboxylic acid amide
  • Hemithioaminal
  • Thioether
  • Slifenyl compound
  • Azacycle
  • Dialkylthioether
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organoslifur compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • cephalosporin (CHEBI:3499 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Bacterial Agents
  • Cephalosporins

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Extracellliar

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility5.21e-01 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.52 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Extracellliar

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01330

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01330

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01330 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    47904 KEGG Compound ID

    C06886 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Cefotetan NuGOwiki Link

    HMDB15425 Metagene Link

    HMDB15425 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    3499

    Product: Amifostine

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    PMID: 21947282

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