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Identification
NameCefacetrile
Accession NumberDB01414
TypeSmall Molecule
GroupsApproved
Description

A derivative of 7-aminocephalosporanic acid.

Structure
Thumb
Synonyms
SynonymLanguageCode
CefacetriloSpanishINN
CefacetrilumLatinINN
CephacetrileNot AvailableNot Available
Vetrimast [veterinary]Not AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
CelosporCiba
CeltolTakeda
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number10206-21-0
WeightAverage: 339.324
Monoisotopic: 339.052505853
Chemical FormulaC13H13N3O6S
InChI KeyRRYMAQUWDLIUPV-BXKDBHETSA-N
InChI
InChI=1S/C13H13N3O6S/c1-6(17)22-4-7-5-23-12-9(15-8(18)2-3-14)11(19)16(12)10(7)13(20)21/h9,12H,2,4-5H2,1H3,(H,15,18)(H,20,21)/t9-,12-/m1/s1
IUPAC Name
(6R,7R)-3-[(acetyloxy)methyl]-7-(2-cyanoacetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CC#N)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
  • Meta-thiazine
  • Acetate salt
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxylic acid ester
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Nitrile
  • Carbonitrile
  • Monocarboxylic acid or derivatives
  • Enamine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationCefacetrile is a broad-spectrum first generation cephalosporin antibiotic effective in Gram-positive and Gram-negative bacterial infections.
PharmacodynamicsCefacetrile is effective against many Gram-positive bacterial strains and somewhat less effective against Gram-negative species. It works by inhibition of bacterial cell wall synthesis. It attains high serum levels and is excreted quickly via the urine.
Mechanism of actionIn vitro tests demonstrate that the bactericidal action of cephalosporins results from inhibition of cell wall synthesis. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins.
AbsorptionNot Available
Volume of distribution

Vd of 0.2 to 0.5L/.kg

Protein binding23 to 38%
MetabolismNot Available
Route of eliminationNot Available
Half life1.2 hours
ClearanceNot Available
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-0.9435
Blood Brain Barrier-0.9965
Caco-2 permeable-0.754
P-glycoprotein substrateSubstrate0.7774
P-glycoprotein inhibitor INon-inhibitor0.7686
P-glycoprotein inhibitor IINon-inhibitor0.9626
Renal organic cation transporterNon-inhibitor0.9013
CYP450 2C9 substrateNon-substrate0.7919
CYP450 2D6 substrateNon-substrate0.823
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.8122
CYP450 2C9 substrateNon-inhibitor0.8282
CYP450 2D6 substrateNon-inhibitor0.9145
CYP450 2C19 substrateNon-inhibitor0.8132
CYP450 3A4 substrateNon-inhibitor0.9152
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8735
Ames testNon AMES toxic0.6895
CarcinogenicityNon-carcinogens0.9237
BiodegradationNot ready biodegradable0.9705
Rat acute toxicity1.8811 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9933
hERG inhibition (predictor II)Non-inhibitor0.9062
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point168-170Bickel, H., Bosshardt, R., Fechtig, B., Schenker, K. and Urech, J.; U.S. Patent 3,483,197; December 9,1969; assigned to Ciba Corporation.
logP-0.45HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.43 mg/mLALOGPS
logP-0.52ALOGPS
logP-1.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)3.31ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area136.8 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity77.51 m3·mol-1ChemAxon
Polarizability31.32 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Bickel, H., Bosshardt, R., Fechtig, B., Schenker, K. and Urech, J.; U.S. Patent 3,483,197;
December 9,1969; assigned to Ciba Corporation.

General ReferenceNot Available
External Links
ATC CodesJ01DB10
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcenocoumarolMay enhance the anticoagulant effect of Vitamin K Antagonists.
ProbenecidProbenecid may increase the serum concentration of Cephalosporins.
Food InteractionsNot Available

Targets

1. Penicillin-binding protein 1A

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 1A P02918 Details

References:

  1. Yotsuji A, Mitsuyama J, Hori R, Yasuda T, Saikawa I, Inoue M, Mitsuhashi S: Mechanism of action of cephalosporins and resistance caused by decreased affinity for penicillin-binding proteins in Bacteroides fragilis. Antimicrob Agents Chemother. 1988 Dec;32(12):1848-53. Pubmed
  2. Truesdell SE, Zurenko GE, Laborde AL: Interaction of cephalosporins with penicillin-binding proteins of methicillin-resistant Staphylococcus aureus. J Antimicrob Chemother. 1989 Apr;23 Suppl D:13-9. Pubmed

2. Penicillin-binding protein 1B

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 1B P02919 Details

References:

  1. Truesdell SE, Zurenko GE, Laborde AL: Interaction of cephalosporins with penicillin-binding proteins of methicillin-resistant Staphylococcus aureus. J Antimicrob Chemother. 1989 Apr;23 Suppl D:13-9. Pubmed
  2. Yotsuji A, Mitsuyama J, Hori R, Yasuda T, Saikawa I, Inoue M, Mitsuhashi S: Mechanism of action of cephalosporins and resistance caused by decreased affinity for penicillin-binding proteins in Bacteroides fragilis. Antimicrob Agents Chemother. 1988 Dec;32(12):1848-53. Pubmed

Transporters

1. Solute carrier family 22 member 6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

References:

  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. Pubmed
  2. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. Pubmed
  3. Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. Pubmed
  4. Uwai Y, Saito H, Inui K: Rat renal organic anion transporter rOAT1 mediates transport of urinary-excreted cephalosporins, but not of biliary-excreted cefoperazone. Drug Metab Pharmacokinet. 2002;17(2):125-9. Pubmed

2. Solute carrier family 22 member 8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 8 Q8TCC7 Details

References:

  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. Pubmed
  2. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. Pubmed
  3. Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. Pubmed
  4. Uwai Y, Saito H, Inui K: Rat renal organic anion transporter rOAT1 mediates transport of urinary-excreted cephalosporins, but not of biliary-excreted cefoperazone. Drug Metab Pharmacokinet. 2002;17(2):125-9. Pubmed

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Drug created on July 23, 2007 06:31 / Updated on April 03, 2014 11:16