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Identification
NameCefapirin
Accession NumberDB01139  (APRD00860)
TypeSmall Molecule
GroupsApproved, Vet Approved
Description

Cefapirin (INN, also spelled cephapirin) is an injectable, first-generation cephalosporin antibiotic. It is marketed under the trade name Cefadyl. Production for use in humans has been discontinued in the United States. Cefapirin is partly plasma-bound and is effective against gram-negative and gram-positive organisms.

Structure
Thumb
Synonyms
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulfanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cefapirin
Cefapirina
Cefapirine
Cefapirinum
Cefaprin
Cephapirin
Cephapirine
CEPR
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CefadylNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Cefapirin benzathine
ThumbNot applicableDBSALT001645
Cefapirin sodium
24356-60-3
Thumb
  • InChI Key: VGEOUKPOQQEQSX-OALZAMAHSA-M
  • Monoisotopic Mass: 445.037821314
  • Average Mass: 445.445
DBSALT000264
Categories
UNII89B59H32VN
CAS number21593-23-7
WeightAverage: 423.463
Monoisotopic: 423.055876671
Chemical FormulaC17H17N3O6S2
InChI KeyInChIKey=UQLLWWBDSUHNEB-CZUORRHYSA-N
InChI
InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1
IUPAC Name
(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(pyridin-4-ylsulfanyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[[email protected]]2NC(=O)CSC1=CC=NC=C1)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
  • Pyridine
  • Meta-thiazine
  • Heteroaromatic compound
  • Acetate salt
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxylic acid ester
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Sulfenyl compound
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • 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 treatment of infections caused by susceptible bacteria.
PharmacodynamicsCephapirin is a first-generation cephalosporin that has a wide spectrum of activity against gram-positive and gram-negative organisms. Cephapirin is more resistant to beta-lactamases than are the penicillins and so is effective against staphylococci, with the exception of methicillin-resistant staphylococci.
Mechanism of actionThe bactericidal activity of cephapirin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Major metabolite detected is desacetylcephapirin.

SubstrateEnzymesProduct
Cefapirin
Not Available
DesacetylcephapirinDetails
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityRats exposed via the oral route to cephapirin displayed low acute toxicity (LD50 = 14000 mg/kg). The most common adverse reactions are hypersensitivity reactions and alterations to liver function. Evidence of white blood cell disorders and anaemia were noted in some subjects.
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-0.959
Blood Brain Barrier-0.9971
Caco-2 permeable-0.7523
P-glycoprotein substrateSubstrate0.8491
P-glycoprotein inhibitor INon-inhibitor0.6578
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterNon-inhibitor0.8236
CYP450 2C9 substrateNon-substrate0.7333
CYP450 2D6 substrateNon-substrate0.8159
CYP450 3A4 substrateSubstrate0.5132
CYP450 1A2 substrateNon-inhibitor0.7695
CYP450 2C9 inhibitorNon-inhibitor0.7348
CYP450 2D6 inhibitorNon-inhibitor0.8753
CYP450 2C19 inhibitorNon-inhibitor0.7075
CYP450 3A4 inhibitorNon-inhibitor0.8003
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5917
Ames testNon AMES toxic0.6996
CarcinogenicityNon-carcinogens0.901
BiodegradationNot ready biodegradable0.9955
Rat acute toxicity1.4439 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9946
hERG inhibition (predictor II)Non-inhibitor0.7588
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubility1030 mg/LNot Available
logP-1.15SANGSTER (1994)
pKa2.15Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.151 mg/mLALOGPS
logP0.18ALOGPS
logP-2ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)3.54ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area125.9 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity102.43 m3·mol-1ChemAxon
Polarizability40.63 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
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

Crast, L.B. Jr.; U.S. Patent 3,422,100; January 14, 1969; assigned to Bristol-Myers Company Silvestri, H.H.and Johnson, D.A.; US. Patent 3,503,967; March 31,1970; assigned to Bristol-Myers Company.
Havranek, R.E. and Crast, L.B. Jr.; U.S. Patent 3,578,661; May 11, 1971; assigned to Bristol-
Myers Company.

General ReferencesNot Available
External Links
ATC CodesJ01DB08
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (31.4 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolCefapirin may increase the anticoagulant activities of Acenocoumarol.
ProbenecidThe serum concentration of Cefapirin can be increased when it is combined with Probenecid.
WarfarinCefapirin may increase the anticoagulant activities of Warfarin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Clostridium perfringens (strain 13 / Type A)
Pharmacological action
yes
Actions
inhibitor
General Function:
Transferase activity, transferring glycosyl groups
Specific Function:
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits) (By similarity).
Gene Name:
pbpA
Uniprot ID:
Q8XJ01
Molecular Weight:
75176.35 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Hamilton TE, Lawrence PJ: The formation of functional penicillin-binding proteins. J Biol Chem. 1975 Aug 25;250(16):6578-85. [PubMed:808545 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23