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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2018-05-20 20:16:39 UTC
HMDB IDHMDB0015270
Secondary Accession Numbers
  • HMDB0030451
  • HMDB15270
  • HMDB30451
Metabolite Identification
Common NameCephapirin
DescriptionCephapirin is an injectable, first-generation cephalosporin antibiotic that has a wide spectrum of activity against gram-positive and gram-negative organisms. The bactericidal activity of cephapirin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Cephapirin is more resistant to beta-lactamases than the penicillins, and therefore is effective against staphylococci, with the exception of methicillin-resistant staphylococci. Cephapirin is FDA approved for use in food-producing animals, especially dairy cattle. Cephapirin is used for the treatment of mastitis in cows. Production for use in humans has been discontinued in the United States. It is marketed under the trade name Cefadyl.
Structure
Thumb
Synonyms
ValueSource
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulfanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidChEBI
CefapirinaChEBI
CefapirineChEBI
CefapirinumChEBI
CefaprinChEBI
CephapirineChEBI
CEPRChEBI
CephapirinKegg
MetricureKegg
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulfanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulphanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulphanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidGenerator
CefadylHMDB
Monosodium salt, cephapirinHMDB
Salt, cephapirin monosodiumHMDB
BL p 1322HMDB
Bristol-myers brand OF cephapirin sodiumHMDB
Cephapirin, sodiumHMDB
Apothecon brand OF cephapirin sodiumHMDB
Cephapirin sodiumHMDB
CéfalojectHMDB
Sodium cephapirinHMDB
BL-p 1322HMDB
BrisfirinaHMDB
Bristol-myers squibb brand OF cephapirin sodiumHMDB
Cephapirin monosodium saltHMDB
CefapirinChEBI
Chemical FormulaC17H17N3O6S2
Average Molecular Weight423.463
Monoisotopic Molecular Weight423.055876671
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
Traditional NameCEPR
CAS Registry Number21593-23-7
SMILES
[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CSC1=CC=NC=C1)C(O)=O
InChI Identifier
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
InChI KeyUQLLWWBDSUHNEB-CZUORRHYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids and derivatives
Alternative Parents
Substituents
  • N-acyl-alpha amino acid or derivatives
  • Cephem
  • Aryl thioether
  • Alkylarylthioether
  • Meta-thiazine
  • Dicarboxylic acid or derivatives
  • Pyridine
  • Heteroaromatic compound
  • Beta-lactam
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid ester
  • Lactam
  • Azetidine
  • Azacycle
  • Organoheterocyclic compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Dialkylthioether
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Thioether
  • Hemithioaminal
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.15 g/LNot Available
LogP-0.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP0.18ALOGPS
logP-2ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)3.54ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area125.9 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity102.43 m³·mol⁻¹ChemAxon
Polarizability40.63 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9373100000-e3d19d32bd32937d2df3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9221200000-5b079bfce3f72569ddd8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ck9-1193200000-dbd8b4f9cdd95af96bebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-3493000000-9715d40cfca13766b646View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0903-9740000000-3730a9b0ee7ce8523e45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-2693100000-30db005d7cf1f9280b9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-5982000000-04fa910b005391b04891View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dl-9470000000-f3f678bd4350e63bc6bdView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01139 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01139 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01139
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002317
KNApSAcK IDNot Available
Chemspider ID28486
KEGG Compound IDC06896
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCephapirin
METLIN IDNot Available
PubChem Compound30699
PDB IDNot Available
ChEBI ID554446
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simonet M, Herrmann JL, Gehanno P, Veron M: [Activity of cefapirin against bacterial strains isolated from acute otitis media in children]. Pathol Biol (Paris). 1990 May;38(5):352-4. [PubMed:2114604 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .