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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2019-01-11 19:36:12 UTC
HMDB IDHMDB0015625
Secondary Accession Numbers
  • HMDB15625
Metabolite Identification
Common NamePrasugrel
DescriptionPrasugrel, a thienopyridine derivative, is a platelet activation and aggregation inhibitor structurally and pharmacologically related to clopidogrel and ticlopidine. Similar to clopidogrel, prasugrel is a prodrug that requires enzymatic transformation in the liver to its active metabolite, R-138727. R-138727 irreversibly binds to P2Y12 type ADP receptors on platelets thereby inhibiting ADP-mediated platelet activation and aggregation. Prasugrel inhibits ADP-mediated platelet aggregation more rapidly, more consistently and to a greater extent (at least 30%) than clopidogrel. The increased potency of prasugrel appears to be due to more efficient conversion to its active metabolite. The relationship, however, between increased platelet aggregation and clinical response has not been determined. Prasugrel carries a higher risk of bleed compared to clopidogrel, which may be a result of its higher potency. Prasugrel was developed by Daiichi Sankyo Co. and is currently marketed in the United States and Canada in cooperation with Eli Lilly and Company for acute coronary syndromes planned for percutaneous coronary intervention (PCI).
Structure
Data?1547235371
Synonyms
ValueSource
CS-747HMDB
747, CSMeSH
HCL, PrasugrelMeSH
Prasugrel HCLMeSH
EffientMeSH
Hydrochloride, prasugrelMeSH
Prasugrel hydrochlorideMeSH
EfientMeSH
Chemical FormulaC20H20FNO3S
Average Molecular Weight373.441
Monoisotopic Molecular Weight373.114792406
IUPAC Name5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4H,5H,6H,7H-thieno[3,2-c]pyridin-2-yl acetate
Traditional Nameprasugrel
CAS Registry Number150322-43-3
SMILES
CC(=O)OC1=CC2=C(CCN(C2)C(C(=O)C2CC2)C2=CC=CC=C2F)S1
InChI Identifier
InChI=1S/C20H20FNO3S/c1-12(23)25-18-10-14-11-22(9-8-17(14)26-18)19(20(24)13-6-7-13)15-4-2-3-5-16(15)21/h2-5,10,13,19H,6-9,11H2,1H3
InChI KeyDTGLZDAWLRGWQN-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as thienopyridines. These are heterocyclic compounds containing a thiophene ring fused to a pyridine ring. Thiophene is 5-membered ring consisting of four carbon atoms and one sulfur atom. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassThienopyridines
Sub ClassNot Available
Direct ParentThienopyridines
Alternative Parents
Substituents
  • Thienopyridine
  • 2,3,5-trisubstituted thiophene
  • Halobenzene
  • Fluorobenzene
  • Aralkylamine
  • Pyridine
  • Aryl fluoride
  • Aryl halide
  • Benzenoid
  • Monocyclic benzene moiety
  • Thiophene
  • Alpha-aminoketone
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Amino acid or derivatives
  • Ketone
  • Tertiary amine
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organofluoride
  • Organic oxygen compound
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0024 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0024 g/LALOGPS
logP3.67ALOGPS
logP4.31ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)14.25ChemAxon
pKa (Strongest Basic)5.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area46.61 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity96.81 m³·mol⁻¹ChemAxon
Polarizability37.7 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03xu-5292000000-363487adeda2803edf87JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-056s-2945000000-7653802e8e3994dc55bcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02mi-3109000000-5df287f035db2dd8d72eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9012000000-4c525511fe781201418cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9110000000-e5719df9692a6db2952dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-4009000000-9044e8f3f643c0735a0aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-9148000000-99e7e9c97dd6cac360acJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9280000000-6aa7847fbc28ebfd9358JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06209 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06209 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06209
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5293653
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPrasugrel
METLIN IDNot Available
PubChem Compound6918456
PDB IDNot Available
ChEBI ID87723
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Dovlatova NL, Jakubowski JA, Sugidachi A, Heptinstall S: The reversible P2Y antagonist cangrelor influences the ability of the active metabolites of clopidogrel and prasugrel to produce irreversible inhibition of platelet function. J Thromb Haemost. 2008 Jul;6(7):1153-9. doi: 10.1111/j.1538-7836.2008.03020.x. Epub 2008 Jul 1. [PubMed:18485086 ]
  2. Tagarakis GI: Ticagrelor and prasugrel: two novel, most-promising antiplatelet agents. Recent Pat Cardiovasc Drug Discov. 2010 Nov;5(3):208-11. [PubMed:20874669 ]
  3. Jeong YH, Tantry US, Gurbel PA: Importance of potent P2Y(12) receptor blockade in acute myocardial infarction: focus on prasugrel. Expert Opin Pharmacother. 2012 Aug;13(12):1771-96. doi: 10.1517/14656566.2012.704909. Epub 2012 Jul 12. [PubMed:22783896 ]
  4. Angiolillo DJ: The evolution of antiplatelet therapy in the treatment of acute coronary syndromes: from aspirin to the present day. Drugs. 2012 Nov 12;72(16):2087-116. doi: 10.2165/11640880-000000000-00000. [PubMed:23083110 ]