| Common Name |
Prasugrel
| Description |
Prasugrel, 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 reslit 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 |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
CS-747HMDB
747, CSMeSH
HCL, PrasugrelMeSH
Prasugrel HCLMeSH
EffientMeSH
Hydrochloride, prasugrelMeSH
Prasugrel hydrochlorideMeSH
EfientMeSH
| Chemical Formlia |
C20H20FNO3S
| Average Molecliar Weight |
373.441
| Monoisotopic Molecliar Weight |
373.114792406
| IUPAC Name |
5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4H,5H,6H,7H-thieno[3,2-c]pyridin-2-yl acetate
| Traditional Name |
prasugrel
| CAS Registry Number |
150322-43-3
| 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 Key |
DTGLZDAWLRGWQN-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This 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 slifur atom. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center.
| Kingdom |
Organic compounds
| Super Class |
Organoheterocyclic compounds
| Class |
Thienopyridines
| Sub Class |
Not Available
| Direct Parent |
Thienopyridines
| Alternative Parents |
2,3,5-trisubstituted thiophenes
Aralkylamines
Fluorobenzenes
Pyridines and derivatives
Aryl fluorides
Alpha-amino ketones
Heteroaromatic compounds
Trialkylamines
Carboxylic acid esters
Amino acids and derivatives
Azacyclic compounds
Monocarboxylic acids and derivatives
Organic oxides
Organofluorides
Organopnictogen compounds
Hydrocarbon derivatives
| 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
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
tertiary amino compound (CHEBI:87723 )
acetate ester (CHEBI:87723 )
cyclopropanes (CHEBI:87723 )
ketone (CHEBI:87723 )
monofluorobenzenes (CHEBI:87723 )
thienopyridine (CHEBI:87723 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Drug
| Biofunction |
Antithrombotic Agents
Platelet Aggregation Inhibitors
| Application |
Pharmaceutical
| Cellliar locations |
Cytoplasm
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.37e-03 g/LNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.0024 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity96.81 m3·mol-1ChemAxon
Polarizability37.7 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| LC-MS/MS |
LC-MS/MS Spectrum – , positivesplash10-056s-2945000000-7653802e8e3994dc55bcView in MoNA
| 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 |
Cytoplasm
Membrane
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06209
21059682
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06209
21059682
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB06209
| 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 |
5293653
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Prasugrel
| NuGOwiki Link |
HMDB15625
| Metagene Link |
HMDB15625
| METLIN ID |
Not Available
| PubChem Compound |
6918456
| PDB ID |
Not Available
| ChEBI ID |
775723
Product: Moguisteine
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- 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 ]
- Tagarakis GI: Ticagrelor and prasugrel: two novel, most-promising antiplatelet agents. Recent Pat Cardiovasc Drug Discov. 2010 Nov;5(3):208-11. [PubMed:20874669 ]
- 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 ]
- 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 ]
|
PMID: 15634002
