prasugrel   Click here for help

GtoPdb Ligand ID: 7562

Synonyms: CS-747 | Effient® | Efient®
Approved drug
prasugrel is an approved drug (FDA and EMA (2009))
Compound class: Synthetic organic
Comment: This drug is metabolised to its active metabolite R-138727.
Marketed formulations may contain prasugrel hydrochloride (PubChem CID 10158453).
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: prasugrel

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 6
Topological polar surface area 74.85
Molecular weight 373.11
XLogP 2.2
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES CC(=O)Oc1sc2c(c1)CN(CC2)C(c1ccccc1F)C(=O)C1CC1
Isomeric SMILES CC(=O)Oc1sc2c(c1)CN(CC2)C(c1ccccc1F)C(=O)C1CC1
InChI 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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Prasugrel is used to prevent to prevent atherothrombotic events in patients with acute coronary syndrome (eg unstable angina, heart attack) undergoing percutaneous coronary intervention. It may also be used in patients with certain disorders of the heart or blood vessels.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
R-138727 is an antagonist of the P2Y12 receptor, which is an adenosine diphosphate (ADP) receptor expressed on platelets. ADP-induced activation of P2Y12 causes platelet aggregation and promotes blood clot formation. Antagonism of ADP binding inhibits these effects.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)