Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1326)
Drug Name
Prasugrel hydrochloride
Synonyms
Prasugrel; Prasugrel (Effient); Prasugrel, 98%; Prasugrel (hydrochloride); Prasugrel HCl; Prasugrel hydrochloride; Prasugren hydrochloride; 2-[2-(Acetyloxy)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl]-1-cyclopropyl-2-(2-fluorophenyl)ethanone Hydrochloride; 389574-19-0; 5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate hydrochloride; DSSTox_CID_28993; DSSTox_GSID_49067; DSSTox_RID_83258; Effient hydrochloride; LY 640315; 150322-43-3; 2-[2-(Acetyloxy)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl]-1-cyclopropyl-2-(2-fluorophenyl)ethanone; 5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate; AK327587; CHEBI:87723; CS 747; CS-747; Ethanone, 2-[2-(acetyloxy)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl]-1-cyclopropyl-2-(2-fluorophenyl)-; Effient; Efient; LY-640315; LY640315; Prasita
Indication Acute coronary syndrome [ICD11: BA4Z] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 409.9 Topological Polar Surface Area 74.8
Heavy Atom Count 27 Rotatable Bond Count 6
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
10158453
CAS Number
389574-19-0
TTD Drug ID
D07IRF
Formula
C20H21ClFNO3S
Canonical SMILES
CC(=O)OC1=CC2=C(S1)CCN(C2)C(C3=CC=CC=C3F)C(=O)C4CC4.Cl
InChI
1S/C20H20FNO3S.ClH/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;1H
InChIKey
JALHGCPDPSNJNY-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
R-95913 DM002895
19919505
Hydrolysis - Esterase Hydrolysis 1 [4] , [5] , [6]
R-138727 DM002896
121230782
Unclear 2 [4] , [5] , [7] , [6]
R-106583 DM002897
69553995
Unclear 3 [4] , [5]
R-119251 DM002898
71751946
Unclear 3 [4] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002091 Prasugrel hydrochloride R-95913 Hydrolysis - Esterase Hydrolysis BCHE [4], [5], [6]
MR002088 R-95913 R-138727 Unclear CYP2B6 ... [4], [5], [7], [6]
MR002089 R-138727 R-106583 Unclear Unclear [4], [5]
MR002090 R-138727 R-119251 Unclear Unclear [4], [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Butyrylcholine esterase (BCHE) DME0069 Homo sapiens
CHLE_HUMAN
3.1.1.8
[2]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
References
1 Prasugrel Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development Curr Med Chem. 2009;16(27):3480-675. doi: 10.2174/092986709789057635.
3 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.
4 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
5 Determination of the active and inactive metabolites of prasugrel in human plasma by liquid chromatography/tandem mass spectrometry Rapid Commun Mass Spectrom. 2007;21(2):169-79. doi: 10.1002/rcm.2813.
6 Pharmacokinetic and Pharmacodynamic Modeling and Simulation Analysis of Prasugrel in Healthy Male Volunteers. Clin Pharmacol Drug Dev. 2023 Jan;12(1):21-29. doi: 10.1002/cpdd.1172.
7 Interactions of fentanyl with blood platelets and plasma proteins: platelet sensitivity to prasugrel metabolite is not affected by fentanyl under in vitro conditions. Pharmacol Rep. 2023 Apr;75(2):423-441. doi: 10.1007/s43440-023-00447-7.

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