PRASUGREL HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C20H20FNO3S.ClH
Molecular Weight	409.902
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CC(=O)OC1=CC2=C(CCN(C2)C(C(=O)C3CC3)C4=CC=CC=C4F)S1

InChI

InChIKey=JALHGCPDPSNJNY-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C20H20FNO3S
Molecular Weight	373.441
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.drugbank.ca/drugs/DB06209
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022307s002lbl.pdf

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 thus preventing activation of the GPIIb/IIIa receptor complex. As a result, inhibition of ADP-mediated platelet activation and aggregation occurs. Prasugrel was developed by Daiichi Sankyo Co. and is currently marketed under the brand name EFFIENT in the United States and Canada in cooperation with Eli Lilly and Company for acute coronary syndromes planned for percutaneous coronary intervention (PCI). FDA approved in 2009.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Purinergic receptor P2Y12 23 Target ID: CHEMBL2001 Sources: http://www.drugbank.ca/drugs/DB06209 \| http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022307s002lbl.pdf	Antagonist 2849
platelet aggregation 80 Target ID: GO:0070527 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18485086	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cardiovascular diseases 72 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022307s002lbl.pdf	Preventing		Approved 8583	EFFIENT Approved Use Acute Coronary Syndrome Effient is indicated to reduce the rate of thrombotic cardiovascular (CV) events (including stent thrombosis) in patients with acute coronary syndrome (ACS) who are to be managed with percutaneous coronary intervention (PCI) as follows: • Patients with unstable angina (UA) or non-ST-elevation myocardial infarction (NSTEMI). • Patients with ST-elevation myocardial infarction (STEMI) when managed with primary or delayed PCI. Launch Date 2009

C_max

Value	Dose	Co-administered	Analyte	Population
163.2 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27474356	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		R-138727 plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
153.3 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28417436	20 mg 1 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:		R-138727 blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
163 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27474356	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		R-138727 plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
178.8 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28417436	20 mg 1 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:		R-138727 blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.2 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27474356	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		R-138727 plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.5 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28417436	20 mg 1 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:		R-138727 blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193 inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741 CYP1A2 2153 CYP2C19 2057 CYP3A 227 CYP2B6 926	CYP2B6 776 CYP2C19 1119 CYP3A5 446	CYP1A2 832 CYP3A 142

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022307s000_ClinPharmR_p3.pdf#PAGE=5 Page: 5.0	no
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=13 Page: 13.0	unlikely
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=13 Page: 13.0	unlikely
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=13 Page: 13.0	unlikely
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=13 Page: 13.0	unlikely
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=13 Page: 13.0	unlikely
CYP3A 317	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=13 Page: 13.0	unlikely
CYP3A 317	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=13 Page: 13.0	unlikely
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=13 Page: 13.0	weak	weak (co-administration study) Comment: prasugrel decreased exposure to hydroxybupropion, a CYP2B6-mediated metabolite of bupropion, by 23% Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=13 Page: 13.0

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2B6 776	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=12 Page: 12.0	major		no (co-administration study) Comment: administration with rifampicin (CYP2B6 inducer) did not significantly change its inhibtion of platelet aggregation Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=12 Page: 12.0
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=12 Page: 12.0	major		no (co-administration study) Comment: administration with ketoconazole (inhibitor) and atorvastatin (CYP3A4 substrate) did not affect prasugrel-mediated inhibition of platelet aggregation Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=12 Page: 12.0
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=12 Page: 12.0	minor		no (co-administration study) Comment: administration with rifampicin (CYP2C19 inducer) did not significantly change its inhibtion of platelet aggregation Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=12 Page: 12.0
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=12 Page: 12.0	minor		no (co-administration study) Comment: administration with rifampicin (CYP2C9 inducer) did not significantly change its inhibtion of platelet aggregation Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=12 Page: 12.0
CYP2B6 776	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=13 Page: 13.0	no	R-138727 6	no (pharmacogenomic study) Comment: There is no relevant effect of genetic variation on the pharmacokinetics of prasugrel’s active metabolite or its inhibition of platelet aggregation Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=13 Page: 13.0
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=13 Page: 13.0	no	R-138727 6	no (pharmacogenomic study) Comment: There is no relevant effect of genetic variation on the pharmacokinetics of prasugrel’s active metabolite or its inhibition of platelet aggregation Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=13 Page: 13.0
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=13 Page: 13.0	no	R-138727 6	no (pharmacogenomic study) Comment: There is no relevant effect of genetic variation on the pharmacokinetics of prasugrel’s active metabolite or its inhibition of platelet aggregation Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=13 Page: 13.0
CYP3A5 446	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=13 Page: 13.0	no	R-138727 6	no (pharmacogenomic study) Comment: There is no relevant effect of genetic variation on the pharmacokinetics of prasugrel’s active metabolite or its inhibition of platelet aggregation Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022307s018lbl.pdf#page=13 Page: 13.0

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022307s000_Pharm_P2.pdf#page=3 Page: 3.0		R-138727 6

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY525916	https://www.001chemical.com/chem/150322-43-3
AA Blocks	AA001MFU	https://www.aablocks.com/goods/Goods/detail?id=AA001MFU
Aaron Chemicals	AR001N7M	http://www.aaronchem.com/150322-43-3
abcr GmbH	AB450331	http://www.abcr.com/shop/en/AB450331
AbMole Bioscience	M2234	http://www.abmole.com/products/prasugrel.html
Acadechem	ACDC-070957	http://acadechemical.com/product/11527
Aceschem	ACF023082	https://www.aceschem.com/catalog/150322-43-3.html
Achemo Scientific Limited	AC-35132	http://www.achemo.com/search/?Keyword= 150322-43-3
Achemtek	0102-024105	http://www.achemtek.com/150322-43-3
Acorn PharmaTech	ACN-040194	http://www.acornpharmatech.com/
Acros Organics	AC461480010	https://www.fishersci.com/shop/products/prasugrel-98-acros-organics-1/AC461480010
Acros Organics	AC461482500	https://www.fishersci.com/shop/products/prasugrel-98-acros-organics/AC461482500
Active Biopharma	ABP000379	http://www.activebiopharma.com/150322-43-3
AEchem Scientific Corp., USA	AE045579	http://www.aechemsc.com/info_products/AE045579.php
AHH Chemical co.,ltd	MT-58137	http://www.ahhchemical.com/product/MT-58137.html
AK Scientific, Inc. (AKSCI)	W0064	http://www.aksci.com/item_detail.php?cat=W0064
Alfa Chemistry	ACM150322433	https://www.alfa-chemistry.com/prasugrel-cas-150322-43-3-item-321833.htm
Alfa Chemistry	AP150322433	https://reagents.alfa-chemistry.com/product/prasugrel-cas-150322-43-3-5401.html
Alsachim	1595	http://www.alsachim.com/product-C2280-glo.bal-view.html
Ambeed	A125835	https://www.ambeed.com/products/150322-43-3.html
Ambinter	Amb15691578	http://www.ambinter.com/reference/15691578
Angel Pharmatech	AG202427	http://www.angelpharmatech.com/150322-43-3.html
Angene	AGN-PC-0Q4L5L	http://www.angenechemical.com/productshow/AGN-PC-0Q4L5L.html
Ark Pharm	AK327587	http://www.arkpharminc.com/products/150322-43-3.html
AstaTech, Inc.	FD7194	http://www.astatechinc.com/CPSResult.php?CRNO=37284
Aurora Fine Chemicals LLC	A17.863.172	http://online.aurorafinechemicals.com/info?ID=A17.863.172
Aurum Pharmatech LLC	Q-1607	http://www.Aurumpharmatech.com/Product/ProductDetails/Q_1607
AvaChem Scientific	2449B	http://www.avachem.com/productSearch.asp?2449B
Avantor Inc	TCP2040-200MG	https://us.vwr.com/store/product/16814123/prasugrel-98-0-by-hplc-titration-analysis
BioChemPartner	BCP01882	http://www.biochempartner.com/150322-43-3-BCP01882
BioCrick	BCC1089	http://www.biocrick.com/Prasugrel-BCC1089.html
BioSynth	Q-101872	https://www.biosynth.com/en/products/chemical-intermediates/advanced-intermediates/products/Q-101872.html
BLD Pharm	BD32021	http://www.bldpharm.com/products/150322-43-3.html
BOC Sciences	1189919-49-0	https://isotope.bocsci.com/product/prasugrel-d5-cas-1189919-49-0-350962.html
Boerchem	BC683564	http://www.boerchem.com/?product_40161.html
Capot Chemical	19523	http://www.capotchem.com/en/19523.htm
Capot Chemical	PubChem19523	http://www.capotchem.com/en/19523.htm
Chem Scene	CS-0657	http://www.chemscene.com/150322-43-3.html
ChemMol	30108479	http://www.chemmol.com/chemmol/30108479.html
ChemMol	44011139	http://www.chemmol.com/chemmol/44011139.html
ChemMol	49400037	http://www.chemmol.com/chemmol/49400037.html
ChemMol	99047007	http://www.chemmol.com/chemmol/99047007.html
ChemShuttle	141148	http://www.chemshuttle.com/catalogsearch/result/?q=150322-43-3&cat=
ChemShuttle	ZB0747	https://www.chemshuttle.com/catalogsearch/result/?q=150322-43-3&cat=
Chemspace	CSSB00015187897	https://chem-space.com/CSSB00015187897
Clearsynth	CS-O-02724	https://www.clearsynth.com/en/CSO02724.html
Clearsynth	CS-O-14426	http://www.clearsynth.com/en/CSO14426.html
Clearsynth	CS-O-32324	https://www.clearsynth.com/en/CSO32324.html
CSNpharm	CSN16171	https://www.csnpharm.com/products/prasugrel.html
DAOGE BIOPHARMA	DG21-10697	https://www.daogechem.com/product/150322-43-3.html
DC Chemicals	DC3161	http://www.dcchemicals.com/product_show-Prasugrel.html
Finetech	FT-0650150	http://www.finetechnology-ind.com/prod/detail/pub/150322-43-3.html
Glentham Life Sciences	GP4257	http://www.glentham.com/products/product/GP4257/
Hairui	HR133591	http://www.hairuichem.com/en/product/150322-43-3.html
iChemical	EBD811	http://www.ichemical.com/products/150322-43-3.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00449136	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00449136
Matrix Scientific	125313	https://www.matrixscientific.com/125313.html
mcule	MCULE-1302242257	https://mcule.com/MCULE-1302242257/
MedChem Express	HY-15284	https://www.medchemexpress.com/prasugrel.html
Molcore	MC525916	https://www.molcore.com/product/150322-43-3
MuseChem	I001860	https://www.musechem.com/product/I001860.html
OChem	24475	http://www.ocheminc.com/index.php?act=psearch&pid=322P433
Renno Tech	RL01920	http://www.rennotech.com/product_show.asp?id=2169
Selleck Chemicals	S1258	http://www.selleckchem.com/products/Prasugrel.html
Sigma-Aldrich	SML0331_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/sml0331?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S540126	http://www.smolecule.com/products/s540126
Specs	AR-270/43507998	http://www.specs.net/enter.php?specsid=AR-270/43507998
Synblock Inc	PB23765	http://www.synblock.com/product/389574-19-0.html
Synblock Inc	SB20805	http://www.synblock.com/product/150322-43-3.html
TCI (Tokyo Chemical Industry)	P2040	http://www.tcichemicals.com/eshop/en/us/commodity/P2040/index.html
THE BioTek	bt-279672	https://www.thebiotek.com/product/inhibitors/bt-279672
Tocris	6317	https://www.tocris.com/products/prasugrel_6317
TripleBond	CP0097	http://www.triplebond-canada.com/prod/1526/
VladaChem	VL279226-10mg	https://www.vladachem.com/product.php?products=150322-43-3
Yuhao Chemical	YH36014	http://www.chemyuhao.com/150322-43-3.html

PubMed

Title	Date	PubMed
Ticagrelor and prasugrel: two novel, most-promising antiplatelet agents.	2010 Nov	20874669
Importance of potent P2Y(12) receptor blockade in acute myocardial infarction: focus on prasugrel.	2012 Aug	22783896
Nonclinical assessment of carcinogenic risk and tumor growth enhancement potential of prasugrel, a platelet-inhibiting therapeutic agent.	2012 Jul-Aug	22692976
The evolution of antiplatelet therapy in the treatment of acute coronary syndromes: from aspirin to the present day.	2012 Nov 12	23083110
Toxicity of thienopyridines on human neutrophil granulocytes and lymphocytes.	2013 Jun 7	23499857

Patents

Sample Use Guides

In Vivo Use Guide

Initiate treatment with a single 60 mg oral loading dose. • Continue at 10 mg once daily with or without food. Consider 5 mg once daily for patients < 60 kg

Route of Administration: Oral

In Vitro Use Guide

Prasugrel used at aconcentration of 10 uM markedly inhibited P-selectin expression on human blood platelets induced by 10 uM ADP

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:31:11 GMT 2025` Edited by `admin` on `Mon Mar 31 18:31:11 GMT 2025`
Record UNII	G89JQ59I13
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EFFIENT

Preferred Name

English

PRASUGREL HYDROCHLORIDE

Official Name

English

ETHANONE, 2-(2-(ACETYLOXY)-6,7-DIHYDROTHIENO(3,2-C)PYRIDIN-5(4H)-YL)-1-CYCLOPROPYL-2-(2-FLUOROPHENYL)-, HYDROCHLORIDE (1:1)

Systematic Name

English

Prasugrel Hydrochloride [WHO-DD]

Common Name

English

PRASUGREL HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

PRASUGREL HYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

PRASU DOC

Brand Name

English

PRASUGREL HYDROCHLORIDE [USAN]

Common Name

English

PRASUGREL HYDROCHLORIDE [USP-RS]

Common Name

English

ETHANONE, 2-(2-(ACETYLOXY)-6,7-DIHYDROTHIENO(3,2-C)PYRIDIN-5(4H)-YL)-1-CYCLOPROPYL-2-(2-FLUOROPHENYL), HYDROCHLORIDE

Common Name

English

PRASUGREL HYDROCHLORIDE [VANDF]

Common Name

English

PRASUGREL HCL

Common Name

English

PRASUGREL HYDROCHLORIDE [MI]

Common Name

English

EFIENT

Brand Name

English

PRASUGREL HYDROCHLORIDE [MART.]

Common Name

English

PRASUGREL HYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

2-ACETOXY-5-(.ALPHA.-CYCLOPROPYLCARBONYL-2-FLUOROBENZYL)-4,5,6,7-TETRAHYDROTHIENO(3,2-C)PYRIDINE HYDROCHLORIDE

Systematic Name

English

LY640315

Code

English

PRASUGREL HYDROCHLORIDE [JAN]

Common Name

English

5-((1RS)-2-CYCLOPROPYL-1-(2-FLUOROPHENYL)-2-OXOETHYL)-4,5,6,7-TETRAHYDROTHIENO(3,2-C)PYRIDIN-2-YL ACETATE HYDROCHLORIDE

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

473015