PRASUGREL

Details

Stereochemistry	RACEMIC
Molecular Formula	C20H20FNO3S
Molecular Weight	373.441
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CC(=O)OC1=CC2=C(CCN(C2)C(C(=O)C3CC3)C4=C(F)C=CC=C4)S1

InChI

InChIKey=DTGLZDAWLRGWQN-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C20H20FNO3S
Molecular Weight	373.441
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

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

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 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	Antagonist 2,778
platelet aggregation 76	Inhibitor 8,297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cardiovascular diseases 71	Preventing		Approved 8,429	EFFIENT

C_max

Value	Dose	Co-administered	Analyte	Population
153.3 ng/mL	20 mg 1 times / day multiple, oral		R-138727 blood	Homo sapiens
163.2 ng/mL	10 mg single, oral		R-138727 plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
178.8 ng × h/mL	20 mg 1 times / day multiple, oral		R-138727 blood	Homo sapiens
163 ng × h/mL	10 mg single, oral		R-138727 plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.5 h	20 mg 1 times / day multiple, oral		R-138727 blood	Homo sapiens
4.2 h	10 mg single, oral		R-138727 plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
20 mg 1 times / day multiple, oral Highest studied dose	healthy, 18–50 years n = 6	Other AEs: Alanine aminotransferase increased...
75 mg single, oral Highest studied dose	healthy, 30.4 years (range: 19.0–48.0 years) n = 5	Other AEs: Dizziness...
10 mg 1 times / day multiple, oral Recommended	unhealthy, ≥ 75 years	Disc. AE: Bleeding...

Showing 1 to 3 of 3 entries

Previous1Next

AEs

Show entries

AE	Significance	Dose	Population
Alanine aminotransferase increased	2 patients	20 mg 1 times / day multiple, oral Highest studied dose	healthy, 18–50 years n = 6
Dizziness	1 patient	75 mg single, oral Highest studied dose	healthy, 30.4 years (range: 19.0–48.0 years) n = 5
Bleeding	grade 5\|severe Disc. AE	10 mg 1 times / day multiple, oral Recommended	unhealthy, ≥ 75 years

Showing 1 to 3 of 3 entries

Previous1Next

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737	substrate 1,037 inhibitor 1,767	inhibitor 1,852	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1,461 CYP1A2 1,524 CYP2C19 1,478 CYP3A 214 CYP2B6 810	CYP2B6 664 CYP2C19 991 CYP3A5 395	CYP1A2 701 CYP3A 129

Drug as perpetrator

Show entries

Target	Modality	Activity
P-gp 1,650	inhibitor 3,277	no
CYP1A2 1,692	inducer 1,573	unlikely
CYP1A2 1,692	inhibitor 3,277	unlikely
CYP2C19 1,553	inhibitor 3,277	unlikely
CYP2C9 1,819	inhibitor 3,277	unlikely

Showing 1 to 5 of 9 entries

Previous1 2Next

Drug as victim

Show entries

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2B6 664	substrate 3,367	major		no (co-administration study)
CYP3A4 1,737	substrate 3,367	major		no (co-administration study)
CYP2C19 991	substrate 3,367	minor		no (co-administration study)
CYP2C9 1,037	substrate 3,367	minor		no (co-administration study)
CYP2B6 664	substrate 3,367	no	R-138727 6	no (pharmacogenomic study)

Showing 1 to 5 of 8 entries

Previous1 2Next

Tox targets

Show entries

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626		R-138727 6

Showing 1 to 1 of 1 entries

Previous1Next

Sourcing

Sourcing

Show entries

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
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

Showing 1 to 5 of 75 entries

Previous1 2 3 4 5…15Next

PubMed

Show entries

Title	Date	PubMed
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

Showing 1 to 4 of 4 entries

Previous1Next

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
Record UNII	34K66TBT99
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

PRASUGREL

Official Name

English

NSC-759625

Code

English

prasugrel [INN]

Common Name

English

Prasugrel [WHO-DD]

Common Name

English

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

Systematic Name

English

Showing 1 to 5 of 13 entries

Previous1 2 3Next

Show entries

Classification Tree

Code System

Code

Established Pharmacologic Class

NDF-RT

N0000182142

Antiplatelet Agent

NCI_THESAURUS

C80483

Platelet aggregation inhibitors excl. heparin

WHO-ATC

B01AC22

Platelet aggregation inhibitors, excl. heparin

WHO-VATC

QB01AC22

Showing 1 to 4 of 4 entries

Previous1Next

Show entries

Code System

Code

Type

Description

LACTMED

Prasugrel

PRIMARY

ChEMBL

CHEMBL1201772

PRIMARY

RXCUI

613391

PRIMARY

RxNorm

DRUG BANK

DB06209

PRIMARY

NCI_THESAURUS

C81566

PRIMARY

Showing 1 to 5 of 22 entries

Previous1 2 3 4 5Next

Show entries

Related Record

Type

Details


					4XFT5Y771R

PRASUGREL HYDROBROMIDE

SALT/SOLVATE -> PARENT


					G89JQ59I13

PRASUGREL HYDROCHLORIDE

SALT/SOLVATE -> PARENT


					K9GA2EPK9H

PRASUGREL SULFATE

SALT/SOLVATE -> PARENT


					6LC6AG47OY

PRASUGREL, (S)-

ENANTIOMER -> RACEMATE


					VC4YSF7KNU

PRASUGREL MALEATE

SALT/SOLVATE -> PARENT

Showing 1 to 5 of 8 entries

Previous1 2Next

Show entries

Related Record

Type

Details


					FLN02B3F1J

R-138727

METABOLITE ACTIVE -> PRODRUG

Interaction Type:

MAJOR

Qualification:

PLASMA

Amount:

122 ng-hour/mL (average)


					1F19E6097Q

PRASUGREL DESACETYL

METABOLITE INACTIVE -> PARENT


					FLN02B3F1J

R-138727

METABOLITE ACTIVE -> PRODRUG

Interaction Type:

MAJOR

Qualification:

PLASMA

Amount:

122 ng-hour/mL (average)


					FLN02B3F1J

R-138727

METABOLITE ACTIVE -> PRODRUG

Interaction Type:

MAJOR

Qualification:

PLASMA

Amount:

122 ng-hour/mL (average)


					FLN02B3F1J

R-138727

METABOLITE ACTIVE -> PRODRUG

Interaction Type:

MAJOR

Qualification:

PLASMA

Amount:

122 ng-hour/mL (average)

Showing 1 to 5 of 5 entries

Previous1Next

Show entries

Related Record

Type

Details


					34K66TBT99

PRASUGREL

ACTIVE MOIETY

Showing 1 to 1 of 1 entries

Previous1Next

Name	Property Type	Amount
Biological Half-life	PHARMACOKINETIC	7 hours (average)

Volume of Distribution	PHARMACOKINETIC	[0.63 to 0.97] Liters/Kilogram (average)

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator