TERUTROBAN

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H22ClNO4S
Molecular Weight	407.911
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CC1=C(CCC(O)=O)C2=C(C[C@@H](CC2)NS(=O)(=O)C3=CC=C(Cl)C=C3)C=C1

InChI

InChIKey=HWEOXFSBSQIWSY-MRXNPFEDSA-N

InChI=1S/C20H22ClNO4S/c1-13-2-3-14-12-16(6-9-19(14)18(13)10-11-20(23)24)22-27(25,26)17-7-4-15(21)5-8-17/h2-5,7-8,16,22H,6,9-12H2,1H3,(H,23,24)/t16-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C20H22ClNO4S
Molecular Weight	407.911
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Terutroban (S18886), a specific thromboxane A2 receptor antagonist, which improves endothelial function and has an antiatherosclerotic effect. The compound is under development by Servier for the potential treatment of cardiovascular diseases and coronary artery disease. In addition, it participated in phase III clinical trials PERFORM (Prevention of cerebrovascular and cardiovascular Events of ischemic origin with teRutroban in patients with a history oF ischemic strOke or tRansient ischeMic attack), but this study was stopped, and the result was not achieved.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Thromboxane A2 receptor 19	Antagonist 2,778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Atherothrombosis 2	Preventing		Phase III 656	Unknown
Coronary artery disease 48	Preventing		Not Provided 504	Unknown

C_max

Value	Dose	Analyte	Population
496 ng/mL	10 mg single, oral	TERUTROBAN plasma	Homo sapiens
1480 ng/mL	30 mg single, oral	TERUTROBAN plasma	Homo sapiens
42 ng/mL	1 mg single, oral	TERUTROBAN plasma	Homo sapiens
236 ng/mL	5 mg single, oral	TERUTROBAN plasma	Homo sapiens
124 ng/mL	2.5 mg single, oral	TERUTROBAN plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
3029 ng × h/mL	10 mg single, oral	TERUTROBAN plasma	Homo sapiens
5852 ng × h/mL	30 mg single, oral	TERUTROBAN plasma	Homo sapiens
283 ng × h/mL	1 mg single, oral	TERUTROBAN plasma	Homo sapiens
1023 ng × h/mL	5 mg single, oral	TERUTROBAN plasma	Homo sapiens
495 ng × h/mL	2.5 mg single, oral	TERUTROBAN plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
8 h	10 mg single, oral	TERUTROBAN plasma	Homo sapiens
6.7 h	30 mg single, oral	TERUTROBAN plasma	Homo sapiens
7.4 h	1 mg single, oral	TERUTROBAN plasma	Homo sapiens
6.8 h	5 mg single, oral	TERUTROBAN plasma	Homo sapiens
7.2 h	2.5 mg single, oral	TERUTROBAN plasma	Homo sapiens

Doses

Doses

Show entries

Dose	Population	Adverse events
30 mg 1 times / day multiple, oral Highest studied dose	unhealthy, ADULT

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
1PlusChem LLC	1P001WOH	https://www.1pchem.com/search?query=1P001WOH
Alfa Chemistry	165537-73-5	http://www.alfa-chemistry.com/search.aspx?q=165537-73-5
BLD Pharm	BD630421	http://www.bldpharm.com/search/Search.html?keyword=BD630421
Cayman Chemical	14059	http://www.caymanchem.com/app/template/Product.vm/catalog/14059
Chem Scene	CS-4806	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-4806

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PubMed

PubMed

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Title	Date	PubMed
The Prevention of cerebrovascular and cardiovascular Events of ischemic origin with teRutroban in patients with a history oF ischemic strOke or tRansient ischeMic attack (PERFORM) study: baseline characteristics of the population.	2009	19407444
Rationale and design of a randomized, double-blind, parallel-group study of terutroban 30 mg/day versus aspirin 100 mg/day in stroke patients: the prevention of cerebrovascular and cardiovascular events of ischemic origin with terutroban in patients with a history of ischemic stroke or transient ischemic attack (PERFORM) study.	2009	19372653
[Update on new antithrombotic treatments].	2010 Jan 20	20170027
Thromboxane Antagonism with terutroban in Peripheral Arterial Disease: the TAIPAD study.	2010 Nov	20723034

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Sample Use Guides

In Vivo Use Guide

30 mg/day

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical
Record UNII	A6WX9391D8
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

TERUTROBAN

Official Name

English

3-((6R)-6-(4-CHLOROBENZENESULFONAMIDO)-2-METHYL-5,6,7,8-TETRAHYDRONAPHTHALEN-1-YL)PROPANOIC ACID

Systematic Name

English

Terutroban [WHO-DD]

Common Name

English

terutroban [INN]

Common Name

English

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Classification Tree

Code System

Code

Agent Affecting Blood or Body Fluid

NCI_THESAURUS

C1327

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Code System

Code

Type

Description

EVMPD

SUB23570

PRIMARY

SMS_ID

100000089023

PRIMARY

INN

8452

PRIMARY

EPA CompTox

DTXSID30870091

PRIMARY

MESH

C501362

PRIMARY

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Related Record

Type

Details


					XX7VY52OOD

THROMBOXANE A2 RECEPTOR

TARGET -> INHIBITOR

Amount:


					KP3SN6UT5P

Terutroban sodium

SALT/SOLVATE -> PARENT

Amount:

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Related Record

Type

Details


					A6WX9391D8

TERUTROBAN

ACTIVE MOIETY

Amount:

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SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

Sourcing

PubMed

Sample Use Guides

C_max

T_1/2