TERUTROBAN

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

Structure Search

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

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12498008 | https://www.ncbi.nlm.nih.gov/pubmed/20490906

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 Target ID: P21731 Gene ID: 6915.0 Gene Symbol: TBXA2R Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12498008	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Atherothrombosis 2 Sources: http://clinicaltrials.servier.com/wp-content/uploads/CL3-18886-012_synopsis_report.pdf	Preventing		Phase III 656	Unknown Approved Use Unknown
Coronary artery disease 48 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12498008	Preventing		Not Provided 504	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
236 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	TERUTROBAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
42 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	TERUTROBAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
496 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	TERUTROBAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
124 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101	2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered:	TERUTROBAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
1480 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	TERUTROBAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
1023 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	TERUTROBAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
283 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	TERUTROBAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
3029 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	TERUTROBAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
495 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101	2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered:	TERUTROBAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
5852 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	TERUTROBAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
6.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	TERUTROBAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
7.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	TERUTROBAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	TERUTROBAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
7.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101	2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered:	TERUTROBAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
6.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	TERUTROBAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
30 mg 1 times / day multiple, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15978101 Page: p.1442	unhealthy, ADULT n = 6 Health Status: unhealthy Condition: peripheral artery disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/15978101 Page: p.1442	Sources: https://pubmed.ncbi.nlm.nih.gov/15978101 Page: p.1442

Sourcing

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
MedChem Express	HY-16991	https://www.medchemexpress.com/search.html?q=HY-16991&ft=&fa=&fp=
MolPort	MolPort-039-101-327	https://www.molport.com/shop/molecule-link/MolPort-039-101-327
Molnova	M12526	https://www.molnova.com/en/serch-list.html?keywords=M12526
MuseChem	I012178	https://www.musechem.com/product/I012178.html
MuseChem	M035092	https://www.musechem.com/product/M035092.html
Tocris	5568	https://www.tocris.com/search.php?Type=QuickSearch&Value=5568
Toronto Research Chemicals	E925683	https://www.trc-canada.com/product-detail/?CatNum=E925683
Toronto Research Chemicals	T116705	https://www.trc-canada.com/product-detail/?CatNum=T116705
eMolecules	49260724	https://orderbb.emolecules.com/search/#?query=49260724
eMolecules	64090119	https://orderbb.emolecules.com/search/#?query=64090119
eNovation Chemicals	D548040	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D548040&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-3371926949	https://mcule.com/MCULE-3371926949/
mcule	MCULE-8884448347	https://mcule.com/MCULE-8884448347/

PubMed

Title	Date	PubMed
Synthesis and biological evaluation of new tetrahydronaphthalene derivatives as thromboxane receptor antagonists.	1998 Jun 2	9871769
[Terutroban and endothelial TP receptors in atherogenesis].	2006 Apr	16597416
The thromboxane receptor antagonist S18886 attenuates renal oxidant stress and proteinuria in diabetic apolipoprotein E-deficient mice.	2006 Jan	16380483
Experimental models of thrombosis and atherosclerosis.	2006 Sep-Oct	17243266
Increased spontaneous tone in renal arteries of spontaneously hypertensive rats.	2007 Sep	17557920
The role of prostaglandin E and thromboxane-prostanoid receptors in the response to prostaglandin E2 in the aorta of Wistar Kyoto rats and spontaneously hypertensive rats.	2008 Apr 1	18093985
Two isoforms of cyclooxygenase contribute to augmented endothelium-dependent contractions in femoral arteries of 1-year-old rats.	2008 Feb	18215347
Antiplatelet therapy for secondary prevention of noncardioembolic ischemic stroke: a critical review.	2008 May	18369175
Negative effects of rofecoxib treatment on cardiac function after ischemia-reperfusion injury in APOE3Leiden mice are prevented by combined treatment with thromboxane prostanoid-receptor antagonist S18886 (terutroban).	2008 Sep	18679128
Hypertension and the absence of EDHF-mediated responses favour endothelium-dependent contractions in renal arteries of the rat.	2008 Sep	18574459
Effect of the thromboxane prostaglandin receptor antagonist terutroban on arterial thrombogenesis after repeated administration in patients treated for the prevention of ischemic stroke.	2009	19752552
Rationale and design of 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	19439938
TP receptor antagonism: a new concept in atherothrombosis and stroke prevention.	2009	19439937
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
New antiplatelet agents: why they are needed.	2009 Dec	19892299
Update on oral antiplatelet therapy: principles, problems and promises.	2009 May	19450051
New antiplatelet agents.	2009 Sep	19587588
Emerging antiplatelet agents, differential pharmacology, and clinical utility.	2010	22282687
Rationale, design and population baseline characteristics of the PERFORM vascular project: an ancillary study of 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) trial.	2010 Apr	20490906
Pharmacokinetic, pharmacodynamic and clinical profile of novel antiplatelet drugs targeting vascular diseases.	2010 Feb 1	20050853
[Update on new antithrombotic treatments].	2010 Jan 20	20170027
Terutroban, a thromboxane/prostaglandin endoperoxide receptor antagonist, increases survival in stroke-prone rats by preventing systemic inflammation and endothelial dysfunction: comparison with aspirin and rosuvastatin.	2010 Jul	20332187
Novel antiplatelet agents in the prevention of cardiovascular complications--focus on ticagrelor.	2010 Jun 1	20539844
Antiplatelet drugs--do we need new options? With a reappraisal of direct thromboxane inhibitors.	2010 May 7	20426498
Thromboxane Antagonism with terutroban in Peripheral Arterial Disease: the TAIPAD study.	2010 Nov	20723034
Controversies and future perspectives of antiplatelet therapy in secondary stroke prevention.	2010 Oct	20738445

Sample Use Guides

In Vivo Use Guide

30 mg/day

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:33:20 GMT 2023` Edited by `admin` on `Fri Dec 15 16:33:20 GMT 2023`
Record UNII	A6WX9391D8
Record Status	`Validated (UNII)`
Record Version

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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

Classification Tree Code System Code

NCI_THESAURUS

C1327