SITAXENTAN SODIUM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H14ClN2O6S2.Na
Molecular Weight	476.8891
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cc1cc2c(cc1CC(=O)c3c(ccs3)S(=O)(=O)N=c4c(c(C)[n-]o4)Cl)OCO2.[Na+]

InChI

InChIKey=MDTNUYUCUYPIHE-UHFFFAOYSA-N

InChI=1S/C18H14ClN2O6S2.Na/c1-9-5-13-14(26-8-25-13)7-11(9)6-12(22)17-15(3-4-28-17)29(23,24)21-18-16(19)10(2)20-27-18;/h3-5,7H,6,8H2,1-2H3;/q-1;+1

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

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

Molecular Formula	C18H15ClN2O6S2
Molecular Weight	454.9073
Charge	0
Count

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

Description
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/000679/WC500037902.pdf
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/9171878 | http://adisinsight.springer.com/drugs/800007312 | http://www.pfizer.com/news/press-release/press-release-detail/pfizer_stops_clinical_trials_of_thelin_and_initiates_voluntary_product_withdrawal_in_the_interest_of_patient_safety

Sitaxentan (TBC11251, trade name Thelin) is a potent and selective Endothelin A receptor antagonist. Sitaxentan was under development by Encysive Pharmaceuticals (now Pfizer) for use in the treatment of pulmonary hypertension, congestive heart failure and asthma. It was launched in the major markets of the European Union (EU) under name Thelin for the treatment of pulmonary arterial hypertension. In December 2010, Pfizer discontinued clinical trials of sitaxentan worldwide and initiated voluntary product withdrawal from markets where it is approved due to life-threatening idiosyncratic risk of liver injury.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Endothelin receptor ET-A 19 Target ID: CHEMBL252 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9171878/	Antagonist 2575		0.43 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Pulmonary arterial hypertension 34 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/000679/WC500037902.pdf	Primary	Withdrawn	THELIN Approved Use Treatment of patients with pulmonary arterial hypertension (PAH) classified as WHO functional class III, to improve exercise capacity. Efficacy has been shown in primary pulmonary hypertension and in pulmonary hypertension associated with connective tissue disease. Launch Date 1.16017922E12
Heart failure 83 Sources: http://adisinsight.springer.com/drugs/800007312	Primary	Phase II 1101	THELIN Approved Use Treatment of patients with pulmonary arterial hypertension (PAH) classified as WHO functional class III, to improve exercise capacity. Efficacy has been shown in primary pulmonary hypertension and in pulmonary hypertension associated with connective tissue disease. Launch Date 1.16017922E12
Asthma 227 Sources: http://adisinsight.springer.com/drugs/800007312	Primary	Phase II 1101	THELIN Approved Use Treatment of patients with pulmonary arterial hypertension (PAH) classified as WHO functional class III, to improve exercise capacity. Efficacy has been shown in primary pulmonary hypertension and in pulmonary hypertension associated with connective tissue disease. Launch Date 1.16017922E12

PubMed

Title	Date	PubMed
Pulmonary arterial hypertension associated to connective tissue diseases.	2005	16218473
Endothelin receptor antagonists.	2006 Jun	16219361
Therapeutic targets in systemic sclerosis.	2007	17767744
[Treatment of pulmonary arterial hypertension by endothelin receptor antagonists in 2008].	2008 Apr	18243424
The management of pulmonary hypertension in children.	2008 Jul	18381346
[Systemic sclerosis].	2008 May	18552072
[Specific drugs for the treatment of pulmonary arterial hypertension - current status].	2008 Oct	18814092
Successful treatment of systemic-sclerosis-related digital ulcers with a selective endothelin type A receptor antagonist (sitaxentan).	2009	19590168
Interaction of acenocoumarol and sitaxentan in pulmonary arterial hypertension.	2009 Jun	19335742
Integrated care and optimal management of pulmonary arterial hypertension.	2009 May 12	21197349
Early intervention in pulmonary arterial hypertension associated with systemic sclerosis: an essential component of disease management.	2010 Dec	21119190
Clinical experience with bosentan and sitaxentan in connective tissue disease-associated pulmonary arterial hypertension.	2010 Nov	20675359

Patents

Sample Use Guides

In Vivo Use Guide

Thelin is to be taken orally as a dose of 100 mg once daily.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Jun 26 08:21:22 UTC 2021` Edited by `admin` on `Sat Jun 26 08:21:22 UTC 2021`
Record UNII	6V9JH46E20
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SITAXENTAN SODIUM

Official Name

English

SITAXENTAN SODIUM [EMA EPAR]

Common Name

English

SITAXSENTAN SODIUM SALT

Common Name

English

SITAXSENTAN SODIUM SALT [MI]

Common Name

English

TBC-11251 SODIUM

Code

English

TBC-11251NA

Code

English

SITAXENTAN SODIUM [WHO-DD]

Common Name

English

TBC-11251Z

Code

English

THELIN

Common Name

English

N-(4-CHLORO-3-METHYL-1,2-OXAZOL-5-YL)-2-(2-(6-METHYL-2H-1,3-BENZODIOXOL-5-YL)ACETYL)THIOPHENE-3-SULFONAMIDE SODIUM SALT

Common Name

English

SITAXENTAN SODIUM [USAN]

Common Name

English

3-THIOPHENESULFONAMIDE, N-(4-CHLORO-3-METHYL-5-ISOXAZOLYL)-2-(2-(6-METHYL-1,3-BENZODIOXOL-5-YL)ACETYL)-, SODIUM SALT (1:1)

Systematic Name

English

SITAXSENTAN SODIUM

Common Name

English

Classification Tree Code System Code

EMA ASSESSMENT REPORTS

THELIN (AUTHORIZED: HYPERTENSION, PULMONARY)