SITAXENTAN SODIUM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H14ClN2O6S2.Na
Molecular Weight	476.886
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].CC1=NOC([N-]S(=O)(=O)C2=C(SC=C2)C(=O)CC3=C(C)C=C4OCOC4=C3)=C1Cl

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	454.905
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 2778		0.43 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Pulmonary arterial hypertension 35 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http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/000679/WC500037902.pdf	Primary	Withdrawn	THELIN Approved Use Treatment of patients with pulmonary arterial hypertension (PAH) classified as WHO functional class III, to improve exercise capacity.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 2006
Heart failure 103 Sources: http://adisinsight.springer.com/drugs/800007312	Primary	Phase II 1132	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 2006
Asthma 241 Sources: http://adisinsight.springer.com/drugs/800007312	Primary	Phase II 1132	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 2006

PubMed

Title	Date	PubMed
Emerging medical therapies for pulmonary arterial hypertension.	2002 Nov-Dec	12525997
The endothelin system in pulmonary arterial hypertension.	2004 Feb 1	14736539
Endothelin receptor antagonists.	2006 Jun	16219361
Bosentan in the treatment of pulmonary arterial hypertension with the focus on the mildly symptomatic patient.	2009	19688101
Long term combination treatment for severe idiopathic pulmonary arterial hypertension.	2010 Mar 26	21160759
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.	2013 Nov	23956101

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 `Fri Dec 15 15:59:18 GMT 2023` Edited by `admin` on `Fri Dec 15 15:59:18 GMT 2023`
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)