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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 of SITAXENTAN SODIUM

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.43 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Primary
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
Primary
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

PubMed

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

Patents

Sample Use Guides

Thelin is to be taken orally as a dose of 100 mg once daily.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment:: Treatment of cultured mesangial cells with endothelin-1 activates the formation of drebrin-positive actin microspikes. These microspikes do not form when cells are treated with the endothelin A receptor antagonist sitaxentan or under conditions of small, interfering RNA knockdown of endothelin A receptor mRNA.
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
  • Download
Name Type Language
SITAXENTAN SODIUM
EMA EPAR   USAN   WHO-DD  
USAN  
Official Name English
SITAXENTAN SODIUM [EMA EPAR]
Common Name English
SITAXSENTAN SODIUM SALT
MI  
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)
Created by admin on Sat Jun 26 08:21:23 UTC 2021 , Edited by admin on Sat Jun 26 08:21:23 UTC 2021
FDA ORPHAN DRUG 180803
Created by admin on Sat Jun 26 08:21:23 UTC 2021 , Edited by admin on Sat Jun 26 08:21:23 UTC 2021
EU-Orphan Drug EU/3/04/234
Created by admin on Sat Jun 26 08:21:23 UTC 2021 , Edited by admin on Sat Jun 26 08:21:23 UTC 2021
Code System Code Type Description
MERCK INDEX
M9962
Created by admin on Sat Jun 26 08:21:23 UTC 2021 , Edited by admin on Sat Jun 26 08:21:23 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL282724
Created by admin on Sat Jun 26 08:21:23 UTC 2021 , Edited by admin on Sat Jun 26 08:21:23 UTC 2021
PRIMARY
CAS
210421-74-2
Created by admin on Sat Jun 26 08:21:23 UTC 2021 , Edited by admin on Sat Jun 26 08:21:23 UTC 2021
PRIMARY
DRUG BANK
DBSALT001120
Created by admin on Sat Jun 26 08:21:23 UTC 2021 , Edited by admin on Sat Jun 26 08:21:23 UTC 2021
PRIMARY
FDA UNII
6V9JH46E20
Created by admin on Sat Jun 26 08:21:23 UTC 2021 , Edited by admin on Sat Jun 26 08:21:23 UTC 2021
PRIMARY
PUBCHEM
11477084
Created by admin on Sat Jun 26 08:21:23 UTC 2021 , Edited by admin on Sat Jun 26 08:21:23 UTC 2021
PRIMARY
EVMPD
SUB22351
Created by admin on Sat Jun 26 08:21:23 UTC 2021 , Edited by admin on Sat Jun 26 08:21:23 UTC 2021
PRIMARY
NCI_THESAURUS
C152373
Created by admin on Sat Jun 26 08:21:23 UTC 2021 , Edited by admin on Sat Jun 26 08:21:23 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY