U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C18H15ClN2O6S2
Molecular Weight 454.905
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SITAXENTAN

SMILES

CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)CC3=C(C)C=C4OCOC4=C3)=C1Cl

InChI

InChIKey=PHWXUGHIIBDVKD-UHFFFAOYSA-N
InChI=1S/C18H15ClN2O6S2/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/h3-5,7,21H,6,8H2,1-2H3

HIDE SMILES / InChI

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
Inhibition of endothelin receptors in the treatment of pulmonary arterial hypertension: does selectivity matter?
2008 Aug
Sitaxentan: new drug. Pulmonary hypertension: better to continue to use bosentan.
2008 Jun
[Systemic sclerosis].
2008 May
Pulmonary arterial hypertension: on the way to a manageable disease.
2008 Sep
Small-molecule endothelin receptor antagonists: a review of patenting activity across therapeutic areas.
2009 Jun
Bleeding events in pulmonary arterial hypertension.
2009 Jun
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.
2013 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
Name Type Language
SITAXENTAN
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
IPI-1040
Code English
sitaxentan [INN]
Common Name English
SITAXSENTAN
MI  
Common Name English
SITAXENTAN [USAN]
Common Name English
TBC-11251
Code English
N-(4-CHLORO-3-METHYL-5-ISOXAZOLYL)-2-(3,4-(METHYLENEDIOXY)-6-METHYL)PHENYLACETYL-3-THIOPHENESULFONAMIDE
Common Name English
Sitaxentan [WHO-DD]
Common Name English
N-(4-CHLORO-3-METHYL-5-ISOXAZOLYL)-2-((4,5-(METHYLENEDIOXY)-O-TOLY)ACETYL)-3-THIOPHENESULFONAMIDE
Common Name English
SITAXSENTAN [MI]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 793420
Created by admin on Thu Jul 06 23:04:04 UTC 2023 , Edited by admin on Thu Jul 06 23:04:04 UTC 2023
WHO-ATC C02KX03
Created by admin on Thu Jul 06 23:04:04 UTC 2023 , Edited by admin on Thu Jul 06 23:04:04 UTC 2023
WHO-VATC QC02KX03
Created by admin on Thu Jul 06 23:04:04 UTC 2023 , Edited by admin on Thu Jul 06 23:04:04 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID0057673
Created by admin on Thu Jul 06 23:04:04 UTC 2023 , Edited by admin on Thu Jul 06 23:04:04 UTC 2023
PRIMARY
MESH
C106276
Created by admin on Thu Jul 06 23:04:04 UTC 2023 , Edited by admin on Thu Jul 06 23:04:04 UTC 2023
PRIMARY
NCI_THESAURUS
C73038
Created by admin on Thu Jul 06 23:04:04 UTC 2023 , Edited by admin on Thu Jul 06 23:04:04 UTC 2023
PRIMARY
WIKIPEDIA
Sitaxentan
Created by admin on Thu Jul 06 23:04:04 UTC 2023 , Edited by admin on Thu Jul 06 23:04:04 UTC 2023
PRIMARY
ChEMBL
CHEMBL282724
Created by admin on Thu Jul 06 23:04:04 UTC 2023 , Edited by admin on Thu Jul 06 23:04:04 UTC 2023
PRIMARY
DRUG BANK
DB06268
Created by admin on Thu Jul 06 23:04:04 UTC 2023 , Edited by admin on Thu Jul 06 23:04:04 UTC 2023
PRIMARY
INN
7952
Created by admin on Thu Jul 06 23:04:04 UTC 2023 , Edited by admin on Thu Jul 06 23:04:04 UTC 2023
PRIMARY
EVMPD
SUB22917
Created by admin on Thu Jul 06 23:04:04 UTC 2023 , Edited by admin on Thu Jul 06 23:04:04 UTC 2023
PRIMARY
DRUG CENTRAL
3548
Created by admin on Thu Jul 06 23:04:04 UTC 2023 , Edited by admin on Thu Jul 06 23:04:04 UTC 2023
PRIMARY
CAS
184036-34-8
Created by admin on Thu Jul 06 23:04:04 UTC 2023 , Edited by admin on Thu Jul 06 23:04:04 UTC 2023
PRIMARY
MERCK INDEX
M9962
Created by admin on Thu Jul 06 23:04:04 UTC 2023 , Edited by admin on Thu Jul 06 23:04:04 UTC 2023
PRIMARY Merck Index
FDA UNII
J9QH779MEM
Created by admin on Thu Jul 06 23:04:04 UTC 2023 , Edited by admin on Thu Jul 06 23:04:04 UTC 2023
PRIMARY
IUPHAR
3950
Created by admin on Thu Jul 06 23:04:04 UTC 2023 , Edited by admin on Thu Jul 06 23:04:04 UTC 2023
PRIMARY
PUBCHEM
216235
Created by admin on Thu Jul 06 23:04:04 UTC 2023 , Edited by admin on Thu Jul 06 23:04:04 UTC 2023
PRIMARY
SMS_ID
100000087992
Created by admin on Thu Jul 06 23:04:04 UTC 2023 , Edited by admin on Thu Jul 06 23:04:04 UTC 2023
PRIMARY