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
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
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 |
DescriptionSources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/000679/WC500037902.pdfCurator'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
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 |
---|---|---|---|
Target ID: CHEMBL252 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9171878/ |
0.43 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | THELIN Approved UseTreatment 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 Date1.16017922E12 |
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Primary | THELIN Approved UseTreatment 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 Date1.16017922E12 |
|||
Primary | THELIN Approved UseTreatment 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 Date1.16017922E12 |
PubMed
Title | Date | PubMed |
---|---|---|
Pulmonary arterial hypertension associated to connective tissue diseases. | 2005 |
|
Endothelin receptor antagonists. | 2006 Jun |
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Therapeutic targets in systemic sclerosis. | 2007 |
|
Clinical trials and basic research: defining mechanisms and improving treatment in connective tissue disease. | 2007 |
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Sitaxentan: in pulmonary arterial hypertension. | 2007 |
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[Treatment of pulmonary arterial hypertension by endothelin receptor antagonists in 2008]. | 2008 Apr |
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Inhibition of endothelin receptors in the treatment of pulmonary arterial hypertension: does selectivity matter? | 2008 Aug |
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The management of pulmonary hypertension in children. | 2008 Jul |
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[Systemic sclerosis]. | 2008 May |
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Cost-utility of treatments for pulmonary arterial hypertension: a Markov state-transition decision analysis model. | 2009 |
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Bosentan in the treatment of pulmonary arterial hypertension with the focus on the mildly symptomatic patient. | 2009 |
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Successful treatment of systemic-sclerosis-related digital ulcers with a selective endothelin type A receptor antagonist (sitaxentan). | 2009 |
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Small-molecule endothelin receptor antagonists: a review of patenting activity across therapeutic areas. | 2009 Jun |
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Severe hepatitis associated with sitaxentan and response to glucocorticoid therapy. | 2009 Jun |
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Bleeding events in pulmonary arterial hypertension. | 2009 Jun |
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Integrated care and optimal management of pulmonary arterial hypertension. | 2009 May 12 |
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Early intervention in pulmonary arterial hypertension associated with systemic sclerosis: an essential component of disease management. | 2010 Dec |
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The emergence of oral tadalafil as a once-daily treatment for pulmonary arterial hypertension. | 2010 May 6 |
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Clinical experience with bosentan and sitaxentan in connective tissue disease-associated pulmonary arterial hypertension. | 2010 Nov |
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Endothelin receptor antagonists are an effective long term treatment option in pulmonary arterial hypertension associated with congenital heart disease with or without trisomy 21. | 2010 Oct |
|
Bioactivation of sitaxentan in liver microsomes, hepatocytes, and expressed human P450s with characterization of the glutathione conjugate by liquid chromatography tandem mass spectrometry. | 2013 Jun 17 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27165837
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
Edited
Fri Dec 15 15:59:18 UTC 2023
by
admin
on
Fri Dec 15 15:59:18 UTC 2023
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Record UNII |
6V9JH46E20
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Record Status |
Validated (UNII)
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Record Version |
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EMA ASSESSMENT REPORTS |
THELIN (AUTHORIZED: HYPERTENSION, PULMONARY)
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FDA ORPHAN DRUG |
180803
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EU-Orphan Drug |
EU/3/04/234
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m9962
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CHEMBL282724
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LL-12
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100000091727
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SUB22351
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C152373
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |