Structure via PubChem · Public domain (PubChem)
sitaxentan
Sign in to saveAlso known as TBC11251 / TBC-11251, Thelin®, Sitaxsentan, N-(4-Chloro-3-methyl-5-isoxazolyl)-2-[(2-methyl-4,5-methylenedioxyphenyl)acetyl]thiophene-3-sulfonamide
Sitaxentan sodium (TBC-11251) is a medication for the treatment of pulmonary arterial hypertension (PAH). It was marketed as Thelin by Encysive Pharmaceuticals until Pfizer purchased Encysive in February 2008. In 2010, Pfizer voluntarily removed sitaxentan from the market due to concerns about liver toxicity.
Chemical data
- Formula
- C18H15ClN2O6S2
- Molecular weight
- 454.9 g/mol
- IUPAC name
- N-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-[2-(6-methyl-1,3-benzodioxol-5-yl)acetyl]thiophene-3-sulfonamide
- SMILES
- CC1=CC2=C(C=C1CC(=O)C3=C(C=CS3)S(=O)(=O)NC4=C(C(=NO4)C)Cl)OCO2
- InChIKey
- PHWXUGHIIBDVKD-UHFFFAOYSA-N
- XLogP
- 3.7
- Polar surface area
- 144 Ų
- H-bond donors
- 1
- H-bond acceptors
- 9
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2006
- Admin. routes
- oral
- Indications
- pulmonary arterial hypertension, hypertension, chronic kidney disease, Proteinuria
via ChEMBL · EBI
Research
262 papers- Sitaxentan: in pulmonary arterial hypertension.Drugs · 2007
- Clinical and cost-effectiveness of epoprostenol, iloprost, bosentan, sitaxentan and sildenafil for pulmonary arterial hypertension within their licensed indications: a systematic review and economic evaluation.Health technology assessment (Winchester, England) · 2009
- Endothelin Receptor Antagonists.2012
- Simultaneous quantification of ambrisentan, macitentan and sitaxentan in human plasma using UPLC-MS/MS.Biomedical chromatography : BMC · 2020
- The effects of sitaxentan on sildenafil pharmacokinetics and pharmacodynamics in healthy subjects.British journal of clinical pharmacology · 2010
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 454.006
- Has use
- medication
Show 5 more facts
- chemical formula
- C₁₈H₁₅ClN₂O₆S₂
- canonical SMILES
- CC1=CC2=C(C=C1CC(=O)C3=C(C=CS3)S(=O)(=O)NC4=C(C(=NO4)C)Cl)OCO2
- defined daily dose
- 0.1
- subject has role
- Endothelin receptor antagonist
- Commons category
- Sitaxentan
Sources (3)
via Wikidata · CC0
~3 min read
Encyclopedic overview
6 sectionsContents
- Mechanism of action
- Regulatory status
- Adverse effects
- References
- Further reading
- External links
Sitaxentan sodium (TBC-11251) is a medication for the treatment of pulmonary arterial hypertension (PAH). It was marketed as Thelin by Encysive Pharmaceuticals until Pfizer purchased Encysive in February 2008. In 2010, Pfizer voluntarily removed sitaxentan from the market due to concerns about liver toxicity.
==Mechanism of action== Sitaxentan is a small molecule that blocks the action of endothelin (ET) on the endothelin-A (ETA) receptor selectively (by a factor of 6000 compared with the ETB). It is a sulfonamide class endothelin receptor antagonist (ERA) and is undergoing Food and Drug Administration (FDA) review for treating pulmonary hypertension. The rationale for benefit compared with bosentan, a nonselective ET blocker, is negligible inhibition of the beneficial effects of ETB stimulation, such as nitric oxide production and clearance of ET from circulation. In clinical trials, the efficacy of sitaxentan has been much the same as bosentan, but the hepatotoxicity of sitaxentan outweighs its benefits. Dosing is once daily, as opposed to twice daily for bosentan.
Excerpted from Wikipedia’s “sitaxentan” article, available under the CC BY-SA 4.0 licence.