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Sitaxentan sodium

CAS No.
210421-74-2
Chemical Name:
Sitaxentan sodium
Synonyms
Thelin;CS-338;CS-777;TBC-11249;TBC-11250;TBC-11251 sodium;sitaxentan sodiuM;SITAXSENTAN SODIUM;TBC11251 sodiuM salt;Sitaxentan sodium salt
CBNumber:
CB32459580
Molecular Formula:
C18H14ClN2NaO6S2
Molecular Weight:
476.89
MDL Number:
MFCD11040990
MOL File:
210421-74-2.mol
Last updated:2024-11-19 23:02:33

Sitaxentan sodium Properties

storage temp. room temp
solubility H2O: soluble10mg/mL (clear solution)
form powder
color white to beige
FDA UNII 6V9JH46E20

SAFETY

Risk and Safety Statements

WGK Germany  3
RTECS  XN0296600

Sitaxentan sodium price More Price(36)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PZ0203 Sitaxentan sodium salt ≥98% (HPLC) 210421-74-2 5mg $122 2024-03-01 Buy
Sigma-Aldrich PZ0203 Sitaxentan sodium salt ≥98% (HPLC) 210421-74-2 25mg $491 2024-03-01 Buy
Cayman Chemical 29244 Sitaxentan (sodium salt) 210421-74-2 5mg $85 2024-03-01 Buy
Cayman Chemical 29244 Sitaxentan (sodium salt) 210421-74-2 25mg $352 2024-03-01 Buy
Cayman Chemical 29244 Sitaxentan (sodium salt) 210421-74-2 10mg $158 2024-03-01 Buy
Product number Packaging Price Buy
PZ0203 5mg $122 Buy
PZ0203 25mg $491 Buy
29244 5mg $85 Buy
29244 25mg $352 Buy
29244 10mg $158 Buy

Sitaxentan sodium Chemical Properties,Uses,Production

Description

In November Encysive Pharmaceuticals launched Thelin® (sitaxsentan sodium) in the U.K. for the treatment of pulmonary arterial hypertension (PAH), following European Commission approval in August 2006. Sitaxsentan is the first selective endothelin A (ETA) receptor antagonist, and the first once-daily oral treatment available for patients with PAH. It is 6,500-fold selective in the targeting of ETA versus ETB receptors. Sitaxsentan is indicated for improving exercise capacity in PAH patients classified as World Health Organization (WHO) functional class III. Efficacy has been shown in primary pulmonary hypertension and pulmonary hypertension associated with connective tissue disease. In the U.S., Encysive has submitted a complete response to an approvable letter received from the FDA in July.

Description

Sitaxentan is a potent nonpeptide endothelin A (ETA) receptor antagonist (IC50 = 1.4 nM). It is selective for ETA over ETB receptors (IC50 = 9,800 nM). Sitaxentan inhibits phosphoinositol hydrolysis induced by endothelin-1 in COS-7 cells (pA2 = 8). In vivo, sitaxentan reduces blood pressure in a rat model of acute hypoxia-induced pulmonary hypertension (ED50 = 0.5 mg/kg). It reduces femoral artery neointimal lesion size in a mouse model of intraluminal injury. Sitaxentan (15 mg/kg) decreases bronchoalveolar lavage fluid (BALF) pleocytosis, as well as pulmonary collagen deposition and fibrosis, and improves lung mechanics in a mouse model of bleomycin-induced lung injury. Formulations containing sitaxentan have been used in the treatment of hypertension.

Uses

Selective endothelin A (ETA) receptor antagonist. Antihypertensive. Used in treatment of chronic heart failure.

General Description

Sitaxentan sodium, belongs to thesulfonamide class of endothelin receptor antagonists.Although it has 6,000-fold selectivity for the ETA receptor,clinical trials have not demonstrated a greater efficacyover bosentan. However, it has much lower liver toxicitythan bosentan. The manufacturer is attempting to meetefficacy outcomes set by the FDA, which must be met beforeapproval of sitaxsentan as a therapeutic agent will begranted.

Biochem/physiol Actions

Sitaxentan (Sitaxsentan) is a potent and selective endothelin ET(A) receptor antagonist once used in the treatment of pulmonary arterial hypertension (PAH), but removed from the market because of hepatotoxicity. It is over 6000-fold selective for the the ETA receptor subtype with an IC50 of 1 nM for ETA versus an IC50 of 9800 nM for ETB.

Synthesis

The synthesis of sitaxentan is depicted in Scheme 12. 5-amino-3- methylisoxazole 85 was treated with NCS in DCM at 0??C to give chloroisoxazole 86 in 87% yield. The amine was then coupled with the commercially available 2-(methoxycarbonyl)- 3-thiophenesulfonyl chloride (87) using sodium hydride in THF at 0??C. The resulting ester was directly hydrolyzed in 1N NaOH to furnish acid 88 in 45% yield. The acid 88 was then coupled with N,O-dimethylhydroxylamine to give Weinreb amide 89. The amide 89 was then treated with benzylic Grignard reagent followed by acidic workup to give the sitaxentan XII in 50% yield in two steps. The Grignard reagent 90 was prepared through the following sequence. The 5-methylbenzodioxole 91 was treated with aqueous formaldehyde and concentrated HCl in ethyl ether to give the desired benzyl chloride 93 and condensation product 92. The mixture of 92 and 93 was used to form the Grignard reagent without separation.

Synthesis_210421-74-2

Sitaxentan sodium Preparation Products And Raw materials

Raw materials

Preparation Products

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Hefei TNJ Chemical Industry Co.,Ltd.
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View Lastest Price from Sitaxentan sodium manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Sitaxsentan sodium pictures 2024-11-19 Sitaxsentan sodium
210421-74-2
US $30.00-103.00 / mg ≥95% 10g TargetMol Chemicals Inc.
Sitaxentan sodium pictures 2019-07-06 Sitaxentan sodium
210421-74-2
US $2.00 / kg 1kg 99% 100kg Career Henan Chemical Co

Sitaxentan sodium Spectrum

Sodium (4-chloro-3-methyl-1,2-oxazol-5-yl)-[2-[2-(6-methyl-1,3-benzodioxol-5-yl)acetyl]thiophen-3-yl]sulfonylazanide SITAXSENTAN SODIUM TBC-11249 Thelin sitaxentan sodiuM N-(4-Chloro-3-Methylisoxazol-5-yl)-2-[2-(6-Methyl-1,3-Benzodioxol-5-yl)acetyl]thiophene-3-sulfonaMide N-(4-Chloro-3-Methyl-5-isoxazolyl)-2-[2-(6-Methyl-1,3-benzodioxol-5-yl)acetyl]-3-thiophenesulfonaMide TBC11251 sodiuM salt Sitaxsentan sodiuM (TBC-11251) N-(4-Chloro-3-methyl-5-isoxazolyl)-2-[2-(6-methyl-1,3-benzodioxol-5-yl)acetyl]-3-thiophenesulfonamide sodium salt Sitaxentan sodium salt Sitaxsentan sodium salt Sitaxsentan sodiuM(TBC-11249) 3-Thiophenesulfonamide, N-(4-chloro-3-methyl-5-isoxazolyl)-2-[2-(6-methyl-1,3-benzodioxol-5-yl)acetyl]-, sodium salt (1:1) TBC-11250 TBC-11251 sodium 4-Chloro-3-methyl-5-[2-[2-(6-methyl-1,3-benzodioxol-5-yl)acetyl]-3-thienylsulfonamido]isoxazole sodium salt CS-338 CS-777 Sitaxentan sodium USP/EP/BP Sodium (4-chloro-3-methylisoxazol-5-yl)((2-(2-(6-methylbenzo[d][1,3]dioxol-5-yl)acetyl)thiophen-3-yl)sulfonyl)amide Sitaxentan sodium (Sitaxsentan TBC11251 sodium salt|||TBC11251|||Thelin|||Sitaxentan sodium 210421-74-2 C18H14ClN2O6S2Na C18H14ClN2NaO6S2 Inhibitors Sitaxsentan Sodium Heterocycles Intermediates & Fine Chemicals Pharmaceuticals Sulfur & Selenium Compounds