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Sitaxentan sodium

Product Name
Sitaxentan sodium
CAS No.
210421-74-2
Chemical Name
Sitaxentan sodium
Synonyms
CS-777;CS-338;Thelin;TBC-11249;TBC-11250;TBC-11251 sodium;sitaxentan sodiuM;SITAXSENTAN SODIUM;TBC11251 sodiuM salt;Sitaxentan sodium salt
CBNumber
CB32459580
Molecular Formula
C18H14ClN2NaO6S2
Formula Weight
476.89
MOL File
210421-74-2.mol
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Sitaxentan sodium Property

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

WGK Germany 
3
RTECS 
XN0296600
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PZ0203
Product name
Sitaxentan sodium salt
Purity
≥98% (HPLC)
Packaging
5mg
Price
$122
Updated
2024/03/01
Sigma-Aldrich
Product number
PZ0203
Product name
Sitaxentan sodium salt
Purity
≥98% (HPLC)
Packaging
25mg
Price
$491
Updated
2024/03/01
Cayman Chemical
Product number
29244
Product name
Sitaxentan (sodium salt)
Packaging
5mg
Price
$85
Updated
2024/03/01
Cayman Chemical
Product number
29244
Product name
Sitaxentan (sodium salt)
Packaging
25mg
Price
$352
Updated
2024/03/01
Cayman Chemical
Product number
29244
Product name
Sitaxentan (sodium salt)
Packaging
10mg
Price
$158
Updated
2024/03/01
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Sitaxentan sodium Chemical Properties,Usage,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.

Sitaxentan sodium Preparation Products And Raw materials

Raw materials

Preparation Products

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Sitaxentan sodium Suppliers

Canada 1 China 93 India 3 United Kingdom 1 United States 16 Global 114
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
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86-10-82849933
Email
jkinfo@jkchemical.com
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China
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94657
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Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
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61
Chemsky (shanghai) International Co.,Ltd
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
15402
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60
Hangzhou Yuhao Chemical Technology Co., Ltd
Tel
0571-82693216
Fax
+86-571-82880190
Email
info@yuhaochemical.com
Country
China
ProdList
9387
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52
Dalian Meilun Biotech Co., Ltd.
Tel
0411-62910999 13889544652
Email
sales@meilune.com
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China
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4727
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58
Beijing Yisiyan Technology Research Center
Tel
010-56645598 13366904824
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01062230033
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bjkaida@163.com
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China
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1638
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Jiangsu Aikon Biopharmaceutical R&D co.,Ltd.
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025-66099280 17798518460
Fax
(1)02557626880
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cfzhang@aikonchem.com
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China
ProdList
19915
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Haoyuan Chemexpress Co., Ltd.
Tel
021-58950125
Fax
(86) 21-58955996
Email
info@chemexpress.com
Country
China
ProdList
7552
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61
Shanghai Aladdin Bio-Chem Technology Co.,LTD
Tel
400-400-6206333 18521732826
Fax
021-50323701
Email
market@aladdin-e.com
Country
China
ProdList
25003
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AdooQ BioScience, LLC
Tel
+1 (866) 930-6790
Fax
+1 (866) 333-9607
Email
info@adooq.com
Country
United States
ProdList
2782
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58
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View Lastest Price from Sitaxentan sodium manufacturers

Career Henan Chemical Co
Product
Sitaxentan sodium 210421-74-2
Price
US $2.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100kg
Release date
2018-12-23

210421-74-2, Sitaxentan sodiumRelated Search:

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  • N-(4-Chloro-3-Methylisoxazol-5-yl)-2-[2-(6-Methyl-1,3-Benzodioxol-5-yl)acetyl]thiophene-3-sulfonaMide
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  • 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
  • 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