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2D Structure
Also known as: 146623-69-0, Gr-138950, Gr 138950, 3-[[3-bromo-2-[2-(trifluoromethylsulfonylamino)phenyl]-1-benzofuran-5-yl]methyl]-5-cyclopropyl-2-ethylimidazole-4-carboxamide, Gr138950, Hs64ng1g69
Molecular Formula
C25H22BrF3N4O4S
Molecular Weight
611.4  g/mol
InChI Key
DUEWVPTZCSAMNB-UHFFFAOYSA-N
FDA UNII
HS64NG1G69

Saprisartan is an AT1 receptor antagonist. It is based on medications of losartan's prototypical chemical structure. The mode of (functional) AT1 receptor antagonism has been characterized as insurmountable/noncompetitive for saprisartan. It is very likely that slow dissociation kinetics from the AT1 receptor underlie insurmountable antagonism.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-[[3-bromo-2-[2-(trifluoromethylsulfonylamino)phenyl]-1-benzofuran-5-yl]methyl]-5-cyclopropyl-2-ethylimidazole-4-carboxamide
2.1.2 InChI
InChI=1S/C25H22BrF3N4O4S/c1-2-19-31-21(14-8-9-14)22(24(30)34)33(19)12-13-7-10-18-16(11-13)20(26)23(37-18)15-5-3-4-6-17(15)32-38(35,36)25(27,28)29/h3-7,10-11,14,32H,2,8-9,12H2,1H3,(H2,30,34)
2.1.3 InChI Key
DUEWVPTZCSAMNB-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCC1=NC(=C(N1CC2=CC3=C(C=C2)OC(=C3Br)C4=CC=CC=C4NS(=O)(=O)C(F)(F)F)C(=O)N)C5CC5
2.2 Other Identifiers
2.2.1 UNII
HS64NG1G69
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Gr 138950

2. Gr-138950

3. Gr138950

4. Gr138950c

5. Sapri-sartan Potassium

6. Saprisartan Potassium

2.3.2 Depositor-Supplied Synonyms

1. 146623-69-0

2. Gr-138950

3. Gr 138950

4. 3-[[3-bromo-2-[2-(trifluoromethylsulfonylamino)phenyl]-1-benzofuran-5-yl]methyl]-5-cyclopropyl-2-ethylimidazole-4-carboxamide

5. Gr138950

6. Hs64ng1g69

7. Saprisartan [inn:ban]

8. Unii-hs64ng1g69

9. 3-((3-bromo-2-(2-(trifluoromethylsulfonylamino)phenyl)-1-benzofuran-5-yl)methyl)-5-cyclopropyl-2-ethylimidazole-4-carboxamide

10. Gr-138950x

11. Saprisartan [inn]

12. Saprisartan [who-dd]

13. Schembl120388

14. Chembl305544

15. Gtpl6899

16. Dtxsid00163422

17. Chebi:190069

18. Zinc3919581

19. Bdbm50469901

20. Db01347

21. L000533

22. Q20817193

23. 1-({3-bromo-2-[2-(trifluoromethane)sulfonamidophenyl]-1-benzofuran-5-yl}methyl)-4-cyclopropyl-2-ethyl-1h-imidazole-5-carboxamide

24. 1-[[3-bromo-2-[2-[[(trifluoromethyl)sulphonyl ]amino ]phenyl]-5-benzofuranyl]methyl]-4-cyclopropyl-2-ethyl-1h-imidazole-5-carboxamide

25. 1-[[3-bromo-2-[2-[[(trifluoromethyl)sulphonyl]amino]phenyl]-5-benzofuranyl]methyl]-4-cyclopropyl-2-ethyl-1h-imidazole-5-carboxamide

26. 1h-imidazole-5-carboxamide, 1-((3-bromo-2-(2-(((trifluoromethyl)sulfonyl)amino)phenyl)-5-benzofuranyl)methyl)-4-cyclopropyl-2-ethyl-

27. 3-[[3-bromo-2-[2-(triluoromethylsulonylamino)phenyl]-1-benzouran-5-yl]methyl]-5-cyclopropyl-2-ethylimidazole-4-carboxamide

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 611.4 g/mol
Molecular Formula C25H22BrF3N4O4S
XLogP35.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count9
Rotatable Bond Count8
Exact Mass610.04972 g/mol
Monoisotopic Mass610.04972 g/mol
Topological Polar Surface Area129 Ų
Heavy Atom Count38
Formal Charge0
Complexity979
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Saprisartan is used in the treatment of hypertension and heart failure.


5 Pharmacology and Biochemistry
5.1 Pharmacology

By inhibiting the angiotensin II receptor, this drug leades to a decrease in sodium reabsorption and a decrease in vasoconstriction. This has the combined effect of decreasing blood pressure.


5.2 MeSH Pharmacological Classification

Angiotensin II Type 1 Receptor Blockers

Agents that antagonize ANGIOTENSIN II TYPE 1 RECEPTOR. Included are ANGIOTENSIN II analogs such as SARALASIN and biphenylimidazoles such as LOSARTAN. Some are used as ANTIHYPERTENSIVE AGENTS. (See all compounds classified as Angiotensin II Type 1 Receptor Blockers.)


Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)


5.3 Mechanism of Action

Saprisartan is a selective, potent, orally active and long-acting nonpeptide Angiotensin II type 1 (AT1) receptor antagonist. Saprisartan blocks the renin-angiotensin-aldosterone system (RAAS) at the level of the AT1 receptor that mediates most, if not all, of the important actions of Ang II. Saprisartan binds reversibly to the AT1 receptors in vascular smooth muscle and the adrenal gland. As angiotensin II is a vasoconstrictor, which also stimulates the synthesis and release of aldosterone, blockage of its effects results in decreases in systemic vascular resistance. AT1 receptor antagonists avoid the nonspecificity of the Ang I converting enzyme (ACE) inhibitors.