DrugBank: Saprisartan (DB01347)

targets (1)

Identification

Name

Saprisartan

Accession Number

DB01347

Type

small molecule

Groups

approved

Description

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.(10579749)

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Not Available

Salts

Not Available

Brand names

Not Available

Brand mixtures

Not Available

Categories

Not Available

CAS number

146623-69-0

Weight

Average: 611.431
Monoisotopic: 610.049723164

Chemical Formula

C₂₅H₂₂BrF₃N₄O₄S

InChI Key

InChIKey=DUEWVPTZCSAMNB-UHFFFAOYSA-N

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)

Plain Text

IUPAC Name

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

SMILES

CCC1=NC(C2CC2)=C(N1CC1=CC2=C(OC(=C2Br)C2=CC=CC=C2NS(=O)(=O)C(F)(F)F)C=C1)C(N)=O

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Benzofurans

Substructures

Benzofurans
Amino Ketones
Sulfonyls
Cyclopropane and Derivatives
Benzene and Derivatives
Carbamates and Derivatives
Aryl Halides
Imidazoles
Heterocyclic compounds
Aromatic compounds
Carboxamides and Derivatives
Sulfonamides
Furans
Imines
Carboxylic Acids and Derivatives
Cyanamides
Anilines

Pharmacology

Indication

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

Pharmacodynamics

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.

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.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
water solubility	1.51e-02 g/l	ALOGPS
logP	5.89	ALOGPS
logP	3.35	ChemAxon
logS	-4.6	ALOGPS
pKa (strongest acidic)	2.27	ChemAxon
pKa (strongest basic)	5.18	ChemAxon
physiological charge	-1	ChemAxon
hydrogen acceptor count	4	ChemAxon
hydrogen donor count	2	ChemAxon
polar surface area	120.22	ChemAxon
rotatable bond count	8	ChemAxon
refractivity	137.15	ChemAxon
polarizability	54.2	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
PubChem Compound	60921
PubChem Substance	46508176
ChemSpider	54892
Therapeutic Targets Database	DAP001257
PharmGKB	PA164746338

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Drug	Interaction
Amiloride	Increased risk of hyperkalemia
Lithium	The ARB increases serum levels of lithium
Potassium	Increased risk of hyperkalemia
Triamterene	Increased risk of hyperkalemia

Food Interactions

Not Available

Targets
1. Type-1 angiotensin II receptor Pharmacological action: yes Actions: antagonist Receptor for angiotensin II. Mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system Organism class: human UniProt ID: P30556 Gene: AGTR1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Timmermans PB: Pharmacological properties of angiotensin II receptor antagonists. Can J Cardiol. 1999 Nov;15 Suppl F:26F-8F. Pubmed Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Targets

1. Type-1 angiotensin II receptor

Pharmacological action: yes
Actions: antagonist

Receptor for angiotensin II. Mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system

Organism class: human
UniProt ID: P30556 Link_out

Gene: AGTR1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Timmermans PB: Pharmacological properties of angiotensin II receptor antagonists. Can J Cardiol. 1999 Nov;15 Suppl F:26F-8F. Pubmed
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Comments

Drug created on June 30, 2007 12:15 / Updated on February 08, 2013 16:20