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Identification
NameSaprisartan
Accession NumberDB01347
TypeSmall Molecule
GroupsApproved
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
Thumb
Synonyms
SynonymLanguageCode
GR-138950Not AvailableNot Available
GR-138950CNot AvailableNot Available
SaprisartanNot AvailableNot Available
Saprisartan potassiumNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number146623-69-0
WeightAverage: 611.431
Monoisotopic: 610.049723164
Chemical FormulaC25H22BrF3N4O4S
InChI KeyDUEWVPTZCSAMNB-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)
IUPAC Name
1-{[3-bromo-2-(2-trifluoromethanesulfonamidophenyl)-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
Class2-arylbenzofuran flavonoids
Sub ClassNot Available
Direct Parent2-arylbenzofuran flavonoids
Alternative Parents
Substituents
  • 2-arylbenzofuran flavonoid
  • Phenylbenzofuran
  • 2-phenylbenzofuran
  • Sulfanilide
  • Benzofuran
  • 1,2,4,5-tetrasubstituted imidazole
  • Benzenoid
  • N-substituted imidazole
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl bromide
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Imidazole
  • Furan
  • Cyclic alcohol
  • Azole
  • Trihalomethane
  • Primary carboxylic acid amide
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Halomethane
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organobromide
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl fluoride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationSaprisartan is used in the treatment of hypertension and heart failure.
PharmacodynamicsBy 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 actionSaprisartan 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.647
Caco-2 permeable-0.6148
P-glycoprotein substrateSubstrate0.5611
P-glycoprotein inhibitor INon-inhibitor0.6454
P-glycoprotein inhibitor IINon-inhibitor0.5279
Renal organic cation transporterNon-inhibitor0.8625
CYP450 2C9 substrateNon-substrate0.653
CYP450 2D6 substrateNon-substrate0.7866
CYP450 3A4 substrateSubstrate0.5105
CYP450 1A2 substrateNon-inhibitor0.6561
CYP450 2C9 substrateInhibitor0.6267
CYP450 2D6 substrateNon-inhibitor0.7996
CYP450 2C19 substrateInhibitor0.5274
CYP450 3A4 substrateNon-inhibitor0.5167
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8837
Ames testNon AMES toxic0.5853
CarcinogenicityNon-carcinogens0.6378
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5781 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9673
hERG inhibition (predictor II)Inhibitor0.6568
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0151 mg/mLALOGPS
logP5.89ALOGPS
logP3.35ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)2.27ChemAxon
pKa (Strongest Basic)5.18ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area120.22 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity137.15 m3·mol-1ChemAxon
Polarizability54.2 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Type-1 angiotensin II receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Type-1 angiotensin II receptor P30556 Details

References:

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

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Drug created on June 30, 2007 12:15 / Updated on September 16, 2013 17:14