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Identification
NameForasartan
Accession NumberDB01342
TypeSmall Molecule
GroupsApproved
Description

Forasartan, a specific angiotensin II antagonist, is used alone or with other antihypertensive agents to treat hypertension. Forasartan competes with angiotensin II for binding at the AT1 receptor subtype. As angiotensin II is a vasoconstrictor which also stimulates the synthesis and release of aldosterone, blockage of its effects results in a decreases in systemic vascular resistance.

Structure
Thumb
Synonyms
SynonymLanguageCode
ForasartanNot AvailableNot Available
SC-52458Not AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number145216-43-9
WeightAverage: 416.522
Monoisotopic: 416.243692936
Chemical FormulaC23H28N8
InChI KeyYONOBYIBNBCDSJ-UHFFFAOYSA-N
InChI
InChI=1S/C23H28N8/c1-3-5-11-21-25-22(12-6-4-2)31(28-21)16-17-13-14-20(24-15-17)18-9-7-8-10-19(18)23-26-29-30-27-23/h7-10,13-15H,3-6,11-12,16H2,1-2H3,(H,26,27,29,30)
IUPAC Name
5-[(dibutyl-1H-1,2,4-triazol-1-yl)methyl]-2-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]pyridine
SMILES
CCCCC1=NN(CC2=CN=C(C=C2)C2=CC=CC=C2C2=NNN=N2)C(CCCC)=N1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPhenylpyridines
Direct ParentPhenylpyridines
Alternative Parents
Substituents
  • 2-phenylpyridine
  • Phenyltetrazole
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • 1,2,4-triazole
  • Tetrazole
  • Azole
  • Azacycle
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of hypertension.
PharmacodynamicsForasartan, a specific angiotensin II antagonist, is used alone or with other antihypertensive agents to treat hypertension. By inhibiting angiotensin II receptors, this drug leads to a decrease in sodium reabsorption (which decreases water content of blood) and a decrease in vasoconstriction. Combined, this has the effect of lowering blood pressure.
Mechanism of actionForasartan competes with angiotensin II for binding at the AT1 receptor subtype. As angiotensin II is a vasoconstrictor which also stimulates the synthesis and release of aldosterone, blockage of its effects results in a decreases in systemic vascular resistance. Also, since angiotensin causes vasoconstriction, the inhibition of this receptor decreases vasoconstriction, which consequently also decreases vascular resistnace.
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
Pathways
PathwayCategorySMPDB ID
Forasartan Action PathwayDrug actionSMP00160
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9069
Caco-2 permeable+0.5
P-glycoprotein substrateSubstrate0.615
P-glycoprotein inhibitor INon-inhibitor0.6612
P-glycoprotein inhibitor IINon-inhibitor0.8805
Renal organic cation transporterInhibitor0.5228
CYP450 2C9 substrateNon-substrate0.7854
CYP450 2D6 substrateNon-substrate0.831
CYP450 3A4 substrateNon-substrate0.5512
CYP450 1A2 substrateNon-inhibitor0.64
CYP450 2C9 substrateNon-inhibitor0.5115
CYP450 2D6 substrateNon-inhibitor0.7168
CYP450 2C19 substrateInhibitor0.7661
CYP450 3A4 substrateInhibitor0.6576
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7192
Ames testNon AMES toxic0.5233
CarcinogenicityNon-carcinogens0.8243
BiodegradationNot ready biodegradable0.9969
Rat acute toxicity2.7970 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6462
hERG inhibition (predictor II)Non-inhibitor0.546
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00667 mg/mLALOGPS
logP4.51ALOGPS
logP5.89ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)7.35ChemAxon
pKa (Strongest Basic)3.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area98.06 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity145.44 m3·mol-1ChemAxon
Polarizability46.79 Å3ChemAxon
Number of Rings4ChemAxon
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. Tokunaga R, Kushiku K, Yamada K, Yamada H, Furukawa T: Possible involvement of calcium-calmodulin pathways in the positive chronotropic response to angiotensin II on the canine cardiac sympathetic ganglia. Jpn J Pharmacol. 2001 Aug;86(4):381-9. Pubmed
  2. Usune S, Furukawa T: Effects of SC-52458, a new nonpeptide angiotensin II receptor antagonist, on increase in cytoplasmic Ca2+ concentrations and contraction induced by angiotensin II and K(+)-depolarization in guinea-pig taenia coli. Gen Pharmacol. 1996 Oct;27(7):1179-85. Pubmed
  3. Hagmann M, Nussberger J, Naudin RB, Burns TS, Karim A, Waeber B, Brunner HR: SC-52458, an orally active angiotensin II-receptor antagonist: inhibition of blood pressure response to angiotensin II challenges and pharmacokinetics in normal volunteers. J Cardiovasc Pharmacol. 1997 Apr;29(4):444-50. Pubmed
  4. 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 12:11 / Updated on September 16, 2013 17:14