Fimasartan
Basic information
- CAS
247257-48-3- Standard SMILES
CCCCc1nc(C)c(CC(=S)N(C)C)c(=O)n1Cc1ccc(-c2ccccc2-c2nn[nH]n2)cc1- InChIKey
AMEROGPZOLAFBN-UHFFFAOYSA-N- Molecular formula
- C27H31N7OS
- Average molar mass
- 501.6 g/mol
- Monoisotopic mass
- 501.23107981
Overview
Fimasartan is a member of biphenyls.
Names & identifiers
- Preferred name
- Fimasartan
- IUPAC
- 2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N,N-dimethylethanethioamide
- English name
- Fimasartan
- Molecular formula
- C27H31N7OS
- Molecular weight
- 501.65
Names & synonyms
FIMASARTAN247257-48-3fimasartanumDTXSID80179460P58222188PRefChem:140452C09CA10DTXCID101019512-(2-butyl-4-methyl-6-oxo-1-((2'-(1H-1,2,3,4-tetrazol-5-yl)-(1,1'-biphenyl)-4-yl)methyl)-1,6-dihydropyrimidin-5-yl)-N,N-dimethylethanethioamide2-(1-((2'-(2H-Tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-butyl-4-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)-N,N-dimethylethanethioamideFimasartan [INN]2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N,N-dimethylethanethioamide
Show more names
BR-A-657Non-masartanFimasartan D4Unii-p58222188pBR-A-657Fimasartan(BR-A-657)FiMasartan USP/EP/BPFimasartan Impurity H
MFCD131947955-Pyrimidineethanethioamide, 2-butyl-1,6-dihydro-N,N,4-trimethyl-6-oxo-1-[[2'-(2H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-CHEMBL1951143Fimasartan (INN)2-(2-Butyl-4-methyl-6-oxo-1-{[2'-(1H-tetrazol-5-yl)-4-biphenylyl]methyl}-1,6-dihydro-5-pyrimidinyl)-N,N-dimethylethanethioamideKanarb2-Butyl-5-dimethylaminothiocarbonylmethyl-6-methyl-3-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidin-4(3H)-one2-((2-BUTYL-4-METHYL-6-OXO-1-((2'-(1H-TETRAZOL-5-YL)BIPHENYL-4-YL)METHYL)-1,6-DIHYDROPYRIMIDIN-5-YL))-N,N-DIMETHYLTHIOACETAMIDE
Properties
Computed structural properties
- XLogP
- 3.5
- Topological polar surface area
- 122 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 9
- Heavy atoms
- 36
- Formal charge
- 0
- Complexity
- 849
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 155 °C · >155°C (dec.)
- Boiling point
- 693 · 693.0±65.0 °C(Predicted)
- Density
- 1.25 · 1.25
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 4.16 · 4.16±0.10(Predicted)
- color
- White to Off-White
- InChIKey
- AMEROGPZOLAFBN-UHFFFAOYSA-N
- SMILES
- C1(CCCC)N(CC2=CC=C(C3=CC=CC=C3C3=NNN=N3)C=C2)C(=O)C(CC(N(C)C)=S)=C(C)N=1
- FDA UNII
- 58222188 P · P58222188P
- ATC code
- 9 CA10 · C09CA10
- UNSPSC Code
- 12352107 · 12352107
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
PharmacodynamicsFimasartan is a selective angiotensin receptor 1 (AR1) inhibitor. It acts to lower blood pressure by inhibiting vasoconstriction
Mechanism of Action
Angiotensin II activates AR1 leading to vasoconstriction and increased noradrenaline release which further increases vasoconstriction via action at α1-adrenergic receptors. It also stimulates secretion of aldosterone which acts to increase sodium and water reabsorption in the renal tubules. Fimasartan bind to and antagonizes AR1 preventing vasoconstriction and reducing aldosterone secretion to increase natriuresis leading to a reduction in blood volume. Together these effects produce an anti-hypertensive effect.
Biological Half-LifeThe half life of elimination is 7-10 h.
Absorption, Distribution and Excretion
Tmax is 0.5-1.3 h.
Most is eliminated unchangd in bile with less than 3% in the urine.
Applications
DescriptionFimasartan is an angiotensin II receptor antagonist (ARB) drug employed in the treatment of both hypertension and heart failure. It has been found to be safe when administered with hydrochlorothiazide (a diuretic) in clinical trials. Fimasartan was initially approved September 9th, 2010 in South Korea and is marketed under the brand name Kanarb by Boryung Pharmaceuticals.
UsesFimasartan is a new angiotensin II receptor blocker antagonist and also functions as an antihypertensive agent.
Upstream & downstream products
Upstream raw materials
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