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SML3256

Sigma-Aldrich

Fimasartan

≥98% (HPLC)

Synonym(s):

2-Butyl-1,6-dihydro-N,N,4-trimethyl-6-oxo-1-[[2′-(2H-tetrazol-5-yl)[1,1′-biphenyl]-4-yl]methyl]-5-pyrimidineethanethioamide, 2-n-Butyl-5-dimethylaminothiocarbonylmethyl-6-methyl-3-[[2′-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidin-4(3H)-one, BR-A-657, BR-A657

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About This Item

Empirical Formula (Hill Notation):
C27H31N7OS
CAS Number:
Molecular Weight:
501.65
MDL number:
UNSPSC Code:
12352107
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

S=C(CC1=C(N=C(N(C1=O)CC2=CC=C(C=C2)C3=CC=CC=C3C4=NNN=N4)CCCC)C)N(C)C

InChI

1S/C27H31N7OS/c1-5-6-11-24-28-18(2)23(16-25(36)33(3)4)27(35)34(24)17-19-12-14-20(15-13-19)21-9-7-8-10-22(21)26-29-31-32-30-26/h7-10,12-15H,5-6,11,16-17H2,1-4H3,(H,29,30,31,32)

InChI key

AMEROGPZOLAFBN-UHFFFAOYSA-N

Biochem/physiol Actions

Fimasartan (BR-A-657) is an orally active, highly potent angiotensin II receptor AT1 (AGTR1) antagonist (blocker) that selectively blocks AngII-, but not KCl- or noradrenaline-, induced contraction of rabbit thoracic aortic rings (IC50 = 0.42 nM) with 615-fold higher AT1 affinity than losartan (IC50 = 0.13 nM vs. 80 nM against 0.05 nM AngII for binding rat adrenal cortex). Fimasartan significantly decreases mean arterial blood pressure with rapid onset (in 0.5 h) in spontaneously hypertensive rats (Emax of 75% reduction, 5-24 hr post 10 mg/kg p.o.) and is ~19-fold more effective than losartan against AngII (100 ng/kg i.v.)-induced pressor response in rats in vivo (ED50 = 18 ng/kg vs. 336 ng/kg i.v.).
Orally active, highly potent angiotensin II receptor AT1 (AGTR1) antagonist with superior in vivo antihypertensive efficacy than Losartan.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Sung-A Chang et al.
Journal of Korean medical science, 30(5), 559-568 (2015-05-02)
Angiotensin receptor blockers (ARBs) have organ-protective effects in heart failure and may be also effective in doxorubicin-induced cardiomyopathy (DOX-CMP); however, the efficacy of ARBs on the prevention of DOX-CMP have not been investigated. We performed a preclinical experiment to evaluate
Suran Ryu et al.
Biological & pharmaceutical bulletin, 36(3), 467-474 (2013-03-02)
Since inhibition of angiotensin II type 1 (AT1) receptor reduces chronic inflammation associated with hypertension, we evaluated the anti-inflammatory potential and the underlying mechanism of fimasartan, a Korean Food and Drug Administration approved anti-hypertension drug, in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages.
Doo Sun Sim et al.
Journal of Korean medical science, 30(1), 34-43 (2015-01-02)
Cardioprotective effect of fimasartan, a new angiotensin receptor blocker (ARB), was evaluated in a porcine model of acute myocardial infarction (MI). Fifty swine were randomized to group 1 (sham, n=10), group 2 (no angiotensin-converting enzyme inhibitor [ACEI] or ARB, n=10)
Xiuli Yang et al.
Experimental neurology, 310, 22-32 (2018-09-02)
Nucleotide-binding and oligomerization domain-like receptor family pyrin domain-containing 3 (NLRP3) inflammasome, which is composed of an NLRP3 domain, the adaptor molecule apoptosis-associated speck-like protein containing a CARD (ASC) domain, and procaspase-1, plays an important role in the immune pathophysiology of
Fabio Angeli et al.
Expert opinion on drug metabolism & toxicology, 14(5), 533-541 (2018-04-21)
Fimasartan is the ninth and latest Angiotensin Receptor Blockers for the treatment of hypertension. Fimasartan is a derivative of losartan in which the imidazole ring has been replaced. It provides a selective type 1 angiotensin II receptor antagonist effect with

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