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Also known as: 247257-48-3, Kanarb, Fimasartan [inn], 2-(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-dimethylethanethioamide, Chembl1951143, Fimasartan (inn)

Molecular Formula

C₂₇H₃₁N₇OS

Molecular Weight

501.6 g/mol

InChI Key

AMEROGPZOLAFBN-UHFFFAOYSA-N

FDA UNII

P58222188P

Fimasartan 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.

1 2D Structure

Fimasartan

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-N,N-dimethylethanethioamide

2.1.2 InChI

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)

2.1.3 InChI Key

AMEROGPZOLAFBN-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCCCC1=NC(=C(C(=O)N1CC2=CC=C(C=C2)C3=CC=CC=C3C4=NNN=N4)CC(=S)N(C)C)C

2.2 Other Identifiers

2.2.1 UNII

P58222188P

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Br-a657

2.3.2 Depositor-Supplied Synonyms

1. 247257-48-3

2. Kanarb

3. Fimasartan [inn]

4. 2-(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-dimethylethanethioamide

5. Chembl1951143

6. Fimasartan (inn)

7. P58222188p

8. 2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]pyrimidin-5-yl]-n,n-dimethylethanethioamide

9. 2-(2-butyl-4-methyl-6-oxo-1-{[2'-(1h-tetrazol-5-yl)-4-biphenylyl]methyl}-1,6-dihydro-5-pyrimidinyl)-n,n-dimethylethanethioamide

10. Br-a657

11. Br-a-657.k

12. Unii-p58222188p

13. 5-pyrimidineethanethioamide, 2-butyl-1,6-dihydro-n,n,4-trimethyl-6-oxo-1-((2'-(2h-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-

14. 5-pyrimidineethanethioamide, 2-butyl-1,6-dihydro-n,n,4-trimethyl-6-oxo-1-[[2'-(2h-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-

15. Fimasartan [who-dd]

16. Schembl2229436

17. Schembl20126833

18. Dtxsid80179460

19. Chebi:136044

20. Bcp11616

21. Ex-a3997

22. Hy-b0780

23. Zinc3842872

24. Bdbm50364573

25. Mfcd13194795

26. S4975

27. Zb1816

28. Akos016011331

29. Akos037643761

30. Ccg-269705

31. Cs-3509

32. Db09279

33. Ncgc00390600-01

34. Ac-30631

35. As-35179

36. D10556

37. 257f483

38. A919293

39. L019170

40. Q8563179

41. 2-((2-butyl-4-methyl-6-oxo-1-((2'-(1h-tetrazol-5-yl)biphenyl-4-yl)methyl)-1,6-dihydropyrimidin-5-yl))-n,n-dimethylthioacetamide

42. 2-(1-((2'-(1h-tetrazol-5-yl)biphenyl-4-yl)methyl)-2-butyl-4-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)-n,n-dimethylethanethioamide

43. 2-(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-dimethylethanethioamide

44. 2-[2-butyl-4-methyl-6-oxo-1-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]met Hyl]pyrimidin-5-yl]-n,n-dimethylethanethioamide

45. 2-butyl-5-dimethylaminothiocarbonylmethyl-6-methyl-3-[[2'-(1h-tetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidin-4(3h)-one

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₃₁N₇OS
Molecular Weight	501.6 g/mol
XLogP3	3.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	9
Exact Mass	501.23107981 g/mol
Monoisotopic Mass	501.23107981 g/mol
Topological Polar Surface Area	123 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	849
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Used for the treatment of hypertension and heart failure.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Fimasartan is a selective angiotensin receptor 1 (AR1) inhibitor. It acts to lower blood pressure by inhibiting vasoconstriction

5.2 ATC Code

C - Cardiovascular system

C09 - Agents acting on the renin-angiotensin system

C09C - Angiotensin ii receptor blockers (arbs), plain

C09CA - Angiotensin ii receptor blockers (arbs), plain

C09CA10 - Fimasartan

5.3 Absorption, Distribution and Excretion

Absorption

Tmax is 0.5-1.3 h.

Route of Elimination

Most is eliminated unchangd in bile with less than 3% in the urine.

5.4 Biological Half-Life

The half life of elimination is 7-10 h.

5.5 Mechanism of Action

Angiotensin II activates AR1 leading to vasoconstriction and increased noradrenaline release which further increases vasoconstriction via action at 1-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.

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