WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H317141
CAS#: 247257-48-3 (free)
Description: Fimasartan is a non-peptide angiotensin II receptor antagonist (ARB) used for the treatment of hypertension and heart failure. Through oral administration, fimasartan blocks angiotensin II receptor type 1 (AT1 receptors), reducing pro-hypertensive actions of angiotensin II, such as systemic vasoconstriction and water retention by the kidneys. Fimasartan was approved for use in South Korea in September 9th, 2010.
Hodoodo Cat#: H317141
Name: Fimasartan
CAS#: 247257-48-3 (free)
Chemical Formula: C27H31N7OS
Exact Mass: 501.23
Molecular Weight: 501.650
Elemental Analysis: C, 64.65; H, 6.23; N, 19.55; O, 3.19; S, 6.39
Related CAS #: 1020110-23-9 (potassium trihydrate) 247257-48-3 (free) 1402813-38-0 (potassium)
Synonym: BR-A657; BR A657; BRA657; BRA 657; BR-A-657.K; Fimasartan. brand name: Kanarb.
IUPAC/Chemical Name: 2-(2-Butyl-4-methyl-6-oxo-1-{[2'-(1H-tetrazol-5-yl)-4-biphenylyl]methyl}-1,6-dihydro-5-pyrimidinyl)-N,N-dimethylethanethioamide
InChi Key: AMEROGPZOLAFBN-UHFFFAOYSA-N
InChi Code: 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)
SMILES Code: S=C(N(C)C)CC1=C(C)N=C(CCCC)N(CC2=CC=C(C3=CC=CC=C3C4=NN=NN4)C=C2)C1=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | Fimasartan(BR-A-657) is a non-peptide angiotensin II receptor antagonist used for the treatment of hypertension and heart failure. |
| In vitro activity: | Cultured microglia cells stimulated by hemolysate demonstrated significant activation of the inflammasome, which was reduced by fimasartan. Reference: Exp Neurol. 2018 Dec;310:22-32. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6203658/ |
| In vivo activity: | Transcription of the p53 gene was also significantly increased in terfenadine-treated larvae, whereas fimasartan-treated larvae showed only a mild increase in p53 mRNA expression. These findings indicated that fimasartan significantly suppressed terfenadine-induced apoptosis in an in vivo zebrafish model of HF. Reference: Korean J Intern Med. 2020 Nov; 35(6): 1400–1410. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7652659/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 74.5 | 148.51 | |
| Ethanol | 24.0 | 47.84 |
The following data is based on the product molecular weight 501.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | 1. Yang X, Sun J, Kim TJ, Kim YJ, Ko SB, Kim CK, Jia X, Yoon BW. Pretreatment with low-dose fimasartan ameliorates NLRP3 inflammasome-mediated neuroinflammation and brain injury after intracerebral hemorrhage. Exp Neurol. 2018 Dec;310:22-32. doi: 10.1016/j.expneurol.2018.08.013. Epub 2018 Aug 29. PMID: 30171865; PMCID: PMC6203658. 2. Lee YJ, Jang YN, Han YM, Kim HM, Jeong JM, Seo HS. Fimasartan Ameliorates Nonalcoholic Fatty Liver Disease through PPARδ Regulation in Hyperlipidemic and Hypertensive Conditions. PPAR Res. 2017;2017:8048720. doi: 10.1155/2017/8048720. Epub 2017 Mar 13. PMID: 28386270; PMCID: PMC5366769. 3. Quan H, Oh GC, Seok SH, Lee HY. Fimasartan, an angiotensin II receptor antagonist, ameliorates an in vivo zebrafish model of heart failure. Korean J Intern Med. 2020 Nov;35(6):1400-1410. doi: 10.3904/kjim.2019.038. Epub 2020 Mar 13. PMID: 32164398; PMCID: PMC7652659. 4. Kim JH, Lim IR, Joo HJ, Park CY, Choi SC, Jeong HS, Hong SJ. Fimasartan reduces neointimal formation and inflammation after carotid arterial injury in apolipoprotein E knockout mice. Mol Med. 2019 Jul 15;25(1):33. doi: 10.1186/s10020-019-0095-0. PMID: 31307370; PMCID: PMC6632006. |
| In vitro protocol: | 1. Yang X, Sun J, Kim TJ, Kim YJ, Ko SB, Kim CK, Jia X, Yoon BW. Pretreatment with low-dose fimasartan ameliorates NLRP3 inflammasome-mediated neuroinflammation and brain injury after intracerebral hemorrhage. Exp Neurol. 2018 Dec;310:22-32. doi: 10.1016/j.expneurol.2018.08.013. Epub 2018 Aug 29. PMID: 30171865; PMCID: PMC6203658. 2. Lee YJ, Jang YN, Han YM, Kim HM, Jeong JM, Seo HS. Fimasartan Ameliorates Nonalcoholic Fatty Liver Disease through PPARδ Regulation in Hyperlipidemic and Hypertensive Conditions. PPAR Res. 2017;2017:8048720. doi: 10.1155/2017/8048720. Epub 2017 Mar 13. PMID: 28386270; PMCID: PMC5366769. |
| In vivo protocol: | 1. Quan H, Oh GC, Seok SH, Lee HY. Fimasartan, an angiotensin II receptor antagonist, ameliorates an in vivo zebrafish model of heart failure. Korean J Intern Med. 2020 Nov;35(6):1400-1410. doi: 10.3904/kjim.2019.038. Epub 2020 Mar 13. PMID: 32164398; PMCID: PMC7652659. 2. Kim JH, Lim IR, Joo HJ, Park CY, Choi SC, Jeong HS, Hong SJ. Fimasartan reduces neointimal formation and inflammation after carotid arterial injury in apolipoprotein E knockout mice. Mol Med. 2019 Jul 15;25(1):33. doi: 10.1186/s10020-019-0095-0. PMID: 31307370; PMCID: PMC6632006. |
1: Kim CK, Yang XL, Kim YJ, Choi IY, Jeong HG, Park HK, Kim D, Kim TJ, Jang H, Ko SB, Yoon BW. Effect of Long-Term Treatment with Fimasartan on Transient Focal Ischemia in Rat Brain. Biomed Res Int. 2015;2015:295925. doi: 10.1155/2015/295925. Epub 2015 Sep 13. PubMed PMID: 26448932; PubMed Central PMCID: PMC4584036.
2: Ghim JL, Paik SH, Hasanuzzaman M, Chi YH, Choi HK, Kim DH, Shin JG. Absolute bioavailability and pharmacokinetics of the angiotensin II receptor antagonist fimasartan in healthy subjects. J Clin Pharmacol. 2015 Aug 13. doi: 10.1002/jcph.618. [Epub ahead of print] PubMed PMID: 26272450.
3: Rhee MY, Baek SH, Kim W, Park CG, Park SW, Oh BH, Kim SH, Kim JJ, Shin JH, Yoo BS, Rim SJ, Ha JW, Doh JH, Ahn Y, Chae JK, Park JB, Kim SK, Kim CH. Efficacy of fimasartan/hydrochlorothiazide combination in hypertensive patients inadequately controlled by fimasartan monotherapy. Drug Des Devel Ther. 2015 Jun 2;9:2847-54. doi: 10.2147/DDDT.S82098. eCollection 2015. PubMed PMID: 26082615; PubMed Central PMCID: PMC4459623.
4: Lee JY, Choi YJ, Oh SJ, Chi YH, Paik SH, Lee KH, Jung JK, Ryu CS, Kim KB, Kim DH, Yoon YR, Kim SK. Characterization of fimasartan metabolites in human liver microsomes and human plasma. Xenobiotica. 2015 Jun 11:1-12. [Epub ahead of print] PubMed PMID: 26068523.
5: Kim TH, Shin S, Landersdorfer CB, Chi YH, Paik SH, Myung J, Yadav R, Horkovics-Kovats S, Bulitta JB, Shin BS. Population Pharmacokinetic Modeling of the Enterohepatic Recirculation of Fimasartan in Rats, Dogs, and Humans. AAPS J. 2015 Sep;17(5):1210-23. doi: 10.1208/s12248-015-9764-2. Epub 2015 May 20. PubMed PMID: 25990964; PubMed Central PMCID: PMC4540730.
6: Chang SA, Lim BK, Lee YJ, Hong MK, Choi JO, Jeon ES. A Novel Angiotensin Type I Receptor Antagonist, Fimasartan, Prevents Doxorubicin-induced Cardiotoxicity in Rats. J Korean Med Sci. 2015 May;30(5):559-68. doi: 10.3346/jkms.2015.30.5.559. Epub 2015 Apr 15. PubMed PMID: 25931786; PubMed Central PMCID: PMC4414639.
7: Lee HY, Kim YJ, Ahn T, Youn HJ, Chull Chae S, Seog Seo H, Kim KS, Rhee MY, Choi DJ, Kim JJ, Chun KJ, Yoo BS, Park JS, Oh SK, Kim DS, Kwan J, Ahn Y, Bae Park J, Jeong JO, Hyon MS, Cho EJ, Han KR, Kim DI, Joo SJ, Shin JH, Sung KC, Jeon ES. A Randomized, Multicenter, Double-Blind, Placebo-Controlled, 3 × 3 Factorial Design, Phase II Study to Evaluate the Efficacy and Safety of the Combination of Fimasartan/Amlodipine in Patients With Essential Hypertension. Clin Ther. 2015 Apr 4. pii: S0149-2918(15)00089-2. doi: 10.1016/j.clinthera.2015.02.019. [Epub ahead of print] PubMed PMID: 25850881.
8: Yoon SH, Oh S, Kim HS, Yi S, Yu KS, Jang IJ, Cho JY. Validated LC-MS/MS Assay for the Quantitative Determination of Fimasartan in Human Plasma: Application to Pharmacokinetic Studies. J Chromatogr Sci. 2015 Sep;53(8):1250-6. doi: 10.1093/chromsci/bmu219. Epub 2015 Jan 22. PubMed PMID: 25616988.
9: Sim DS, Jeong MH, Song HC, Kim J, Chong A, Bom HS, Jeong IS, Oh SG, Kim JM, Park DS, Kim JH, Lim KS, Kim MS, Ryu SH, Kim HK, Kim SS, Jang SY, Cho JY, Jeong HC, Lee KH, Park KH, Yoon NS, Yoon HJ, Kim KH, Hong YJ, Park HW, Kim JH, Ahn Y, Cho JG, Park JC, Kang JC. Cardioprotective effect of fimasartan, a new angiotensin receptor blocker, in a porcine model of acute myocardial infarction. J Korean Med Sci. 2015 Jan;30(1):34-43. doi: 10.3346/jkms.2015.30.1.34. Epub 2014 Dec 23. PubMed PMID: 25552881; PubMed Central PMCID: PMC4278025.
10: Kim S, Lee J, Shin D, Lim KS, Kim YS, Jang IJ, Yu KS. Effect of renal function on the pharmacokinetics of fimasartan: a single-dose, open-label, Phase I study. Drug Des Devel Ther. 2014 Oct 6;8:1723-31. doi: 10.2147/DDDT.S68784. eCollection 2014. PubMed PMID: 25336916; PubMed Central PMCID: PMC4199969.
11: Youn JC, Ihm SH, Bae JH, Park SM, Jeon DW, Jung BC, Park TH, Lee NH, Song JM, Yoon YW, Shin ES, Sung KC, Jung IH, Pyun WB, Joo SJ, Park WJ, Shin JH, Kang SM. Efficacy and safety of 30-mg fimasartan for the treatment of patients with mild to moderate hypertension: an 8-week, multicenter, randomized, double-blind, phase III clinical study. Clin Ther. 2014 Oct 1;36(10):1412-21. doi: 10.1016/j.clinthera.2014.07.004. Epub 2014 Aug 3. PubMed PMID: 25092393.
12: Jeong ES, Kim YW, Kim HJ, Shin HJ, Shin JG, Kim KH, Chi YH, Paik SH, Kim DH. Glucuronidation of fimasartan, a new angiotensin receptor antagonist, is mainly mediated by UGT1A3. Xenobiotica. 2015 Jan;45(1):10-8. doi: 10.3109/00498254.2014.942810. Epub 2014 Jul 18. PubMed PMID: 25034008.
13: Kim TH, Shin S, Bashir M, Chi YH, Paik SH, Lee JH, Choi HJ, Choi JH, Yoo SD, Bulitta JB, Ma E, Joo SH, Shin BS. Pharmacokinetics and metabolite profiling of fimasartan, a novel antihypertensive agent, in rats. Xenobiotica. 2014 Oct;44(10):913-25. doi: 10.3109/00498254.2014.915359. Epub 2014 Apr 30. PubMed PMID: 24786684.
14: Kim CO, Lee HW, Oh ES, Seong SJ, Kim do Y, Lee J, Ahn SH, Yoon YR, Cho CM, Park MS. Influence of hepatic dysfunction on the pharmacokinetics and safety of fimasartan. J Cardiovasc Pharmacol. 2013 Dec;62(6):524-9. doi: 10.1097/FJC.0000000000000010. PubMed PMID: 24084213.
15: Lee H, Kim KS, Chae SC, Jeong MH, Kim DS, Oh BH. Ambulatory blood pressure response to once-daily fimasartan: an 8-week, multicenter, randomized, double-blind, active-comparator, parallel-group study in Korean patients with mild to moderate essential hypertension. Clin Ther. 2013 Sep;35(9):1337-49. doi: 10.1016/j.clinthera.2013.06.021. Epub 2013 Aug 7. PubMed PMID: 23932463.
16: Han J, Park SJ, Thu VT, Lee SR, Long le T, Kim HK, Kim N, Park SW, Jeon ES, Kim EJ, Yoon CH, Cho GY, Choi DJ. Effects of the novel angiotensin II receptor type I antagonist, fimasartan on myocardial ischemia/reperfusion injury. Int J Cardiol. 2013 Oct 3;168(3):2851-9. doi: 10.1016/j.ijcard.2013.03.151. Epub 2013 May 1. PubMed PMID: 23642815.
17: Lee JY, Lee CW, Kim WJ, Ahn JM, Park DW, Kang SJ, Lee SW, Kim YH, Son WC, Jung S, Park SW, Park SJ. Antiatherosclerotic effects of the novel angiotensin receptor antagonist Fimasartan on plaque progression and stability in a rabbit model: a double-blind placebo-controlled trial. J Cardiovasc Pharmacol. 2013 Aug;62(2):229-36. doi: 10.1097/FJC.0b013e318297458b. PubMed PMID: 23615162.
18: Ryu S, Shin JS, Cho YW, Kim HK, Paik SH, Lee JH, Chi YH, Kim JH, Kim JH, Lee KT. Fimasartan, anti-hypertension drug, suppressed inducible nitric oxide synthase expressions via nuclear factor-kappa B and activator protein-1 inactivation. Biol Pharm Bull. 2013;36(3):467-74. PubMed PMID: 23449332.
19: Lim HJ, Lee SK, Lim DY. Influence of Fimasartan (a Novel AT(1) Receptor Blocker) on Catecholamine Release in the Adrenal Medulla of Spontaneously Hypertensive Rats. Korean J Physiol Pharmacol. 2013 Feb;17(1):99-109. doi: 10.4196/kjpp.2013.17.1.99. Epub 2013 Feb 14. PubMed PMID: 23441003; PubMed Central PMCID: PMC3579112.
20: Kim JW, Yi S, Kim TE, Lim KS, Yoon SH, Cho JY, Lee MG, Song IS, Shin SG, Jang IJ, Yu KS. Increased systemic exposure of fimasartan, an angiotensin II receptor antagonist, by ketoconazole and rifampicin. J Clin Pharmacol. 2013 Jan;53(1):75-81. doi: 10.1177/0091270011433328. Epub 2013 Jan 24. PubMed PMID: 23400746.
