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MedKoo Cat#: 525084 | Name: FR 139317

Description:

WARNING: This product is for research use only, not for human or veterinary use.

FR 139317 is a highly potent and selective ETA endothelin receptor antagonist (Ki values are 1 nM and 7.3 μM at ETA and ETB subtypes respectively). It is active in vivo.

Chemical Structure

FR 139317
FR 139317
CAS#142375-60-8

Theoretical Analysis

MedKoo Cat#: 525084

Name: FR 139317

CAS#: 142375-60-8

Chemical Formula: C33H44N6O5

Exact Mass: 604.3373

Molecular Weight: 604.74

Elemental Analysis: C, 65.54; H, 7.33; N, 13.90; O, 13.23

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Synonym
FR 139317; FR-139317; FR139317
IUPAC/Chemical Name
(2R)-2-[[(2R)-2-[[(2S)-2-(azepane-1-carbonylamino)-4-methylpentanoyl]amino]-3-(1-methylindol-3-yl)propanoyl]amino]-3-pyridin-2-ylpropanoic acid
InChi Key
LIOKMIQQPDDTNO-UPRLRBBYSA-N
InChi Code
InChI=1S/C33H44N6O5/c1-22(2)18-26(37-33(44)39-16-10-4-5-11-17-39)30(40)35-27(19-23-21-38(3)29-14-7-6-13-25(23)29)31(41)36-28(32(42)43)20-24-12-8-9-15-34-24/h6-9,12-15,21-22,26-28H,4-5,10-11,16-20H2,1-3H3,(H,35,40)(H,36,41)(H,37,44)(H,42,43)/t26-,27+,28+/m0/s1
SMILES Code
O=C(N[C@H](CC1=CN(C)C2=CC=CC=C12)C(N[C@@H](C(O)=O)CC3=NC=CC=C3)=O)[C@@H](NC(N4CCCCCC4)=O)CC(C)C
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

Preparing Stock Solutions

The following data is based on the product molecular weight 604.74 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.

Recalculate based on batch purity %
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
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Positron emission tomography of [18F]-big endothelin-1 reveals renal excretion but tissue-specific conversion to [18F]-endothelin-1 in lung and liver. Br J Pharmacol. 2010 Feb;159(4):812-9. doi: 10.1111/j.1476-5381.2010.00641.x. PubMed PMID: 20388128; PubMed Central PMCID: PMC2829207. 7: Yang YL, Liu DD, Hsieh NK, Chen HI. Endothelin and gelatinases in renal changes following blockade of nitric oxide synthase in hypertensive rats. Chin J Physiol. 2008 Jun 30;51(3):186-95. PubMed PMID: 18935914. 8: Johnsson E, Maddahi A, Wackenfors A, Edvinsson L. Enhanced expression of contractile endothelin ET(B) receptors in rat coronary artery after organ culture. Eur J Pharmacol. 2008 Mar 17;582(1-3):94-101. doi: 10.1016/j.ejphar.2007.12.030. Epub 2008 Jan 7. PubMed PMID: 18242601. 9: Qi W, Wei JX, Dorairaj I, Mahajan RP, Wilson VG. Evidence that a prostanoid produced by cyclo-oxygenase-2 enhances contractile responses of the porcine isolated coronary artery following exposure to lipopolysaccharide. Br J Anaesth. 2007 Mar;98(3):323-30. Epub 2007 Feb 1. PubMed PMID: 17272385. 10: Kato G, Ishino K, Mohri M, Hisamochi K, Takagaki M, Sano S. Efficacy of an endothelin-A receptor antagonist in heart transplantation from asphyxiated canine non-heart-beating donors. Jpn J Thorac Cardiovasc Surg. 2006 Dec;54(12):511-5. PubMed PMID: 17236652. 11: O'Sullivan SE, Kendall DA, Randall MD. The effects of Delta9-tetrahydrocannabinol in rat mesenteric vasculature, and its interactions with the endocannabinoid anandamide. Br J Pharmacol. 2005 Jun;145(4):514-26. PubMed PMID: 15821751; PubMed Central PMCID: PMC1576168. 12: Chu L, Zhang JX, Norota I, Endoh M. Receptor subtypes mediating the inotropic effects and Ca(2+) signaling induced by endothelin-1 through crosstalk with norepinephrine in canine ventricular myocardium. J Pharmacol Sci. 2005 Mar;97(3):417-28. Epub 2005 Mar 12. PubMed PMID: 15764840. 13: Goto K. [Discovery of endothelin and its significance]. Nihon Rinsho. 2004 Sep;62 Suppl 9:575-83. Review. Japanese. PubMed PMID: 15506451. 14: Granström B, Nilsson E, Hultkvist-Bengtsson U, Edvinsson L. Analysis of ET-A and ET-B receptors using an isolated perfused rat lung preparation. Acta Physiol Scand. 2004 Jun;181(2):259-64. PubMed PMID: 15180799. 15: Yomogida S, Maruya J, Norota I, Ishii K, Endoh M. Differential inhibition by TAK-044 of the inotropic effects of endothelin-1 and endothelin-3. Eur J Pharmacol. 2004 May 25;492(2-3):217-24. PubMed PMID: 15178368. 16: Di Filippo C, Rossi F, Ongini E, Del Soldato P, Perretti M, D'Amico M. The distinct alterations produced in cardiovascular functions by prednisolone and nitro-prednisolone (NCX-1015) in the rat highlight a causal role for endothelin-1. J Pharmacol Exp Ther. 2004 Sep;310(3):1133-41. Epub 2004 Apr 27. PubMed PMID: 15113846. 17: Getting SJ, Di Filippo C, Lam CW, Rossi F, D'Amico M. Investigation into the potential anti-inflammatory effects of endothelin antagonists in a murine model of experimental monosodium urate peritonitis. J Pharmacol Exp Ther. 2004 Jul;310(1):90-7. Epub 2004 Mar 2. PubMed PMID: 14996949. 18: Kumada M, Cao W, Kuwaki T. Effect of endothelin on vasomotor and respiratory neurons in the rostral ventrolateral medulla in rats. Cell Mol Neurobiol. 2003 Oct;23(4-5):691-707. PubMed PMID: 14514025. 19: Di Filippo C, Filippelli A, Rinaldi B, Piegari E, Esposito F, Rossi F, D'Amico M. Chronic peripheral ouabain treatment affects the brain endothelin system of rats. J Hypertens. 2003 Apr;21(4):747-53. PubMed PMID: 12658021. 20: Wackenfors A, Ingemansson R, Malmsjö M. Endothelin receptors in endothelium-denuded human coronary artery bypass grafts and coronary arteries. Ann Thorac Surg. 2003 Mar;75(3):874-81. PubMed PMID: 12645710.