Rilmakalim | CAS#132014-21-2 | K channel opener

MedKoo Cat#: 461330 | Name: Rilmakalim

Description:

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

Rilmakalim is a potassium channel opener with a antivasoconstrictor effect.

Chemical Structure

Rilmakalim

CAS#132014-21-2

Theoretical Analysis

MedKoo Cat#: 461330

Name: Rilmakalim

CAS#: 132014-21-2

Chemical Formula: C21H23NO5S

Exact Mass: 401.1297

Molecular Weight: 401.47

Elemental Analysis: C, 62.83; H, 5.77; N, 3.49; O, 19.93; S, 7.99

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Rilmakalim;

IUPAC/Chemical Name

1-((3S,4R)-3-hydroxy-2,2-dimethyl-6-(phenylsulfonyl)chroman-4-yl)pyrrolidin-2-one

InChi Key

LKAQWOWWTKFLNX-UXHICEINSA-N

InChi Code

InChI=1S/C21H23NO5S/c1-21(2)20(24)19(22-12-6-9-18(22)23)16-13-15(10-11-17(16)27-21)28(25,26)14-7-4-3-5-8-14/h3-5,7-8,10-11,13,19-20,24H,6,9,12H2,1-2H3/t19-,20+/m1/s1

SMILES Code

O=C1N([C@H]2[C@H](O)C(C)(C)OC3=C2C=C(S(=O)(C4=CC=CC=C4)=O)C=C3)CCC1

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

Shelf Life

>3 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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 401.47 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

1: Wuest M, Kaden S, Hakenberg OW, Wirth MP, Ravens U. Effect of rilmakalim on detrusor contraction in the presence and absence of urothelium. Naunyn Schmiedebergs Arch Pharmacol. 2005 Nov;372(3):203-12. Epub 2005 Nov 11. PubMed PMID: 16283254. 2: Riccioppo Neto F, Mesquita Júnior O, Olivera GB. Antiarrhythmic and electrophysiological effects of the novel KATP channel opener, rilmakalim, in rabbit cardiac cells. Gen Pharmacol. 1997 Aug;29(2):201-5. PubMed PMID: 9251899. 3: Novaković A, Gojković-Bukarica L, Beleslin-Cokić B, Japundzić-Zigon N, Sajić Z, Nezić D, Perić M, Djukanović B, Kazić T. Differential antivasoconstrictor effects of levcromakalim and rilmakalim on the isolated human mammary artery and saphenous vein. J Pharmacol Sci. 2003 Jun;92(2):108-14. PubMed PMID: 12832838. 4: Olbrich HG, Müller M, Lindner S, Henke B, Zarse M, Riehle M, Oremek G, Mutschler E. Glimepiride (Hoe490) inhibits the rilmakalim induced decrease in intracellular free calcium and contraction of isolated heart muscle cells from guinea pigs to a lesser extent than glibenclamide. Int J Cardiol. 1999 Dec 15;72(1):53-63. PubMed PMID: 10636633. 5: Kocic I, Hirano Y, Hiraoka M. Hypotonic stress increases efficacy of rilmakalim, but not pinacidil, to activate ATP-sensitive K(+) current in guinea pig ventricular myocytes. J Pharmacol Sci. 2004 Jun;95(2):189-95. PubMed PMID: 15215643. 6: Krause E, Englert H, Gögelein H. Adenosine triphosphate-dependent K currents activated by metabolic inhibition in rat ventricular myocytes differ from those elicited by the channel opener rilmakalim. Pflugers Arch. 1995 Mar;429(5):625-35. PubMed PMID: 7792140. 7: Kocić I, Dabrowski M, Petrusewicz J. Different mechanisms of positive chronotropic actions of isoprenaline and noradrenaline on isolated guinea pig right atria revealed by pretreatment with rilmakalim. Pol J Pharmacol. 2000 Sep-Oct;52(5):383-8. PubMed PMID: 11334231. 8: Balana B, Dobrev D, Wettwer E, Christ T, Knaut M, Ravens U. Decreased ATP-sensitive K(+) current density during chronic human atrial fibrillation. J Mol Cell Cardiol. 2003 Dec;35(12):1399-405. PubMed PMID: 14654366. 9: Kääb S, Zwermann L, Barth A, Hinterseer M, Englert HC, Gögelein H, Näbauer M. Selective block of sarcolemmal IKATP in human cardiomyocytes using HMR 1098. Cardiovasc Drugs Ther. 2003 Sep-Nov;17(5-6):435-41. PubMed PMID: 15107598. 10: Kocić I, Hirano Y, Hiraoka M. Early exposure to hypertonic solution strongly intensifies the effects of K+ channel opener, rilmakalim, in guinea pig ventricular myocytes. Pol J Pharmacol. 2003 Nov-Dec;55(6):1159-62. PubMed PMID: 14730116. 11: Gögelein H, Hartung J, Englert HC, Schölkens BA. HMR 1883, a novel cardioselective inhibitor of the ATP-sensitive potassium channel. Part I: effects on cardiomyocytes, coronary flow and pancreatic beta-cells. J Pharmacol Exp Ther. 1998 Sep;286(3):1453-64. PubMed PMID: 9732411. 12: Kocic I, Sztormowska K. Pulmonary hypertension modifies responsiveness of sinoatrial cells of rat hearts to adrenomimetics and activators of ATP-sensitive K+ channels in a gender-dependent way. J Physiol Pharmacol. 2009 Mar;60(1):165-9. PubMed PMID: 19439819. 13: Langheinrich U, Mederos y Schnitzler M, Daut J. Ca2+-transients induced by K+ channel openers in isolated coronary capillaries. Pflugers Arch. 1998 Feb;435(3):435-8. PubMed PMID: 9426303. 14: Kocić I, Gruchała M, Petrusewicz J. Selective inhibition of pinacidil effects by estrogen in guinea pig heart. Int J Cardiol. 2006 Jun 7;110(1):22-6. Epub 2005 Aug 10. PubMed PMID: 16095733. 15: Mederos y Schnitzler M, Derst C, Daut J, Preisig-Müller R. ATP-sensitive potassium channels in capillaries isolated from guinea-pig heart. J Physiol. 2000 Jun 1;525 Pt 2:307-17. PubMed PMID: 10835035; PubMed Central PMCID: PMC2269954. 16: Hambrock A, Kayar T, Stumpp D, Osswald H. Effect of two amino acids in TM17 of Sulfonylurea receptor SUR1 on the binding of ATP-sensitive K+ channel modulators. Diabetes. 2004 Dec;53 Suppl 3:S128-34. PubMed PMID: 15561900. 17: Kocić I, Hirano Y, Petrusewicz J, Hiraoka M. Hypotonic stress enhances slope conductivity of ATP-sensitive K+ channels activated pharmacologically. Int J Cardiol. 2007 Apr 4;116(3):423-4. Epub 2006 Jul 24. PubMed PMID: 16860891. 18: Buchheit KH, Hofmann A. KATP channel openers reverse immune complex-induced airways hyperreactivity independently of smooth muscle relaxation. Naunyn Schmiedebergs Arch Pharmacol. 1996 Aug-Sep;354(3):355-61. PubMed PMID: 8878067. 19: Grunow B, Wenzel J, Terlau H, Langner S, Gebert M, Kruse C. In vitro developed spontaneously contracting cardiomyocytes from rainbow trout as a model system for human heart research. Cell Physiol Biochem. 2011;27(1):1-12. doi: 10.1159/000325212. Epub 2011 Feb 11. PubMed PMID: 21325816. 20: Goegelein H, Gautier P, Roccon A, O'Connor S, Ruetten H. Effects of the novel amiodarone-like compound SAR114646A on cardiac ion channels and ventricular arrhythmias in rats. Naunyn Schmiedebergs Arch Pharmacol. 2011 Sep;384(3):231-44. doi: 10.1007/s00210-011-0664-4. Epub 2011 Jul 16. PubMed PMID: 21766160.