Synonym
BRL 34915; BRL-34915; BRL34915; Cromakalim; (±)-Cromakalim;
IUPAC/Chemical Name
(3S,4R)-3-hydroxy-2,2-dimethyl-4-(2-oxopyrrolidin-1-yl)chromane-6-carbonitrile
InChi Key
TVZCRIROJQEVOT-CABCVRRESA-N
InChi Code
InChI=1S/C16H18N2O3/c1-16(2)15(20)14(18-7-3-4-13(18)19)11-8-10(9-17)5-6-12(11)21-16/h5-6,8,14-15,20H,3-4,7H2,1-2H3/t14-,15+/m1/s1
SMILES Code
N#CC1=CC([C@@H](N2C(CCC2)=O)[C@H](O)C(C)(C)O3)=C3C=C1
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
286.33
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: Cecchetti V, Tabarrini O, Sabatini S. From cromakalim to different structural classes of K(ATP) channel openers. Curr Top Med Chem. 2006;6(10):1049-68. Review. PubMed PMID: 16787279.
2: Moreau C, Prost AL, Dérand R, Vivaudou M. SUR, ABC proteins targeted by KATP channel openers. J Mol Cell Cardiol. 2005 Jun;38(6):951-63. Epub 2005 Feb 19. Review. PubMed PMID: 15910880.
3: Khan IA, Gowda RM. Novel therapeutics for treatment of long-QT syndrome and torsade de pointes. Int J Cardiol. 2004 May;95(1):1-6. Review. PubMed PMID: 15159030.
4: Sebille S, De Tullio P, Boverie S, Antoine MH, Lebrun P, Pirotte B. Recent developments in the chemistry of potassium channel activators: the cromakalim analogs. Curr Med Chem. 2004 May;11(9):1213-22. Review. PubMed PMID: 15134515.
5: Muraki K. [Analyses of Ca-related ion channel currents and their involvement in Ca mobilization in smooth muscle and endothelial cells]. Nihon Yakurigaku Zasshi. 2003 Mar;121(3):143-51. Review. Japanese. PubMed PMID: 12673948.
6: Brayden JE. Functional roles of KATP channels in vascular smooth muscle. Clin Exp Pharmacol Physiol. 2002 Apr;29(4):312-6. Review. PubMed PMID: 11985542.
7: Ng GY, da S, Ohlsson A. Bronchodilators for the prevention and treatment of chronic lung disease in preterm infants. Cochrane Database Syst Rev. 2001;(3):CD003214. Review. Update in: Cochrane Database Syst Rev. 2012;6:CD003214. PubMed PMID: 11687053.
8: Ashcroft FM, Gribble FM. New windows on the mechanism of action of K(ATP) channel openers. Trends Pharmacol Sci. 2000 Nov;21(11):439-45. Review. PubMed PMID: 11121575.
9: Doggrell SA. Tedisamil: master switch of nature? Expert Opin Investig Drugs. 2001 Jan;10(1):129-38. Review. PubMed PMID: 11116286.
10: Lawson K. Potassium channel openers as potential therapeutic weapons in ion channel disease. Kidney Int. 2000 Mar;57(3):838-45. Review. PubMed PMID: 10720937.
11: Miller TR, Taber RD, Molinari EJ, Whiteaker KL, Monteggia LM, Scott VE, Brioni JD, Sullivan JP, Gopalakrishnan M. Pharmacological and molecular characterization of ATP-sensitive K+ channels in the TE671 human medulloblastoma cell line. Eur J Pharmacol. 1999 Apr 9;370(2):179-85. Review. PubMed PMID: 10323267.
12: Grover GJ. Pharmacology of ATP-sensitive potassium channel (KATP) openers in models of myocardial ischemia and reperfusion. Can J Physiol Pharmacol. 1997 Apr;75(4):309-15. Review. PubMed PMID: 9196857.
13: Lawson K. Is there a therapeutic future for "potassium channel openers'? Clin Sci (Lond). 1996 Dec;91(6):651-63. Review. PubMed PMID: 8976800.
14: Lawson K. Potassium channel activation: a potential therapeutic approach? Pharmacol Ther. 1996;70(1):39-63. Review. PubMed PMID: 8804110.
15: Zhang H, Cook D. Cerebral vascular smooth muscle potassium channels and their possible role in the management of vasospasm. Pharmacol Toxicol. 1994 Dec;75(6):327-36. Review. PubMed PMID: 7899253.
16: Haeusler G, Lues I. Therapeutic potential of potassium channel activators in coronary heart disease. Eur Heart J. 1994 Aug;15 Suppl C:82-8. Review. PubMed PMID: 7995277.
17: Hellwig B. [Potassium agonists]. Med Monatsschr Pharm. 1994 Jun;17(6):164-7. Review. German. PubMed PMID: 8052166.
18: Henry P, Escande D. Do potassium channel openers compete with ATP to activate ATP sensitive potassium channels? Cardiovasc Res. 1994 Jun;28(6):754-9. Review. PubMed PMID: 7923275.
19: Grover GJ. Protective effects of ATP-sensitive potassium-channel openers in experimental myocardial ischemia. J Cardiovasc Pharmacol. 1994;24 Suppl 4:S18-27. Review. PubMed PMID: 7898104.
20: Atwal KS. Pharmacology and structure-activity relationships for KATP modulators: tissue-selective KATP openers. J Cardiovasc Pharmacol. 1994;24 Suppl 4:S12-7. Review. PubMed PMID: 7898103.