MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 584385 | Name: Levcromakalim
Featured

Description:

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

Levcromakalim, also known as Lemakalim, is an anti-asthmatic, antihypertensive, and potassium-ATP channel opener.

Chemical Structure

Levcromakalim
CAS#94535-50-9

Theoretical Analysis

MedKoo Cat#: 584385

Name: Levcromakalim

CAS#: 94535-50-9

Chemical Formula: C16H18N2O3

Exact Mass: 286.1317

Molecular Weight: 286.33

Elemental Analysis: C, 67.12; H, 6.34; N, 9.78; O, 16.76

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 600.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Levcromakalim; Lemakalim; BRL 38227; BRL-38227; BRL38227
IUPAC/Chemical Name
2H-1-Benzopyran-6-carbonitrile, 3,4-dihydro-3-hydroxy-2,2-dimethyl-4-(2-oxo-1-pyrrolidinyl)-, (3S,trans)-
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=C2C([C@@H](N3C(CCC3)=O)[C@H](O)C(C)(C)O2)=C1
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
>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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Levcromakalim ((-)-Cromakalim) is an ATP-sensitive K+ channel (KATP) activator.
In vitro activity:
In contrast, in human bronchi, cromakalim was capable of inducing powerful concentration-dependent relaxations against carbachol-induced tone [cromakalim (20 microM) induced relaxations of 0.77 +/- 0.09 (relative to isoprenaline = 1.0, mean +/- S.E.M.) against carbachol, compared to 0.95 +/- 0.04 against histamine]. Reference: J Pharmacol Exp Ther. 1992 May;261(2):429-37. https://pubmed.ncbi.nlm.nih.gov/1578358/
In vivo activity:
One compound in particular, 1,1-dimethyl-5-nitro-3-(2-pyridon-1-yl)indan-2-ol, (levcromakalim) was identified as a potent relaxant of airways smooth muscle in vitro with IC50 = 0.15 microM and was found to significantly inhibit histamine-induced dyspnoea in conscious guinea pigs when given orally 30-45 min prior to challenge. Reference: J Med Chem. 1991 Mar;34(3):919-26. https://pubmed.ncbi.nlm.nih.gov/2002472/
Solvent mg/mL mM comments
Solubility
DMSO 26.4 92.31
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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
Formulation protocol:
1. Kajioka S, Nakayama S, Asano H, Seki N, Naito S, Brading AF. Levcromakalim and MgGDP activate small conductance ATP-sensitive K+ channels of K+ channel pore 6.1/sulfonylurea receptor 2A in pig detrusor smooth muscle cells: uncoupling of cAMP signal pathways. J Pharmacol Exp Ther. 2008 Oct;327(1):114-23. doi: 10.1124/jpet.108.140269. Epub 2008 Jul 2. PMID: 18596222. 2. Taylor SG, Arch JR, Bond J, Buckle DR, Shaw DJ, Taylor JF, Ward JS. The inhibitory effects of cromakalim and its active enantiomer BRL 38227 against various agonists in guinea pig and human airways: comparison with pinacidil and verapamil. J Pharmacol Exp Ther. 1992 May;261(2):429-37. PMID: 1578358. 3. Owolabi OJ, Omogbai EK. Evaluation of the potassium channel activator levcromakalim (BRL38227) on the lipid profile, electrolytes and blood glucose levels of streptozotocin-diabetic rats. J Diabetes. 2013 Mar;5(1):88-94. doi: 10.1111/1753-0407.12001. PMID: 23374501. 4. Buckle DR, Arch JR, Edge C, Foster KA, Houge-Frydrych CS, Pinto IL, Smith DG, Taylor JF, Taylor SG, Tedder JM, et al. Synthesis and smooth muscle relaxant activity of a new series of potassium channel activators: 3-amido-1,1-dimethylindan-2-ols. J Med Chem. 1991 Mar;34(3):919-26. doi: 10.1021/jm00107a008. PMID: 2002472.
In vitro protocol:
1. Kajioka S, Nakayama S, Asano H, Seki N, Naito S, Brading AF. Levcromakalim and MgGDP activate small conductance ATP-sensitive K+ channels of K+ channel pore 6.1/sulfonylurea receptor 2A in pig detrusor smooth muscle cells: uncoupling of cAMP signal pathways. J Pharmacol Exp Ther. 2008 Oct;327(1):114-23. doi: 10.1124/jpet.108.140269. Epub 2008 Jul 2. PMID: 18596222. 2. Taylor SG, Arch JR, Bond J, Buckle DR, Shaw DJ, Taylor JF, Ward JS. The inhibitory effects of cromakalim and its active enantiomer BRL 38227 against various agonists in guinea pig and human airways: comparison with pinacidil and verapamil. J Pharmacol Exp Ther. 1992 May;261(2):429-37. PMID: 1578358.
In vivo protocol:
1. Owolabi OJ, Omogbai EK. Evaluation of the potassium channel activator levcromakalim (BRL38227) on the lipid profile, electrolytes and blood glucose levels of streptozotocin-diabetic rats. J Diabetes. 2013 Mar;5(1):88-94. doi: 10.1111/1753-0407.12001. PMID: 23374501. 2. Buckle DR, Arch JR, Edge C, Foster KA, Houge-Frydrych CS, Pinto IL, Smith DG, Taylor JF, Taylor SG, Tedder JM, et al. Synthesis and smooth muscle relaxant activity of a new series of potassium channel activators: 3-amido-1,1-dimethylindan-2-ols. J Med Chem. 1991 Mar;34(3):919-26. doi: 10.1021/jm00107a008. PMID: 2002472.
1: Owolabi OJ, Omogbai EK. Evaluation of the potassium channel activator levcromakalim (BRL38227) on the lipid profile, electrolytes and blood glucose levels of streptozotocin-diabetic rats. J Diabetes. 2013 Mar;5(1):88-94. doi: 10.1111/1753-0407.12001. PubMed PMID: 23374501. 2: Silberberg SD, van Breemen C. A potassium current activated by lemakalim and metabolic inhibition in rabbit mesenteric artery. Pflugers Arch. 1992 Jan;420(1):118-20. PubMed PMID: 1553259. 3: White R, Hiley CR. Endothelium and cannabinoid receptor involvement in levcromakalim vasorelaxation. Eur J Pharmacol. 1997 Nov 27;339(2-3):157-60. PubMed PMID: 9473130. 4: Florence X, Desvaux V, Goffin E, de Tullio P, Pirotte B, Lebrun P. Influence of the alkylsulfonylamino substituent located at the 6-position of 2,2-dimethylchromans structurally related to cromakalim: from potassium channel openers to calcium entry blockers? Eur J Med Chem. 2014 Jun 10;80:36-46. doi: 10.1016/j.ejmech.2014.04.024. Epub 2014 Apr 13. PubMed PMID: 24763361. 5: Sugai K, Yanagisawa T, Motohashi O, Suzuki M, Yoshimoto T. Levcromakalim decreases vascular tone, cytoplasmic Ca2+ and Ca2+ sensitivity in canine basilar artery. Fundam Clin Pharmacol. 1998;12(4):403-10. PubMed PMID: 9711462. 6: Clapp LH, Gurney AM, Standen NB, Langton PD. Properties of the ATP-sensitive K+ current activated by levcromakalim in isolated pulmonary arterial myocytes. J Membr Biol. 1994 Jun;140(3):205-13. PubMed PMID: 7932655. 7: Lindeman KS, Freed AN. Lemakalim attenuates hypocapnia- and dry air-induced bronchoconstriction in canine peripheral airways. J Appl Physiol (1985). 1993 Jul;75(1):86-92. PubMed PMID: 8376305. 8: Li L, Vapaatalo H, Vaali K, Paakkari I, Kankaanranta H. Flufenamic and tolfenamic acids and lemakalim relax guinea-pig isolated trachea by different mechanisms. Life Sci. 1998;62(20):PL 303-8. PubMed PMID: 9600333. 9: Gantenbein M, Attolini L, Bruguerolle B. Kinetics of bupivacaine after levcromakalim treatment in mice. J Pharm Pharmacol. 1997 Mar;49(3):293-5. PubMed PMID: 9231348. 10: Suzuki S, Yano K, Kusano S, Hashimoto T. Antihypertensive effect of levcromakalim in patients with essential hypertension. Study by 24-h ambulatory blood pressure monitoring. Arzneimittelforschung. 1995 Aug;45(8):859-64. PubMed PMID: 7575747. 11: Mellemkjaer S, Nielsen-Kudsk JE. Effects of levcromakalim and glibenclamide on paced guinea-pig atrial strips exposed to hypoxia. Eur J Pharmacol. 1995 Apr 13;277(1):51-6. PubMed PMID: 7635172. 12: Movahed P, Högestätt ED, Petersson J. Effect of hypoxia on vasodilator responses to S-nitroso-N-acetylpenicillamine and levcromakalim in guinea pig basilar artery. Naunyn Schmiedebergs Arch Pharmacol. 2003 May;367(5):532-7. Epub 2003 Mar 25. PubMed PMID: 12669187. 13: Sugai K, Yaganisawa T, Motohashi O, Suzuki M, Yoshimoto T. Levcromakalim decreases cytoplasmic Ca2+ and vascular tone in basilar artery of SAH model dogs. J Cardiovasc Pharmacol. 1999 Jun;33(6):868-75. PubMed PMID: 10367589. 14: Ambalavanan N, Bulger A, Ware J, Philips J. Hemodynamic effects of levcromakalim in neonatal porcine pulmonary hypertension. Biol Neonate. 2001 Jul;80(1):74-80. PubMed PMID: 11474154. 15: Zhang H, Stockbridge N, Weir B, Vollrath B, Cook D. Vasodilatation of canine cerebral arteries by nicorandil, pinacidil and lemakalim. Gen Pharmacol. 1992 Mar;23(2):197-201. PubMed PMID: 1353469. 16: Benton DC. The effects of cetiedil and its congeners on levcromakalim-stimulated 86Rb efflux from smooth and skeletal muscle. Eur J Pharmacol. 1996 Dec 19;317(2-3):329-33. PubMed PMID: 8997618. 17: Jung YS, Moon CH, Cho TS, Yoo SE, Shin HS. Cardioprotective effects of KR-30450, a novel K+(ATP) opener, and its major metabolite KR-30818 on isolated rat hearts. Jpn J Pharmacol. 1998 Jan;76(1):65-73. PubMed PMID: 9517406. 18: Florence X, Dilly S, de Tullio P, Pirotte B, Lebrun P. Modulation of the 6-position of benzopyran derivatives and inhibitory effects on the insulin releasing process. Bioorg Med Chem. 2011 Jul 1;19(13):3919-28. doi: 10.1016/j.bmc.2011.05.040. Epub 2011 May 24. PubMed PMID: 21664825. 19: Smits GJ, Perrone MH, Cox BF. Regional hemodynamic dose-response of lemakalim and glybenclamide in anesthetized rats. J Cardiovasc Pharmacol. 1997 Jan;29(1):49-56. PubMed PMID: 9007670. 20: Teramoto N, Brading AF. Activation by levcromakalim and metabolic inhibition of glibenclamide-sensitive K channels in smooth muscle cells of pig proximal urethra. Br J Pharmacol. 1996 Jun;118(3):635-42. PubMed PMID: 8762088; PubMed Central PMCID: PMC1909732.