MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 577821 | Name: Bimakalim
Featured New

Description:

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

Bimakalim, an ATP-sensitive potassium channel opener, mimics the effects of ischemic preconditioning to reduce infarct size, adenosine release, and neutrophil function in dogs

Chemical Structure

Bimakalim
Bimakalim
CAS#117545-11-6

Theoretical Analysis

MedKoo Cat#: 577821

Name: Bimakalim

CAS#: 117545-11-6

Chemical Formula: C17H14N2O2

Exact Mass: 278.1055

Molecular Weight: 278.31

Elemental Analysis: C, 73.37; H, 5.07; N, 10.07; O, 11.50

Price and Availability

Size Price Availability Quantity
1mg USD 90.00 Ready to Ship
5mg USD 250.00 Ready to Ship
10mg USD 450.00 Ready to Ship
25mg USD 750.00 Ready to Ship
50mg USD 1,250.00 Ready to Ship
100mg USD 2,250.00 Ready to Ship
Show More
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Bimakalim; EMD 52692; EMD-52692; EMD52692; SR 44866; SR-44866; SR44866;
IUPAC/Chemical Name
2,2-dimethyl-4-(2-oxopyridin-1(2H)-yl)-2H-chromene-6-carbonitrile
InChi Key
JTVSKASWNROQQF-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H14N2O2/c1-17(2)10-14(19-8-4-3-5-16(19)20)13-9-12(11-18)6-7-15(13)21-17/h3-10H,1-2H3
SMILES Code
CC1(C=C(C2=C(O1)C=CC(=C2)C#N)N3C=CC=CC3=O)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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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:
Bimakalim is an ATP-sensitive potassium channel opener.
In vitro activity:
Pretreatment with bimakalim restores the response expected in the absence of hypoxia, and glibenclamide blocks the effect of bimakalim or further impairs the response to dobutamine when used alone before long-duration hypoxia. Evidence is provided for protective effects of the K(ATP) opener bimakalim on the human myocardial contractile function in conditions of hypoxia/reoxygenation, at concentrations at which negative inotropism and APD90 shortening are not contributory. Reference: J Cardiovasc Pharmacol. 1999 Jul;34(1):162-72. https://pubmed.ncbi.nlm.nih.gov/10413083/
In vivo activity:
Ventricular ERP and repolarization were significantly shortened only by the second and third dose of BIM (bimakalim). Of 14 pigs receiving the highest BIM dosage, 3 revealed polymorphic VTs degenerating into ventricular fibrillation (VF). These data suggest that high BIM doses may lead to faster and more aggressive pacing-induced reentrant VTs after subacute MI. Reference: J Cardiovasc Pharmacol Ther. 2009 Sep;14(3):222-30. https://pubmed.ncbi.nlm.nih.gov/19587223/

Preparing Stock Solutions

The following data is based on the product molecular weight 278.31 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. Picard S, Criniti A, Iwashiro K, Rouet R, Monti F, Tonelli E, Ruvolo G, Ducouret P, del Monte F, Papalia U, Puddu PE. Protection of human myocardium in vitro by K(ATP) activation with low concentrations of bimakalim. J Cardiovasc Pharmacol. 1999 Jul;34(1):162-72. doi: 10.1097/00005344-199907000-00025. PMID: 10413083. 2. Rouet R, Picard S, Criniti A, Monti F, Dawodu AA, Ruvolo G, La Francesca S, Macrina F, Tonelli E, Ducouret P, Puddu PE. Effects of bimakalim on human cardiac action potentials: comparison with guinea pig and nicorandil and use-dependent study. J Cardiovasc Pharmacol. 1999 Feb;33(2):255-63. doi: 10.1097/00005344-199902000-00012. PMID: 10028934. 3. Aidonidis I, Poyatzi A, Stamatiou G, Lymberi M, Stamatoyannis N, Molyvdas PA. Dose-related shortening of ventricular tachycardia cycle length after administration of the KATP channel opener bimakalim in a 4-day-old chronic infarct anesthetized pig model. J Cardiovasc Pharmacol Ther. 2009 Sep;14(3):222-30. doi: 10.1177/1074248409338929. Epub 2009 Jul 8. PMID: 19587223. 4. Lathrop DA, Contney SJ, Bosnjak ZJ, Stowe DF. Reversal of hypothermia-induced action potential lengthening by the KATP channel agonist bimakalim in isolated guinea pig ventricular muscle. Gen Pharmacol. 1998 Jul;31(1):125-31. doi: 10.1016/s0306-3623(97)00395-9. PMID: 9595290.
In vitro protocol:
1. Picard S, Criniti A, Iwashiro K, Rouet R, Monti F, Tonelli E, Ruvolo G, Ducouret P, del Monte F, Papalia U, Puddu PE. Protection of human myocardium in vitro by K(ATP) activation with low concentrations of bimakalim. J Cardiovasc Pharmacol. 1999 Jul;34(1):162-72. doi: 10.1097/00005344-199907000-00025. PMID: 10413083. 2. Rouet R, Picard S, Criniti A, Monti F, Dawodu AA, Ruvolo G, La Francesca S, Macrina F, Tonelli E, Ducouret P, Puddu PE. Effects of bimakalim on human cardiac action potentials: comparison with guinea pig and nicorandil and use-dependent study. J Cardiovasc Pharmacol. 1999 Feb;33(2):255-63. doi: 10.1097/00005344-199902000-00012. PMID: 10028934.
In vivo protocol:
1. Aidonidis I, Poyatzi A, Stamatiou G, Lymberi M, Stamatoyannis N, Molyvdas PA. Dose-related shortening of ventricular tachycardia cycle length after administration of the KATP channel opener bimakalim in a 4-day-old chronic infarct anesthetized pig model. J Cardiovasc Pharmacol Ther. 2009 Sep;14(3):222-30. doi: 10.1177/1074248409338929. Epub 2009 Jul 8. PMID: 19587223. 2. Lathrop DA, Contney SJ, Bosnjak ZJ, Stowe DF. Reversal of hypothermia-induced action potential lengthening by the KATP channel agonist bimakalim in isolated guinea pig ventricular muscle. Gen Pharmacol. 1998 Jul;31(1):125-31. doi: 10.1016/s0306-3623(97)00395-9. PMID: 9595290.
1: Alexandre J, Puddu PE, Simard C, Hof T, Sallé L, Guinamard R, Manrique A, Rouet R, Beygui F, Milliez P. Proarrhythmic effects of aldosterone during myocardial ischemia-reperfusion: implication of the sarcolemmal-KATP channels. J Cardiovasc Pharmacol. 2014 Aug;64(2):134-41. doi: 10.1097/FJC.0000000000000097. PMID: 24662493. 2: Aidonidis I, Poyatzi A, Stamatiou G, Lymberi M, Stamatoyannis N, Molyvdas PA. Dose-related shortening of ventricular tachycardia cycle length after administration of the KATP channel opener bimakalim in a 4-day-old chronic infarct anesthetized pig model. J Cardiovasc Pharmacol Ther. 2009 Sep;14(3):222-30. doi: 10.1177/1074248409338929. Epub 2009 Jul 8. PMID: 19587223. 3: Stephan D, Salamon E, Weber H, Russ U, Lemoine H, Quast U. KATP channel openers of the benzopyran type reach their binding site via the cytosol. Br J Pharmacol. 2006 Sep;149(2):199-205. doi: 10.1038/sj.bjp.0706858. Epub 2006 Aug 14. PMID: 16921394; PMCID: PMC2013803. 4: Merkus D, Sorop O, Houweling B, Hoogteijling BA, Duncker DJ. KCa+ channels contribute to exercise-induced coronary vasodilation in swine. Am J Physiol Heart Circ Physiol. 2006 Nov;291(5):H2090-7. doi: 10.1152/ajpheart.00315.2006. Epub 2006 May 12. PMID: 16699076. 5: Gumina RJ, El Schultz J, Moore J, Beier N, Schelling P, Gross GJ. Cardioprotective-mimetics reduce myocardial infarct size in animals resistant to ischemic preconditioning. Cardiovasc Drugs Ther. 2005 Oct;19(5):315-22. doi: 10.1007/s10557-005-3693-8. PMID: 16382293. 6: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2005 Mar;27(2):145-59. PMID: 15834466. 7: Burian M, Piske M, Petkovic D, Mitrovic V. Lack of anti-ischemic efficacy of the potassium channel opener bimakalim in patients with stable angina pectoris. Cardiovasc Drugs Ther. 2004 Jan;18(1):37-46. doi: 10.1023/B:CARD.0000025754.08942.03. PMID: 15115902. 8: Camara AK, Chen Q, Rhodes SS, Riess ML, Stowe DF. Negative inotropic drugs alter indexes of cytosolic [Ca(2+)]-left ventricular pressure relationships after ischemia. Am J Physiol Heart Circ Physiol. 2004 Aug;287(2):H667-80. doi: 10.1152/ajpheart.01142.2003. Epub 2004 Apr 1. PMID: 15059780. 9: Gauthier KM, Jagadeesh SG, Falck JR, Campbell WB. 14,15-epoxyeicosa-5(Z)-enoic-mSI: a 14,15- and 5,6-EET antagonist in bovine coronary arteries. Hypertension. 2003 Oct;42(4):555-61. doi: 10.1161/01.HYP.0000091265.94045.C7. Epub 2003 Sep 2. PMID: 12953017. 10: Fujimoto K, Bosnjak ZJ, Kwok WM. Isoflurane-induced facilitation of the cardiac sarcolemmal K(ATP) channel. Anesthesiology. 2002 Jul;97(1):57-65. doi: 10.1097/00000542-200207000-00009. PMID: 12131104. 11: Gauthier KM, Deeter C, Krishna UM, Reddy YK, Bondlela M, Falck JR, Campbell WB. 14,15-Epoxyeicosa-5(Z)-enoic acid: a selective epoxyeicosatrienoic acid antagonist that inhibits endothelium-dependent hyperpolarization and relaxation in coronary arteries. Circ Res. 2002 May 17;90(9):1028-36. doi: 10.1161/01.res.0000018162.87285.f8. PMID: 12016270. 12: Salamon E, Mannhold R, Weber H, Lemoine H, Frank W. 6-Sulfonylchromenes as highly potent K(ATP)-channel openers. J Med Chem. 2002 Feb 28;45(5):1086-97. doi: 10.1021/jm010999g. PMID: 11855989. 13: Das B, Sarkar C, Karanth KS. Effects of administration of nicorandil or bimakalim prior to and during ischemia or reperfusion on survival rate, ischemia/reperfusion-induced arrhythmias and infarct size in anesthetized rabbits. Naunyn Schmiedebergs Arch Pharmacol. 2001 Nov;364(5):383-96. doi: 10.1007/s002100100457. PMID: 11692221. 14: Pountney DJ, Sun ZQ, Porter LM, Nitabach MN, Nakamura TY, Holmes D, Rosner E, Kaneko M, Manaris T, Holmes TC, Coetzee WA. Is the molecular composition of K(ATP) channels more complex than originally thought? J Mol Cell Cardiol. 2001 Aug;33(8):1541-6. doi: 10.1006/jmcc.2001.1407. PMID: 11448141. 15: Pratt PF, Li P, Hillard CJ, Kurian J, Campbell WB. Endothelium-independent, ouabain-sensitive relaxation of bovine coronary arteries by EETs. Am J Physiol Heart Circ Physiol. 2001 Mar;280(3):H1113-21. doi: 10.1152/ajpheart.2001.280.3.H1113. PMID: 11179054. 16: Eells JT, Henry MM, Gross GJ, Baker JE. Increased mitochondrial K(ATP) channel activity during chronic myocardial hypoxia: is cardioprotection mediated by improved bioenergetics? Circ Res. 2000 Nov 10;87(10):915-21. doi: 10.1161/01.res.87.10.915. PMID: 11073888. 17: Holmes DS, Sun ZQ, Porter LM, Bernstein NE, Chinitz LA, Artman M, Coetzee WA. Amiodarone inhibits cardiac ATP-sensitive potassium channels. J Cardiovasc Electrophysiol. 2000 Oct;11(10):1152-8. doi: 10.1111/j.1540-8167.2000.tb01762.x. PMID: 11059980. 18: Mitrovic V, Oehm E, Thormann J, Pitschner H, Hamm C. Potassium channel openers and blockers in coronary artery disease. Comparison to betablockers and calcium antagonists. Herz. 2000 Mar;25(2):130-42. doi: 10.1007/pl00001951. PMID: 10829253. 19: Buchheit KH, Hofmann A, Manley P, Pfannkuche HJ, Quast U. Atypical effect of minoxidil sulphate on guinea pig airways. Naunyn Schmiedebergs Arch Pharmacol. 2000 Apr;361(4):418-24. doi: 10.1007/s002100000218. PMID: 10763857. 20: Monti F, Iwashiro K, Picard S, Criniti A, La Francesca S, Ruvolo G, Papalia U, Campa PP, Marino B, Puddu PE. Adenosine triphosphate-dependent potassium channel modulation and cardioplegia-induced protection of human atrial muscle in an in vitro model of myocardial stunning. J Thorac Cardiovasc Surg. 2000 Apr;119(4 Pt 1):842-8. doi: 10.1016/S0022-5223(00)70022-5. PMID: 10733778.