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MedKoo Cat#: 461439 | Name: Aprikalim

Description:

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

Aprikalim is a potent, specific, and selective opener of ATP-sensitive K+ (KATP) channels. Aprikalim affords cardioprotection and at higher doses also causes peripheral or coronary vasodilatation.

Chemical Structure

Aprikalim
Aprikalim
CAS#132562-26-6

Theoretical Analysis

MedKoo Cat#: 461439

Name: Aprikalim

CAS#: 132562-26-6

Chemical Formula: C12H16N2O2S2

Exact Mass: 284.0653

Molecular Weight: 284.39

Elemental Analysis: C, 50.68; H, 5.67; N, 9.85; O, 11.25; S, 22.55

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 #
135912-05-9 132562-26-6 89544-10-5 (racemic)
Synonym
RP 49356; RP-49356; RP49356; Aprikalim; RP 52891; RP-52891; RP-52891;
IUPAC/Chemical Name
2H-Thiopyran-2-carbothioamide, tetrahydro-N-methyl-2-(3-pyridinyl)-, 1-oxide, (1R-trans)-
InChi Key
GKEMHVLBZNVZOI-SJKOYZFVSA-N
InChi Code
InChI=1S/C12H16N2OS2/c1-13-11(16)12(6-2-3-8-17(12)15)10-5-4-7-14-9-10/h4-5,7,9H,2-3,6,8H2,1H3,(H,13,16)/t12-,17-/m1/s1
SMILES Code
S=C([C@]1(C2=CC=CN=C2)CCCC[S@]1=O)NC
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 284.39 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
1: Lozos VA, Toumpoulis IK, Agrogiannis G, Giamarellos-Bourboulis EJ, Chamogeorgakis TP, Rizos IK, Patsouris ES, Anagnostopoulos CE, Rokkas CK. Aprikalim a potassium adenosine triphosphate channel opener reduces neurologic injury in a rabbit model of spinal cord ischemia. Int J Surg. 2013;11(4):354-9. doi: 10.1016/j.ijsu.2013.02.025. Epub 2013 Mar 5. PubMed PMID: 23473993. 2: He GW, Yang CQ. Inhibition of vasoconstriction by potassium channel opener aprikalim in human conduit arteries used as bypass grafts. Br J Clin Pharmacol. 1997 Oct;44(4):353-9. PubMed PMID: 9354310; PubMed Central PMCID: PMC2042851. 3: Pignac J, Lacaille C, Dumont L. Protective effects of the K+ ATP channel opener, aprikalim, against free radicals in isolated rabbit hearts. Free Radic Biol Med. 1996;20(3):383-9. PubMed PMID: 8720909. 4: Belin V, Hodge T, Picaut P, Jordan R, Algate C, Gosselin S, Nohynek G, Cavero I. The myocardial lesions produced by the potassium channel opener aprikalim in monkeys and rats are prevented by blockade of cardiac beta-adrenoceptors. Fundam Appl Toxicol. 1996 Jun;31(2):259-67. PubMed PMID: 8789792. 5: Li HY, Wu S, He GW, Wong TM. Aprikalim reduces the Na+-Ca2+ exchange outward current enhanced by hyperkalemia in rat ventricular myocytes. Ann Thorac Surg. 2002 Apr;73(4):1253-9; discussion 1259-60. PubMed PMID: 11996269. 6: Liu MH, Floten HS, Furnary AP, Yim AP, He GW. Effects of potassium channel opener aprikalim on the receptor-mediated vasoconstriction in the human internal mammary artery. Ann Thorac Surg. 2001 Feb;71(2):636-41. PubMed PMID: 11235720. 7: Bastin R, Albadri H, Gaumont AC, Gulea M. Pyridinedithioesters as heterodienophiles: application to the synthesis of aprikalim. Org Lett. 2006 Mar 16;8(6):1033-6. PubMed PMID: 16524261. 8: Thuringer D, Cavero I, Coraboeuf E. Time-dependent fading of the activation of KATP channels, induced by aprikalim and nucleotides, in excised membrane patches from cardiac myocytes. Br J Pharmacol. 1995 May;115(1):117-27. PubMed PMID: 7647966; PubMed Central PMCID: PMC1908735. 9: Ibbotson T, Edwards G, Noack T, Weston AH. Effects of P1060 and aprikalim on whole-cell currents in rat portal vein; inhibition by glibenclamide and phentolamine. Br J Pharmacol. 1993 Apr;108(4):991-8. PubMed PMID: 8485637; PubMed Central PMCID: PMC1908130. 10: Pignac J, Bourgouin J, Dumont L. Cold cardioplegia and the K+ channel modulator aprikalim (RP 52891): improved cardioprotection in isolated ischemic rabbit hearts. Can J Physiol Pharmacol. 1994 Feb;72(2):126-32. PubMed PMID: 8050052. 11: Chevalier P, Rouillard C, Montay G, Frydman A. Aprikalim: radioimmunoassay and pharmacokinetic studies in mouse, monkey, and dog. J Pharm Sci. 1994 Mar;83(3):372-8. PubMed PMID: 8207684. 12: Auchampach JA, Maruyama M, Cavero I, Gross GJ. The new K+ channel opener Aprikalim (RP 52891) reduces experimental infarct size in dogs in the absence of hemodynamic changes. J Pharmacol Exp Ther. 1991 Dec;259(3):961-7. PubMed PMID: 1762089. 13: Maskal SL, Cohen NM, Hsia PW, Wechsler AS, Damiano RJ Jr. Hyperpolarized cardiac arrest with a potassium-channel opener, aprikalim. J Thorac Cardiovasc Surg. 1995 Oct;110(4 Pt 1):1083-95. PubMed PMID: 7475137. 14: Borg C, Mondot S, Mestre M, Cavero I. Nicorandil: differential contribution of K+ channel opening and guanylate cyclase stimulation to its vasorelaxant effects on various endothelin-1-contracted arterial preparations. Comparison to aprikalim (RP 52891) and nitroglycerin. J Pharmacol Exp Ther. 1991 Nov;259(2):526-34. PubMed PMID: 1682478. 15: Dumas JP, Dumas M, Sgro C, Advenier C, Giudicelli JF. Effects of two K+ channel openers, aprikalim and pinacidil, on hypoxic pulmonary vasoconstriction. Eur J Pharmacol. 1994 Sep 22;263(1-2):17-23. PubMed PMID: 7821349. 16: Guo AC, Diacono J, Feuvray D. Comparison of effects of aprikalim and of hypoxic and ischaemic preconditioning on extracellular potassium accumulation, metabolism, and functional recovery of the globally ischaemic rat heart. Cardiovasc Res. 1994 Jun;28(6):864-71. PubMed PMID: 7923293. 17: Auchampach JA, Gross GJ. Anti-ischaemic actions of potassium channel openers in experimental myocardial ischaemia/reperfusion injury in dogs. Eur Heart J. 1993 Jul;14 Suppl B:10-5. PubMed PMID: 8370365. 18: Sobey CG, Heistad DD, Faraci FM. Effect of subarachnoid hemorrhage on cerebral vasodilatation in response to activation of ATP-sensitive K+ channels in chronically hypertensive rats. Stroke. 1997 Feb;28(2):392-6; discussion 396-7. PubMed PMID: 9040696. 19: Veltkamp R, Domoki F, Bari F, Busija DW. Potassium channel activators protect the N-methyl-D-aspartate-induced cerebral vascular dilation after combined hypoxia and ischemia in piglets. Stroke. 1998 Apr;29(4):837-42; discussion 842-3. PubMed PMID: 9550520. 20: Kitazono T, Heistad DD, Faraci FM. ATP-sensitive potassium channels in the basilar artery during chronic hypertension. Hypertension. 1993 Nov;22(5):677-81. PubMed PMID: 8225527.