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MedKoo Cat#: 464709 | Name: Nicorandil-d4
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Description:

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

Nicorandil-d4 is intended for use as an internal standard for the quantification of nicorandil by GC- or LC-MS. Nicorandil is an activator of sulfonylurea receptor 2B (SUR2B) linked to ATP-sensitive potassium channel Kir6.2 (EC50 = ~10 µM) and a nitric oxide (NO) donor. It is selective for SUR2B/Kir6.2 over the SUR2A/Kir6.2 channel (EC50 = >500 µM). Nicorandil activates soluble guanylate cyclase in a cell-free assay and relaxes partially depolarized isolated bovine coronary artery strips (EC50 = 4.4 µM). It decreases mean blood pressure, coronary resistance, and heart rate, as well as increases coronary sinus outflow, in dogs when administered intravenously at a dose of 1 mg/kg. Nicorandil increases survival and decreases infarct size in a rabbit model of myocardial ischemia-reperfusion injury induced by left coronary artery occlusion. Formulations containing nicorandil have been used in the treatment of angina pectoris.

Chemical Structure

Nicorandil-d4
CAS#1132681-23-2

Theoretical Analysis

MedKoo Cat#: 464709

Name: Nicorandil-d4

CAS#: 1132681-23-2

Chemical Formula: C8H5D4N3O4

Exact Mass: 215.0844

Molecular Weight: 215.20

Elemental Analysis: C, 44.65; H, 6.09; N, 19.53; O, 29.74

Price and Availability

Size Price Availability Quantity
1mg USD 450.00 2 Weeks
5mg USD 750.00 2 Weeks
10mg USD 1,250.00 2 Weeks
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Synonym
Nicorandil-d4; Nicorandil d4;
IUPAC/Chemical Name
2-(nicotinamido-2,4,5,6-d4)ethyl nitrate
InChi Key
LBHIOVVIQHSOQN-VTBMLFEUSA-N
InChi Code
InChI=1S/C8H9N3O4/c12-8(7-2-1-3-9-6-7)10-4-5-15-11(13)14/h1-3,6H,4-5H2,(H,10,12)/i1D,2D,3D,6D
SMILES Code
O=C(NCCO[N+]([O-])=O)C1=C(N=C(C([2H])=C1[2H])[2H])[2H]
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Nicorandil-d4 (SG-75-d4) is the deuterium labeled Nicorandil. Nicorandil (SG-75) is a potent potassium channel activator.
In vitro activity:
Nicorandil (100 micromol/liter) increased flavoprotein oxidation but not membrane current; a 10-fold higher concentration recruits both mitoK(ATP) and surfaceK(ATP) channels. Nicorandil blunted the rate of cell death in a pelleting model of ischemia; this cardioprotective effect was prevented by the mitoK(ATP) channel blocker 5-hydroxydecanoate but was unaffected by the surfaceK(ATP) channel blocker HMR1098. Reference: J Am Coll Cardiol. 2000 Feb;35(2):514-8. https://pubmed.ncbi.nlm.nih.gov/10676702/
In vivo activity:
This study’s aim was to assess whether pharmacologic activation of the K(ATP) channel by nicorandil contributes to endothelial nitric oxide synthase (eNOS) levels. A total of 21 7-week old male Sprague-Dawley rats were used. Nicorandil caused tachycardia without a change in blood pressure, whereas glibenclamide had no effect on the nicorandil-induced change in heart rate or on blood pressure. RT-PCR revealed that nicorandil increased the eNOS and SUR2 mRNA levels by 2.2- and 2.0-fold, respectively, (p < 0.01 versus control), and that these increases were completely inhibited by glibenclamide. Reference: J Cardiovasc Pharmacol. 2001 Aug;38(2):200-10. https://pubmed.ncbi.nlm.nih.gov/11483869/

Preparing Stock Solutions

The following data is based on the product molecular weight 215.20 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. Akao M, Teshima Y, Marbán E. Antiapoptotic effect of nicorandil mediated by mitochondrial atp-sensitive potassium channels in cultured cardiac myocytes. J Am Coll Cardiol. 2002 Aug 21;40(4):803-10. doi: 10.1016/s0735-1097(02)02007-7. PMID: 12204514. 2. Sato T, Sasaki N, O'Rourke B, Marbán E. Nicorandil, a potent cardioprotective agent, acts by opening mitochondrial ATP-dependent potassium channels. J Am Coll Cardiol. 2000 Feb;35(2):514-8. doi: 10.1016/s0735-1097(99)00552-5. PMID: 10676702. 3. Liu Y, Shu J, Liu T, Xie J, Li T, Li H, Li L. Nicorandil protects against coronary microembolization-induced myocardial injury by suppressing cardiomyocyte pyroptosis via the AMPK/TXNIP/NLRP3 signaling pathway. Eur J Pharmacol. 2022 Dec 5;936:175365. doi: 10.1016/j.ejphar.2022.175365. Epub 2022 Nov 3. PMID: 36336011. 4. Horinaka S, Kobayashi N, Higashi T, Hara K, Hara S, Matsuoka H. Nicorandil enhances cardiac endothelial nitric oxide synthase expression via activation of adenosine triphosphate-sensitive K channel in rat. J Cardiovasc Pharmacol. 2001 Aug;38(2):200-10. doi: 10.1097/00005344-200108000-00005. PMID: 11483869.
In vitro protocol:
1. Akao M, Teshima Y, Marbán E. Antiapoptotic effect of nicorandil mediated by mitochondrial atp-sensitive potassium channels in cultured cardiac myocytes. J Am Coll Cardiol. 2002 Aug 21;40(4):803-10. doi: 10.1016/s0735-1097(02)02007-7. PMID: 12204514. 2. Sato T, Sasaki N, O'Rourke B, Marbán E. Nicorandil, a potent cardioprotective agent, acts by opening mitochondrial ATP-dependent potassium channels. J Am Coll Cardiol. 2000 Feb;35(2):514-8. doi: 10.1016/s0735-1097(99)00552-5. PMID: 10676702.
In vivo protocol:
1. Liu Y, Shu J, Liu T, Xie J, Li T, Li H, Li L. Nicorandil protects against coronary microembolization-induced myocardial injury by suppressing cardiomyocyte pyroptosis via the AMPK/TXNIP/NLRP3 signaling pathway. Eur J Pharmacol. 2022 Dec 5;936:175365. doi: 10.1016/j.ejphar.2022.175365. Epub 2022 Nov 3. PMID: 36336011. 2. Horinaka S, Kobayashi N, Higashi T, Hara K, Hara S, Matsuoka H. Nicorandil enhances cardiac endothelial nitric oxide synthase expression via activation of adenosine triphosphate-sensitive K channel in rat. J Cardiovasc Pharmacol. 2001 Aug;38(2):200-10. doi: 10.1097/00005344-200108000-00005. PMID: 11483869.
1: Li W, Zhang G. Impact of administration of nicorandil prior to percutaneous coronary intervention in treatment of acute myocardial infarction: A protocol for systematic review and meta-analysis. Medicine (Baltimore). 2021 Apr 30;100(17):e25565. doi: 10.1097/MD.0000000000025565. PMID: 33907105; PMCID: PMC8084019. 2: Ikeno Y, Ghincea CV, Roda GF, Cheng L, Meng X, Weyant MJ, Cleveland JC Jr, Fullerton DA, Aftab M, Reece TB. Reactive Oxygen Species Mediate Nicorandil- induced Metabolic Tolerance to Spinal Cord Injury. Ann Thorac Surg. 2020 Oct 22:S0003-4975(20)31729-X. doi: 10.1016/j.athoracsur.2020.08.038. Epub ahead of print. PMID: 33902895. 3: Liu Z, Zhu H, He C, He T, Pan S, Zhao N, Zhu L, Guan G, Liu P, Zhang Y, Wang J. Nicorandil attenuates high glucose-induced insulin resistance by suppressing oxidative stress-mediated ER stress PERK signaling pathway. BMJ Open Diabetes Res Care. 2021 Apr;9(1):e001884. doi: 10.1136/bmjdrc-2020-001884. PMID: 33888540; PMCID: PMC8070885. 4: Zhang W, Dai J, Zheng X, Xu K, Yang X, Shen L, Wang X, Hao Z, Qiu X, Jiang L, Shi H, Shen L, He B. Myocardial protective effect of intracoronary administration of nicorandil and alprostadil via targeted perfusion microcatheter in patients undergoing elective percutaneous coronary intervention: A randomized controlled trial. Medicine (Baltimore). 2021 Apr 16;100(15):e25551. doi: 10.1097/MD.0000000000025551. PMID: 33847683; PMCID: PMC8052047. 5: An S, Huang H, Wang H, Jiang Y. Prophylactically injection of Nicorandil to reduce no-reflow phenomenon during PCI in acute STEMI patients: Protocol of a double-blinded, randomized, placebo-controlled trial. Medicine (Baltimore). 2021 Apr 16;100(15):e25500. doi: 10.1097/MD.0000000000025500. PMID: 33847663; PMCID: PMC8052050. 6: Shibutani H, Fujii K, Hashimoto K, Tsujimoto S, Matsumura K, Otagaki M, Morishita S, Shiojima I. Additional decrease in fractional flow reserve in the left anterior descending artery after hand-grip exercise during pharmacological coronary hyperemia. Heart Vessels. 2021 Apr 8. doi: 10.1007/s00380-021-01846-7. Epub ahead of print. PMID: 33830316. 7: Castrisos G, Hoff J, Hewerdine S, Ho YM, Lamparelli M. Non-healing parastomal ulcer: think nicorandil. ANZ J Surg. 2021 Mar 31. doi: 10.1111/ans.16844. Epub ahead of print. PMID: 33788367. 8: Noyes JD, Mordi IR, Zeb Q, Lang CC. Nicorandil-induced colovesical fistula in a patient with diverticular disease. Clin Case Rep. 2021 Feb 10;9(3):1737-1741. doi: 10.1002/ccr3.3888. PMID: 33768926; PMCID: PMC7981709. 9: Mir TH, Zargar PA, Jabeen B, Zahoor A. Nicorandil a magic bullet or a double edged sword in critically ill COVID-19 patients? Clin Exp Pharmacol Physiol. 2021 Jun;48(6):938-939. doi: 10.1111/1440-1681.13487. Epub 2021 Mar 8. PMID: 33684970. 10: Martsevich SY, Lukina YV, Kutishenko NP, Semenova YV. Comparison of the outcomes of the prolonged antianginal therapy use in stable coronary artery disease patients according to the data of randomized and observational studies. Contemp Clin Trials Commun. 2021 Feb 17;21:100743. doi: 10.1016/j.conctc.2021.100743. PMID: 33665472; PMCID: PMC7905070. 11: Herbst DA, Atluri P. Commentary: Teaching an Old Drug New Tricks-Spinal Cord Protection with Nicorandil. Semin Thorac Cardiovasc Surg. 2021 Mar 1:S1043-0679(21)00095-2. doi: 10.1053/j.semtcvs.2021.02.015. Epub ahead of print. PMID: 33662549. 12: Otsuka H, Miyoshi T, Ejiri K, Kohno K, Nakahama M, Doi M, Munemasa M, Murakami M, Nakamura K, Ito H. Possible Protective Effect of Remote Ischemic Preconditioning on Acute Kidney Injury Following Elective Percutaneous Coronary Intervention: Secondary Analysis of a Multicenter, Randomized Study. Acta Med Okayama. 2021 Feb;75(1):45-53. doi: 10.18926/AMO/61433. PMID: 33649613. 13: Thompson D, Al-Lamee R, Foley M, Dehbi HM, Thom S, Davies JE, Francis DP, Patel P, Gupta P; ORBITA Investigators. Achieving optimal adherence to medical therapy by telehealth: Findings from the ORBITA medication adherence sub-study. Pharmacol Res Perspect. 2021 Feb;9(1):e00710. doi: 10.1002/prp2.710. PMID: 33570248; PMCID: PMC7876856. 14: Kojima A, Shirayama T, Shiraishi J, Sawada T. Subcutaneous implantable cardioverter-defibrillator was inappropriate for use in a patient with aborted sudden cardiac death due to coronary spastic angina: a case report. Eur Heart J Case Rep. 2020 Dec 12;4(6):1-5. doi: 10.1093/ehjcr/ytaa471. PMID: 33442640; PMCID: PMC7793180. 15: Liu H, Zhao J, Pan S, Zhu Y, Fu G, Tang W, Peng F. Shexiang Tongxin dropping pill protects against sodium laurate-induced coronary microcirculatory dysfunction in rats. J Tradit Chin Med. 2021 Feb;41(1):89-97. doi: 10.19852/j.cnki.jtcm.2021.01.011. PMID: 33522201. 16: Lenz M, Kaun C, Krychtiuk KA, Haider P, Brekalo M, Maier N, Goederle L, Binder CJ, Huber K, Hengstenberg C, Wojta J, Hohensinner PJ, Speidl WS. Effects of Nicorandil on Inflammation, Apoptosis and Atherosclerotic Plaque Progression. Biomedicines. 2021 Jan 27;9(2):120. doi: 10.3390/biomedicines9020120. PMID: 33513743; PMCID: PMC7912627. 17: Sánchez-Duarte S, Márquez-Gamiño S, Montoya-Pérez R, Villicaña-Gómez EA, Vera-Delgado KS, Caudillo-Cisneros C, Sotelo-Barroso F, Melchor-Moreno MT, Sánchez-Duarte E. Nicorandil decreases oxidative stress in slow- and fast-twitch muscle fibers of diabetic rats by improving the glutathione system functioning. J Diabetes Investig. 2021 Jan 27. doi: 10.1111/jdi.13513. Epub ahead of print. PMID: 33503290. 18: Zhao Y, Yang Z, He Y, Sun R, Yuan H. The KATP channel opener, nicorandil, ameliorates brain damage by modulating synaptogenesis after ischemic stroke. PLoS One. 2021 Jan 26;16(1):e0246019. doi: 10.1371/journal.pone.0246019. PMID: 33497397; PMCID: PMC7837460. 19: Foley M, Rajkumar CA, Shun-Shin M, Ganesananthan S, Seligman H, Howard J, Nowbar AN, Keeble TR, Davies JR, Tang KH, Gerber R, O'Kane P, Sharp ASP, Petraco R, Malik IS, Nijjer S, Sen S, Francis DP, Al-Lamee R. Achieving Optimal Medical Therapy: Insights From the ORBITA Trial. J Am Heart Assoc. 2021 Feb 2;10(3):e017381. doi: 10.1161/JAHA.120.017381. Epub 2021 Jan 26. PMID: 33496201; PMCID: PMC7955412. 20: Zhang Y, Wang X, Liu R, Li Q, Tian W, Lei H, Shi C. The effectiveness and safety of nicorandil in the treatment of patients with microvascular angina: A protocol for systematic review and meta-analysis. Medicine (Baltimore). 2021 Jan 15;100(2):e23888. doi: 10.1097/MD.0000000000023888. PMID: 33466132; PMCID: PMC7808505.