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| Clinical data | |
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| Trade names | Ikorel, others |
| AHFS/Drugs.com | International Drug Names |
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| Routes of administration | By mouth |
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| Pharmacokinetic data | |
| Bioavailability | 75 to 80% |
| Protein binding | 25% |
| Metabolism | Liver |
| Eliminationhalf-life | 1 hour |
| Excretion | Kidney (21%) |
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| DrugBank |
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| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.059.541 |
| Chemical and physical data | |
| Formula | C8H9N3O4 |
| Molar mass | 211.177 g·mol−1 |
| 3D model (JSmol) | |
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Nicorandil is avasodilatordrug used to treatangina, which is chest pain that results from episodes of transient myocardialischemia. Angina can be caused by diseases such asatherosclerosis,coronary artery disease, andaortic stenosis.[2]
It was patented in 1976 and approved for medical use in 1983.[3]
Side effects listed in theBritish National Formulary include flushing,palpitations, weakness and vomiting. More recently,perianal,ileal, and peristomal ulceration has been reported as a side effect. Anal ulceration is now included in the British National Formulary as a reported side effect. Other side effects include severemigraine, toothache, and nasal congestion.[citation needed]
Nicorandil is ananti-angina medication that has the dual properties of anitrate andATP-sensitiveK+
channel opener.[4] In humans, the nitrate action of nicorandil dilates the large coronary arteries at low plasma concentrations.[4] At high plasma concentrations nicorandil reduces coronary vascular resistance, which is associated with increased ATP-sensitiveK+ channel (KATP) opening.[4]
Nicorandil stimulatesguanylate cyclase to increase formation ofcyclic GMP (cGMP).[5] cGMP activatesprotein kinase G (PKG), which phosphorylates and inhibitsGTPase RhoA and decreases Rho-kinase activity.[5] Reduced Rho-kinase activity permits an increase inmyosin phosphatase activity, decreasing the calcium sensitivity of the smooth muscle.[5]
PKG also activates thesarcolemma calcium pump to remove activating calcium.[6] PKG acts onK+
channels to promote K+ efflux and the ensuinghyperpolarization inhibitsvoltage-gated calcium channels.[4] Overall, this leads to relaxation of the smooth muscle and coronary vasodilation.[citation needed]
The effect of nicorandil as avasodilator is mainly attributed to its nitrate property.[4] Yet, nicorandil is effective in cases where nitrates, such asnitroglycerine, are not effective.[4] Studies show that this is due to its KATP channel agonist action which causes pharmacological preconditioning and provides cardioprotective effects against ischemia.[4] Nicorandil activates KATP channels in the mitochondria of the myocardium, which appears to relay the cardioprotective effects, although the mechanism is still unclear.[7] In experimental animal models of theLong QT syndrome, Nicorandil normalizes the prolongedcardiac action potential duration and theQT interval.[8]
Amide reaction between Nicotinoyl Chloride [10400-19-8] & 2-Aminoethyl Nitrate [646-02-6].
.svg)
The reaction of N-(2-Hydroxyethyl)Nicotinamide [6265-73-2] with nitric acid gives nicorandil.
Nicorandil is marketed under the brand names Ikorel (in the United Kingdom, Australia and most of Europe), Cordinic (in Russia), Angedil (in Romania, Poland), Dancor (in Switzerland), Nikoran, PCA (in India), Aprior (in the Philippines), Nitorubin (in Japan), and Sigmart (in Japan, South Korea, Taiwan and China). Nicorandil is not available in the United States.[citation needed]