Nicorandil
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Grundinformationen
- CAS
65141-46-0- Standard-SMILES
O=C(NCCO[N+](=O)[O-])c1cccnc1- InChIKey
LBHIOVVIQHSOQN-UHFFFAOYSA-N- Summenformel
- C8H9N3O4
- Durchschnittliche Molmasse
- 211,177 g/mol
- Monoisotopische Masse
- 211,05930577
Namen und Bezeichner
- Bevorzugter Name
- Nicorandil
- IUPAC
- 2-[(Pyridine-3-carbonyl)amino]ethyl nitrate
- Lokaler Name
- Nicorandil
- Englischer Name
- Nicorandil
- Summenformel
- C8H9N3O4
- Molmasse
- 211.17
Namen und Synonyme
Nicorandi2-[(Pyridin-3-ylcarbonyl)amino]ethyl nitrate, N-[2-(Nitroxy)ethyl]pyridine-3-carboxamideSG-75DancorIKORELZynicorSIGMARTADANCORNicodilNicordil
Datenbank-Bezeichner
- CAS
65141-46-0- PubChem CID
- 47528
- DTXSID
DTXSID8045692- ChEMBL
CHEMBL284906- ChEBI
CHEBI:31905- UNII
- 260456HAM0
- EC Number
- 265-514-1
- Nikkaji
- J4.534I
Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 92 °C · 92°C
- Siedepunkt
- 350.85 °C · 350.85°C (rough estimate)
- Dichte
- 1.4271 · 1.4271 (rough estimate)
- Brechungsindex
- 1.74 · 1.7400 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 10 mg/mL · DMSO: >10mg/mL
- Aggregatzustand
- powder
- pka
- 12.7 · 12.70±0.46(Predicted)
- Farbe
- white to off-white
- Merck
- 14 · 14,6521
- InChI
- 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)
- InChIKey
- LBHIOVVIQHSOQN-UHFFFAOYSA-N
- SMILES
- C1=NC=CC=C1C(NCCO[N+]([O-])=O)=O
- CAS Datenbank
- 65141 · 65141-46-0
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- 3
- hs_code
- 29333990
- risk_code
- 22-41
- Toxizität
- LD50 in rats (mg/kg): 1200-1300 orally; 800-1000 i.v. (Nagano)
- hazard_code
- Xn
- safety_code
- 26-39
- Speicherklasse
- 5.2 - Organic peroxides and self-reacting hazardous materials
- Hazard Classifications
- Acute Tox. 4 OralOrg. Perox. D
Chemie und Industrie
Anwendungen
VerwendenNicorandil is a vasodilator used for the prophylaxis and treatment of angina. This medication widens blood vessels thus increasing the blood and oxygen flow to the heart. It is not currently available in the US.Nicorandil is a nitric oxide donor and ATP-sensitive potassium channel opener. A study showed that Nicorandil is able to protect against stress-induced cell death in dystrophin-deficient cardiomyocytes and also preserve cardiac function in the mdx mouse heart subjected to ischemia and reperfusion injury.
Darstellung
synthetischeNicorandil is obtained by treating nicotinic acid chloride hydrochloride with nitro-oxy-ethyl-amine nitrate in an organic solvent.Nicorandil was synthesized from 2-aminoethanol by a four step process. In order to protect the amino group during nitration, 2-aminoethanol was first treated with phthalic anhydride. The amide formed was then nitrated using a nitrating mixture and was subsequently deprotected by reacting with hydrazine hydrate. The 2- nitroxyethylamine obtained was condensed with nicotinoyl chloride in pyridine. Treatment with aqueous sodium bicarbonate solution gave nicorandil as free base.synthesis of Nicorandil
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