2-(Benzylmethylamino)ethylmethyl-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridin-3,5-dicarboxylatmonohydrochlorid

Nicardipine Hydrochloride

HCID 41114CAS 54527-84-3

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Grundinformationen

Standard-SMILES: COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)Cc2ccccc2)C1c1cccc([N+](=O)[O-])c1.Cl
InChIKey: AIKVCUNQWYTVTO-UHFFFAOYSA-N
Summenformel: C26H30ClN3O6
Durchschnittliche Molmasse: 516 g/mol
Monoisotopische Masse: 515,18231336

Überblick

Nicardipine hydrochloride is a dihydropyridine. It has a role as a geroprotector.

Namen und Bezeichner

Bevorzugter Name: Nicardipine Hydrochloride
IUPAC: 5-O-[2-[benzyl(methyl)amino]ethyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate;hydrochloride
Lokaler Name: 2-(Benzylmethylamino)ethylmethyl-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridin-3,5-dicarboxylatmonohydrochlorid
Englischer Name: Nicardipine hydrochloride
Summenformel: C26H30ClN3O6
Molmasse: 515.99

Namen und Synonyme

NICARDIPINE HYDROCHLORIDE54527-84-3Nicardipine HClLoxenPerdipineNicodelPerdipinaYC-93VasonaseCardene SRBarizinCardepine

Weitere Namen anzeigen

Naratriptan HCldafildaganlincilVasonas

DacarelLecibraLecibralLescodilNerdipinaNicapressNicardalNicarpin

Datenbank-Bezeichner

CAS: 54527-84-3、69441-18-5
PubChem CID: 41114
DTXSID: DTXSID9046992
ChEMBL: CHEMBL1200326、CHEMBL3199626
ChEBI: CHEBI:7551
UNII: K5BC5011K3
EC Number: 259-198-4、274-007-4

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA): 114 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 8
Frei drehbare Bindungen: 10
Schwere Atome: 36
Formalladung: 0
Komplexität: 856

Experimentelle und physikochemische Eigenschaften

Human Drugs · 2 Einträge

FDA approved drugs -> Active ingredient

Collision Cross Section211.9 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physikochemische Eigenschaften

Schmelzpunkt: 176 · 176-1780C
storage temp.: 2 · 2-8°C
Löslichkeit: 1 mg/mL · DMSO: ~1 mg/mL
Aggregatzustand: powder
Farbe: yellow
Merck: 14 · 14,6495
Stabilität: 1 year · Stable for 1 year from date of purchase as supplied. Solutions in distilled water or ethanol may be stored at -20°C for up to 1 month.
InChI: 1S/C26H29N3O6.ClH/c1-17-22(25(30)34-4)24(20-11-8-12-21(15-20)29(32)33)23(18(2)27-17)26(31)35-14-13-28(3)16-19-9-6-5-7-10-19;/h5-12,15,24,27H,13-14,16H2,1-4H3;1H
InChIKey: AIKVCUNQWYTVTO-UHFFFAOYSA-N
SMILES: C1(C(C(=O)OC)=C(NC(C)=C1C(=O)OCCN(C)CC1C=CC=CC=1)C)C1C=CC=C([N+]([O-])=O)C=1.Cl
CAS Datenbank: 54527 · 54527-84-3(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 2% (1 of 49) of reports.

Danger

H301 (89.8%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 49 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Other Safety InformationIMAP assessments - 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl 2-[methyl(phenylmethyl)amino]ethyl ester, monohydrochloride: Environment tier I assessment

Hazard Classes and CategoriesAcute Tox. 3 (89.8%)

Toxikologische Informationen

Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Nicardipine hydrochloride

Ambiguous-DILI-concern

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Sicherheitsdaten

wgk: 3
ridadr: UN 2811 6.1/PG 3
hs_code: 2933399090
RTECS-Nr.: US7972100
risk_code: 23/24/25
Toxizität: LD50 in male, female rats (mg/kg): 634, 557 orally; 18.1, 25.0 i.v.; in male, female mice: 634, 650 orally; 20.7, 19.9 i.v. (Odani, Sado)
hazard_code: T
safety_code: 36/37/39-45
hazard_class: 6.1(b)
packing_group: III
Speicherklasse: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications: Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 Oral

Chemie und Industrie

Pharmakologische Informationen

FDA Pharmacological Classification · 2 Einträge

NICARDIPINE HYDROCHLORIDE

Dihydropyridines [CS]; Cytochrome P450 2C8 Inhibitors [MoA]; Dihydropyridine Calcium Channel Blocker [EPC]; Cytochrome P450 3A4 Inhibitors [MoA]; Calcium Channel Antagonists [MoA]; Cytochrome P450 2C19 Inhibitors [MoA]; Cytochrome P450 2D6 Inhibitors [MoA]

MeSH Pharmacological Classification · 3 Einträge

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.

A class of drugs that act by selective inhibition of calcium influx through cellular membranes.

Drugs used to cause dilation of the blood vessels.

Anwendungen · 2 Einträge

BeschreibungNicardipine is a dihydropyridine L-type calcium channel antagonist that displays antihypertensive and antianginal activity. It is reported to inhibit adenosine A1, A2A, and A3 receptors with Ki values of 19.6, 63.8, and 3.25 μM, respectively, and can inhibit cytochrome P450 3A4 catalytic activity with an IC50 value of 0.148 μM. Additionally, nicardipine has been shown to activate transient receptor potential A1 channels, producing an increase in Ca2+ (EC50 = 0.5 μM).

VerwendenDihydropyridine calcium channel blocker. Antianginal; antihypertensive