Nicardipine Hydrochloride

HCID 41114
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Basic information

CAS
54527-84-3
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
Molecular formula
C26H30ClN3O6
Average molar mass
516 g/mol
Monoisotopic mass
515.18231336

Overview

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

Names & identifiers

Preferred 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
English name
Nicardipine hydrochloride
Molecular formula
C26H30ClN3O6
Molecular weight
515.99

Names & synonyms

NICARDIPINE HYDROCHLORIDE54527-84-3Nicardipine HClLoxenPerdipineNicodelPerdipinaYC-93VasonaseCardene SRBarizinCardepine
Show more names
Naratriptan HCldafildaganlincilVasonas
DacarelLecibraLecibralLescodilNerdipinaNicapressNicardalNicarpin

Database identifiers

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

Properties

Computed structural properties

Topological polar surface area
114 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
8
Rotatable bonds
10
Heavy atoms
36

Experimental & physicochemical properties

Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

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

Physicochemical properties

Melting point
176 · 176-1780C
storage temp.
2 · 2-8°C
solubility
1 mg/mL · DMSO: ~1 mg/mL
form
powder
color
yellow
Merck
14 · 14,6495

Safety & regulation

GHS classification

GHS Classification · 5 items

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.

Hazard information

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%)

Toxicology

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Nicardipine hydrochloride

Ambiguous-DILI-concern

3

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Safety data

PPE
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk
3
rtecs
US7972100
ridadr
UN 2811 6.1/PG 3
hs_code
2933399090
Toxicity
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)

Chemistry & industry

Pharmacology

FDA Pharmacological Classification · 2 items

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 items

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.

Applications · 5 items

DescriptionNicardipine 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).

Usesanesthetic (topical)

UsesNicardipine 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).

UsesDihydropyridine calcium channel blocker. Antianginal; antihypertensive

General DescriptionNicardipine hydrochloride,1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylicacid methyl 2-[methyl(phenylmethyl)amino]ethylester hydrochloride (Cardene), is a more potent vasodilator ofthe systemic, coronary, cerebral, and renal vasculature andhas been used in the treatment of mild, moderate, and severehypertension. The drug is also used in the management of stableangina.

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
济南百隆化学有限公司[email protected] · [email protected]

Additional notes

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

Related reactions

4 records
New reaction record

Compound notes

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