Nicardipine

HCID 4474CAS 55985-32-5

Basic information

Standard SMILES
COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)Cc2ccccc2)C1c1cccc([N+](=O)[O-])c1
InChIKey
ZBBHBTPTTSWHBA-UHFFFAOYSA-N
Molecular formula
C26H29N3O6
Average molar mass
479.5 g/mol
Monoisotopic mass
479.20563565

Overview

Nicardipine is a racemate comprising equimolar amounts of (R)- and (S)-nicardipine. It is a calcium channel blocker which is used to treat hypertension. It has a role as a vasodilator agent, an antihypertensive agent, a calcium channel blocker and an autophagy inhibitor. It contains a (S)-nicardipine and a (R)-nicardipine.

Names & identifiers

Preferred name
Nicardipine
IUPAC
5-O-[2-[benzyl(methyl)amino]ethyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
English name
Nicardipine
Molecular formula
C26H29N3O6
Molecular weight
479.53

Names & synonyms

nicardipine55985-32-5NicardipinoNicardipinumPerpidineNicardipine (stn)CHEBI:7550DTXSID6023363CZ5312222S5-O-[2-[benzyl(methyl)amino]ethyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate3-(2-(benzyl(methyl)amino)ethyl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateDTXCID903363
Show more names
NicardipineBaseNicardipine USP/EP/BPNicardipine, 10 mM in DMSObenzylmethylamino)ethylmethylesterNICARDIPINE 20% SR, 33% SR PELLETSNicardipine (base and/or unspecified salts)2-(benzylmethylamino)ethyl methyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)pyridine-3,5-dicarboxylateMethyl 2-(benzyl-methyl-amino)ethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl 2-(methyl(phenylmethyl)amino)ethyl ester3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl 2-[methyl(phenylmethyl)amino]ethyl ester3-{2-[benzyl(methyl)amino]ethyl} 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylatenicardipinaLA, Nicardipine5-O-(2-(benzyl(methyl)amino)ethyl) 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateO5-methyl O3-(2-(methyl-(phenylmethyl)amino)ethyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateO5-methyl O3-[2-(methyl-(phenylmethyl)amino)ethyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Database identifiers

CAS
55985-32-5
PubChem CID
4474
DTXSID
DTXSID6023363
ChEMBL
CHEMBL1484、CHEMBL3302409
ChEBI
CHEBI:7550
UNII
CZ5312222S
EC Number
259-932-3
Nikkaji
J11.098A

Properties

Computed structural properties

XLogP
3.8
Topological polar surface area
114 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
8
Rotatable bonds
10
Heavy atoms
35

Experimental & physicochemical properties

LogP3.6
Solubility2.47e-03 g/L
Human Drugs · 2 items

Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Calcium Channel Blockers; Vasodilator Agents

Pharmaceuticals

Melting Point · 2 items

136-138 °C

136 - 138 °C

Physical DescriptionSolid
Collision Cross Section · 3 items

211.2 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID9046992]

212.1 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

208.67 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
136 · 136-138 °C
Boiling point
603.4 · 603.4±55.0 °C(Predicted)
Density
1.23 · 1.230±0.06 g/cm3(Predicted)
storage temp.
-20 °C · Store at -20°C
solubility
Dichloromethane; Methanol
form
Solid

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

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: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxicology

Hepatotoxicity · 1 item

Nicardipine has not been associated with significant increases in rates of elevations in serum aminotransferase or alkaline phosphatase levels, even with chronic long term therapy. Cases of idiosyncratic liver injury have not been published, although a single instance of marked serum enzyme elevations without jaundice has been reported with the use of intravenous nicardipine. Large trials of nicardipine have not mentioned liver injury, serum aminotransferase elevations or discontinuation of drug because of hepatic adverse events. Thus, clinically apparent liver injury with jaundice due to nicardipine must be rare, if it occurs at all.

Drug Induced Liver Injury · 5 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

nicardipine

DILI Negative

Oral

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H302
Precautionary statements
P264-P270-P301+P312-P330-P501

Chemistry & industry

Pharmacology

ATC Code · 3 items

C08CA04

C - Cardiovascular system

QC - Cardiovascular system

Protein Binding>95%
Pharmacodynamics · 1 item

Nicardipine, a dihydropyridine calcium-channel blocker, is used alone or with an angiotensin-converting enzyme inhibitor, to treat hypertension, chronic stable angina pectoris, and Prinzmetal's variant angina. Nicardipine is similar to other peripheral vasodilators. Nicardipine inhibits the influx of extra cellular calcium across the myocardial and vascular smooth muscle cell membranes possibly by deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum. The decrease in intracellular calcium inhibits the contractile processes of the myocardial smooth muscle cells, causing dilation of the coronary and systemic arteries, increased oxygen delivery to the myocardial tissue, decreased total peripheral resistance, decreased systemic blood pressure, and decreased afterload.

Mechanism of Action · 1 item

By deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum, nicardipine inhibits the influx of extracellular calcium across the myocardial and vascular smooth muscle cell membranes The decrease in intracellular calcium inhibits the contractile processes of the myocardial smooth muscle cells, causing dilation of the coronary and systemic arteries, increased oxygen delivery to the myocardial tissue, decreased total peripheral resistance, decreased systemic blood pressure, and decreased afterload.

Biological Half-Life8.6 hours
Metabolism/Metabolites · 2 items

Nicardipine HCl is metabolized extensively by the liver.

Nicardipine has known human metabolites that include Dehydronicardipine and De-benzylated nicardipine.

Uses & manufacturing

Use ClassificationPharmaceuticals
Applications · 3 items

UsesVasodilator.

UsesIt is used for arterial hypertension, chronic, stable angina pectoris, preventing angina pectoris, and for ischemic-type abnormalities of brain blood flow.

UsesNicardipine is a dihydropyridine calcium channel blocker. Antianginal; antihypertensive. Neuroprotective & Neuroresearch products.

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]
苏州道澜生物医药科技有限公司15952404857 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
广州佳途科技股份有限公司81960175 18933936954 · [email protected]
咸宁深蓝生物医药研发有限公司18171815831 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Nicardipine is a racemate comprising equimolar amounts of (R)- and (S)-nicardipine. It is a calcium channel blocker which is used to treat hypertension. It has a role as an antihypertensive agent, a calcium channel blocker, a vasodilator agent and an autophagy inhibitor. It contains a (S)-nicardipine and a (R)-nicardipine.

Related reactions

6 records

Linked notes

Loading…