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
Show more names
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
- Formal charge
- 0
- Complexity
- 856
Experimental & physicochemical properties
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Calcium Channel Blockers; Vasodilator Agents
Pharmaceuticals
Melting Point
136-138 °C
136 - 138 °C
Collision Cross Section
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
- pka
- 7.3 · 7.30±0.50(Predicted)
- color
- Yellow
- CAS DataBase Reference
- 55985 · 55985-32-5(CAS DataBase Reference)
- FDA UNII
- 5312222 S · CZ5312222S
- NCI Drug Dictionary
- nicardipine
- ATC code
- 8 CA04 · C08CA04
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 264 · P264-P270-P301+P312-P330-P501
Safety & regulation
GHS classification
GHS Classification
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
Toxicology
Hepatotoxicity
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
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
nicardipine
DILI Negative
Oral
DOI:10.1016/j.drudis.2019.09.022
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302
- Precautionary statements
- P264-P270-P301+P312-P330-P501
Chemistry & industry
Pharmacology
ATC Code
C08CA04
C - Cardiovascular system
QC - Cardiovascular system
Pharmacodynamics
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
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.
Metabolism/Metabolites
Nicardipine HCl is metabolized extensively by the liver.
Nicardipine has known human metabolites that include Dehydronicardipine and De-benzylated nicardipine.
FDA Pharmacological Classification
CZ5312222S
NICARDIPINE
Mechanisms of Action [MoA] - Calcium Channel Antagonists
Established Pharmacologic Class [EPC] - Dihydropyridine Calcium Channel Blocker
Chemical Structure [CS] - Dihydropyridines
Mechanisms of Action [MoA] - Cytochrome P450 3A4 Inhibitors
MeSH Pharmacological Classification
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.
Absorption, Distribution and Excretion
While nicardipine is completely absorbed, it is subject to saturable first pass metabolism and the systemic bioavailability is about 35% following a 30 mg oral dose at steady state.
Nicardipine has been shown to be rapidly and extensively metabolized by the liver.
8.3 L/kg
0.4 L/hr∙kg [Following infusion]
Uses & manufacturing
Applications
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
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
Linked notes
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