Nicardipine
Completing data — refresh the page later to see the latest
Basic information
- CAS
55985-32-5- 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:7550DTXSID60233635-O-[2-[benzyl(methyl)amino]ethyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateCZ5312222S3-(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
Properties
Computed structural propertiesFilling in
- 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
LogP
3.6
3.67
Solubility2.47e-03 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Calcium Channel Blockers; Vasodilator Agents
Pharmaceuticals
Melting Point
136-138 °C
136 - 138 °C
Physical DescriptionSolid
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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
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
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
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
Chemistry & industry
Pharmacology
ATC Code
C08CA04
C - Cardiovascular system
QC - Cardiovascular system
Protein Binding>95%
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.
Biological Half-Life8.6 hours
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
Related reactions
6 records
Compound notes
Loading…