3,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, 3-methyl 5-((1-oxobutoxy)methyl) ester

HCID 153994
NotesReactions
Substructure searchFind similar structures

Basic information

CAS
166432-28-6
Standard SMILES
CCCC(=O)OCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cccc(Cl)c1Cl
InChIKey
KPBZROQVTHLCDU-UHFFFAOYSA-N
Molecular formula
C21H23Cl2NO6
Average molar mass
456.3 g/mol
Monoisotopic mass
455.09024282

Overview

Clevidipine is a dihydropyridine.

Names & identifiers

Preferred name
3,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, 3-methyl 5-((1-oxobutoxy)methyl) ester
IUPAC
5-O-(butanoyloxymethyl) 3-O-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
English name
Clevidipine
Molecular formula
C21H23Cl2NO6
Molecular weight
456.32

Names & synonyms

Clevidipine167221-71-8CleveloxClevidepineClevidepine butyrateClevidipino3,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, 3-methyl 5-[(1-oxobutoxy)methyl] esterDTXSID6057661H-324/3819O2GP3B7QH324/38METHYL 5-{[(BUTANOYLOXY)METHOXY]CARBONYL}-4-(2,3-DICHLOROPHENYL)-2,6-DIMETHYL-1,4-DIHYDROPYRIDINE-3-CARBOXYLATE
Show more names
Clevidipine impuritylevidipineClevidipine USP/EP/BP3-((butyryloxy)Methyl) 5-Methyl 4-(2,3-dichlorophenyl)-2,6-diMethylpyridine-3,5-dicarboxylate(±)-4-(2,3-Dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid butoxy methyl methyl diester
DTXCID70314503,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, methyl (1-oxobutoxy)methyl esterbutyroxymethyl methyl 4-(2',3'-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate3,5-PYRIDINEDICARBOXYLIC ACID, 4-(2,3-DICHLOROPHENYL)-1,4-DIHYDRO-2,6-DIMETHYL-, 3-METHYL 5-((1-OXOBUTOXY)METHYL) ESTERO3-(butanoyloxymethyl) O5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylateclevidipinumclevipidinemethyl 5-(((butanoyloxy)methoxy)carbonyl)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylate

Database identifiers

CAS
166432-28-6、167221-71-8
PubChem CID
153994
DTXSID
DTXSID6057661
ChEMBL
CHEMBL1237132
ChEBI
CHEBI:135738
UNII
19O2GP3B7Q
EC Number
682-702-2、814-032-5
Nikkaji
J772.200A

Properties

Computed structural properties

XLogP
4.3
Topological polar surface area
90.9 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
7
Rotatable bonds
10
Heavy atoms
30

Experimental & physicochemical properties

Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physicochemical properties

Melting point
137 · 137-139°C
storage temp.
Refrigerator
solubility
DMSO (Slightly), Methanol (Slightly)
form
Solid
color
White to Off-White
FDA UNII
19 O2GP3B7Q · 19O2GP3B7Q

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H301 (33.3%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P260, P264, P270, P280, P301+P316, P308+P316, P318, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

Hazard information

Hazard Classes and Categories · 2 items

Acute Tox. 3 (33.3%)

Repr. 2 (100%)

Toxicology

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Clevidipine

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

Safety data

Signal word
Warning
Symbol(GHS)
GHS08
Hazard statements
H361
Precautionary statements
P201-P202-P281-P308+P313-P405-P501

Chemistry & industry

Pharmacology

ATC Code · 3 items

C08CA16

C - Cardiovascular system

QC - Cardiovascular system

Protein Binding>99.5%
Pharmacodynamics · 1 item

Clevidipine belongs to a well-known class of drugs called dihydropyridine calcium channel antagonists. Clevidpine is the first third generation intravenous dihydropyridine calcium channel blocker. In vitro studies demonstrated that clevidipine acts by selectively relaxing the smooth muscle cells that line small arteries, resulting in arterial dilation, widening of the artery opening, and without reducing central venous pressure or reducing cardiac output.

Mechanism of Action · 1 item

Possibly by deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum, clevidipine inhibits the influx of extracellular calcium across both the myocardial and vascular smooth muscle cell membranes. The resultant inhibition of the contractile processes of the myocardial smooth muscle cells leads to dilation of the coronary and systemic arteries and improved oxygen delivery to the myocardial tissue.

Biological Half-Life1 minute
Metabolism/MetabolitesClevidipine is rapidly hydrolyzed to inactive metabolites by esterases in arterial blood.

Applications

UsesAntihypertensive.

Suppliers100 total

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]
上海波以尔化工有限公司[email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
广州市亿邦医药科技有限公司+86 (20) 28996708,29078958,28139708,29076128,28133708,28139728,28139738,28133718,021-31663278,021-31663578,021-60538387

Additional notes

DefinitionChEBI: Clevidipine is a dihydropyridine.

Related reactions

2 records
New reaction record

Compound notes

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