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Details

Stereochemistry RACEMIC
Molecular Formula C36H41N3O6
Molecular Weight 611.7286
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LERCANIDIPINE

SMILES

CC1=C(C(c2cccc(c2)N(=O)=O)C(=C(C)N1)C(=O)OC(C)(C)CN(C)CCC(c3ccccc3)c4ccccc4)C(=O)OC

InChI

InChIKey=ZDXUKAKRHYTAKV-UHFFFAOYSA-N
InChI=1S/C36H41N3O6/c1-24-31(34(40)44-6)33(28-18-13-19-29(22-28)39(42)43)32(25(2)37-24)35(41)45-36(3,4)23-38(5)21-20-30(26-14-9-7-10-15-26)27-16-11-8-12-17-27/h7-19,22,30,33,37H,20-21,23H2,1-6H3

HIDE SMILES / InChI

Molecular Formula C36H41N3O6
Molecular Weight 611.7286
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment:: description was created based on several sources, including https://www.drugs.com/history/lercanidipine.html | https://www.ncbi.nlm.nih.gov/pubmed/27794423

Lercanidipine is antihypertensive drugs which acts by blocking L-type calcium channels, allowing relaxation and opening of blood vessels. Lercanidipine exists as a racemate, with anti-hypertensive activity residing primarily in S-enantiomer. NDA for lercanidipine was submitted to FDA in 2002 by Forest Laboratories, but FDA refused to approve the drug, and lercanidipine is not marketed in USA. Lercanidipine is also investigated in preclinical models of epilepsy and ischemic stroke.

CNS Activity

Curator's Comment:: Active in a preclinical models of epilepsy on mice

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.2 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ZANIDIP

Approved Use

Lercanidipine is indicated for the treatment of mild to moderate essential hypertension
Primary
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Lercanidipine: a review of its use in hypertension.
2000 Nov
Nephroprotective effect of treatment with calcium channel blockers in spontaneously hypertensive rats.
2000 Sep
Tolerability of long-term treatment with lercanidipine versus amlodipine and lacidipine in elderly hypertensives.
2002 Nov
Increased vascular selectivity and prolonged pharmacological efficacy of the L-type Ca2+ channel antagonist lercanidipine in human cardiovascular tissue.
2005 Sep
Lercanidipine and losartan effects on blood pressure and fibrinolytic parameters.
2006 Apr
[The effect of calcium channel blocker lercanidipine on lowgrade inflammation parameters in essential hypertension patients].
2006 Dec
Lercanidipine reduces matrix metalloproteinase-9 activity in patients with hypertension.
2006 Jan
Efficacy and safety of lercanidipine versus hydrochlorothiazide as add-on to enalapril in diabetic populations with uncontrolled hypertension.
2006 Jan
Fixed-dose combination lercanidipine/enalapril.
2007
Lercanidipine in the treatment of hypertension.
2007 Mar
Lercanidipine inhibits vascular smooth muscle cell proliferation and neointimal formation via reducing intracellular reactive oxygen species and inactivating Ras-ERK1/2 signaling.
2009 Jan
Neuroprotective Effect of Lercanidipine- A Novel Calcium Channel Blocker in Albino Mice.
2015 Nov
Neuroprotective effect of lercanidipine in middle cerebral artery occlusion model of stroke in rats.
2017 Feb
Patents

Sample Use Guides

The recommended dosage is 10 mg orally once a day at least 15 minutes before meals; the dose may be increased to 20 mg depending on the individual patient's response. In preclinical models lercanidipine is administered intraperitoneally.
Route of Administration: Other
Lercanidipine demonstrated vasodilation effect in isolated vessel ring obtained from human arteria mammaria preparation (EC50 approx. 1 nM). Isolated vessel rings were precontracted by 0.3 mol/L prostaglandin F2.
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:56:57 UTC 2021
Edited
by admin
on Fri Jun 25 22:56:57 UTC 2021
Record UNII
V7XTJ4R0BH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LERCANIDIPINE
INN   MI   WHO-DD  
INN  
Official Name English
3,5-PYRIDINEDICARBOXYLIC ACID, 1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-, 2-((3,3-DIPHENYLPROPYL)METHYLAMINO)-1,1-DIMETHYLETHYL METHYL ESTER
Common Name English
LERCANIDIPINE [MI]
Common Name English
LERCANIDIPINE [WHO-DD]
Common Name English
LERCANIDIPINE [INN]
Common Name English
LERCANIL
Brand Name English
2-((3,3-DIPHENYLPROPYL)METHYLAMINO)-1,1-DIMETHYLETHYL METHYL (4RS)-2,6-DIMETHYL-4-(3-NITROPHENYL)-1,4-DIHYDROPYRIDINE-3,5-DICARBOXYLATE
Systematic Name English
Classification Tree Code System Code
WHO-ATC C09DB08
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
NCI_THESAURUS C333
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
WHO-ATC C08CA13
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
WHO-ATC C09BB02
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
WHO-VATC QC09BB02
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
WHO-VATC QC08CA13
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
Code System Code Type Description
MESH
C060343
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
PRIMARY
FDA UNII
V7XTJ4R0BH
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
PRIMARY
WIKIPEDIA
LERCANIDIPINE
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
PRIMARY
DRUG BANK
DB00528
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
PRIMARY
DRUG CENTRAL
4157
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
PRIMARY
INN
6971
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
PRIMARY
PUBCHEM
65866
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
PRIMARY
NCI_THESAURUS
C81687
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
PRIMARY
ChEMBL
CHEMBL250270
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
PRIMARY
CAS
100427-26-7
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
PRIMARY
EPA CompTox
100427-26-7
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
PRIMARY
MERCK INDEX
M6770
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
PRIMARY Merck Index
EVMPD
SUB08437MIG
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
PRIMARY
RXCUI
135056
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
PRIMARY RxNorm
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY