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Details

Stereochemistry RACEMIC
Molecular Formula C36H41N3O6.ClH
Molecular Weight 648.188
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LERCANIDIPINE HYDROCHLORIDE

SMILES

Cl.COC(=O)C1=C(C)NC(C)=C(C1C2=CC=CC(=C2)[N+]([O-])=O)C(=O)OC(C)(C)CN(C)CCC(C3=CC=CC=C3)C4=CC=CC=C4

InChI

InChIKey=WMFYOYKPJLRMJI-UHFFFAOYSA-N
InChI=1S/C36H41N3O6.ClH/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;1H

HIDE SMILES / InChI

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

CNS Active
3913
Curator's Comment: Active in a preclinical models of epilepsy on mice

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Blocker
537
 2.2 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
ZANIDIP

Approved Use

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

Approved Use

Unknown
Palliative
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Tolerability of long-term treatment with lercanidipine versus amlodipine and lacidipine in elderly hypertensives.
2002 Nov
Lercanidipine reduces matrix metalloproteinase-9 activity in patients with hypertension.
2006 Jan
Fixed-dose combination lercanidipine/enalapril.
2007
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 in middle cerebral artery occlusion model of stroke in rats.
2017 Feb
Patents

Patents

20020068740
18
20020137755
7
EP0153016A2
3
JP2007512338A
11
JP2007512339A
43

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.
Name Type Language
LERCANIDIPINE HYDROCHLORIDE
JAN   MART.   MI   USAN   WHO-DD  
USAN  
Official Name English
Lercanidipine hydrochloride [WHO-DD]
Common Name English
LERCANIDIPINE HYDROCHLORIDE [JAN]
Common Name English
2-[(3,3-Diphenylpropyl)methylamino]-1,1-dimethylethyl methyl (4RS)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate monohydrochloride
Systematic Name English
LERCANIDIPINE HYDROCHLORIDE [MART.]
Common Name English
LERCANIDIPINE HYDROCHLORIDE [MI]
Common Name English
REC-15/2375
Code English
3,5-PYRIDINEDICARBOXYLIC ACID, 1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-, 2-((3,3-DIPHENYLPROPYL)METHYLAMINO)-1,1-DIMETHYLETHYL METHYL ESTER, MONOHYDROCHLORIDE
Common Name English
LERCANIDIPINE HCL
Common Name English
LERCANIDIPINE HYDROCHLORIDE [USAN]
Common Name English
CARDIOVASC
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C333
Created by admin on Fri Dec 15 16:37:03 UTC 2023 , Edited by admin on Fri Dec 15 16:37:03 UTC 2023
Code System Code Type Description
MERCK INDEX
m6770
Created by admin on Fri Dec 15 16:37:03 UTC 2023 , Edited by admin on Fri Dec 15 16:37:03 UTC 2023
PRIMARY Merck Index
FDA UNII
OA8TFX68PE
Created by admin on Fri Dec 15 16:37:03 UTC 2023 , Edited by admin on Fri Dec 15 16:37:03 UTC 2023
PRIMARY
NCI_THESAURUS
C87685
Created by admin on Fri Dec 15 16:37:03 UTC 2023 , Edited by admin on Fri Dec 15 16:37:03 UTC 2023
PRIMARY
MESH
C060343
Created by admin on Fri Dec 15 16:37:03 UTC 2023 , Edited by admin on Fri Dec 15 16:37:03 UTC 2023
PRIMARY
ChEMBL
CHEMBL250270
Created by admin on Fri Dec 15 16:37:03 UTC 2023 , Edited by admin on Fri Dec 15 16:37:03 UTC 2023
PRIMARY
EPA CompTox
DTXSID3046665
Created by admin on Fri Dec 15 16:37:03 UTC 2023 , Edited by admin on Fri Dec 15 16:37:03 UTC 2023
PRIMARY
USAN
OO-76
Created by admin on Fri Dec 15 16:37:03 UTC 2023 , Edited by admin on Fri Dec 15 16:37:03 UTC 2023
PRIMARY
SMS_ID
100000091632
Created by admin on Fri Dec 15 16:37:03 UTC 2023 , Edited by admin on Fri Dec 15 16:37:03 UTC 2023
PRIMARY
CAS
132866-11-6
Created by admin on Fri Dec 15 16:37:03 UTC 2023 , Edited by admin on Fri Dec 15 16:37:03 UTC 2023
PRIMARY
EVMPD
SUB02894MIG
Created by admin on Fri Dec 15 16:37:03 UTC 2023 , Edited by admin on Fri Dec 15 16:37:03 UTC 2023
PRIMARY
PUBCHEM
157917
Created by admin on Fri Dec 15 16:37:03 UTC 2023 , Edited by admin on Fri Dec 15 16:37:03 UTC 2023
PRIMARY
CAS
100427-27-8
Created by admin on Fri Dec 15 16:37:03 UTC 2023 , Edited by admin on Fri Dec 15 16:37:03 UTC 2023
NON-SPECIFIC STOICHIOMETRY
RXCUI
153679
Created by admin on Fri Dec 15 16:37:03 UTC 2023 , Edited by admin on Fri Dec 15 16:37:03 UTC 2023
PRIMARY RxNorm
ACTIVE MOIETY
Structure of LERCANIDIPINE
NIH
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