LERCANIDIPINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C36H41N3O6
Molecular Weight	611.7272
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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=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

Description
Sources: http://www.mhra.gov.uk/home/groups/par/documents/websiteresources/con071101.pdf
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-gated L-type calcium channel 92 Target ID: CHEMBL2095229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16173926	Blocker 537		2.2 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Essential hypertension 17 Sources: http://www.mhra.gov.uk/home/groups/par/documents/websiteresources/con071101.pdf	Primary	Approved 8429	ZANIDIP Approved Use Lercanidipine is indicated for the treatment of mild to moderate essential hypertension
Epilepsy 121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26673531	Primary	Preclinical	Unknown Approved Use Unknown
Stroke 144 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27794423	Palliative	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Lercanidipine: a review of its use in hypertension.	2000 Nov	11129125
Nephroprotective effect of treatment with calcium channel blockers in spontaneously hypertensive rats.	2000 Sep	10945845
Efficacy and safety of lercanidipine versus hydrochlorothiazide as add-on to enalapril in diabetic populations with uncontrolled hypertension.	2006 Jan	16331117
Lercanidipine in the treatment of hypertension.	2007 Mar	17341540
Lercanidipine inhibits vascular smooth muscle cell proliferation and neointimal formation via reducing intracellular reactive oxygen species and inactivating Ras-ERK1/2 signaling.	2009 Jan	18973813

Patents

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

Official Name

English

Lercanidipine [WHO-DD]

Common 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 [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