LERCANIDIPINE

Possibly Marketed Outside US

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

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

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 95	Blocker 555		2.2 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Essential hypertension 17	Primary	Approved 8,583	ZANIDIP
Epilepsy 121	Primary	Preclinical	Unknown
Stroke 144	Palliative	Preclinical	Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
2.37 ng/mL	20 mg single, oral		LERCANIDIPINE, (S)- plasma	Homo sapiens
1.68 ng/mL	20 mg single, oral		LERCANIDIPINE. (R)- plasma	Homo sapiens
2.244 ng/mL	10 mg single, oral	VALSARTAN	LERCANIDIPINE plasma	Homo sapiens
3.231 ng/mL	10 mg single, oral		LERCANIDIPINE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
13.68 ng × h/mL	20 mg single, oral		LERCANIDIPINE, (S)- plasma	Homo sapiens
11.24 ng × h/mL	20 mg single, oral		LERCANIDIPINE. (R)- plasma	Homo sapiens
12.741 ng × h/mL	10 mg single, oral	VALSARTAN	LERCANIDIPINE plasma	Homo sapiens
12.04 ng × h/mL	10 mg single, oral		LERCANIDIPINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
9.3 h	20 mg single, oral		LERCANIDIPINE, (S)- plasma	Homo sapiens
7.5 h	20 mg single, oral		LERCANIDIPINE. (R)- plasma	Homo sapiens
5.221 h	10 mg single, oral	VALSARTAN	LERCANIDIPINE plasma	Homo sapiens
9.2 h	10 mg single, oral		LERCANIDIPINE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
2%			LERCANIDIPINE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
560 mg single, oral Overdose	healthy, ADULT	Disc. AE: seizure, hypotension...
10 mg 1 times / day steady-state, oral Recommended	unhealthy, ADULT	Other AEs: abdominal distension, dyspepsia...
10 mg 1 times / day steady-state, oral Studied dose	unhealthy, ADULT	Other AEs: headache...
10 mg 1 times / day steady-state, oral Studied dose	unhealthy, ADULT	Disc. AE: flushing, headache... Other AEs: headache...

Showing 1 to 4 of 4 entries

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AEs

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AE	Significance	Dose	Population
bradycardia	1 pt Disc. AE	560 mg single, oral Overdose	healthy, ADULT
hypotension	1 pt Disc. AE	560 mg single, oral Overdose	healthy, ADULT
seizure	1 pt Disc. AE	560 mg single, oral Overdose	healthy, ADULT
abdominal distension	1 pt	10 mg 1 times / day steady-state, oral Recommended	unhealthy, ADULT
dyspepsia	1 pt	10 mg 1 times / day steady-state, oral Recommended	unhealthy, ADULT

Showing 1 to 5 of 12 entries

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PubMed

Show entries

Title	Date	PubMed
Lercanidipine and losartan effects on blood pressure and fibrinolytic parameters.	2006 Apr	16679299
[The effect of calcium channel blocker lercanidipine on lowgrade inflammation parameters in essential hypertension patients].	2006 Dec	17220028
Fixed-dose combination lercanidipine/enalapril.	2007	17209666
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

Showing 1 to 5 of 7 entries

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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.

Show entries

Name

Type

Language

LERCANIDIPINE

Official Name

English

LERCANIL

Preferred 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

Showing 1 to 5 of 7 entries

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Classification Tree

Code System

Code

Angiotensin II antagonists and calcium channel blockers

WHO-ATC

C09DB08

Cation Channel Blocker

NCI_THESAURUS

C333

Dihydropyridine derivatives

WHO-ATC

C08CA13

ACE inhibitors and calcium channel blockers

WHO-ATC

C09BB02

ACE inhibitors and calcium channel blockers

WHO-VATC

QC09BB02

Showing 1 to 5 of 6 entries

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Show entries

Code System

Code

Type

Description

MESH

C060343

PRIMARY

FDA UNII

V7XTJ4R0BH

PRIMARY

WIKIPEDIA

LERCANIDIPINE

PRIMARY

DRUG BANK

DB00528

PRIMARY

DRUG CENTRAL

4157

PRIMARY

Showing 1 to 5 of 15 entries

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ACTIVE MOIETY


					V7XTJ4R0BH

LERCANIDIPINE

SALT/SOLVATE (PARENT)


					9YZG49F7RC

LERCANIDIPINE HYDROCHLORIDE HEMIHYDRATE

SALT/SOLVATE (PARENT)


					OA8TFX68PE

LERCANIDIPINE HYDROCHLORIDE

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound