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Details

Stereochemistry RACEMIC
Molecular Formula 2C36H41N3O6.2ClH.H2O
Molecular Weight 1314.392
Optical Activity ( + / - )
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LERCANIDIPINE HYDROCHLORIDE HEMIHYDRATE

SMILES

O.Cl.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.COC(=O)C5=C(C)NC(C)=C(C5C6=CC=CC(=C6)[N+]([O-])=O)C(=O)OC(C)(C)CN(C)CCC(C7=CC=CC=C7)C8=CC=CC=C8

InChI

InChIKey=ZFZXJUJPHGPYAJ-UHFFFAOYSA-N
InChI=1S/2C36H41N3O6.2ClH.H2O/c2*1-24-31(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;;;/h2*7-19,22,30,33,37H,20-21,23H2,1-6H3;2*1H;1H2

HIDE SMILES / InChI
Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C36H41N3O6
Molecular Weight 611.7272
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

CNS Active
4002
Curator's Comment: Active in a preclinical models of epilepsy on mice

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Blocker
555
 2.2 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.37 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15556551/
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LERCANIDIPINE, (S)- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.68 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15556551/
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LERCANIDIPINE. (R)- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.244 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27405507/
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered: VALSARTAN
VALSARTAN
 LERCANIDIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
3.231 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27232153/
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LERCANIDIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
13.68 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15556551/
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LERCANIDIPINE, (S)- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
11.24 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15556551/
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LERCANIDIPINE. (R)- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
12.741 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27405507/
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered: VALSARTAN
VALSARTAN
 LERCANIDIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
12.04 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27232153/
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LERCANIDIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
9.3 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15556551/
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LERCANIDIPINE, (S)- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
7.5 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15556551/
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LERCANIDIPINE. (R)- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
5.221 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27405507/
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered: VALSARTAN
VALSARTAN
 LERCANIDIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
9.2 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27232153/
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LERCANIDIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15556551/
LERCANIDIPINE plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse events​
560 mg single, oral
Overdose
Dose: 560 mg
Route: oral
Route: single
Dose: 560 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/21251326/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/21251326/
Disc. AE: seizure, hypotension...
AEs leading to
discontinuation/dose reduction:
seizure (1 pt)
hypotension (1 pt)
bradycardia (1 pt)
Sources:
https://pubmed.ncbi.nlm.nih.gov/21251326/
10 mg 1 times / day steady-state, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: steady-state
Dose: 10 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28485829/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/28485829/
Other AEs: abdominal distension, dyspepsia...
Other AEs:
abdominal distension (1 pt)
dyspepsia (1 pt)
nausea (1 pt)
Sources:
https://pubmed.ncbi.nlm.nih.gov/28485829/
10 mg 1 times / day steady-state, oral
Studied dose
Dose: 10 mg, 1 times / day
Route: oral
Route: steady-state
Dose: 10 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17581601/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/17581601/
Other AEs: headache...
Other AEs:
headache (2.9%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/17581601/
10 mg 1 times / day steady-state, oral
Studied dose
Dose: 10 mg, 1 times / day
Route: oral
Route: steady-state
Dose: 10 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17581601/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/17581601/
Disc. AE: flushing, headache...
Other AEs: headache...
AEs leading to
discontinuation/dose reduction:
flushing (2 patients)
headache (1 pt)
fatigue (1 pt)
vertigo (1 pt)
Other AEs:
headache (4.2%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/17581601/
AEs

AEs

AESignificanceDosePopulation
bradycardia 1 pt
Disc. AE
560 mg single, oral
Overdose
Dose: 560 mg
Route: oral
Route: single
Dose: 560 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/21251326/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/21251326/
hypotension 1 pt
Disc. AE
560 mg single, oral
Overdose
Dose: 560 mg
Route: oral
Route: single
Dose: 560 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/21251326/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/21251326/
seizure 1 pt
Disc. AE
560 mg single, oral
Overdose
Dose: 560 mg
Route: oral
Route: single
Dose: 560 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/21251326/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/21251326/
abdominal distension 1 pt
10 mg 1 times / day steady-state, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: steady-state
Dose: 10 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28485829/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/28485829/
dyspepsia 1 pt
10 mg 1 times / day steady-state, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: steady-state
Dose: 10 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28485829/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/28485829/
nausea 1 pt
10 mg 1 times / day steady-state, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: steady-state
Dose: 10 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28485829/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/28485829/
headache 2.9%
10 mg 1 times / day steady-state, oral
Studied dose
Dose: 10 mg, 1 times / day
Route: oral
Route: steady-state
Dose: 10 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17581601/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/17581601/
fatigue 1 pt
Disc. AE
10 mg 1 times / day steady-state, oral
Studied dose
Dose: 10 mg, 1 times / day
Route: oral
Route: steady-state
Dose: 10 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17581601/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/17581601/
headache 1 pt
Disc. AE
10 mg 1 times / day steady-state, oral
Studied dose
Dose: 10 mg, 1 times / day
Route: oral
Route: steady-state
Dose: 10 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17581601/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/17581601/
vertigo 1 pt
Disc. AE
10 mg 1 times / day steady-state, oral
Studied dose
Dose: 10 mg, 1 times / day
Route: oral
Route: steady-state
Dose: 10 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17581601/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/17581601/
flushing 2 patients
Disc. AE
10 mg 1 times / day steady-state, oral
Studied dose
Dose: 10 mg, 1 times / day
Route: oral
Route: steady-state
Dose: 10 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17581601/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/17581601/
headache 4.2%
10 mg 1 times / day steady-state, oral
Studied dose
Dose: 10 mg, 1 times / day
Route: oral
Route: steady-state
Dose: 10 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17581601/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/17581601/
PubMed

PubMed

TitleDatePubMed
Neuroprotective effect of lercanidipine in middle cerebral artery occlusion model of stroke in rats.
2017-02
Neuroprotective Effect of Lercanidipine- A Novel Calcium Channel Blocker in Albino Mice.
2015-11
Lercanidipine inhibits vascular smooth muscle cell proliferation and neointimal formation via reducing intracellular reactive oxygen species and inactivating Ras-ERK1/2 signaling.
2009-01
Lercanidipine in the treatment of hypertension.
2007-03
Fixed-dose combination lercanidipine/enalapril.
2007
[The effect of calcium channel blocker lercanidipine on lowgrade inflammation parameters in essential hypertension patients].
2006-12
Lercanidipine and losartan effects on blood pressure and fibrinolytic parameters.
2006-04
Lercanidipine reduces matrix metalloproteinase-9 activity in patients with hypertension.
2006-01
Efficacy and safety of lercanidipine versus hydrochlorothiazide as add-on to enalapril in diabetic populations with uncontrolled hypertension.
2006-01
Increased vascular selectivity and prolonged pharmacological efficacy of the L-type Ca2+ channel antagonist lercanidipine in human cardiovascular tissue.
2005-09
Tolerability of long-term treatment with lercanidipine versus amlodipine and lacidipine in elderly hypertensives.
2002-11
Lercanidipine: a review of its use in hypertension.
2000-11
Nephroprotective effect of treatment with calcium channel blockers in spontaneously hypertensive rats.
2000-09
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.
Substance Class Chemical
Created
by admin
on Wed Apr 02 10:33:15 GMT 2025
Edited
by admin
on Wed Apr 02 10:33:15 GMT 2025
Record UNII
9YZG49F7RC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
3,5-PYRIDINEDICARBOXYLIC ACID, 1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-, 3-(2-((3,3-DIPHENYLPROPYL)METHYLAMINO)-1,1-DIMETHYLETHYL) 5-METHYL ESTER, HYDROCHLORIDE, HYDRATE (2:2:1)
Preferred Name English
LERCANIDIPINE HYDROCHLORIDE HEMIHYDRATE
Common Name English
Code System Code Type Description
FDA UNII
9YZG49F7RC
Created by admin on Wed Apr 02 10:33:15 GMT 2025 , Edited by admin on Wed Apr 02 10:33:15 GMT 2025
PRIMARY
SMS_ID
100000159821
Created by admin on Wed Apr 02 10:33:15 GMT 2025 , Edited by admin on Wed Apr 02 10:33:15 GMT 2025
PRIMARY
CAS
957215-04-2
Created by admin on Wed Apr 02 10:33:15 GMT 2025 , Edited by admin on Wed Apr 02 10:33:15 GMT 2025
PRIMARY
PUBCHEM
163203543
Created by admin on Wed Apr 02 10:33:15 GMT 2025 , Edited by admin on Wed Apr 02 10:33:15 GMT 2025
PRIMARY
Related Record Type Details
Structure of LERCANIDIPINE
PARENT -> SALT/SOLVATE
Structure of LERCANIDIPINE HYDROCHLORIDE
ANHYDROUS->SOLVATE
Related Record Type Details
Structure of LERCANIDIPINE
ACTIVE MOIETY
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