U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 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 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 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
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
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

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 Sat Dec 16 18:16:31 GMT 2023
Edited
by admin
on Sat Dec 16 18:16:31 GMT 2023
Record UNII
9YZG49F7RC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LERCANIDIPINE HYDROCHLORIDE HEMIHYDRATE
Common Name English
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)
Systematic Name English
Code System Code Type Description
FDA UNII
9YZG49F7RC
Created by admin on Sat Dec 16 18:16:32 GMT 2023 , Edited by admin on Sat Dec 16 18:16:32 GMT 2023
PRIMARY
SMS_ID
100000159821
Created by admin on Sat Dec 16 18:16:32 GMT 2023 , Edited by admin on Sat Dec 16 18:16:32 GMT 2023
PRIMARY
CAS
957215-04-2
Created by admin on Sat Dec 16 18:16:32 GMT 2023 , Edited by admin on Sat Dec 16 18:16:32 GMT 2023
PRIMARY
PUBCHEM
163203543
Created by admin on Sat Dec 16 18:16:32 GMT 2023 , Edited by admin on Sat Dec 16 18:16:32 GMT 2023
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
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966