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Details

Stereochemistry ABSOLUTE
Molecular Formula C36H41N3O6
Molecular Weight 611.7286
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LERCANIDIPINE. (R)-

SMILES

CC1=C([C@@]([H])(c2cccc(c2)N(=O)=O)C(=C(C)N1)C(=O)OC(C)(C)CN(C)CCC(c3ccccc3)c4ccccc4)C(=O)OC

InChI

InChIKey=ZDXUKAKRHYTAKV-MGBGTMOVSA-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/t33-/m1/s1

HIDE SMILES / InChI

Molecular Formula C36H41N3O6
Molecular Weight 611.7286
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/9850438 | https://www.ncbi.nlm.nih.gov/pubmed/9818292

(R)-Lercanidipine is enantiomer of antihypertensive drugs Lercanidipine, that acts by blocking L-type calcium channels, allowing relaxation and opening of blood vessels. The dihydropyridine calcium antagonists promote systemic vasodilatation by a reversible blockade of voltagedependent Ca2+ influx through L-type channels in the cell membrane. (S)-Lercanidipine has 100- to 200-fold greater affinity than the (R)-enantiomer for the L-type calcium channel. The pharmacokinectics of (S)- Lercanidipine has been evaluated in healthy volunteers, in elderly and non-elderly patients with hypertension, and in patients with renal or hepatic impairment. Patients from these studies were investigated after receiving a single 10 or 20 mgdose of [14C]-labeled rac-Lercanidipine as a solution. The maximum plasma concentrations of (S)-Lercanidipine were reached within 2–3 h and the area under the plasma concentration–time curves were not linearly related to the dose, indicating a saturable first-pass metabolism. The absorption of (S)-LER increases after the ingestion of a highfat meal. Lercanidipine is highly bound to plasma protein (>98%) in humans. Its volume of distribution of 2–2.5 L/kg was determined in healthy volunteers after intravenous infusion of 2 mg. Lercanidipine is extensively metabolized by CYP 3A4 to inactive pyridine derivatives. A crossover study involving a single administration of either 10 mg of (R)- or (S)-LER or 20 mg of rac-LER as a solution demonstrated no in vivo enantiomer interconversion

CNS Activity

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
84.83 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ZANIDIP

Approved Use

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

Approved Use

Unknown
Primary
ZANIDIP

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Enantioselective pharmacokinetics of lercanidipine in healthy volunteers.
2004 Dec 25
Patents

Patents

Sample Use Guides

Single administration of 10 mg as a solution.
Route of Administration: Oral
In Vitro Use Guide
Migration of rat Smooth muscle cells (SMC) was induced by fibrinogen and examined using a 48-well microchemotaxis chamber (Neuro-Probe, Cabin John, MD, USA). SMC that migrated to the lower surface of the filters were counted under a high-power (100x) field (HPF). Six HPF were counted per sample and the results were averaged. To investigate the proliferation of SMC, cells were seeded at various densities for rat (2 x 10^5) and human (5 x 10^4) myocytes/Petri dish (dia. 35 mm) and incubated with MEM supplemented with 10% FCS. Cell proliferation was evaluated by cell count after trypsinization of the monolayers using a Coulter Counter model ZM SMC doubling time was computed according to Elmore and Swift. Cell proliferation was then estimated by nuclear incorporation of [3H]thymidine.
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:56:57 UTC 2021
Edited
by admin
on Fri Jun 25 22:56:57 UTC 2021
Record UNII
J3YZX94597
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LERCANIDIPINE. (R)-
Common Name English
(-)-LERCANIDIPINE
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, (4R)-
Systematic Name English
(R)-LERCANIDIPINE
Common Name English
Code System Code Type Description
CAS
185197-70-0
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
PRIMARY
FDA UNII
J3YZX94597
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
PRIMARY
PUBCHEM
9809926
Created by admin on Fri Jun 25 22:56:57 UTC 2021 , Edited by admin on Fri Jun 25 22:56:57 UTC 2021
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER