Details
Stereochemistry | RACEMIC |
Molecular Formula | C36H41N3O6.ClH |
Molecular Weight | 648.188 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
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
InChI
InChIKey=WMFYOYKPJLRMJI-UHFFFAOYSA-N
InChI=1S/C36H41N3O6.ClH/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;1H
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 | ( + / - ) |
DescriptionCurator'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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26673531
Curator's Comment: Active in a preclinical models of epilepsy on mice
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2095229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16173926 |
2.2 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | ZANIDIP Approved UseLercanidipine is indicated for the treatment of mild to moderate essential hypertension |
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Primary | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Tolerability of long-term treatment with lercanidipine versus amlodipine and lacidipine in elderly hypertensives. | 2002 Nov |
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Increased vascular selectivity and prolonged pharmacological efficacy of the L-type Ca2+ channel antagonist lercanidipine in human cardiovascular tissue. | 2005 Sep |
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[The effect of calcium channel blocker lercanidipine on lowgrade inflammation parameters in essential hypertension patients]. | 2006 Dec |
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Lercanidipine reduces matrix metalloproteinase-9 activity in patients with hypertension. | 2006 Jan |
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Lercanidipine in the treatment of hypertension. | 2007 Mar |
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Lercanidipine inhibits vascular smooth muscle cell proliferation and neointimal formation via reducing intracellular reactive oxygen species and inactivating Ras-ERK1/2 signaling. | 2009 Jan |
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Neuroprotective Effect of Lercanidipine- A Novel Calcium Channel Blocker in Albino Mice. | 2015 Nov |
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Neuroprotective effect of lercanidipine in middle cerebral artery occlusion model of stroke in rats. | 2017 Feb |
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16173926
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
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admin
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Edited
Fri Dec 15 16:37:03 GMT 2023
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Fri Dec 15 16:37:03 GMT 2023
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Record UNII |
OA8TFX68PE
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C333
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ENANTIOMER -> RACEMATE |
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ENANTIOMER -> RACEMATE |
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PARENT -> SALT/SOLVATE |
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SOLVATE->ANHYDROUS |
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ACTIVE MOIETY |
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