Identification
- Summary
Lercanidipine is a calcium channel blocker for the management of hypertension.
- Generic Name
- Lercanidipine
- DrugBank Accession Number
- DB00528
- Background
Lercanidipine is a calcium channel blocker of the dihydropyridine class. It is sold under various commercial names including Zanidip.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Lercanidipine (DB00528)
- Weight
- Average: 611.7272
Monoisotopic: 611.299536059 - Chemical Formula
- C36H41N3O6
- Synonyms
- Lercanidipine
- Lercanidipino
Pharmacology
- Indication
For the treatment of Hypertension, management of angina pectoris and Raynaud's syndrome
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat High blood pressure (hypertension) Combination Product in combination with: Enalapril (DB00584) •••••••••••• ••••• •••••••• ••••••••• •••• ••••••••••••• ••••••• •••••• Treatment of Mild hypertension •••••••••••• •••••• Treatment of Moderate essential hypertension •••••••••••• •••••• - Contraindications & Blackbox Warnings
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Lercanidipine, a dihydropyridine calcium-channel blocker, is used alone or with an angiotensin-converting enzyme inhibitor, to treat hypertension, chronic stable angina pectoris, and Prinzmetal's variant angina. Lercanidipine is similar to other peripheral vasodilators. Lercanidipine inhibits the influx of extra cellular calcium across the myocardial and vascular smooth muscle cell membranes possibly by deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum. The decrease in intracellular calcium inhibits the contractile processes of the myocardial smooth muscle cells, causing dilation of the coronary and systemic arteries, increased oxygen delivery to the myocardial tissue, decreased total peripheral resistance, decreased systemic blood pressure, and decreased afterload.
- Mechanism of action
By deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum, Lercanidipine inhibits the influx of extracellular calcium across the myocardial and vascular smooth muscle cell membranes The decrease in intracellular calcium inhibits the contractile processes of the myocardial smooth muscle cells, causing dilation of the coronary and systemic arteries, increased oxygen delivery to the myocardial tissue, decreased total peripheral resistance, decreased systemic blood pressure, and decreased afterload.
Target Actions Organism AVoltage-dependent calcium channel gamma-1 subunit inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbaloparatide The risk or severity of adverse effects can be increased when Lercanidipine is combined with Abaloparatide. Abametapir The serum concentration of Lercanidipine can be increased when it is combined with Abametapir. Abatacept The metabolism of Lercanidipine can be increased when combined with Abatacept. Acalabrutinib The metabolism of Lercanidipine can be decreased when combined with Acalabrutinib. Acarbose The risk or severity of hypoglycemia can be increased when Lercanidipine is combined with Acarbose. - Food Interactions
- Avoid alcohol. Alcohol may increase the vasodilatory effects of lercanidipine, which may lead to hypotension.
- Avoid grapefruit products. Grapefruit inhibits the metabolism of lercanidipine through CYP3A4, which causes increased serum levels of lercanidipine, and may increase the risk of hypotension.
- Exercise caution with St. John's Wort. Lercanidipine is metabolized by CYP3A4, and St. John's Wort is a CYP3A4 inducer.
- Take on an empty stomach. Taking lercanidipine after meals increases its bioavailability, therefore lercanidipine should be taken least 15 minutes before meals.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Lercanidipine hydrochloride OA8TFX68PE 132866-11-6 WMFYOYKPJLRMJI-UHFFFAOYSA-N - International/Other Brands
- Cardiovasc / Carmen / Corifeo / Lercanil / Lercaton / Lerzam / Renovia / Vasodip / Zandip / Zanicor / Zanidip
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ATOVER Lercanidipine hydrochloride (10 MG) + Enalapril maleate (10 MG) Tablet, coated Oral Recordati Industria Chimica E Farmaceutica S.P.A. 2014-07-08 Not applicable Italy 
ATOVER Lercanidipine hydrochloride (10 MG) + Enalapril maleate (20 MG) Tablet, coated Oral Recordati Industria Chimica E Farmaceutica S.P.A. 2014-07-08 Not applicable Italy ATOVER Lercanidipine hydrochloride (20 MG) + Enalapril maleate (20 MG) Tablet, coated Oral Recordati Industria Chimica E Farmaceutica S.P.A. 2015-09-22 Not applicable Italy ATOVER Lercanidipine hydrochloride (10 MG) + Enalapril maleate (20 MG) Tablet, coated Oral Recordati Industria Chimica E Farmaceutica S.P.A. 2014-07-08 Not applicable Italy ATOVER Lercanidipine hydrochloride (10 MG) + Enalapril maleate (10 MG) Tablet, coated Oral Recordati Industria Chimica E Farmaceutica S.P.A. 2014-07-08 Not applicable Italy
Categories
- ATC Codes
- C09DB08 — Valsartan and lercanidipine
- C09DB — Angiotensin II receptor blockers (ARBs) and calcium channel blockers
- C09D — ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), COMBINATIONS
- C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
- C — CARDIOVASCULAR SYSTEM
- C09BB — ACE inhibitors and calcium channel blockers
- C09B — ACE INHIBITORS, COMBINATIONS
- C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
- C — CARDIOVASCULAR SYSTEM
- Drug Categories
- ACE Inhibitors and Calcium Channel Blockers
- Agents causing hyperkalemia
- Agents Causing Muscle Toxicity
- Angiotensin II receptor blockers (ARBs) and calcium channel blockers
- Antiarrhythmic agents
- Antihypertensive Agents
- Bradycardia-Causing Agents
- Calcium Channel Blockers
- Calcium-Regulating Hormones and Agents
- Cardiovascular Agents
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (moderate)
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Dihydropyridine Derivatives
- Hypotensive Agents
- Membrane Transport Modulators
- Pyridines
- Selective Calcium Channel Blockers With Mainly Vascular Effects
- Vasodilating Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Diphenylmethanes
- Direct Parent
- Diphenylmethanes
- Alternative Parents
- Nitrobenzenes / Dihydropyridinecarboxylic acids and derivatives / Nitroaromatic compounds / Aralkylamines / Dicarboxylic acids and derivatives / Vinylogous amides / Methyl esters / Enoate esters / Trialkylamines / Amino acids and derivatives show 9 more
- Substituents
- Allyl-type 1,3-dipolar organic compound / Alpha,beta-unsaturated carboxylic ester / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / C-nitro compound / Carbonyl group / Carboxylic acid derivative show 28 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- V7XTJ4R0BH
- CAS number
- 100427-26-7
- InChI Key
- ZDXUKAKRHYTAKV-UHFFFAOYSA-N
- InChI
- 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
- IUPAC Name
- 3-{1-[(3,3-diphenylpropyl)(methyl)amino]-2-methylpropan-2-yl} 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
- SMILES
- COC(=O)C1=C(C)NC(C)=C(C1C1=CC(=CC=C1)[N+]([O-])=O)C(=O)OC(C)(C)CN(C)CCC(C1=CC=CC=C1)C1=CC=CC=C1
References
- Synthesis Reference
Bandi Parthasaradhi Reddy, Kura Rathnakar Reddy, Rapolu Raji Reddy, Dasari Muralidhara Reddy, Dandamudi Satish Kumar, " NOVEL PROCESS FOR THE PREPARATION OF LERCANIDIPINE." U.S. Patent US20090227800, issued September 10, 2009.
US20090227800- General References
- Lin TH, Voon WC, Yen HW, Huang CH, Su HM, Lai WT, Sheu SH: Lercanidipine and losartan effects on blood pressure and fibrinolytic parameters. Kaohsiung J Med Sci. 2006 Apr;22(4):177-83. [Article]
- Martinez ML, Lopes LF, Coelho EB, Nobre F, Rocha JB, Gerlach RF, Tanus-Santos JE: Lercanidipine reduces matrix metalloproteinase-9 activity in patients with hypertension. J Cardiovasc Pharmacol. 2006 Jan;47(1):117-22. [Article]
- Agrawal R, Marx A, Haller H: Efficacy and safety of lercanidipine versus hydrochlorothiazide as add-on to enalapril in diabetic populations with uncontrolled hypertension. J Hypertens. 2006 Jan;24(1):185-92. [Article]
- External Links
- Human Metabolome Database
- HMDB0014669
- PubChem Compound
- 65866
- PubChem Substance
- 46508865
- ChemSpider
- 59276
- 135056
- ChEBI
- 135930
- ChEMBL
- CHEMBL250270
- Therapeutic Targets Database
- DAP001261
- PharmGKB
- PA164769058
- Wikipedia
- Lercanidipine
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Cardiovascular Disease (CVD) / Chronic Kidney Disease (CKD) / Hypertension, Essential Hypertension / Stroke 1 4 Completed Treatment Hypertension 2 4 Completed Treatment Hypertension / Hypertension, Essential Hypertension 1 4 Terminated Treatment Hypertension 1 4 Unknown Status Treatment Human Immunodeficiency Virus (HIV) Infections / Hypertension 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, film coated Oral 10 MG Tablet, film coated Oral 20 MG Tablet, film coated Oral 10 mg/1 Tablet, coated Oral Tablet, film coated Oral Capsule Oral Tablet, film coated Oral Tablet Oral 10.00 mg Tablet Oral Tablet Oral 10.000 mg Tablet Oral Tablet, coated Oral 20 mg Tablet, coated Oral 10 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 6.4 Not Available - Predicted Properties
Property Value Source Water Solubility 0.000156 mg/mL ALOGPS logP 6.42 ALOGPS logP 6.41 Chemaxon logS -6.6 ALOGPS pKa (Strongest Acidic) 16.96 Chemaxon pKa (Strongest Basic) 9.36 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 111.01 Å2 Chemaxon Rotatable Bond Count 14 Chemaxon Refractivity 176.85 m3·mol-1 Chemaxon Polarizability 66.2 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9474 Blood Brain Barrier - 0.9611 Caco-2 permeable - 0.7039 P-glycoprotein substrate Substrate 0.9085 P-glycoprotein inhibitor I Inhibitor 0.9132 P-glycoprotein inhibitor II Inhibitor 0.8957 Renal organic cation transporter Non-inhibitor 0.7439 CYP450 2C9 substrate Non-substrate 0.8448 CYP450 2D6 substrate Non-substrate 0.8924 CYP450 3A4 substrate Substrate 0.7579 CYP450 1A2 substrate Inhibitor 0.6321 CYP450 2C9 inhibitor Inhibitor 0.7247 CYP450 2D6 inhibitor Inhibitor 0.5933 CYP450 2C19 inhibitor Inhibitor 0.7625 CYP450 3A4 inhibitor Inhibitor 0.5715 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7709 Ames test Non AMES toxic 0.5517 Carcinogenicity Non-carcinogens 0.668 Biodegradation Not ready biodegradable 0.9895 Rat acute toxicity 2.8614 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.5761 hERG inhibition (predictor II) Non-inhibitor 0.6908
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-000i-2191010000-9a91ea6a126944a1a4fb - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 263.2200967 predictedDarkChem Lite v0.1.0 [M-H]- 213.56602 predictedDeepCCS 1.0 (2019) [M+H]+ 264.0823967 predictedDarkChem Lite v0.1.0 [M+H]+ 215.50316 predictedDeepCCS 1.0 (2019) [M+Na]+ 263.9323967 predictedDarkChem Lite v0.1.0 [M+Na]+ 221.24358 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Voltage-gated calcium channel activity
- Specific Function
- This protein is a subunit of the dihydropyridine (DHP) sensitive calcium channel. Plays a role in excitation-contraction coupling. The skeletal muscle DHP-sensitive Ca(2+) channel may function only...
- Gene Name
- CACNG1
- Uniprot ID
- Q06432
- Uniprot Name
- Voltage-dependent calcium channel gamma-1 subunit
- Molecular Weight
- 25028.105 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Burnier M, Pruijm M, Wuerzner G: Treatment of essential hypertension with calcium channel blockers: what is the place of lercanidipine? Expert Opin Drug Metab Toxicol. 2009 Aug;5(8):981-7. doi: 10.1517/17425250903085135. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- Klotz U: Interaction potential of lercanidipine, a new vasoselective dihydropyridine calcium antagonist. Arzneimittelforschung. 2002;52(3):155-61. doi: 10.1055/s-0031-1299873. [Article]
- Borghi C: Lercanidipine in hypertension. Vasc Health Risk Manag. 2005;1(3):173-82. [Article]
- Flockhart Table of Drug Interactions [Link]
- LERCANIDIPINE - Australian Prescribing Information [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57525.03 Da
References
- Flockhart Table of Drug Interactions [Link]
Drug created at June 13, 2005 13:24 / Updated at November 03, 2023 23:43