Lercanidipine

Identification

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
Thumb
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

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

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.

TargetActionsOrganism
AVoltage-dependent calcium channel gamma-1 subunit
inhibitor
Humans
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
Medicalerrors
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AbametapirThe serum concentration of Lercanidipine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Lercanidipine can be increased when combined with Abatacept.
AcalabrutinibThe metabolism of Lercanidipine can be decreased when combined with Acalabrutinib.
AcarboseThe risk or severity of hypoglycemia can be increased when Lercanidipine is combined with Acarbose.
AcebutololThe risk or severity of bradycardia can be increased when Lercanidipine is combined with Acebutolol.
AceclofenacThe therapeutic efficacy of Lercanidipine can be decreased when used in combination with Aceclofenac.
AcemetacinThe therapeutic efficacy of Lercanidipine can be decreased when used in combination with Acemetacin.
AcetohexamideThe risk or severity of hypoglycemia can be increased when Lercanidipine is combined with Acetohexamide.
AcetyldigitoxinLercanidipine may increase the arrhythmogenic activities of Acetyldigitoxin.
Acetylsalicylic acidAcetylsalicylic acid may decrease the antihypertensive activities of Lercanidipine.
Interactions
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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

Products
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Product Ingredients
IngredientUNIICASInChI Key
Lercanidipine hydrochlorideOA8TFX68PE132866-11-6WMFYOYKPJLRMJI-UHFFFAOYSA-N
International/Other Brands
Cardiovasc / Carmen / Corifeo / Lercanil / Lercaton / Lerzam / Renovia / Vasodip / Zandip / Zanicor / Zanidip
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ZANIPRESS 10 MG/10 MG FILM TABLET, 30 ADETLercanidipine hydrochloride (10 mg) + Enalapril maleate (10 mg)Tablet, film coatedOralRECORDATİ İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
ZANIPRESS 10 MG/10 MG FILM TABLET, 90 ADETLercanidipine hydrochloride (10 mg) + Enalapril maleate (10 mg)Tablet, film coatedOralRECORDATİ İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
ZANIPRESS 20 MG/10 MG FILM TABLET, 30 ADETLercanidipine hydrochloride (10 mg) + Enalapril maleate (20 mg)Tablet, film coatedOralRECORDATİ İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
ZANIPRESS 20 MG/10 MG FILM TABLET, 90 ADETLercanidipine hydrochloride (10 mg) + Enalapril maleate (20 mg)Tablet, film coatedOralRECORDATİ İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
ZANIPRESS 20 MG/20 MG FILM TABLET,30 ADETLercanidipine hydrochloride (20 mg) + Enalapril maleate (20 mg)Tablet, film coatedOralRECORDATİ İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
ZANIPRESS 20 MG/20 MG FILM TABLET,90 ADETLercanidipine hydrochloride (20 mg) + Enalapril maleate (20 mg)Tablet, film coatedOralRECORDATİ İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
ZANITEK 10 MG/10MG FILM TABLET, 30 ADETLercanidipine hydrochloride (10 mg) + Enalapril maleate (10 mg)Tablet, film coatedOralRECOFARMA İLAÇ VE HAMMADDELERİ SAN.VE TİC. LTD. ŞTİ.2020-08-14Not applicableTurkey flag
ZANITEK 10 MG/10MG FILM TABLET,90 ADETLercanidipine hydrochloride (10 mg) + Enalapril maleate (10 mg)Tablet, film coatedOralRECOFARMA İLAÇ VE HAMMADDELERİ SAN.VE TİC. LTD. ŞTİ.2020-08-14Not applicableTurkey flag
ZANITEK 20 MG/10MG FILM TABLET, 30 ADETLercanidipine hydrochloride (10 mg) + Enalapril maleate (20 mg)Tablet, film coatedOralRECOFARMA İLAÇ VE HAMMADDELERİ SAN.VE TİC. LTD. ŞTİ.2020-08-14Not applicableTurkey flag
ZANITEK 20 MG/10MG FILM TABLET, 30 ADETLercanidipine hydrochloride (10 mg) + Enalapril maleate (20 mg)Tablet, film coatedOralRECOFARMA İLAÇ VE HAMMADDELERİ SAN.VE TİC. LTD. ŞTİ.2020-08-14Not applicableTurkey flag

Categories

ATC Codes
C09DB08 — Valsartan and lercanidipineC09BB02 — Enalapril and lercanidipineC08CA13 — Lercanidipine
Drug Categories
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
  1. 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]
  2. 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]
  3. 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]
Human Metabolome Database
HMDB0014669
PubChem Compound
65866
PubChem Substance
46508865
ChemSpider
59276
RxNav
135056
ChEBI
135930
ChEMBL
CHEMBL250270
Therapeutic Targets Database
DAP001261
PharmGKB
PA164769058
Wikipedia
Lercanidipine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentCardiovascular Disease (CVD) / Chronic Kidney Disease (CKD) / Hypertension,Essential / Stroke1
4CompletedTreatmentHigh Blood Pressure (Hypertension)2
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Hypertension,Essential1
4RecruitingTreatmentProteinuria / Renal Insufficiency,Chronic1
4TerminatedTreatmentHigh Blood Pressure (Hypertension)1
4Unknown StatusTreatmentHigh Blood Pressure (Hypertension) / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentHigh Blood Pressure (Hypertension)1
2CompletedTreatmentHypertension,Essential2
Not AvailableCompletedNot AvailableHigh Blood Pressure (Hypertension)1
Not AvailableRecruitingNot AvailableObesity, Morbid1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, coatedOral
Tablet, coatedOral
Tablet, film coatedOral
Tablet, film coatedOral
TabletOral
Tablet, coatedOral20 mg
Tablet, coatedOral10 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP6.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000156 mg/mLALOGPS
logP6.42ALOGPS
logP6.41ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)16.96ChemAxon
pKa (Strongest Basic)9.36ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area111.01 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity176.85 m3·mol-1ChemAxon
Polarizability66.2 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9474
Blood Brain Barrier-0.9611
Caco-2 permeable-0.7039
P-glycoprotein substrateSubstrate0.9085
P-glycoprotein inhibitor IInhibitor0.9132
P-glycoprotein inhibitor IIInhibitor0.8957
Renal organic cation transporterNon-inhibitor0.7439
CYP450 2C9 substrateNon-substrate0.8448
CYP450 2D6 substrateNon-substrate0.8924
CYP450 3A4 substrateSubstrate0.7579
CYP450 1A2 substrateInhibitor0.6321
CYP450 2C9 inhibitorInhibitor0.7247
CYP450 2D6 inhibitorInhibitor0.5933
CYP450 2C19 inhibitorInhibitor0.7625
CYP450 3A4 inhibitorInhibitor0.5715
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7709
Ames testNon AMES toxic0.5517
CarcinogenicityNon-carcinogens0.668
BiodegradationNot ready biodegradable0.9895
Rat acute toxicity2.8614 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5761
hERG inhibition (predictor II)Non-inhibitor0.6908
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. 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
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
  1. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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
  1. 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]
  2. 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]
  3. Borghi C: Lercanidipine in hypertension. Vasc Health Risk Manag. 2005;1(3):173-82. [Article]
  4. Flockhart Table of Drug Interactions [Link]
  5. 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
  1. Flockhart Table of Drug Interactions [Link]
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
  1. 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]

Drug created on June 13, 2005 13:24 / Updated on February 24, 2021 23:06