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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:42 UTC
HMDB IDHMDB0014669
Secondary Accession Numbers
  • HMDB14669
Metabolite Identification
Common NameLercanidipine
DescriptionLercanidipine is only found in individuals that have used or taken this drug. It is a calcium channel blocker of the dihydropyridine class. It is sold under various commercial names including Zanidip.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.
Structure
Data?1582753206
Synonyms
ValueSource
LercanilKegg
ZanidipHMDB
Biohorm brand OF lercanidipine hydrochlorideHMDB
LercadipHMDB
LerdipHMDB
Lercanidipine hydrochlorideHMDB
Methyl-1,1-dimethyl-2-(N-(3,3-diphenylpropyl)-N-methylamino)ethyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateHMDB
Chemical FormulaC36H41N3O6
Average Molecular Weight611.7272
Monoisotopic Molecular Weight611.299536059
IUPAC Name3-{1-[(3,3-diphenylpropyl)(methyl)amino]-2-methylpropan-2-yl} 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Traditional Namelercanidipine
CAS Registry Number100427-26-7
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
InChI Identifier
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
InChI KeyZDXUKAKRHYTAKV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassBenzodiazines
Direct ParentQuinazolines
Alternative Parents
Substituents
  • Quinazoline
  • Secondary aliphatic/aromatic amine
  • Toluene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Organosulfonic acid amide
  • Organic sulfonic acid or derivatives
  • Vinylogous amide
  • Aminosulfonyl compound
  • Tertiary carboxylic acid amide
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Amino acid or derivatives
  • Carboxamide group
  • Lactam
  • Carboxylic acid derivative
  • Secondary amine
  • Azacycle
  • Organic oxide
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00016 g/LNot Available
LogP6.4Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM249.830932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00016 g/LALOGPS
logP6.42ALOGPS
logP6.41ChemAxon
logS-6.6ALOGPS
pKa (Strongest Basic)9.36ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area113.69 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity177.85 m³·mol⁻¹ChemAxon
Polarizability65.78 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+240.55331661259
DarkChem[M-H]-230.55631661259
DeepCCS[M+H]+215.50330932474
DeepCCS[M-H]-213.56630932474
DeepCCS[M-2H]-246.80530932474
DeepCCS[M+Na]+221.24430932474
AllCCS[M+H]+247.732859911
AllCCS[M+H-H2O]+246.432859911
AllCCS[M+NH4]+248.932859911
AllCCS[M+Na]+249.232859911
AllCCS[M-H]-240.432859911
AllCCS[M+Na-2H]-242.632859911
AllCCS[M+HCOO]-245.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LercanidipineCOC(=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=C15680.5Standard polar33892256
LercanidipineCOC(=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=C13800.8Standard non polar33892256
LercanidipineCOC(=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=C14408.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lercanidipine,1TMS,isomer #1COC(=O)C1=C(C)N([Si](C)(C)C)C(C)=C(C(=O)OC(C)(C)CN(C)CCC(C2=CC=CC=C2)C2=CC=CC=C2)C1C1=CC=CC([N+](=O)[O-])=C14076.3Semi standard non polar33892256
Lercanidipine,1TMS,isomer #1COC(=O)C1=C(C)N([Si](C)(C)C)C(C)=C(C(=O)OC(C)(C)CN(C)CCC(C2=CC=CC=C2)C2=CC=CC=C2)C1C1=CC=CC([N+](=O)[O-])=C13087.9Standard non polar33892256
Lercanidipine,1TMS,isomer #1COC(=O)C1=C(C)N([Si](C)(C)C)C(C)=C(C(=O)OC(C)(C)CN(C)CCC(C2=CC=CC=C2)C2=CC=CC=C2)C1C1=CC=CC([N+](=O)[O-])=C15485.5Standard polar33892256
Lercanidipine,1TBDMS,isomer #1COC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OC(C)(C)CN(C)CCC(C2=CC=CC=C2)C2=CC=CC=C2)C1C1=CC=CC([N+](=O)[O-])=C14339.1Semi standard non polar33892256
Lercanidipine,1TBDMS,isomer #1COC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OC(C)(C)CN(C)CCC(C2=CC=CC=C2)C2=CC=CC=C2)C1C1=CC=CC([N+](=O)[O-])=C13362.0Standard non polar33892256
Lercanidipine,1TBDMS,isomer #1COC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OC(C)(C)CN(C)CCC(C2=CC=CC=C2)C2=CC=CC=C2)C1C1=CC=CC([N+](=O)[O-])=C15415.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lercanidipine GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-2191010000-9a91ea6a126944a1a4fb2017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lercanidipine 10V, Positive-QTOFsplash10-03di-0000009000-9d9d3cd84299b9a1b7182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lercanidipine 20V, Positive-QTOFsplash10-00di-0000019000-b7c19cb600de37512b6b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lercanidipine 40V, Positive-QTOFsplash10-0006-5094013000-61550404c96e9879a0522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lercanidipine 10V, Negative-QTOFsplash10-03di-0000009000-c5578a9d7353dd1253992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lercanidipine 20V, Negative-QTOFsplash10-03di-0000009000-93862893f933ac09e4de2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lercanidipine 40V, Negative-QTOFsplash10-006x-4092013000-f3bb297f4ce55e9fbe122016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lercanidipine 10V, Negative-QTOFsplash10-03di-0000119000-0687db4621b20c64d0bc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lercanidipine 20V, Negative-QTOFsplash10-0329-5897346000-a2e4782ffaec352368fc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lercanidipine 40V, Negative-QTOFsplash10-0002-9500010000-35785b7411b57538ca962021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lercanidipine 10V, Positive-QTOFsplash10-01q9-0937146000-3dbff6a5bec63ea954062021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lercanidipine 20V, Positive-QTOFsplash10-000t-0942011000-5b5db8b5b9de4bd20d102021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lercanidipine 40V, Positive-QTOFsplash10-014i-1920000000-573f0fda3422bc5dde782021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00528 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00528 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00528
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID59276
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLercanidipine
METLIN IDNot Available
PubChem Compound65866
PDB IDNot Available
ChEBI ID518487
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:16331117 ]
  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. [PubMed:16424795 ]
  3. 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. [PubMed:16679299 ]

Enzymes

General function:
Involved in monooxygenase 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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase 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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase 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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
General function:
Involved in monooxygenase 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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular weight:
57525.03
General function:
Involved in 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 as a multiple subunit complex
Gene Name:
CACNG1
Uniprot ID:
Q06432
Molecular weight:
25028.1
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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  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. [PubMed:19619074 ]