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Showing metabocard for Amlodipine (HMDB0005018)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
enzymes (4) Show 4 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-10-17 08:50:19 UTC
Update Date2020-04-22 23:33:42 UTC
HMDB IDHMDB0005018
Secondary Accession Numbers
  • HMDB05018
Metabolite Identification
Common NameAmlodipine
DescriptionAmlodipine is a long-acting calcium channel blocker used as an anti-hypertensive and in the treatment of angina. As other calcium channel blockers, amlodipine acts by relaxing the smooth muscle in the arterial wall, decreasing peripheral resistance and hence improving blood pressure; in angina it improves blood flow to the myocardium. It was developed under the direction of Dr. Simon Campbell; A long acting dihydropyridine calcium channel blocker. It is effective in the treatment of angina pectoris and hypertension; in angina it improves blood flow to the myocardium. Amlodipine (as besylate, mesylate or maleate) is a long-acting calcium channel blocker used as an anti hypertensive and in the treatment of angina. Amlodipine is marketed as Norvasc in North America and as Istin in the United Kingdom as well as under various other names. As other calcium channel blockers, amlodipine acts by relaxing the smooth muscle in the arterial wall, decreasing peripheral resistance and hence improving blood pressure; Amlodipine (as besylate, mesylate or maleate) is a long-acting calcium channel blocker used as an anti-hypertensive and in the treatment of angina. Amlodipine is marketed as Norvasc in North America and as Istin in the United Kingdom as well as under various other names. As other calcium channel blockers, amlodipine acts by relaxing the smooth muscle in the arterial wall, decreasing peripheral resistance and hence improving blood pressure; in angina it improves blood flow to the myocardium. It was developed under the direction of Dr. Simon Campbell.
Structure
Data?1582752340
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Ethyl-5-methyl (+-)-2-(2-aminoethoxymethyl)-4-(O-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylateChEBI
Amlodipine free baseChEBI
AmlodipinoChEBI
AmlodipinumChEBI
NorvascKegg
3-Ethyl-5-methyl (+-)-2-(2-aminoethoxymethyl)-4-(O-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acidGenerator
Amlodipine besilateHMDB
Amlodipine besylateHMDB
AMVAZHMDB
IstinHMDB
PelmecHMDB
Racemic amlodipineHMDB
Amlodipine, (+-)-isomerHMDB
Amlodipine, (+-)-isomer, maleate (1:1)HMDB
Amlodipine, (S)-isomer, maleate (1:1)HMDB
AmlorHMDB
Amlodipine, (R)-isomerHMDB
Pfizer brand OF amlodipine besilateHMDB
Amlodipine maleateHMDB
Amlodipine maleate (1:1)HMDB
AmlodisHMDB
AstudalHMDB
Mack brand OF amlodipine besilateHMDB
Almirall brand OF amlodipine besilateHMDB
Eczacibasi brand OF amlodipine besilateHMDB
Chemical FormulaC20H25ClN2O5
Average Molecular Weight408.876
Monoisotopic Molecular Weight408.145199627
IUPAC Name3-ethyl 5-methyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
Traditional Name(+-)-amlodipine
CAS Registry Number88150-42-9
SMILES
CCOC(=O)C1=C(COCCN)NC(C)=C(C1C1=CC=CC=C1Cl)C(=O)OC
InChI Identifier
InChI=1S/C20H25ClN2O5/c1-4-28-20(25)18-15(11-27-10-9-22)23-12(2)16(19(24)26-3)17(18)13-7-5-6-8-14(13)21/h5-8,17,23H,4,9-11,22H2,1-3H3
InChI KeyHTIQEAQVCYTUBX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dihydropyridinecarboxylic acids and derivatives. Dihydropyridinecarboxylic acids and derivatives are compounds containing a dihydropyridine moiety bearing a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassHydropyridines
Direct ParentDihydropyridinecarboxylic acids and derivatives
Alternative Parents
Substituents
  • Dihydropyridinecarboxylic acid derivative
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Vinylogous amide
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Methyl ester
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Dialkyl ether
  • Secondary aliphatic amine
  • Azacycle
  • Enamine
  • Ether
  • Secondary amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Amine
  • Primary amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Primary aliphatic amine
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.00AUSTIN,RP ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0074 g/LALOGPS
logP2.22ALOGPS
logP1.64ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)19.12ChemAxon
pKa (Strongest Basic)9.45ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area99.88 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity108.64 m³·mol⁻¹ChemAxon
Polarizability42.31 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-003r-9008000000-1fbca2d37d687cf7db0bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4u-0192000000-988fbef9dd83defbfbe0Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-002o-1392000000-3e9bc5dcf61b0f4cae6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4j-2029500000-6f84285a27a09d3975adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gw3-3189000000-2934b69ddcfba1ecb708Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ffx-3293000000-4459172f2e0c2c8495efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-3007900000-5363cd8b8ca60ece4eeaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-4029200000-2a9e3badde424295bb13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dl-9085000000-7db6de7520133d8f4045Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue Locations
  • Epidermis
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00381
Phenol Explorer Compound IDNot Available
FooDB IDFDB023590
KNApSAcK IDNot Available
Chemspider ID2077
KEGG Compound IDC06825
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmlodipine
METLIN ID955
PubChem Compound2162
PDB IDNot Available
ChEBI ID2668
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceKim, Seok-Chan; Choi, Kwan-Min; Cheong, Chan-Seong. Synthesis of amlodipine using aza Diels-Alder reaction. Bulletin of the Korean Chemical Society (2002), 23(1), 143-144.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Iabichella ML, Dell'Omo G, Melillo E, Pedrinelli R: Calcium channel blockers blunt postural cutaneous vasoconstriction in hypertensive patients. Hypertension. 1997 Mar;29(3):751-6. [PubMed:9052891 ]
  2. Pedrinelli R, Dell'Omo G, Nuti M, Menegato A, Balbarini A, Mariani M: Heterogeneous effect of calcium antagonists on leg oedema: a comparison of amlodipine versus lercanidipine in hypertensive patients. J Hypertens. 2003 Oct;21(10):1969-73. [PubMed:14508205 ]

Enzymes

Enzyme Details
1. Cytochrome P450 3A4
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
Enzyme Details
2. Carbonic anhydrase 1
General function:
Involved in carbonate dehydratase activity
Specific function:
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:
CA1
Uniprot ID:
P00915
Molecular weight:
28870.0
Enzyme Details
3. Voltage-dependent N-type calcium channel subunit alpha-1B
General function:
Involved in ion channel activity
Specific function:
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1B gives rise to N-type calcium currents. N-type calcium channels belong to the 'high-voltage activated' (HVA) group and are blocked by omega-conotoxin-GVIA (omega-CTx-GVIA) and by omega-agatoxin- IIIA (omega-Aga-IIIA). They are however insensitive to dihydropyridines (DHP), and omega-agatoxin-IVA (omega-Aga-IVA). Calcium channels containing alpha-1B subunit may play a role in directed migration of immature neurons
Gene Name:
CACNA1B
Uniprot ID:
Q00975
Molecular weight:
262493.8
Enzyme Details
4. Voltage-dependent calcium channel gamma-1 subunit
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