Human Metabolome Database: Showing metabocard for Amlodipine (HMDB0005018)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

enzymes (4) Show 4 proteins

Record Information

Version

4.0

Status

Detected but not Quantified

Creation Date

2006-10-17 08:50:19 UTC

Update Date

2020-11-09 23:29:03 UTC

HMDB ID

HMDB0005018

Secondary Accession Numbers

HMDB05018

Metabolite Identification

Common Name

Amlodipine

Description

Amlodipine 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Ethyl-5-methyl (+-)-2-(2-aminoethoxymethyl)-4-(O-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate	ChEBI
Amlodipine free base	ChEBI
Amlodipino	ChEBI
Amlodipinum	ChEBI
Norvasc	Kegg
3-Ethyl-5-methyl (+-)-2-(2-aminoethoxymethyl)-4-(O-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid	Generator
Amlodipine besilate	HMDB
Amlodipine besylate	HMDB
AMVAZ	HMDB
Istin	HMDB
Pelmec	HMDB
Racemic amlodipine	HMDB
Amlodipine, (+-)-isomer	HMDB
Amlodipine, (+-)-isomer, maleate (1:1)	HMDB
Amlodipine, (S)-isomer, maleate (1:1)	HMDB
Amlor	HMDB
Amlodipine, (R)-isomer	HMDB
Pfizer brand OF amlodipine besilate	HMDB
Amlodipine maleate	HMDB
Amlodipine maleate (1:1)	HMDB
Amlodis	HMDB
Astudal	HMDB
Mack brand OF amlodipine besilate	HMDB
Almirall brand OF amlodipine besilate	HMDB
Eczacibasi brand OF amlodipine besilate	HMDB

Chemical Formula

C₂₀H₂₅ClN₂O₅

Average Molecular Weight

408.876

Monoisotopic Molecular Weight

408.145199627

IUPAC Name

3-ethyl 5-methyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

Traditional Name

(+-)-amlodipine

CAS Registry Number

88150-42-9

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 Key

HTIQEAQVCYTUBX-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Hydropyridines

Direct Parent

Dihydropyridinecarboxylic 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

ethyl ester (CHEBI:2668 )
primary amino compound (CHEBI:2668 )
methyl ester (CHEBI:2668 )
monochlorobenzenes (CHEBI:2668 )
dihydropyridine (CHEBI:2668 )

Ontology

Disposition

Biological location:

Organ and components:

Skin

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Amlodipine Action Pathway

Role

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	3.00	AUSTIN,RP ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	0.0074 g/L	ALOGPS
logP	2.22	ALOGPS
logP	1.64	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	19.12	ChemAxon
pKa (Strongest Basic)	9.45	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.88 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	108.64 m³·mol⁻¹	ChemAxon
Polarizability	42.31 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-003r-9008000000-1fbca2d37d687cf7db0b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4u-0192000000-988fbef9dd83defbfbe0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-002o-1392000000-3e9bc5dcf61b0f4cae6a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4j-2029500000-6f84285a27a09d3975ad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gw3-3189000000-2934b69ddcfba1ecb708	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ffx-3293000000-4459172f2e0c2c8495ef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-3007900000-5363cd8b8ca60ece4eea	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08fr-4029200000-2a9e3badde424295bb13	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03dl-9085000000-7db6de7520133d8f4045	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Epidermis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Amlodipine Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00381

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023590

KNApSAcK ID

Not Available

Chemspider ID

2077

KEGG Compound ID

C06825

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Amlodipine

METLIN ID

955

PubChem Compound

2162

PDB ID

Not Available

ChEBI ID

2668

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

References

Synthesis Reference

Kim, 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

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 ]
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

Showing metabocard for Amlodipine (HMDB0005018)

Structure for HMDB0005018 (Amlodipine)

Enzymes