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Record Information |
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Version | 4.0 |
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Status | Detected but not Quantified |
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Creation Date | 2006-10-17 08:50:19 UTC |
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Update Date | 2020-11-09 23:29:03 UTC |
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HMDB ID | HMDB0005018 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Amlodipine |
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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. |
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Structure | |
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Synonyms | Value | Source |
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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 |
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Chemical Formula | C20H25ClN2O5 |
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Average Molecular Weight | 408.876 |
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Monoisotopic Molecular Weight | 408.145199627 |
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IUPAC Name | 3-ethyl 5-methyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate |
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Traditional Name | (+-)-amlodipine |
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CAS Registry Number | 88150-42-9 |
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SMILES | CCOC(=O)C1=C(COCCN)NC(C)=C(C1C1=CC=CC=C1Cl)C(=O)OC |
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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 |
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InChI Key | HTIQEAQVCYTUBX-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pyridines and derivatives |
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Sub Class | Hydropyridines |
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Direct Parent | Dihydropyridinecarboxylic acids and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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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) |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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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 |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB00381 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB023590 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 2077 |
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KEGG Compound ID | C06825 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Amlodipine |
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METLIN ID | 955 |
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PubChem Compound | 2162 |
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PDB ID | Not Available |
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ChEBI ID | 2668 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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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. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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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 ]
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