Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:52 UTC |
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Update Date | 2022-03-07 02:52:03 UTC |
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HMDB ID | HMDB0015636 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Agomelatine |
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Description | Agomelatine is structurally closely related to melatonin. Agomelatine is a potent agonist at melatonin receptors and an antagonist at serotonin-2C (5-HT2C) receptors, tested in an animal model of depression. Agomelatine was discovered and developed by the European pharmaceutical company Servier Laboratories Ltd. Servier continue to develop the drug and conduct phase III trials in the European Union. In 2005 Servier submitted Agomelatine to the European Medicines Agency (EMEA). On 27 July 2006 the Committee for Medical Products for Human Use (CHMP) of the EMEA recommended a refusal of the marketing authorisation of Valdoxan/Thymanax. The major concern was that efficacy had not been sufficiently shown. In 2006 Servier sold the rights to develop Agomelatine in the US to Novartis. The development for the US market was discontinued in October 2011. It is currently sold in Australia under the Valdoxan trade name. |
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Structure | COC1=CC2=C(C=CC=C2CCNC(C)=O)C=C1 InChI=1S/C15H17NO2/c1-11(17)16-9-8-13-5-3-4-12-6-7-14(18-2)10-15(12)13/h3-7,10H,8-9H2,1-2H3,(H,16,17) |
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Synonyms | Value | Source |
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Valdoxan | Kegg | S-20098 | HMDB | S20098 | HMDB | N-(2-(7-Methoxy-1-naphthyl)ethyl)acetamide | HMDB | Thymanax | HMDB | Ago 178 | HMDB | Ago-178 | HMDB |
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Chemical Formula | C15H17NO2 |
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Average Molecular Weight | 243.301 |
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Monoisotopic Molecular Weight | 243.125928793 |
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IUPAC Name | N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide |
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Traditional Name | agomelatine |
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CAS Registry Number | 138112-76-2 |
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SMILES | COC1=CC2=C(C=CC=C2CCNC(C)=O)C=C1 |
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InChI Identifier | InChI=1S/C15H17NO2/c1-11(17)16-9-8-13-5-3-4-12-6-7-14(18-2)10-15(12)13/h3-7,10H,8-9H2,1-2H3,(H,16,17) |
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InChI Key | YJYPHIXNFHFHND-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as n-acetyl-2-arylethylamines. N-acetyl-2-arylethylamines are compounds containing an acetamide group that is N-linked to an arylethylamine. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Carboxylic acid derivatives |
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Direct Parent | N-acetyl-2-arylethylamines |
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Alternative Parents | |
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Substituents | - N-acetyl-2-arylethylamine
- Naphthalene
- Anisole
- Alkyl aryl ether
- Benzenoid
- Secondary carboxylic acid amide
- Ether
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Organic nitrogen compound
- Carbonyl group
- Organic oxygen compound
- Hydrocarbon derivative
- Aromatic homopolycyclic compound
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Molecular Framework | Aromatic homopolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.0078 g/L | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross SectionsAdduct Type | Data Source | CCS Value (Å2) | Reference |
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[M+H]+ | CBM | 156.3 | 30932474 |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Agomelatine,1TMS,isomer #1 | COC1=CC=C2C=CC=C(CCN(C(C)=O)[Si](C)(C)C)C2=C1 | 2210.6 | Semi standard non polar | 33892256 | Agomelatine,1TMS,isomer #1 | COC1=CC=C2C=CC=C(CCN(C(C)=O)[Si](C)(C)C)C2=C1 | 2477.3 | Standard non polar | 33892256 | Agomelatine,1TMS,isomer #1 | COC1=CC=C2C=CC=C(CCN(C(C)=O)[Si](C)(C)C)C2=C1 | 2924.4 | Standard polar | 33892256 | Agomelatine,1TBDMS,isomer #1 | COC1=CC=C2C=CC=C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)C2=C1 | 2417.0 | Semi standard non polar | 33892256 | Agomelatine,1TBDMS,isomer #1 | COC1=CC=C2C=CC=C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)C2=C1 | 2670.0 | Standard non polar | 33892256 | Agomelatine,1TBDMS,isomer #1 | COC1=CC=C2C=CC=C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)C2=C1 | 2987.6 | Standard polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Agomelatine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0096-9870000000-12644f5c2eef8ac161ff | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Agomelatine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Agomelatine , positive-QTOF | splash10-000i-1910000000-17cebfbe6b9845617b5d | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Agomelatine 10V, Positive-QTOF | splash10-0udl-0290000000-2f32e7333df35f0d31e0 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Agomelatine 20V, Positive-QTOF | splash10-0udi-1890000000-f8670d6acc856a2aef34 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Agomelatine 40V, Positive-QTOF | splash10-103c-1900000000-44f5e0bbe33a080e259b | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Agomelatine 10V, Negative-QTOF | splash10-0006-1190000000-60e7560fd8d53fc46465 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Agomelatine 20V, Negative-QTOF | splash10-0zfu-3590000000-b1f2b056df1b588a9894 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Agomelatine 40V, Negative-QTOF | splash10-052f-9200000000-7d7eb2751fc51b48fda4 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Agomelatine 10V, Positive-QTOF | splash10-000l-0960000000-1b1a339607ebe3d5742f | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Agomelatine 20V, Positive-QTOF | splash10-000i-0900000000-84ce72fe2cc1bb7fae00 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Agomelatine 40V, Positive-QTOF | splash10-0a4i-1900000000-0471137531ade7533965 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Agomelatine 10V, Negative-QTOF | splash10-00di-0910000000-64f66595ca495c9bd240 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Agomelatine 20V, Negative-QTOF | splash10-0a4i-1900000000-5cf1d78282a06e7b1962 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Agomelatine 40V, Negative-QTOF | splash10-0a4l-5900000000-9ed4ac12ad0427b40af3 | 2021-10-11 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB06594 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB06594 | | 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 | DB06594 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 74141 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Agomelatine |
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METLIN ID | Not Available |
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PubChem Compound | 82148 |
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PDB ID | Not Available |
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ChEBI ID | 108209 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Millan MJ, Brocco M, Gobert A, Dekeyne A: Anxiolytic properties of agomelatine, an antidepressant with melatoninergic and serotonergic properties: role of 5-HT2C receptor blockade. Psychopharmacology (Berl). 2005 Feb;177(4):448-58. Epub 2004 Jul 31. [PubMed:15289999 ]
- Racagni G, Riva MA, Popoli M: The interaction between the internal clock and antidepressant efficacy. Int Clin Psychopharmacol. 2007 Oct;22 Suppl 2:S9-S14. [PubMed:17917564 ]
- Hardeland R, Poeggeler B, Srinivasan V, Trakht I, Pandi-Perumal SR, Cardinali DP: Melatonergic drugs in clinical practice. Arzneimittelforschung. 2008;58(1):1-10. doi: 10.1055/s-0031-1296459. [PubMed:18368944 ]
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