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Record Information |
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Version | 4.0 |
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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 | 2020-02-26 21:41:51 UTC |
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HMDB ID | HMDB0015568 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Vorinostat |
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Description | Vorinostat, also known as SAHA or zolinza, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Vorinostat is a drug which is used for the treatment of cutaneous manifestations in patients with cutaneous t-cell lymphoma who have progressive, persistent or recurrent disease on or following two systemic therapies. A recent study suggested that vorinostat also possesses some activity against recurrent glioblastoma multiforme, resulting in a median overall survival of 5.7 months (compared to 4 - 4.4 months in earlier studies). Vorinostat is an extremely weak basic (essentially neutral) compound (based on its pKa). In some cancer cells, there is an overexpression of HDACs, or an aberrant recruitment of HDACs to oncogenic transcription factors causing hypoacetylation of core nucleosomal histones. Vorinostat (rINN) or Vorinostat (SAHA), is a drug currently under investigation for the treatment of cutaneous T cell lymphoma (CTCL), a type of skin cancer, to be used when the disease persists, gets worse, or comes back during or after treatment with other medicines. Further brain tumor trials are planned using combinations of vorinostat with other drugs. The mechanism of the antineoplastic effect of vorinostat has not been fully characterized. I) and HDAC6 (Class. It is the first in a new class of agents known as histone deacetylase inhibitors. Both metabolites are pharmacologically inactive. |
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Structure | |
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Synonyms | Value | Source |
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Octanedioic acid hydroxyamide phenylamide | ChEBI | SAHA | ChEBI | SHH | ChEBI | Suberanilohydroxamic acid | ChEBI | Suberoylanilide hydroxamic acid | ChEBI | Vorinostatum | ChEBI | Zolinza | ChEBI | Octanedioate hydroxyamide phenylamide | Generator | Suberanilohydroxamate | Generator | Suberoylanilide hydroxamate | Generator | MK0683 | HMDB | N-Hydroxy-n'-phenyloctanediamide | HMDB | N-Hyrdroxy-n'-phenyloctanediamide | HMDB | 18F-SAHA | HMDB | 18F-Suberoylanilide hydroxamic acid | HMDB | Merck brand OF vorinostat | HMDB | N1-Hydroxy-N8-phenyloctanediamide | HMDB | NHNPODA | HMDB | Suberoyl anilide hydroxamic acid | MeSH | 18F Suberoylanilide hydroxamic acid | MeSH | N Hydroxy n' phenyloctanediamide | MeSH | N1 Hydroxy N8 phenyloctanediamide | MeSH |
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Chemical Formula | C14H20N2O3 |
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Average Molecular Weight | 264.3202 |
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Monoisotopic Molecular Weight | 264.147392516 |
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IUPAC Name | N-hydroxy-N'-phenyloctanediamide |
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Traditional Name | SAHA |
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CAS Registry Number | 149647-78-9 |
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SMILES | ONC(=O)CCCCCCC(=O)NC1=CC=CC=C1 |
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InChI Identifier | InChI=1S/C14H20N2O3/c17-13(15-12-8-4-3-5-9-12)10-6-1-2-7-11-14(18)16-19/h3-5,8-9,19H,1-2,6-7,10-11H2,(H,15,17)(H,16,18) |
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InChI Key | WAEXFXRVDQXREF-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Not Available |
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Direct Parent | Benzene and substituted derivatives |
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Alternative Parents | |
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Substituents | - Monocyclic benzene moiety
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Carboximidic acid derivative
- Carboximidic acid
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic 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 | Biological 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 | 0.072 g/L | Not Available | LogP | Not Available | Not Available |
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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 | splash10-006x-4920000000-0b60d0a81534425ab7be | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-Hybrid FT , Positive | splash10-0udi-0859000000-0a83404097a3e01eb158 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-001l-9750000000-d26ffebbce9b1bc73b92 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00kf-7190000000-877b56b4601e9fa6d5b1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9220000000-99ea61440739c3064b34 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9100000000-6506e221f51e0d54cbd7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-2190000000-9403e0edb1371ac82130 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-06ry-9360000000-2ac5220873ae653bb80d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9100000000-81d3844e3cacdfb678fa | Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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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 DB02546 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB02546 | | 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 | DB02546 |
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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 | 5120 |
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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 | Vorinostat |
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METLIN ID | Not Available |
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PubChem Compound | 5311 |
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PDB ID | SHH |
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ChEBI ID | 45716 |
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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 | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Munshi A, Tanaka T, Hobbs ML, Tucker SL, Richon VM, Meyn RE: Vorinostat, a histone deacetylase inhibitor, enhances the response of human tumor cells to ionizing radiation through prolongation of gamma-H2AX foci. Mol Cancer Ther. 2006 Aug;5(8):1967-74. [PubMed:16928817 ]
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