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 15:16:49 UTC |
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Update Date | 2020-02-26 21:39:56 UTC |
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HMDB ID | HMDB0014586 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Betamethasone |
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Description | A glucocorticoid given orally, parenterally, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. Its lack of mineralocorticoid properties makes betamethasone particularly suitable for treating cerebral edema and congenital adrenal hyperplasia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p724) |
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Structure | |
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Synonyms | Value | Source |
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16beta-Methyl-1,4-pregnadiene-9alpha-fluoro-11beta,17alpha,21-triol-3,20-dione | ChEBI | 9-Fluoro-16beta-methylprednisolone | ChEBI | 9alpha-Fluoro-16beta-methylprednisolone | ChEBI | beta-Methasone alcohol | ChEBI | Betadexamethasone | ChEBI | Betametasona | ChEBI | Betamethasonum | ChEBI | Rinderon | ChEBI | Celestone | Kegg | 16b-Methyl-1,4-pregnadiene-9a-fluoro-11b,17a,21-triol-3,20-dione | Generator | 16Β-methyl-1,4-pregnadiene-9α-fluoro-11β,17α,21-triol-3,20-dione | Generator | 9-Fluoro-16b-methylprednisolone | Generator | 9-Fluoro-16β-methylprednisolone | Generator | 9a-Fluoro-16b-methylprednisolone | Generator | 9Α-fluoro-16β-methylprednisolone | Generator | b-Methasone alcohol | Generator | Β-methasone alcohol | Generator | Celestona | HMDB | Celeston | HMDB | Cellestoderm | HMDB | Flubenisolone | HMDB |
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Chemical Formula | C22H29FO5 |
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Average Molecular Weight | 392.4611 |
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Monoisotopic Molecular Weight | 392.199902243 |
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IUPAC Name | (1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one |
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Traditional Name | betamethasone |
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CAS Registry Number | 378-44-9 |
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SMILES | [H][C@@]12C[C@H](C)[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C |
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InChI Identifier | InChI=1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1 |
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InChI Key | UREBDLICKHMUKA-DVTGEIKXSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Hydroxysteroids |
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Direct Parent | 21-hydroxysteroids |
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Alternative Parents | |
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Substituents | - Progestogin-skeleton
- 21-hydroxysteroid
- Pregnane-skeleton
- 20-oxosteroid
- 3-oxo-delta-1,4-steroid
- 3-oxosteroid
- 17-hydroxysteroid
- 11-hydroxysteroid
- 11-beta-hydroxysteroid
- 9-halo-steroid
- Halo-steroid
- Oxosteroid
- Delta-1,4-steroid
- Alpha-hydroxy ketone
- Cyclic alcohol
- Tertiary alcohol
- Ketone
- Fluorohydrin
- Halohydrin
- Secondary alcohol
- Cyclic ketone
- Organooxygen compound
- Alcohol
- Primary alcohol
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organic oxygen compound
- Alkyl halide
- Alkyl fluoride
- Organohalogen compound
- Organofluoride
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: 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 | 231 - 234 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.05 g/L | Not Available | LogP | 1.1 | Not Available |
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Predicted Properties | |
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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 | splash10-02ai-2923000000-e31987dc12e5a702a42e | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-0006-2414490000-490d5cc0ad1eca76d44e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-00dj-3960000000-a7dc9d06200fd3114dc2 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-0ab9-0239000000-6da1b4bf9567b7486622 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-05i4-2930000000-bc11f96b96bcca3051a8 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-00dj-3960000000-a7dc9d06200fd3114dc2 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-002f-0009000000-6926653590903a3ace6c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06vl-0019000000-301b3962f9291bee1ee9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0g4r-1294000000-8f3712f110452655373e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0009000000-a4ddb0d0eed36d96b76f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-05uu-1009000000-badd4f30582cf375bbdf | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-8019000000-2bad3a1904cfc0e5431f | Spectrum |
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General References | - Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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