Cortodoxone
From DrugPedia: A Wikipedia for Drug discovery
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| - | + | [http://crdd.osdd.net/raghava/hmrbase/test_extract.php?db=arun&table=nphormonet&id=1031&show=SHOW-3D Show 3-D Structure] | |
| - | [http:// | + | {{Drugbox |
| + | | IUPAC_name = (8R,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one | ||
| + | | CAS_number = 152-58-9 | ||
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| + | | PubChem = 440707 | ||
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| + | | chemical_formula =C<sub>2</sub><sub>1</sub>H<sub>3</sub><sub>0</sub>O<sub>4</sub> | ||
| + | | molecular_weight = 346.46 | ||
| + | | smiles = CC12CCC(=O)C=C1CCC3C2CCC4(C3CCC4(C(=O)CO)O)C | ||
| + | | synonyms = Cortexolone | ||
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| + | 17,21-Dihydroxypregn-4-ene-3,20-dione. A 17-hydroxycorticosteroid with glucocorticoid and anti-inflammatory activities.'''Cortexolone''' or '''cortodoxone''' or '''11-[[deoxycortisol]]''' or '''11-desoxycortisol''' or '''11-deoxyhydrocortisone''' or '''11-desoxyhydrocortisone''' or '''Reichstein's Substance S''' or, most commonly, '''Compound S''', is a [[steroid]] that can be oxygenated to [[cortisol]] (hydrocortisone). It was first synthesized by [[Tadeusz Reichstein]]. | ||
| - | + | On April 5, 1952, [[biochemist]] Durey Peterson and [[microbiologist]] Herbert Murray at [[Upjohn]] published the first report of a breakthrough [[industrial fermentation|fermentation]] process for the microbial 11α-oxygenation of steroids (e.g. [[progesterone]]) in a single step by common [[mold]]s of the order [[Mucorales]].<ref>{{cite journal |author=Peterson DH, Murray, HC |year=1952 |title=Microbiological oxygenation of steroids at carbon 11 |journal=[[Journal of the American Chemical Society|J Am Chem Soc]] |volume=74 |issue=7 |pages=1871–2 |doi=10.1021/ja01127a531}}</ref> | |
| + | 11α-oxygenation of Compound S produces 11α-hydrocortisone, which can be chemically oxidized to [[cortisone]], or converted by further chemical steps to 11β-hydrocortisone (cortisol). | ||
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| + | Subsequent fermentation processes for the microbial 11β-oxygenation of steroids in a single step were developed that could convert Compound S directly to 11β-hydrocortisone (cortisol). | ||
==General Properties== | ==General Properties== | ||
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C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C | C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C | ||
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Current revision
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| Cortodoxone
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| Systematic (IUPAC) name | |
| (8R,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one | |
| Identifiers | |
| CAS number | |
| ATC code | ? |
| PubChem | |
| Chemical data | |
| Formula | C21H30O4 |
| Mol. mass | 346.46 |
| SMILES | & |
| Synonyms | Cortexolone |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | ? |
17,21-Dihydroxypregn-4-ene-3,20-dione. A 17-hydroxycorticosteroid with glucocorticoid and anti-inflammatory activities.Cortexolone or cortodoxone or 11-deoxycortisol or 11-desoxycortisol or 11-deoxyhydrocortisone or 11-desoxyhydrocortisone or Reichstein's Substance S or, most commonly, Compound S, is a steroid that can be oxygenated to cortisol (hydrocortisone). It was first synthesized by Tadeusz Reichstein.
On April 5, 1952, biochemist Durey Peterson and microbiologist Herbert Murray at Upjohn published the first report of a breakthrough fermentation process for the microbial 11α-oxygenation of steroids (e.g. progesterone) in a single step by common molds of the order Mucorales.<ref>Peterson DH, Murray, HC (1952). "Microbiological oxygenation of steroids at carbon 11". J Am Chem Soc 74 (7): 1871–2. doi:.</ref> 11α-oxygenation of Compound S produces 11α-hydrocortisone, which can be chemically oxidized to cortisone, or converted by further chemical steps to 11β-hydrocortisone (cortisol).
Subsequent fermentation processes for the microbial 11β-oxygenation of steroids in a single step were developed that could convert Compound S directly to 11β-hydrocortisone (cortisol).
[edit] General Properties
*Molecular Weight
346.46
*Molecular Formula
C21H30O4
*IUPAC NAME
(8R,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
*Canonical Smiles
CC12CCC(=O)C=C1CCC3C2CCC4(C3CCC4(C(=O)CO)O)C
*Isomeric Smiles
C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C
