Cortodoxone

From DrugPedia: A Wikipedia for Drug discovery

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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 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: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).

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

[edit] External Links

• [1]Pubchem
• [2]]KEGG Compound
• [3]]KEGG Drug
• [4]Human Metabolome DataBase