Cortodoxone

Cortodoxone

Names
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
Other names 11-Deoxycortisol; Cortoxelone; 17,21-Dihydroxypregn-4-ene-3,20-dione; 17,21-Dihydroxyprogesterone; 11-Desoxycortisol; 11-Deoxyhydrocortisone; 11-Desoxyhydrocortisone; Reichstein's Substance S; Compound S
Identifiers
CAS Number	152-58-9
ChEBI	CHEBI:28324
ChEMBL	ChEMBL253144
ChemSpider	389582
IUPHAR/BPS	5100
Jmol interactive 3D	Image
KEGG	D03595
PubChem	440707
UNII	WDT5SLP0HQ
InChI InChI=1S/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16+,17+,19+,20+,21+/m1/s1 Key: WHBHBVVOGNECLV-OBQKJFGGSA-N InChI=1/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16+,17+,19+,20+,21+/m1/s1 Key: WHBHBVVOGNECLV-OBQKJFGGBG
SMILES O=C4\C=C2/[C@]([C@H]1CC[C@@]3([C@@](O)(C(=O)CO)CC[C@H]3[C@@H]1CC2)C)(C)CC4
Properties
Chemical formula	C21H30O4
Molar mass	346.47 g·mol^−1
Melting point	215 °C (419 °F; 488 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

11-Deoxycortisol, also known as cortodoxone (INN, USAN, BAN), as well as 17-hydroxy-11-deoxycorticosterone, 17α,21-dihydroxyprogesterone, and cortexolone,^[1] is a glucocorticoid steroid hormone that can be oxygenated to cortisol (hydrocortisone). It was first synthesized by Tadeusz Reichstein, and has also been referred to as Reichstein's Substance.^[1]

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.^[2]

11α-oxygenation of cortodoxone produces 11α-hydrocortisone, which can be chemically oxidized to cortisone, or converted by further chemical steps to cortisol.

Subsequent fermentation processes for the microbial 11β-oxygenation of steroids in a single step were developed that could convert cortodoxone directly to cortisol.

Cortodoxone functions as a glucocorticoid, though is less potent than cortisol. It can be synthesized from 17-hydroxyprogesterone. In 11β-hydroxylase deficiency, cortodoxone levels increase dramatically, causing hypertension (as opposed to 21α-hydroxylase deficiency, in which patients have low blood pressure from a lack of mineralocorticoids).

Cortodoxone can also be converted to androstenedione.^[3] This could explain, at least in part, the marked increase in androstenedione levels in 11β-hydroxylase deficiency.^[3]

See also

• 11-Deoxycorticosterone

References

1. R.A. Hill; H.L.J. Makin; D.N. Kirk; G.M. Murphy (23 May 1991). Dictionary of Steroids. CRC Press. pp. 338–. ISBN 978-0-412-27060-4.
2. Peterson DH, Murray, HC (1952). "Microbiological oxygenation of steroids at carbon 11". J Am Chem Soc 74 (7): 1871–2. doi:10.1021/ja01127a531.
3. Auzéby A, Bogdan A, Touitou Y (January 1991). "Evidence for a new biologic pathway of androstenedione synthesis from 11-deoxycortisol". Steroids 56 (1): 33–6. doi:10.1016/0039-128X(91)90112-9. PMID 2028480.