11-Deoxycortisol
(Redirected from
Cortodoxone
)
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| Names | |
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| IUPAC name
17α,21-Dihydroxypregn-4-ene-3,20-dione
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| Systematic IUPAC name
(1R,3aS,3bR,9aR,9bS,11aS)-1-Hydroxy-1-(2-hydroxy-1-oxoethyl)-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one | |
| Other names
11-Deoxycortisol; 11-Deoxycortisone; Cortoxelone; 17α,21-Dihydroxyprogesterone; 11-Desoxycortisol; 11-Deoxyhydrocortisone; 11-Desoxyhydrocortisone; 17α-Hydroxy-11-deoxycorticosterone; Reichstein's Substance S; Compound S; Cortodoxone; Cortexolone,
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| Identifiers | |
3D model (
JSmol ) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
ECHA InfoCard
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100.005.279 |
IUPHAR/BPS |
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| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C21H30O4 | |
| Molar mass | 346.467 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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11-Deoxycortisol, also known as cortodoxone (
endogenous glucocorticoid steroid hormone, and a metabolic intermediate toward cortisol. It was first described by Tadeusz Reichstein in 1938 as Substance S,[6] thus has also been referred to as Reichstein's Substance S[5] or Compound S.[7][8]
Function
Steroidogenesis, showing 11-deoxycortisol in the pathway from cholesterol to cortisol.[9]
Although 11-deoxycortisol itself has weaker glucocorticoid activity compared to cortisol, it can still bind to glucocorticoid receptors and exert certain metabolic and anti-inflammatory effects, and participates in feedback mechanisms involved in regulating the secretion of adrenocorticotropic hormone (ACTH) from the pituitary gland by inhibiting its production.
11-Deoxycortisol acts as a glucocorticoid, though is less potent than cortisol.[10]
11-Deoxycortisol is synthesized from
11β-hydroxylase
.
11-Deoxycortisol in mammals has limited
11β-hydroxylase enzyme may not have been present early in vertebrate evolution.[14]
Clinical significance
11-Deoxycortisol in mammals has limited glucocorticoid activity, but it is the direct precursor of the major mammalian glucocorticoid, cortisol.[15] As a result, the level of 11-deoxycortisol is measured to diagnose impaired cortisol synthesis, to find out the enzyme deficiency that causes impairment along the pathway to cortisol, and to differentiate adrenal disorders.[16]
In
11-deoxycorticosterone
levels increase, and
excess of 11β-hydroxylase deficiency, 11-deoxycortisol can also be converted to androstenedione in a pathway that could explain the increase in androstenedione levels this condition.[23]
In
21-hydroxylase deficiency, 11-deoxycortisol levels are low.[24]
History
In 1934,
adrenal glands in order to isolate physiologically active compounds.[25] He was publishing results of his findings along the way. By 1944, he already isolated and elucidated the chemical structure of 29 pure substances.[26] He was assigning names that consisted of the word "Substance" and a letter from the Latin alphabet to the newly found substances. In 1938, he published an article about "Substance R" and "Substance S" describing their chemical structures and properties.[6] The Substance S since about 1955 became known as 11-Deoxycortisol.[27]
In the 1930s and 1940s clinicians were discovering many uses for the newly discovered hormones, however, only minute quantities could be extracted from animal organs. Chemists were looking for the production of these hormones on a larger industrial scale.
In 1949, American research chemist Percy Lavon Julian, in looking for ways to produce cortisone, announced the synthesis of the Compound S, from the cheap and readily available pregnenolone (synthesized from the soybean oil sterol stigmasterol).[28][29]
On 5 April 1952,
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).See also
Wikimedia Commons has media related to Cortodoxone.
- 11-Deoxycorticosterone
- Cortexolone 17α-propionate
References
- S2CID 221345484.
- PMID 18173113.
- PMID 17066954.
- S2CID 384672.
- ^ ISBN 978-0-412-27060-4.
- ^ from the original on 10 October 2020. Retrieved 5 October 2020.
- S2CID 29970823.
- PMID 12466339.
- ISSN 2002-4436.
- PMID 31090904.
- ^ "Congenital Adrenal Hyperplasia Caused by 11Beta-Hydroxylase Deficiency". Merck Manuals Professional Edition. Archived from the original on 25 September 2020. Retrieved 3 October 2020.
- S2CID 232296805.
- PMID 32699304.
- PMID 20643930.
- S2CID 45997341.
- ^ "Serum steroid levels can help differentiate adrenal disorders". Archived from the original on 7 November 2020. Retrieved 3 October 2020.
- PMID 22145132.
- PMID 32368967.
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- ISBN 978-1-4899-1692-1.
- ^ "Chemistry of the Adrenal Cortex Hormones". Archived from the original on 10 October 2020. Retrieved 5 October 2020.
- PMID 22435119.
- from the original on 17 November 2020. Retrieved 9 November 2020.
- ^ "Science gets synthetic key to rare drug; discovery is made in Chicago". Chicago Tribune. 30 September 1949. p. 1.
Dr. Julian's new method for synthesizing the anti-arthritis compound, cortisone, is less costly than present methods, because it eliminates the need for utilizing osmium tetroxide, a rare and expensive chemical, the Glidden company declared....But whether has Dr. Julian has also synthesized cortisone from soybeans neither he nor the Glidden company would reveal.
- .
Quote: A new synthesis of cortisone, eliminating the need for expensive osmium tetroxide, and the synthesis of three other compounds related to cortisone, which may possible be useful in the treatment of arthritis, have been announced by Percy L. Julian, director of research of the soya products division of the Glidden Co., Chicago. No statement was made as to further details of the new synthesis, but it was revealed that soybean products were not involved...all three [other compounds] were made from soybean sterols.
- .