21-Hydroxypregnenolone
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Preferred IUPAC name
2-Hydroxy-1-[(1S,3aS,3bS,7S,9aR,9bS,11aS)-7-hydroxy-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-1-yl]ethan-1-one | |
Other names
Prebediolone; 3β,21-Dihydroxypregn-5-en-20-one; Pregn-5-en-3β,21-diol-20-one
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3D model (JSmol)
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Properties | |
C21H32O3 | |
Molar mass | 332.484 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
21-Hydroxypregnenolone, also known as prebediolone, as well as 3β,21-dihydroxypregn-5-en-20-one, is a naturally occurring and endogenous pregnane steroid, and an intermediate in the biosynthesis of 11-deoxycorticosterone (21-hydroxyprogesterone), corticosterone (11β,21-dihydroxyprogesterone), and other corticosteroids.[1] It is formed from pregnenolone in the adrenal glands.[1]
The 21-acetate ester of 21-hydroxypregnenolone, prebediolone acetate, is described as a glucocorticoid and has been used in the treatment of rheumatoid arthritis.[2][3][4]
See also[]
References[]
- ^ a b Wishart, David S.; Djombou Feunang, Yannick; Marcu, Ana; Guo, An Chi; Liang, Kevin; Vázquez Fresno, Rosa; Sajed, Tanvir; Johnson, Daniel; Li, Carin; Karu, Naama; Sayeeda, Zinat; Lo, Elvis; Assempour, Nazanin; Berjanskii, Mark; Singhal, Sandeep; Arndt, David; Liang, Yonjie; Badran, Hasan; Grant, Jason; Serra Cayuela, Arnau; Liu, Yifeng; Mandal, Rupa; Neveu, Vanessa; Pon, Allison; Knox, Craig; Wilson, Michael; Manach, Claudine; Scalbert, Augustin. "Showing metabocard for 21-Hydroxypregnenolone (HMDB04026)". Human Metabolome Database, HMDB. 4.0.
- ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 665–. ISBN 978-1-4757-2085-3.
- ^ BRUGSCH HG, MANNING RA (1951). "A comparative study of pregnenolone, 21-acetoxypregnenolone and ACTH". N. Engl. J. Med. 244 (17): 628–32. doi:10.1056/NEJM195104262441703. PMID 14815736.
- ^ LEFKOVITS AM (1953). "Artisone therapy in rheumatoid arthritis". Rheumatism. 9 (4): 70–6. PMID 13101380.
Categories:
- Diols
- Human metabolites
- Ketones
- Pregnanes
- Steroid stubs