21-Hydroxypregnenolone
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Names | |
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IUPAC name 3β,21-Dihydroxypregn-5-en-20-one | |
Systematic 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; Pregn-5-en-3β,21-diol-20-one | |
Identifiers | |
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). |
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
[edit]References
[edit]- ^ a b Wishart, David S.; Guo, An Chi; Oler, Eponine; Wang, Fel; Anjum, Afia; Peters, Harrison; Dizon, Raynard; Sayeeda, Zinat; Tian, Siyang; Lee, Brian L.; Berjanskii, Mark; Mah, Robert; Yamamoto, Mai; Jovel Castillo, Juan; Torres Calzada, Claudia; Hiebert Giesbrecht, Mickel; Lui, Vicki W.; Varshavi, Dorna; Varshavi, Dorsa; Allen, Dana; Arndt, David; Khetarpal, Nitya; Sivakumaran, Aadhavya; Harford, Karxena; Sanford, Selena; Yee, Kristen; Cao, Xuan; Budinsky, Zachary; Liigand, Jaanus; Zhang, Lun; Zheng, Jiamin; Mandal, Rupasri; Karu, Naama; Dambrova, Maija; Schiöth, Helgi B.; Gautam, Vasuk. "Showing metabocard for 21-Hydroxypregnenolone (HMDB04026)". Human Metabolome Database, HMDB. 5.0.
- ^ 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.