21-Hydroxypregnenolone - Misplaced Pages

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21-Hydroxypregnenolone
Names


IUPAC name 3β,21-Dihydroxypregn-5-en-20-one
Systematic IUPAC name 2-Hydroxy-1-phenanthren-1-yl]ethan-1-one
Other names Prebediolone; Pregn-5-en-3β,21-diol-20-one
Identifiers
CAS Number	1164-98-3
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28043
ChEMBL	ChEMBL1908012
ChemSpider	216208
PubChem CID	247020
UNII	A1L3K6161X
CompTox Dashboard (EPA)	DTXSID301314382
InChI InChI=1S/C21H32O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h3,14-18,22-23H,4-12H2,1-2H3/t14-,15-,16-,17-,18+,20-,21-/m0/s1Key: MOIQRAOBRXUWGN-WPWXJNKXSA-N
SMILES C12CC3(1CC2C(=O)CO)CC=C43(CC(C4)O)C
Properties
Chemical formula	C₂₁H₃₂O₃
Molar mass	332.484 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

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. It is formed from pregnenolone in the adrenal glands.

The 21-acetate ester of 21-hydroxypregnenolone, prebediolone acetate, is described as a glucocorticoid and has been used in the treatment of rheumatoid arthritis.

References

^ 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.

Others

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