21-Hydroxypregnenolone

21-Hydroxypregnenolone
Names
	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
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/s1 Key: MOIQRAOBRXUWGN-WPWXJNKXSA-N;
	SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)CO)CC=C4[C@@]3(CC[C@@H](C4)O)C;
Properties
Chemical formula	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]

References

^ ^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.

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