Prebediolone acetate

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Prebediolone acetate
Prebediolone acetate.svg
Clinical data
Trade namesAcetoxanon, Acetoxy-Prenolon, Artisone, Artivis, Pregnartrone, Sterosone
Synonyms21-Hydroxypregnenolone 21-acetate; Pregnenolone 21-acetate; 21-Acetoxypregnenolone; A.O.P.; 3β,21-Dihydroxypregn-5-en-20-one 21-acetate; Pregn-5-en-3β,21-diol-20-one 21-acetate
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
ECHA InfoCard100.008.454 Edit this at Wikidata
Chemical and physical data
FormulaC23H34O4
Molar mass374.521 g·mol−1
3D model (JSmol)

Prebediolone acetate (brand names Acetoxanon, Acetoxy-Prenolon, Artisone, Artivis, Pregnartrone, Sterosone), also known as 21-hydroxypregnenolone 21-acetate or 21-acetoxypregnenolone (A.O.P.), as well as 3β,21-dihydroxypregn-5-en-20-one 21-acetate, is a synthetic pregnane steroid which is described as a glucocorticoid and has been used in the treatment of rheumatoid arthritis.[1][2][3] It is the C21 acetate ester of prebediolone (21-hydroxypregnenolone), the C21 hydroxylated derivative of pregnenolone.[1] Prebediolone acetate has been known since at least 1950.[4] The compound is also an intermediate in a synthesis of deoxycorticosterone acetate (21-acetoxyprogesterone).[5]

See also[edit]

References[edit]

  1. ^ a b 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.
  2. ^ 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.
  3. ^ LEFKOVITS AM (1953). "Artisone therapy in rheumatoid arthritis". Rheumatism. 9 (4): 70–6. PMID 13101380.
  4. ^ Spring, F. S. (1950). "Recent advances in the chemistry of the steroids". Journal of the Chemical Society (Resumed): 3352. doi:10.1039/jr9500003352. ISSN 0368-1769.
  5. ^ Rheumatism. Rolls House Publishing Company. 1953. Artisone is a steroid of the 21-carbon type. It is 5-pregnene 3 beta, 21-dial-20-one 21 acetate.4 It is also known as 21-acetoxy-pregnenolone, acetoxanon, prebediolone acetate. It is an intermediate product in the synthesis of desoxycorticosterone acetate and is prepared by reacting 5,6-pregnene-3-ol-20-one with bromine and chloroform and treating the obtained oily bromide with potassium I acetate in alcohol.