Prebediolone acetate

Prebediolone acetate (brand names Acetoxanon, Acetoxanone, 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]

Prebediolone acetate
Clinical data
Trade namesAcetoxanon, Acetoxanone, Acetoxy-Prenolon, Artisone, Artivis, Pregnartrone, Sterosone
Other names21-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
  • [2-[(3S,8S,9S,10R,13S,14S,17S)-3-Hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.008.454
Chemical and physical data
FormulaC23H34O4
Molar mass374.521 g·mol−1
3D model (JSmol)
  • CC(=O)OCC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
  • InChI=1S/C23H34O4/c1-14(24)27-13-21(26)20-7-6-18-17-5-4-15-12-16(25)8-10-22(15,2)19(17)9-11-23(18,20)3/h4,16-20,25H,5-13H2,1-3H3/t16-,17-,18-,19-,20+,22-,23-/m0/s1
  • Key:MDJRZSNPHZEMJH-MTMZYOSNSA-N

See also

References
  1. 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.



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