16-Methylene-17α-hydroxyprogesterone acetate

16-Methylene-17α-hydroxyprogesterone acetate is a progestin of the 17α-hydroxyprogesterone group which was never marketed.[1][2][3][4][5] Given orally, it shows about 2.5-fold the progestogenic activity of parenteral progesterone in animal bioassays.[5] It is a parent compound of the following clinically used progestins:[6][7]

16-Methylene-17α-hydroxyprogesterone acetate
Clinical data
Other names16-Methylene-17α-acetoxyprogesterone; 16-Methylene-17α-acetoxypregn-4-en-3,20-dione
Drug classProgestogen; Progestin; Progestogen ester
Identifiers
IUPAC name
  • [(8R,9S,10R,13S,14S,17R)-17-Acetyl-10,13-dimethyl-16-methylidene-3-oxo-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-17-yl] acetate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H32O4
Molar mass384.516 g·mol−1
3D model (JSmol)
SMILES
  • CC(=O)[C@]1(C(=C)C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)OC(=O)C
InChI
  • InChI=1S/C24H32O4/c1-14-12-21-19-7-6-17-13-18(27)8-10-22(17,4)20(19)9-11-23(21,5)24(14,15(2)25)28-16(3)26/h13,19-21H,1,6-12H2,2-5H3/t19-,20+,21+,22+,23+,24+/m1/s1
  • Key:XSNMCQGNVPSIQM-CKOZHMEPSA-N

References
  1. Kirk, D. N.; Petrow, V.; Stansfield, M.; Williamson, D. M. (1960). "481. Modified steroid hormones. Part XIV. 17α-Acetoxy-16-methylenepregn-4-ene-3,20-dione". J. Chem. Soc.: 2385–2388. doi:10.1039/JR9600002385. ISSN 0368-1769.
  2. Mannhardt, HJ; von Werder, F; Bork, KH; Ketz, H; Bruckner, K (1960). "Preparation of 16-methylene steroids of the corticoid and progesterone series". Tetrahedron Letters. 1 (16): 21–32. doi:10.1016/S0040-4039(01)99336-0. ISSN 0040-4039.
  3. Syhora, K (1961). "Steroid derivatives. IX. Partial synthesis of 17α-acetoxy-16-methyleneprogesterone". Collection of Czechoslovak Chemical Communications. 26: 1034–8. doi:10.1135/cccc19611034. ISSN 0010-0765.
  4. Shapiro E, Legatt T, Weber L, Steinberg M, Watnick A, Eisler M, Hennessey MG, Coniglio CT, Charney W, Oliveto EP (September 1962). "16-Alkylated Progesterones". J Med Pharm Chem. 91 (5): 975–88. doi:10.1021/jm01240a010. PMID 14056440.
  5. Čekan, Z.; Šeda, M.; Mikulášková, J.; Syhora, K. (1964). "Steroid derivatives XXXIV. On the progestational activity of 6-dehydro-16-methylene-17α-acetoxyprogesterone". Steroids. 4 (3): 415–421. doi:10.1016/0039-128X(64)90154-0. ISSN 0039-128X.
  6. G.W.A Milne (1 November 2017). Ashgate Handbook of Endocrine Agents and Steroids. Taylor & Francis. pp. 158–162. ISBN 978-1-351-74347-1.
  7. R. G. Denkewalter; M. Tishler; G. Ehrhart; J. H. Biel; B. K. B. Lum; J. Büchi; C. A. Winter; K. Münzel; W. Kunz; E. J. Ariëns; F. Labhardt (8 March 2013). Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques. Birkhäuser. pp. 407–. ISBN 978-3-0348-7059-7.


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