16-Methylene-17α-hydroxyprogesterone acetate

16-Methylene-17α-hydroxyprogesterone acetate

Clinical data
Other names	16-Methylene-17α-acetoxyprogesterone; 16-Methylene-17α-acetoxypregn-4-en-3,20-dione
Drug class	Progestogen; 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	6815-51-6
PubChem CID	151431
ChemSpider	133463
UNII	XYO20AWR0I
CompTox Dashboard (EPA)	DTXSID20987647
Chemical and physical data
Formula	C24H32O4
Molar mass	384.516 g·mol^−1
3D model (JSmol)	Interactive image
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

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]

• Chlormethenmadinone acetate (6-chloro-16-methylene-17α-hydroxy-Δ⁶-progesterone acetate)
• Melengestrol acetate (6-methyl-16-methylene-17α-hydroxy-Δ⁶-progesterone acetate)
• Methenmadinone acetate (16-methylene-17α-hydroxy-Δ⁶-progesterone acetate)
• Segesterone acetate (16-methylene-17α-hydroxy-19-norprogesterone acetate)

References

1. Kirk DN, Petrow V, Stansfield M, Williamson DM (1960). "481. Modified steroid hormones. Part XIV. 17α-Acetoxy-16-methylenepregn-4-ene-3,20-dione". Journal of the Chemical Society (Resumed): 2385–2388. doi:10.1039/JR9600002385. ISSN 0368-1769.
2. Mannhardt HJ, Werder FV, Bork KH, Metz H, Brückner 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, et al. (September 1962). "16-Alkylated Progesterones". Journal of Medicinal and Pharmaceutical Chemistry. 5 (5): 975–988. 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. Milne GW (1 November 2017). Ashgate Handbook of Endocrine Agents and Steroids. Taylor & Francis. pp. 158–162. ISBN 978-1-351-74347-1.
7. Denkewalter RG, Tishler M, Ehrhart G, Biel JH, Lum BK, Büchi J, Winter CA, Münzel K, Kunz W, Ariëns EJ, Labhardt F (8 March 2013). Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques. Birkhäuser. pp. 407–. ISBN 978-3-0348-7059-7.