Amadinone

Amadinone (INN), also known as 19-norchlormadinone, is a steroidal progestin of the 19-norprogesterone and 17α-hydroxyprogesterone groups that was synthesized and characterized in 1968 but was never marketed.[1][2] It has antigonadotropic properties, and for this reason, is a functional antiandrogen.[3][4] An acetate ester, amadinone acetate, also exists, but similarly was never marketed.[1]

Amadinone

Clinical data
Other names	6-Chloro-17α-hydroxy-19-norpregna-4,6-dione
Identifiers
IUPAC name (1S,2R,10R,11S,14R,15S)-14-acetyl-8-chloro-14-hydroxy-15-methyltetracyclo[8.7.0.0^2,7.0^11,15]heptadeca-6,8-dien-5-one
CAS Number	30781-27-2
PubChem CID	10315768
ChemSpider	8491233
UNII	6MB06022N0
Chemical and physical data
Formula	C20H25ClO3
Molar mass	348.87 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C=C(C4=CC(=O)CC[C@H]34)Cl)C)O
InChI InChI=1S/C20H25ClO3/c1-11(22)20(24)8-6-17-15-10-18(21)16-9-12(23)3-4-13(16)14(15)5-7-19(17,20)2/h9-10,13-15,17,24H,3-8H2,1-2H3/t13-,14-,15-,17+,19+,20+/m1/s1 Key:ANJGIFXUFSBZPX-WLCXVKOPSA-N

See also

• Chlormadinone
• Chlormadinone acetate

References

1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 35–. ISBN 978-1-4757-2085-3.
2. William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 206–. ISBN 978-0-8155-1856-3.
3. Hughes A, Hasan SH, Oertel GW, Voss HE, Bahner F, Neumann G, Steinbeck H, Gräf KJ, Brotherton J, Horn HJ, Wagner RK (27 November 2013). Androgens II and Antiandrogens / Androgene II und Antiandrogene. Springer Science & Business Media. pp. 495–. ISBN 978-3-642-80859-3.
4. Kent JR, Hill M, Huix FJ, Segre EJ (1972). "Seminal acid phosphatase content in the clinical bioassay of androgens and antiandrogens". Clinical Pharmacology and Therapeutics. 13 (2): 205–11. doi:10.1002/cpt1972132205. PMID 5017374. S2CID 40886901.