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Amadinone

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Chemical compound Pharmaceutical compound
Amadinone
Clinical data
Other names6-Chloro-17α-hydroxy-19-norpregna-4,6-dione
Identifiers
IUPAC name
  • (1S,2R,10R,11S,14R,15S)-14-acetyl-8-chloro-14-hydroxy-15-methyltetracycloheptadeca-6,8-dien-5-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H25ClO3
Molar mass348.87 g·mol
3D model (JSmol)
SMILES
  • CC(=O)1(CC21(CC32C=C(C4=CC(=O)CC34)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

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. It has antigonadotropic properties, and for this reason, is a functional antiandrogen. An acetate ester, amadinone acetate, also exists, but similarly was never marketed.

See also

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.
Progesterone receptor modulators
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens
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