Tigestol

Last updated
Tigestol
Tigestol structure.svg
Identifiers
  • (8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-2,3,4,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
Formula C20H28O
Molar mass 284.443 g·mol−1
3D model (JSmol)
  • CC12CCC3C(C1CCC2(C#C)O)CCC4=C3CCCC4
  • InChI=InChI=1S/C20H28O/c1-3-20(21)13-11-18-17-9-8-14-6-4-5-7-15(14)16(17)10-12-19(18,20)2/h1,16-18,21H,4-13H2,2H3/t16-,17-,18+,19+,20+/m1/s1
  • Key:DHOKBGHAEUVRMO-SLHNCBLASA-N

Tigestol (INN, USAN), also known as 17α-ethynylestr-5(10)-en-17β-ol, [1] is a steroidal progestin of the 19-nortestosterone group that was developed by Organon in the 1960s but was never marketed. [2] [3] [4] [5] It is an isomer of the related 19-nortestosterone derivative progestins lynestrenol and cingestol. [6]

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<span class="mw-page-title-main">Progestogen ester</span>

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<span class="mw-page-title-main">Cingestol</span> Chemical compound

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<span class="mw-page-title-main">Allyltestosterone</span> Chemical compound

Allyltestosterone, or 17α-allyltestosterone, also known as 17α-allylandrost-4-en-17β-ol-3-one, is a steroid derived from testosterone that was first synthesized in 1936 and was never marketed. Along with propyltestosterone (topterone), it has been patented as a topical antiandrogen and hair growth inhibitor. Allyltestosterone is the parent structure of two marketed 19-nortestosterone progestins, allylestrenol and altrenogest. These progestins are unique among testosterone derivatives in that they appear to be associated with few or no androgenic effects.

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References

  1. List PH, Hörhammer L (12 March 2013). Chemikalien und Drogen Teil C: T–Z. Springer-Verlag. pp. 179–. ISBN   978-3-642-67085-5.
  2. Hill RA, Makin HL, Kirk DN, Murphy GM (23 May 1991). Dictionary of Steroids. CRC Press. pp. 424–. ISBN   978-0-412-27060-4.
  3. United States Adopted Names (USAN). United States Pharmacopeial Convention. 1969. p. 65,85.
  4. Lednicer D, Mitscher LA (13 May 1980). The Organic Chemistry of Drug Synthesis. John Wiley & Sons. pp. 145–. ISBN   978-0-471-04392-8.
  5. Lednicer D (1998). Strategies for Organic Drug Synthesis and Design. Wiley. p. 95. ISBN   978-0-471-19657-0.
  6. GB 841411,"New 19-Nor-Steroid Compounds and process for the preparation thereof",published 1960-07-13, assigned to Organon Laboratories Ltd.