Silandrone

Silandrone (INN, USAN) (developmental code name SC-16148), also known as testosterone 17β-trimethylsilyl ether or 17β-trimethylsilyltestosterone, as well as 17β-(trimethylsiloxy)androst-4-en-3-one, is a synthetic anabolic-androgenic steroid (AAS) and an androgen ether – specifically, the 17β-trimethylsilyl ether of testosterone – which was developed by the G. D. Searle & Company in the 1960s but was never marketed.[1] It has a very long duration of action when given via subcutaneous or intramuscular injection, as well as significantly greater potency than that of testosterone propionate.[2][3] In addition, silandrone, unlike testosterone and most esters of testosterone like testosterone propionate, is orally active.[4]

Silandrone
Clinical data
Other namesTestosterone 17β-trimethylsilyl ether; Testosterone O-trimethylsilyl ether; 17β-Trimethylsilyltestosterone; O-Trimethylsilyltestosterone; 17β-(trimethylsiloxy)androst-4-en-3-one; SC-16148; NSC-95147
Routes of
administration		By mouth, intramuscular injection, subcutaneous injection
Identifiers
IUPAC name
  • (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-17-trimethylsilyloxy-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.023.414
Chemical and physical data
FormulaC22H36O2Si
Molar mass360.613 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O[Si](C)(C)C)CCC4=CC(=O)CC[C@]34C
InChI
  • InChI=1S/C22H36O2Si/c1-21-12-10-16(23)14-15(21)6-7-17-18-8-9-20(24-25(3,4)5)22(18,2)13-11-19(17)21/h14,17-20H,6-13H2,1-5H3/t17-,18-,19-,20-,21-,22-/m0/s1
  • Key:HNZDTAXZHUDITM-WLNPFYQQSA-N

See also

References
  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 642–. ISBN 978-1-4757-2085-3.
  2. Saunders FJ (November 1966). "A singularly long-acting ether of testosterone". Proceedings of the Society for Experimental Biology and Medicine. 123 (2): 303–4. doi:10.3181/00379727-123-31472. PMID 5951069. S2CID 21363508.
  3. Le Boeuf BJ, Allen JL (1970). "Prolonged reinstatement of sexual behavior in castrated male rats with an ether of testosterone, SC-16148". Hormones and Behavior. 1 (2): 121–125. doi:10.1016/0018-506X(70)90004-8.
  4. Chinn LJ (1969). The Chemistry and Biochemistry of Steroids. Geron-X. p. 97. ISBN 9780876720035.


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