Silandrone

Silandrone

Clinical data
Routes of administration	Oral, 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
Synonyms	Testosterone 17β-trimethylsilyl ether; Testosterone O-trimethylsilyl ether; 17β-Trimethylsilyltestosterone; O-Trimethylsilyltestosterone; 17β-(trimethylsiloxy)androst-4-en-3-one; SC-16148; NSC-95147
CAS Number	5055-42-5
PubChem (CID)	68627
ChemSpider	61886
UNII	YY7GL3CCE9
KEGG	D05837
ChEBI	CHEBI:607921
ChEMBL	CHEMBL485687
Chemical and physical data
Formula	C22H36O2Si
Molar mass	360.613 g/mol
3D model (Jmol)	Interactive image
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

Silandrone (INN, USAN) (developmental code names SC-16148, NSC-95147), 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, notably, significantly greater potency than that of testosterone propionate.^[2][3] In addition, it is notable that silandrone, unlike testosterone and most esters of testosterone like testosterone propionate, is orally active.^[4]

See also

• Cloxotestosterone
• Cloxotestosterone acetate

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". Proc. Soc. Exp. Biol. Med. 123 (2): 303–4. doi:10.3181/00379727-123-31472. PMID 5951069.
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). doi:10.1016/0018-506X(70)90004-8.
4. Leland J. Chinn (1969). The Chemistry and Biochemistry of Steroids. Geron-X. p. 97.