9179. Testolactone
Nomenclature
CAS number: 968-93-4
(4aS,4bR,10aR,10bS,12aS)-3,4,4a,5,6,10a,10b,11,12,12a-Decahydro-10a,12a-dimethyl-2H-phenanthro[2,1-b]pyran-2,8(4bH)-dione; D-homo-17a-oxaandrosta-1,4-diene-3,17-dione; 13-hydroxy-3-oxo-13,17-secoandrosta-1,4-dien-17-oic acid δ-lactone; 1,2,3,4,4a,4b,7,9,10,10a-decahydro-2-hydroxy-2,4b-dimethyl-7-oxo-1-phenanthrenepropionic
acid δ-lactone; delta-1-testololactone; 1-dehydrotestololactone; 17α-oxo-D-homo-1,4-androstadiene-3,17-dione; Δ1-testolactone; NSC-23759; SQ-9538; Fludestrin (BMS); Teslac (BMS). C19H24O3; mol wt 300.39.
C 75.97%, H 8.05%, O 15.98%.
Description and references
Obtained by microbial transformation of progesterone, Reichstein's substance S, or testosterone: Fried et al., J. Am. Chem. Soc. 75, 5764 (1953); eidem, US 2744120 (1956 to Olin Mathieson); Brannon et al., J. Org. Chem. 30, 760 (1965). Comprehensive description: K. Florey, Anal. Profiles Drug Subs. 5, 533-553 (1976).
Properties
Crystals from acetone, mp 218-219°. [α]D23 -45.6° (c = 1.24 in chloroform). uv max (ethanol): 242 nm (ε 15800).Note
This is a controlled substance (anabolic steroid): 21 CFR, 1308.13, as defined in 1300.01.Therapeutic Category
Antineoplastic.
Keywords
Antineoplastic (Hormonal); Androgens