Estradiol stearate
Estradiol stearate (brand name Depofollan), or estradiol octadecanoate, is a naturally occurring steroidal estrogen and an estrogen ester – specifically, the C17β stearate ester of estradiol. It occurs in the body as a very long-lasting metabolite and prohormone of estradiol. In addition, estradiol stearate is or has been available as a pharmaceutical drug for use via depot intramuscular injection. The drug was introduced in 1941 as Depofollan and was the first long-acting estrogen, although it has never been widely used. It has been reported in at least one source to have a duration of at least one month.
Cyclodiol
Cyclodiol (developmental code name ZK-115194; also known as 14α,17α-ethano-17β-estradiol) is a synthetic estrogen which was studied in the 1990s and was never marketed. It is a derivative of estradiol with a bridge between the C14α and C17α positions. Cyclodiol has 100% of the relative binding affinity of estradiol for the human ERα and similar transactivational capacity as estradiol at the receptor. It has comparable potency to estradiol when administered by subcutaneous injection. The drug shows genotoxicity similarly to estradiol. Cyclodiol showed an absolute bioavailability of 33 ± 19% and a terminal half-life of 28.7 hours in pharmacokinetic studies in women.