6-alpha-methyl-20-oxopregn-4-en-17-alpha-yl acetate

Originator

ORF 1658,ZYF Pharm Chemical

Uses

Progestin.

Definition

ChEBI: Anagestone acetate is a steroid ester.

Manufacturing Process

To solution of 6α-methyl-4-pregnen-17α-ol-3,20-dione (1.0 g) in ethane-dithiol (1 ml) and methylene chloride (2 ml) pyridine chlorhydrate (1 g) was added and mixed 3 min at room temperature. Then to reaction mixture methanol (30 ml) was added and cooled in ice bath during of 2 min. Precipitate was filtered and washed with cool methanol. 6α-Methyl-4-pregnen- 17α-ol-20-one-3-thioacetal was obtained (0.9 g), melting point 186°-188°C (recrystalisation from methanol-dichlormethane).
To the solution of 6α-methyl-4-pregnen-17α-ol-20-one-3-thioacetal (2 g) in 95% ethanol (200 ml) Ni (Renney) (50 g) was added and mixed at heating. Then reaction mixture was cooled to room temperature. The mixture was filtered, and filtrate was evaporated, obtaining residue was crystallisated from methanol with dichloromethane and in the result 6α-methyl-4-pregnen-17α- ol-20-one (0.95 g) was produced, melting point 190°-193°C.
To the solution of 6α-methyl-4-pregnen-17α-ol-20-one (1.5 g) in acetic acid (75 ml) and acetic anhydride (15 ml) p-toluenesulfonic acid was added and the reaction mixture allayed to stand at room temperature any time. Then crystals were recrystallised from methanol with dichlormethane. Acetate 6α- methyl-4-pregnen-17α-ol-20-one (1.3 g) was obtained, melting point 173°- 175°C.

brand name

Anatropin (Ortho Pharmaceutical).

Therapeutic Function

Progestin

World Health Organization (WHO)

Anagestone acetate, a synthetic progestogen, was introduced in 1968 as a component in oral contraceptive preparations. In 1969, it was shown to be associated with an increased risk of mammary tumours in dogs which led the United States Food and Drug Administration to order the termination of its use in all clinical trials. Subsequently the manufacturer withdrew preparations containing anagestone acetate, ultimately on a worldwide basis.

Raw materials

Preparation Products