240. Algestone Acetophenide

Nomenclature

CAS number: 24356-94-3
[16α(R)]-16,17-[(1-Phenylethylidene)bis(oxy)]pregn-4-ene-3,20-dione; 16α,17-dihydroxypregn-4-ene-3,20-dione cyclic acetal with acetophenone; 16α,17α-dihydroxyprogesterone acetophenide; alphasone acetophenide; P-DHP; SQ-15101; Deladroxone (obsolete) (BMS); Droxone (obsolete) (BMS); Neolutin Depositum (Medici).
C29H36O4; mol wt 448.59.
C 77.65%, H 8.09%, O 14.27%.

Description and references

Progestogen. Prepn: J. Fried, US 2941997 (1960 to Olin Mathieson); J. Fried et al., Chem. Ind. (London) 1961, 465. Improved prepn: IE 6800457; S. J. Brancato et al., US 3488347 (1968, 1970 both to Smith Kline & French). In estrus synchronization: J. N. Wiltbank et al., J. Anim. Sci. 26, 764 (1967). Clinical evaluations of combination with estradiol enanthate as injectable contraceptive: R. Plesner, Acta Endocrinol. 61, 494 (1969); idem, ibid. 65, 683 (1970); R. Recio et al., Contraception 33, 579 (1986).

Chemical structure

Properties

Crystals from 95% ethanol, mp 150-151°. [α]D23 +51° (CHCl3). Stable to boiling mineral acids; readily cleaved by warming with formic acid, with subsequent deformylation.

Therapeutic Category

Antiacne.

Keywords

Antiacne