Trade names Enol-Luteovis ATC code G03A (WHO) Molar mass 382.5787 g/mol | Routes of
administration Oral CAS Number 67-95-8 | |
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Legal status In general: ℞ (Prescription only) Synonyms W-3399; Progesterone 3-cyclopentyl enol ether; 3-Cyclopentyloxypregna-3,5-dien-20-one | ||
How to pronounce quingestrone
Quingestrone (INN, USAN) (brand name Enol-Luteovis; former developmental code name W-3399), also known as progesterone 3-cyclopentyl enol ether (PCPE) or as 3-cyclopentyloxypregna-3,5-dien-20-one, is a synthetic, steroidal, pure progestogen that was developed by Vister and introduced in Italy as an oral contraceptive (in combination with ethinylestradiol or mestranol) in 1962. It is closely related to progesterone, being the 3-cyclopentyl enol ether of the progestogen sex hormone.
Contents
Pharmacology
Along with the retroprogesterone derivative dydrogesterone, quingestrone is described as a "true" progesterone derivative due to its close similarity to natural progesterone. Similarly to progesterone, dydrogesterone, and hydroxyprogesterone caproate, quingestrone is a pure progestogen and lacks any androgenic effects. As such, it poses no risk of androgenic side effects or virilizing teratogenic effects on female fetuses. Accordingly, the drug was studied in the clinical prevention of miscarriage during pregnancy; however, insufficient efficacy was observed at the dosage assessed (100 mg/day orally). Quingestrone is said to influence the hypothalamic-pituitary-adrenal axis similarly to progesterone and medroxyprogesterone acetate, producing adrenal suppression at sufficiently high doses, and this suggests that it possesses weak or very weak glucocorticoid properties similarly to progesterone.
Pharmacokinetics
Quingestrone has been suggested to act as a prodrug of progesterone via slow hydrolysis in the body. Indeed, it produces similar metabolites (e.g., pregnanediols and allopregnanediols) to progesterone, although with differing ratios, and notably is the only progestin that is known to produce pregnanediol as a metabolite. Subsequent research has cast doubt on the notion that quingestrone is a prodrug of progesterone however, and indicates that it instead is directly metabolized into pregnanediols without intermediate conversion into progesterone.
Relative to progesterone, quingestrone shows improved pharmacokinetics, including higher potency, oral activity, and a longer half-life and hence duration of action. This is considered to be due to its higher lipophilicity, being stored into and slowly released from fat. Quingestrone also shows slower metabolism and more stable blood levels, with a longer time to peak concentrations and a less intense peak compared to progesterone.
The bioavailability of quingestrone is highest when it is given as a sesame seed oil solution (compared to an oil suspension (~2-fold less) or micronization (~7-fold less)).