Dienogest

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Cat Number

API65928587

CAS Number

65928-58-7

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Product Detail Description Scientific Support Customer Q&A

CAS Number

65928-58-7

EINECS

639-448-2

Storage

Store at room temperature

Synonyms

Dienogestril; Dienogestum; Endometrion; STS-557; MJR-35; 17alpha-17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile

Molecular Formula

C20H25NO2

Molecular Weight

311.4

Smiles

C[C@]12CCC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@]2(CC#N)O

Appearance

White to light yellow powder

Melting Point

210-214°C (dec.)

Boiling Point

549.0±50.0°C at 760 mmHg

Relative Density

1.2±0.1

General Description

Dienogest is a hybrid progestin derived from 19-nortestosterone but with a cyanomethyl group at the 17α position and an additional double bond between carbons 9 and 10. Its structure also features an ethinyl group absent, unlike other 19-nortestosterone derivatives. This unique configuration confers high oral bioavailability (over 90%), a short half-life (8-10 hours), and lack of androgenic or estrogenic activity.

Mechanism of Action

Dienogest binds with high affinity to progesterone receptors and exhibits antiandrogenic activity (blocking androgen receptors) and moderate anti-gonadotropic effects. It suppresses ovulation, induces decidualization of endometrial tissue, and reduces endometrial cell proliferation. The drug also inhibits angiogenesis, reduces local prostaglandin and inflammatory cytokine production, and increases endometrial cell apoptosis.

Application

Dienogest is indicated for the treatment of endometriosis, reducing endometriotic lesion size and alleviating pelvic pain, dysmenorrhea, and dyspareunia. It is also used as an oral contraceptive (in combination with estradiol valerate) and for the management of abnormal uterine bleeding. In endometriosis, continuous administration produces a pseudodecidualization and atrophy of ectopic endometrial tissue without systemic estrogen withdrawal effects.

Meta‑analysis of 11 studies (up to November 2020) evaluated dienogest (DNG) as maintenance therapy after conservative surgery for endometriosis. DNG significantly reduced disease recurrence compared to no treatment (NT) but not compared to other treatments (OT: LNG‑IUS, GnRH‑a). Pregnancy rates were higher with DNG vs. NT but not vs. OT. Adverse effects included increased vaginal bleeding and weight gain. DNG is recommended to decrease recurrence, but it does not improve pregnancy rates over other active treatments.

Fig. 1 Forest plots of outcomes comparing the Dienogest (DNG) group with the control group in terms of disease recurrence. (Liu Y, et al., 2021)

References

Liu Y, et al. Dienogest as a Maintenance Treatment for Endometriosis Following Surgery: A Systematic Review and Meta-Analysis. Front Med (Lausanne). 2021;8:652505.

Does Dienogest require protection from light during long-term storage?

Yes, it is photosensitive. UV light can cause photodegradation and isomerization. Store in light-resistant containers, preferably amber glass.

What is the recommended storage temperature for Dienogest?

Store at controlled room temperature (15-25°C). Avoid excessive heat above 30°C, which can accelerate oxidation of the cyanomethyl group.

Is Dienogest stable in oral contraceptive formulations with ethinyl estradiol?

Yes, when formulated with standard excipients and protected from moisture.

How is the impurity dienogest 3-oxo (a process-related impurity) monitored?

This impurity is quantified using a stability-indicating HPLC method, ensuring it remains within pharmacopoeial limits.