Dienogest
[CAS# 65928-58-7]

Identification

• Classification: Biochemical >> Inhibitor >> Endocrinology & hormones >> Estrogen/progestogen receptor chemical
• Name: Dienogest
• Synonyms: 2-[(8S,13S,14S,17R)-17-hydroxy-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]acetonitrile
• Molecular Formula: C₂₀H₂₅NO₂
• Molecular Weight: 311.42
• CAS Registry Number: 65928-58-7
• EC Number: 639-448-2
• SMILES: C[C@]12CCC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@]2(CC#N)O

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*
• Boiling point: 549.0±50.0 ºC 760 mmHg (Calc.)^*
• Flash point: 285.8±30.1 ºC (Calc.)^*
• Solubility: DMSO 10 mM (Expl.)
• Index of refraction: 1.589 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Danger
• Hazard Statements: H315-H319-H335-H341-H351-H360-H360FD-H361-H362-H400-H410
• Precautionary Statements: P203-P260-P261-P263-P264-P264+P265-P270-P271-P273-P280-P302+P352-P304+P340-P305+P351+P338-P318-P319-P321-P332+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Carcinogenicity	Carc.	2	H351
Reproductive toxicity	Lact.	-	H362
Reproductive toxicity	Repr.	1A	H360
Reproductive toxicity	Repr.	2	H361
Reproductive toxicity	Repr.	1B	H360
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Germ cell mutagenicity	Muta.	2	H341

Discovory and Applicatios

Dienogest is a synthetic steroid belonging to the class of progestins, which are compounds structurally related to the natural hormone progesterone. It was developed and introduced for clinical use in the late 20th century as part of hormonal therapies, particularly in gynecology and reproductive medicine.

Chemically, dienogest is a 19-nortestosterone derivative with a unique molecular structure that imparts strong progestogenic activity while minimizing androgenic effects commonly associated with some other progestins. This profile allows dienogest to exert targeted effects on the female reproductive system with fewer side effects related to androgen excess.

Pharmacologically, dienogest binds selectively to progesterone receptors in target tissues such as the endometrium, ovaries, and pituitary gland. Its action modulates the hormonal regulation of the menstrual cycle by inducing changes in the endometrial lining, inhibiting ovulation, and reducing the secretion of gonadotropins (luteinizing hormone and follicle-stimulating hormone). These effects make dienogest effective for contraception and the treatment of hormone-dependent conditions.

Clinically, dienogest is widely used in combination oral contraceptives as well as in progestin-only therapies. One of its key therapeutic applications is the treatment of endometriosis, a chronic gynecological condition characterized by the growth of endometrial tissue outside the uterus, causing pain and infertility. Dienogest’s ability to suppress endometrial growth and inflammation helps alleviate symptoms and improve quality of life for affected patients.

Dienogest has also been used to treat other menstrual disorders, including heavy menstrual bleeding and dysmenorrhea. Its efficacy in these conditions stems from its influence on endometrial stability and hormone regulation.

Pharmacokinetically, dienogest is rapidly absorbed after oral administration with good bioavailability. It is metabolized predominantly in the liver through hydroxylation and conjugation pathways. The metabolites are excreted mainly in the urine. The elimination half-life of dienogest ranges approximately from 9 to 10 hours, supporting once-daily dosing regimens.

Adverse effects associated with dienogest are generally related to its hormonal activity and include menstrual irregularities, headache, breast tenderness, and mood changes. Due to its low androgenic activity, it has a lower risk of causing acne, weight gain, or other androgen-related side effects compared to some other progestins.

In summary, dienogest is a selective progestin used primarily for contraception and the treatment of endometriosis and menstrual disorders. Its strong progestogenic effects combined with minimal androgenic activity provide therapeutic benefits with a relatively favorable safety profile. The compound’s pharmacokinetics allow convenient dosing and effective hormone modulation in clinical practice.

References

2001. [Treatment of endometriosis with dienogest: preliminary report]. Ginekologia polska, 72(5).
PMID: 11526761

2011. Maintenance therapy with dienogest following gonadotropin-releasing hormone agonist treatment for endometriosis-associated pelvic pain. European Journal of Obstetrics & Gynecology and Reproductive Biology, 157(2).
DOI: 10.1016/j.ejogrb.2011.03.012

2022. Challenges of and possible solutions for living with endometriosis: a qualitative study. BMC Women's Health, 22(1).
DOI: 10.1186/s12905-022-01603-6