Dienogest, sold under the brand name Visanne among others, is a progestin medication which is used in birth control pills and in the treatment of endometriosis.

[1] Side effects of dienogest include menstrual irregularities, headaches, nausea, breast tenderness, depression, and acne, among others.

[23] Dienogest is used primarily in birth control pills in combination with ethinylestradiol under the brand name Valette.

[24][7][25] It is also available in a quadriphasic birth control pill combined with estradiol valerate, marketed as Natazia in the United States and Qlaira in some European countries and Russia.

[26][27][28] Dienogest is approved as a standalone medication under the brand names Visanne and Dinagest in various places such as Europe, Australia, Japan, Singapore, and Malaysia for the treatment of endometriosis.

[29] Birth control pills containing dienogest and estradiol valerate are approved in the United States for the treatment of menorrhagia (heavy menstrual bleeding).

[13] Contraindications of dienogest include active venous thromboembolism, previous or current cardiovascular disease, diabetes with cardiovascular complications, previous or current severe liver disease or tumors, hormone-dependent cancers such as breast cancer, and undiagnosed vaginal bleeding.

[7] They include menstrual irregularities, headaches, nausea, breast tenderness, depression, acne, weight gain, flatulence, and others.

[35] However, they are associated with a significantly lower risk of venous thromboembolism than birth control pills containing ethinylestradiol and a progestin.

[2] This is a property that ethinylestradiol does not share with estradiol, because of its resistance to metabolism in the endometrium and hence its greater relative effects in this part of the body.

[2] Such levels are insufficient for reactivation of endometrioses, but are sufficient to avoid menopausal-like symptoms such as hot flashes and bone loss.

[1] Dienogest has no affinity for sex hormone-binding globulin (SHBG), and hence does not displace testosterone or estradiol from this plasma protein or increase the free fractions of these hormones.

[2] Dienogest weakly stimulates the proliferation of MCF-7 breast cancer cells in vitro, an action that is independent of the classical PRs and is instead mediated via the progesterone receptor membrane component-1 (PGRMC1).

[45] It is unclear if these findings may explain the different risks of breast cancer observed with progesterone and progestins in clinical studies.

[2][7][3][5] The short half-life of dienogest relative to other 19-nortestosterone progestins is in part due to its lack of binding to SHBG and hence prolongation in the circulation.

[47] In terms of structure–activity relationships, the C17α cyanomethyl group of dienogest is responsible for its unique antiandrogenic instead of androgenic activity relative to other 19-nortestosterone progestins.

[50][51] Studies with steroids similar to dienogest (e.g., dienolone) have found that the introduction of a double bond between the C9 and C10 positions is associated with similar/almost unchanged affinity for the PR and AR.

[53][54] Dienogest was synthesized in 1979 in Jena, Germany under the leadership of Kurt Ponsold, was initially referred to as STS-557.

[55] The first product on the market to contain dienogest was a combined birth control pill (with ethinylestradiol), Valette, introduced in 1995 and made by Jenapharm.

[19] In 2007, dienogest was introduced as Dinagest in Japan for the treatment of endometriosis, and it was subsequently marketed for this indication as Visanne in Europe and Australia in December 2009 and April 2010, respectively.

[13] In the case of the dienogest and estradiol valerate birth control pill, these other brand names include Gianda and Klaira.

[13] Dienogest is available both alone and in combination with ethinylestradiol and estradiol valerate widely throughout the world, including but not limited to Canada, Europe, Latin America, and Southeast Asia.