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Dydrogesterone, sold under the brand name Duphaston among others, is a progestin medication which is used for a variety of indications, including threatened or recurrent miscarriage during pregnancy, dysfunctional bleeding, infertility due to luteal insufficiency, dysmenorrhea, endometriosis, secondary amenorrhea, irregular cycles, premenstrual syndrome, and as a component of menopausal hormone therapy.
Side effects of dydrogesterone include menstrual irregularities, headache, nausea, breast tenderness, and others.
Dydrogesterone was developed in the 1950s and introduced for medical use in 1961.
Contents
1 Medical uses
1.1 Gynecological disorders
1.2 Infertility and miscarriage
1.3 Hormone therapy
1.4 Available forms
2 Contraindications
3 Side effects
4 Overdose
5 Interactions
6 Pharmacology
6.1 Pharmacodynamics
6.2 Pharmacokinetics
7 Chemistry
7.1 Analogues
7.2 Synthesis
8 History
9 Society and culture
9.1 Generic names
9.2 Brand names
9.3 Availability
10 References
Medical uses
Dydrogesterone has proven effective in a variety of conditions associated with progesterone deficiency, to counteract the effects of unopposed estrogen on the endometrium in women with an intact uterus.
Gynecological disorders
Primary or essential dysmenorrhea is a very common gynecological phenomenon experienced by women during their reproductive years. Clinical studies have shown symptom relief and a reduction in pain with dydrogesterone treatment for dysmenorrhea.
Endometriosis is a chronic disease which can cause severe, progressive, and at times, incapacitating dysmenorrhea, pelvic pain, dyspareunia and infertility. Dydrogesterone relieves pain without inhibiting ovulation, so that patients are able to become pregnant during treatment. Dydrogesterone is particularly suitable in cases where the woman desires to become pregnant and to prevent bleeding problems. The amount and duration of menstrual bleeding is also significantly reduced, and from the end of the third month onwards, bleeding was considered normal in the majority of patients. Improvement of endometriosis was observed in 71% of patients and cure in 21%.
Dydrogesterone has shown reasonable efficacy in relieving a number of premenstrual syndrome symptoms like mood swings and physical symptoms.
Infertility and miscarriage
Oral dydrogesterone is effective drug, well tolerated and accepted among patients and can be considered for routine luteal support. Advantage of dydrogesterone is oral administration, easy to use and better patient compliance which results in high satisfaction score of oral dydrogesterone in luteal support of IVF / ICSI cycles. According to the latest Cochrane review (2015), no evidence showed a difference between synthetic and micronized progesterone for luteal phase support in terms of successful pregnancies.
Dydrogesterone is used for luteal support in IVF protocols, for treatment of recurrent pregnancy loss.
Threatened miscarriage is defined as bleeding during the first 20 weeks of pregnancy while the cervix is closed. It is the most common complication in pregnancy, occurring in 20% of all pregnancies. Recurrent abortion is defined as the loss of three or more consecutive pregnancies. Dydrogesterone is associated with approximately two-fold significant reduction in the miscarriage rate as compared to standard care in threatened and recurrent miscarriages with minimal side effects.
Hormone therapy
The objective behind menopausal hormone therapy is to actively increase the circulating levels of estrogen to control hot flashes and to prevent the long-term effects of the menopause, such as bone resorption and unfavourable changes in blood lipids. The administration of estradiol halts, or reverses atrophic changes that occur due to the loss of endogenous estradiol during the menopause.
Estrogen promotes endometrial cell growth and in postmenopausal women with an intact uterus, estrogen monotherapy results in continued endometrial development without the physiological secretory changes normally brought on by progesterone. This action is associated with an increased incidence of endometrial hyperplasia and carcinoma. Additional protection with progestogens is therefore important in patients with an intact uterus who receive estrogen therapy. Dydrogesterone counters the proliferative effect of estrogens on the endometrium and ensures the transition to a secretory pattern and cyclical shedding of the endometrium in serial menopausal hormone therapy regimes. Dydrogesterone effectively protects against the ontogenesis of endometrial hyperplasia. Unlike androgenic progestogens, dydrogesterone does not reverse the benefits brought on by estradiol on lipid profiles and carbohydrate metabolism. In a continuous, combined menopausal hormone therapy regimen, dydrogesterone retards the proliferation of the endometrium so that it remains atrophic or inactive.
Available forms
Dydrogesterone is available in the form of 10 mg oral tablets both alone and in combination with estradiol.
Contraindications
See also: Progestin § Contraindications
Side effects
The most commonly reported drug related adverse reactions of patients treated with dydrogesterone without estrogen treatment in clinical trials of indications include menstrual irregularities, headaches, migraines, nausea, breast tenderness, bloating, and weight gain.
Dydrogesterone has been prescribed and used in over 10 million pregnancies worldwide. There have been no harmful effects exhibited due to the use of dydrogesterone while pregnant. Dydrogesterone is safe to use during pregnancy only when prescribed and indicated by a medical practitioner.
Overdose
There is not enough clinical data to support overdose in humans. The maximum dose of dydrogesterone administered to humans to date was 360 mg orally and the drug was found to be well-tolerated at this dose. There are no antidotes to overdose and treatment should be based on symptoms.
Interactions
In menopausal hormone therapy, dydrogesterone is administered together with an estrogen. Therefore, the interaction between dydrogesterone and estrogens has been assessed, and no clinically significant interaction has been observed.
Pharmacology
Pharmacodynamics
20α-Dihydrodydrogesterone, the main active form of dydrogesterone.
Dydrogesterone is a highly selective progestogen, and due to its unique structure, unlike progesterone and many other progestins, binds almost exclusively to the progesterone receptor (PR).
Due to its progestogenic activity, dydrogesterone can produce antigonadotropic effects at sufficient doses in animals.
Dydrogesterone does not bind importantly to the androgen, estrogen, or glucocorticoid receptor.
Affinities of dydrogesterone and related steroids
Progestogen
PR
AR
GR
ERα
K i (nM)
RBA (%)
K i (nM)
RBA (%)
K i (nM)
RBA (%)
K i (nM)
Dydrogesterone
125.9
15.9
251.2
10.0
361.2
17.5
>10,000
20α-Dihydrodydrogesterone
125.9
15.9
3162.3
0.8
3162.3
2.0
>10,000
Progesterone
20.0
100
25.1
100
63.1
100
>10,000
Pharmacokinetics
Dydrogesterone and its major metabolite, 20α-DHD, have predictable pharmacokinetics. The single-dose kinetics are linear in the oral dose range of 2.5 to 10 mg. The pharmacokinetics do not change during repeated administration of up to 20 mg dydrogesterone once daily. Dydrogesterone is readily absorbed after oral administration. The absolute bioavailability of dydrogesterone is on average 28%.
Dydrogesterone is virtually completely metabolized, which occurs in the liver. All of the metabolites of dydrogesterone retain the 4,6-diene-3-one structure, and are metabolically stable. As such, dydrogesterone does not undergo aromatization, which is consistent with its absence of estrogenic effects.
The mean elimination half-lives of DHD and dydrogesterone vary between 14 to 17 hours and 5 to 7 hours, respectively. Dydrogesterone and its metabolites are excreted predominantly in urine. Total clearance of plasma is at a rate of 6.4 L/min. Within 72 hours, excretion is virtually complete. DHD is preponderantly present in the urine as a conjugate of glucuronic acid. Approximately 85% of the oral dose is successfully egested from the body within 24 hours.
The pharmacokinetics of dydrogesterone have been reviewed.
Chemistry
See also: Retroprogesterone and List of progestogens § Retroprogesterone derivatives
A 3D schematic representation of the chemical structures of progesterone (top) and dydrogesterone (bottom), showing the retrosteroid spatial configuration of dydrogesterone.
Dydrogesterone, also known as 6-dehydro-9β,10α-progesterone or as 9β,10α-pregna-4,6-diene-3,20-dione, is a synthetic pregnane steroid and a derivative of progesterone and retroprogesterone (9β,10α-progesterone).
Analogues
Other retroprogesterone derivatives, and analogues of dydrogesterone, include trengestone (1,6-didehydro-6-chlororetroprogesterone) and Ro 6-3129 (16α-ethylthio-6-dehydroretroprogesterone).
Synthesis
Dydrogesterone is synthesized and manufactured by treatment of progesterone with ultraviolet light exposure.
Chemical syntheses of dydrogesterone have been published.
History
Dydrogesterone is a progestin which was first synthesized by Duphar in the 1950s and was first introduced to the market in 1961. It is unique, being the only retrosteroid that is commercially available and its molecular structure is closely related to that of natural progesterone,
Society and culture
Generic names
Dydrogesterone is the generic name of the drug and its INN, USAN, and BAN, while dydrogestérone is its DCF and didrogesterone is its DCIT.
Brand names
Dydrogesterone is marketed mainly under the brand names Duphaston (alone) and Femoston (in combination with estradiol ).
Availability
Dydrogesterone is available widely throughout the world.

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