Dydrogesterone
Chemical compound / From Wikipedia, the free encyclopedia
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Dydrogesterone, sold under the brand name Dydroboon & Duphaston among others,[1] 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.[7] It is taken by mouth.[7]
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Trade names | Duphaston, others[1] |
Other names | Isopregnenone; Dehydroprogesterone; Didrogesteron; 6-Dehydroretroprogesterone; 9β,10α-Pregna-4,6-diene-3,20-dione; NSC-92336[2][3] |
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Routes of administration | By mouth |
Drug class | Progestogen; Progestin |
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Bioavailability | 28%[4][5] |
Protein binding | ? (probably to albumin)[6][7] |
Metabolism | Hepatic: AKR1C1, AKR1C3, CYP3A4[8][9] |
Metabolites | 20α-DHDTooltip 20α-Dihydrodydrogesterone (exclusively via AKR1C1 and AKRC13)[9] |
Elimination half-life | Parent: 5–7 hours[10] Metabolite: 14–17 hours[10] |
Excretion | Urine |
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ECHA InfoCard | 100.005.280 |
Chemical and physical data | |
Formula | C21H28O2 |
Molar mass | 312.453 g·mol−1 |
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Melting point | 144 °C (291 °F) |
Boiling point | 463 °C (865 °F) |
Solubility in water | Insoluble mg/mL (20 °C) |
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Side effects of dydrogesterone include menstrual irregularities, headache, nausea, breast tenderness, and others.[11][12] Dydrogesterone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[7][13] The medication is an atypical progestogen and does not inhibit ovulation.[7][14] It has weak antimineralocorticoid activity and no other important hormonal activity.[7][13]
Dydrogesterone was developed in the 1950s and introduced for medical use in 1961.[15] It is available widely throughout Europe, including in the United Kingdom, and is also marketed in Australia and elsewhere in the world.[3][15] The medication was previously available in the United States,[15] but it has been discontinued in this country.[16]