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Clinical data | |
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Trade names | Surgestone |
Other names | PMG; R-5020; RU-5020; 17α,21-Dimethyl-δ9-19-norprogesterone; 17α,21-Dimethyl-19-norpregna-4,9-diene-3,20-dione |
Routes of administration | By mouth[1] |
Drug class | Progestogen; Progestin |
ATC code | |
Pharmacokinetic data | |
Protein binding | To albumin[1] |
Metabolism | Liver (hydroxylation)[1][3] |
Metabolites | • Trimegestone |
Elimination half-life | Promegestone: ? Trimegestone: 13.8–15.6 hours[1][2] |
Identifiers | |
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CAS Number | |
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ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.207.681 |
Chemical and physical data | |
Formula | C22H30O2 |
Molar mass | 326.480 g·mol−1 |
3D model (JSmol) | |
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Promegestone, sold under the brand name Surgestone, is a progestin medication which is used in menopausal hormone therapy and in the treatment of gynecological disorders.[4][1][5][6] It is taken by mouth.[1]
Side effects of promegestone include menstrual irregularities among others.[7] Promegestone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[1] It has weak antiandrogenic, glucocorticoid, and antimineralocorticoid activity and no other important hormonal activity.[1][8][2] The medication is largely a prodrug of trimegestone.[7][1]
Promegestone was first described in 1973 and was introduced for medical use in France in 1983.[9][10][11] It has only been marketed in a few countries, including France, Portugal, Tunisia, and Argentina.[6][12] In addition to its use as a medication, promegestone has been widely used in scientific research as a radioligand of the progesterone receptor.[4][13]
Promegestone is used in menopausal hormone therapy and in the treatment of gynecological conditions caused by luteal insufficiency, including premenopausal disorders, dysmenorrhea and other menstrual disorders, and premenstrual syndrome.[1][5] It has also been used to treat benign breast disorders such as mastalgia (breast pain).[14] Promegestone tablets have a contraceptive effect and are used as a form of progestogen-only birth control, although it is not specifically licensed as such.[15]
See also: Progestin § Side effects |
Side effects of promegestone include menstrual irregularities among others.[7] It has no androgenic side effects.[4][5]
Promegestone is a progestogen, or an agonist of the progesterone receptor.[1][3] It has about 200% of the affinity of progesterone for the PR.[1][3] The endometrial transformation dosage of promegestone is 10 mg per cycle and its ovulation-inhibiting dosage is 0.5 mg/day.[1][3] Promegestone has weak glucocorticoid activity in addition to its progestogenic activity.[1][3] Conversely, it has no androgenic, estrogenic, mineralocorticoid, or other hormonal activity.[1][3][5] It appears to possess antiandrogenic activity.[13] Its major metabolite trimegestone has weak antimineralocorticoid and antiandrogenic activity.[8][2] In addition, promegestone has been found to possess some neurosteroid activity by acting as a non-competitive antagonist of the nicotinic acetylcholine receptor, similarly to progesterone.[16]
Following oral administration, peak serum levels of promegestone are reached after 1 to 2 hours.[1][3] The medication is mainly bound to albumin; it does not bind to sex hormone-binding globulin, and binds only weakly to corticosteroid-binding globulin.[1][3][17] The metabolism of promegestone is mainly via hydroxylation at the C21 position and at other positions.[1][3] Progesterone is similarly hydroxylated at the C21 position, into 11-deoxycorticosterone (21-hydroxyprogesterone).[18] However, the C9(10) double bond of promegestone greatly limits the A-ring reduction that progesterone undergoes, resulting in 21-hydroxylation being the main route of metabolism for promegestone.[18] The medication is stereoselectively metabolized into trimegestone, the 21(S)-hydroxy metabolite, which is the main compound found in plasma; it circulates at levels approximately twice those of promegestone itself.[7] In addition, trimegestone has more than three-fold higher affinity for the PR than does promegestone.[1] As such, promegestone is largely a prodrug of trimegestone.[7][19] A second metabolite, 21(R)-hydroxypromegestone, circulates at far lower concentrations (AUC ratio for the (S)- and (R)-isomers of about 21).[7] The elimination half-life of trimegestone is 13.8 to 15.6 hours.[1][2] Promegestone, trimegestone, and 21(R)-hydroxypromegestone are not excreted in urine, while 3% of a dose is recovered as the glucuronide and/or sulfate conjugate of trimegestone and 1% of a dose is recovered as the glucuronide and/or sulfate conjugate of 21(R)-hydroxypromegestone.[7]
See also: List of progestogens |
Promegestone, also known as 17α,21-dimethyl-δ9-19-norprogesterone or as 17α,21-dimethyl-19-norpregna-4,9-diene-3,20-dione, is a synthetic norpregnane steroid and a derivative of progesterone.[9][12][11][1] It is specifically a combined derivative of 17α-methylprogesterone and 19-norprogesterone, or of 17α-methyl-19-norprogesterone.[9][11][1] Related derivatives of 17α-methyl-19-norprogesterone include demegestone and trimegestone.[9][12][1]
Promegestone was first described in the literature in 1973 and was introduced for medical use in France in 1983.[9][10][11][5] It was developed by Roussel Uclaf in France.[5]
Promegestone is the generic name of the drug and its INN , while promégestone is its DCF .[6][9][12] It is also known by its developmental code name R-5020 or RU-5020.[6][9][12]
Promegestone is marketed exclusively under the brand name Surgestone.[6][12]
Promegestone is or has been marketed in France, Portugal, Tunisia, and Argentina.[6][12]