Trimegestone

Trimegestone
Clinical data
Trade namesGinotex, Lovelle, Minique, Ondeva, Totelle, others
Other namesTMG; RU-27987; 21(S)-Hydroxypromegestone; 21β-Hydroxypromegestone; 21(S)-Hydroxy-17α,21-dimethyl-9-dehydro-19-norprogesterone; 21(S)-Hydroxy-17α,21-dimethyl-19-norpregna-4,9-dien-3,20-dione; 17β-(S)-Lactoyl-17α-methylestra-4,9-dien-3-one; 17β-((S)-2-Hydroxypropanoyl)-17α-methylestra-4,9-dien-3-one
Routes of
administration		By mouth
Drug classProgestogen; Progestin
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability100%[1]
Protein binding98% (to albumin)[2]
MetabolismMainly hydroxylation[2]
Elimination half-lifeRange: 12–20 hours[3]
Mean: 13.8–15.6 hours[2][4]
Identifiers
IUPAC name
  • (8S,13S,14S,17S)-17-[(2S)-2-hydroxypropanoyl]-13,17-dimethyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.189.099
Chemical and physical data
FormulaC22H30O3
Molar mass342.479 g·mol−1
3D model (JSmol)
SMILES
  • C[C@@H](C(=O)[C@]1(CC[C@@H]2[C@@]1(CCC3=C4CCC(=O)C=C4CC[C@@H]23)C)C)O
InChI
  • InChI=1S/C22H30O3/c1-13(23)20(25)22(3)11-9-19-18-6-4-14-12-15(24)5-7-16(14)17(18)8-10-21(19,22)2/h12-13,18-19,23H,4-11H2,1-3H3/t13-,18+,19-,21-,22+/m0/s1
  • Key:JUNDJWOLDSCTFK-MTZCLOFQSA-N

Trimegestone, sold under the brand names Ondeva and Totelle among others, is a progestin medication which is used in menopausal hormone therapy and in the prevention of postmenopausal osteoporosis.[4][2][3] It was also under development for use in birth control pills to prevent pregnancy, but ultimately was not marketed for this purpose.[5] The medication is available alone or in combination with an estrogen.[6][7] It is taken by mouth.[2]

Side effects of trimegestone include headache, breast tenderness, nervousness, abdominal pain, bloating, muscle cramps, nausea, depression, and vaginal bleeding among others.[8][4] Trimegestone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[2][4] It has weak antiandrogenic and antimineralocorticoid activity and no other important hormonal activity.[2][4]

Trimegestone was first described in 1979 and was introduced for medical use in 2001.[9][10][11] It is sometimes described as a "fourth-generation" progestin.[12][13] The medication is marketed throughout Europe and Latin America.[14][6] It is not available in the United States or Canada.[15][14][6]

  1. ^ Cite error: The named reference FRCOG2015 was invoked but never defined (see the help page).
  2. ^ a b c d e f g Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
  3. ^ a b Stanczyk FZ (2002). "Pharmacokinetics and potency of progestins used for hormone replacement therapy and contraception". Rev Endocr Metab Disord. 3 (3): 211–24. doi:10.1023/A:1020072325818. PMID 12215716. S2CID 27018468.
  4. ^ a b c d e Sitruk-Ware R, Bossemeyer R, Bouchard P (June 2007). "Preclinical and clinical properties of trimegestone: a potent and selective progestin". Gynecol. Endocrinol. 23 (6): 310–9. doi:10.1080/09513590701267727. PMID 17616854. S2CID 39422122.
  5. ^ Cite error: The named reference AdisInsight-EE-TMG was invoked but never defined (see the help page).
  6. ^ a b c Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  7. ^ "Trimegestone". AdisInsight. Springer Nature Switzerland AG.
  8. ^ Cite error: The named reference pmid11772282 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference Beato1980 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference AcademicPress2012 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference TaylorTriggle2007 was invoked but never defined (see the help page).
  12. ^ Sitruk-Ware R (2004). "New progestogens: a review of their effects in perimenopausal and postmenopausal women". Drugs Aging. 21 (13): 865–83. doi:10.2165/00002512-200421130-00004. PMID 15493951. S2CID 9543491.
  13. ^ Briggs P, Kovacs G (11 July 2013). Contraception: A Casebook from Menarche to Menopause. Cambridge University Press. pp. 52–. ISBN 978-1-107-43611-4.
  14. ^ a b Cite error: The named reference Micromedex was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference LemkeWilliams2012 was invoked but never defined (see the help page).
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