Gestrinone

Gestrinone
Clinical data
Trade namesDimetriose, Dimetrose, Nemestran, others
Other namesEthylnorgestrienone; A-46745; R2323; R-2323; RU-2323; 17α-Ethynyl-18-methyl-δ9,11-19-nortestosterone; 17α-Ethynyl-18-methylestra-4,9,11-trien-17β-ol-3-one; 13β-Ethyl-18,19-dinor-17α-pregna-4,9,11-trien-20-yn-17β-ol-3-one
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • X
Routes of
administration		By mouth, vaginal[1]
Drug classProgestogen; Progestin; Antiprogestogen; Androgen; Anabolic steroid; Steroidogenesis inhibitor; Antiestrogen
ATC code
Legal status
Legal status
  • BR: Class C5 (Anabolic steroids)[2]
Pharmacokinetic data
Protein bindingTo albumin[1]
MetabolismLiver (hydroxylation)[1]
Elimination half-life27.3 hours[1]
ExcretionUrine and bile[1]
Identifiers
IUPAC name
  • (8S,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.210.606
Chemical and physical data
FormulaC21H24O2
Molar mass308.421 g·mol−1
3D model (JSmol)
SMILES
  • O=C4\C=C3/C(=C2/C=C\[C@]1([C@@H](CC[C@]1(C#C)O)[C@@H]2CC3)CC)CC4
InChI
  • InChI=1S/C21H24O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,9,11,13,18-19,23H,3,5-8,10,12H2,1H3/t18-,19+,20+,21+/m1/s1 Y
  • Key:BJJXHLWLUDYTGC-ANULTFPQSA-N Y
  (verify)

Gestrinone, sold under the brand names Dimetrose and Nemestran among others, is a medication which is used in the treatment of endometriosis.[3][4] It has also been used to treat other conditions such as uterine fibroids and heavy menstrual bleeding and has been investigated as a method of birth control.[5][6][1] Gestrinone is used alone and is not formulated in combination with other medications.[7] It is taken by mouth or in through the vagina.[1][8]

Side effects of gestrinone include menstrual abnormalities, estrogen deficiency, and symptoms of masculinization like acne, seborrhea, breast shrinkage, increased hair growth, and scalp hair loss, among others.[1][8][9][10] Gestrinone has a complex mechanism of action, and is characterized as a mixed progestogen and antiprogestogen, a weak androgen and anabolic steroid, a weak antigonadotropin, a weak steroidogenesis inhibitor, and a functional antiestrogen.[11][1][12][13]

Gestrinone was introduced for medical use in 1986.[14] It has been used extensively in Europe but appears to remains marketed only in a few countries throughout the world.[10][15][7] The medication is not available in the United States.[16] Due to its anabolic effects, the use of gestrinone in competition has been banned by the International Olympic Committee.[17]

  1. ^ a b c d e f g h i Thomas EJ, Rock J (6 December 2012). Modern Approaches to Endometriosis. Springer Science & Business Media. pp. 228, 232, 234. ISBN 978-94-011-3864-2.
  2. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  3. ^ Coutinho EM (1990). "Therapeutic experience with gestrinone". Prog. Clin. Biol. Res. 323: 233–40. PMID 2406749.
  4. ^ Cite error: The named reference MortonHall1999 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference pmid15589885 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference pmid14717620 was invoked but never defined (see the help page).
  7. ^ a b Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  8. ^ a b Cite error: The named reference Carp2015 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference DesaiPatel2012 was invoked but never defined (see the help page).
  10. ^ a b Cite error: The named reference BlackwellOlive2012 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference Berek2007 was invoked but never defined (see the help page).
  12. ^ Carp HJ (9 April 2015). Progestogens in Obstetrics and Gynecology. Springer. pp. 141–. ISBN 978-3-319-14385-9.
  13. ^ Bromham DR, Booker MW, Rose GL, Wardle PG, Newton JR (1995). "A multicentre comparative study of gestrinone and danazol in the treatment of endometriosis". Journal of Obstetrics and Gynaecology. 15 (3): 188–194. doi:10.3109/01443619509015498. ISSN 0144-3615.
  14. ^ Cite error: The named reference AcademicPress1988 was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference Index Nominum2000 was invoked but never defined (see the help page).
  16. ^ Cite error: The named reference LedgerSchlaff2014 was invoked but never defined (see the help page).
  17. ^ "Helping athletes compete drug-free" (PDF). Canadian Centre for Ethics in Sport. May 2000. p. 34. Archived from the original (PDF) on 2006-05-17. Retrieved 2006-06-01.
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