Gestrinone

Gestrinone, sold under the brand names Dimetrose and Nemestran among others, is a medication which is used in the treatment of endometriosis. 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. Gestrinone is used alone and is not formulated in combination with other medications. It is taken by mouth or in through the vagina.

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
Drug classProgestogen; Progestin; Antiprogestogen; Androgen; Anabolic steroid; Steroidogenesis inhibitor; Antiestrogen
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein bindingTo albumin
MetabolismLiver (hydroxylation)
Elimination half-life27.3 hours
ExcretionUrine and bile
Identifiers
  • (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=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)

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. 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.

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

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