Structure via PubChem · Public domain (PubChem)
gestrinone
Sign in to saveAlso known as Tridomose, 13-Ethyl-17-hydroxy-18,19-Dinor-17a-pregna-4,9,11-trien-20-yn-3-one, Gestrinona, Dimetriose, Ethylnorgestrienone, (17a)-13-ethyl-17-hydroxy-18,19-Dinorpregna-4,9,11-trien-20-yn-3-one, 13-Ethyl-17a-ethynyl-17b-hydroxygona-4,9,11-trien-3-one, Gestrigone
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.
Chemical data
- Formula
- C21H24O2
- Molecular weight
- 308.4 g/mol
- 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
- SMILES
- CC[C@]12C=CC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@]2(C#C)O
- InChIKey
- BJJXHLWLUDYTGC-ANULTFPQSA-N
- XLogP
- 2.2
- Polar surface area
- 37.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
299 papers- Effects, Doses, and Applicability of Gestrinone in Estrogen-Dependent Conditions and Post-Menopausal Women.Pharmaceuticals (Basel, Switzerland) · 2024
- Safety Profile of Gestrinone: A Systematic Review.Pharmaceutics · 2025
- Evaluation of safety and effectiveness of gestrinone in the treatment of endometriosis: a systematic review and meta-analysis.Archives of gynecology and obstetrics · 2023
- Lack of Scientific Evidence for the Use of Gestrinone in the Treatment of Lipedema: A Systematic Review.Cureus · 2025
- Repurposing gestrinone for tumor suppressor through P21 reduction regulated by JNK in gynecological cancer.Translational research : the journal of laboratory and clinical medicine · 2022
via PubMed
Wikidata facts
- Mass
- 308.178
Show 6 more facts
- defined daily dose
- 0.7
- chemical formula
- C₂₁H₂₄O₂
- canonical SMILES
- CCC12C=CC3=C4CCC(=O)C=C4CCC3C1CCC2(C#C)O
- isomeric SMILES
- CC[C@]12C=CC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@]2(C#C)O
- subject has role
- oral contraceptive
- Commons category
- Gestrinone
Sources (3)
via Wikidata · CC0
~7 min read
Encyclopedic overview
14 sectionsContents
- Medical uses
- Contraindications
- Side effects
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Generic names
- Brand names
- Availability
- References
- Further reading
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.
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.
Excerpted from Wikipedia’s “gestrinone” article, available under the CC BY-SA 4.0 licence.