Structure via PubChem · Public domain (PubChem)
dimethisterone
Sign in to saveAlso known as Dimethisterone anhydrous
Dimethisterone, formerly sold under the brand names Lutagan and Secrosteron among others, is a progestin medication which was used in birth control pills and in the treatment of gynecological disorders but is now no longer available. It was used both alone and in combination with an estrogen. It is taken by mouth.
Chemical data
- Formula
- C23H32O2
- Molecular weight
- 340.5 g/mol
- IUPAC name
- (6S,8R,9S,10R,13S,14S,17S)-17-hydroxy-6,10,13-trimethyl-17-prop-1-ynyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
- SMILES
- CC#C[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C[C@@H](C4=CC(=O)CC[C@]34C)C)C)O
- InChIKey
- LVHOURKCKUYIGK-RGUJTQARSA-N
- XLogP
- 4.4
- 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
103 papers- Dimethisterone.Medicamentos de actualidad. Drugs of today · 1968
- Dimethisterone.IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans · 1979
- Autoxidation of dimethisterone.Steroids · 1970
- Steroids.Chemical week · 1969
- Antifertility agents.Annual review of pharmacology · 1967
via PubMed
Wikidata facts
- Mass
- 340.24
Show 4 more facts
- chemical formula
- C₂₃H₃₂O₂
- canonical SMILES
- CC#CC1(CCC2C1(CCC3C2CC(C4=CC(=O)CCC34C)C)C)O
- isomeric SMILES
- CC#C[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C[C@@H](C4=CC(=O)CC[C@]34C)C)C)O
- Commons category
- Dimethisterone
Sources (2)
via Wikidata · CC0
~4 min read
Encyclopedic overview
11 sectionsContents
- Medical uses
- Side effects
- Pharmacology
- Pharmacodynamics
- Chemistry
- Synthesis
- History
- Society and culture
- Generic names
- Brand names
- References
Dimethisterone, formerly sold under the brand names Lutagan and Secrosteron among others, is a progestin medication which was used in birth control pills and in the treatment of gynecological disorders but is now no longer available. It was used both alone and in combination with an estrogen. It is taken by mouth.
Side effects of dimethisterone are similar to those of other progestins. When used in combination with high doses of an estrogen, an increased risk of endometrial cancer can occur. Dimethisterone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has some antimineralocorticoid activity and no other important hormonal activity.
Excerpted from Wikipedia’s “dimethisterone” article, available under the CC BY-SA 4.0 licence.