Structure via PubChem · Public domain (PubChem)
norethisterone
Sign in to saveAlso known as Micronor®, Noriday®, 19-Nor-17alpha-ethynyl-17beta-hydroxy-4-androsten-3-one, 19-Norethisterone, 17alpha-ethynyl-19-nor-4-androsten-17beta-ol-3-one, 19-nor-17alpha-ethynyltestosterone, Primolut-N, Micronor
Norethisterone, also known as norethindrone and sold under the brand name Norlutin among others, is a progestin medication used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders. The medication is available in both low-dose and high-dose formulations and both alone and in combination with an estrogen. It is used by mouth or, as norethisterone enanthate, by injection into muscle.
Chemical data
- Formula
- C20H26O2
- Molecular weight
- 298.4 g/mol
- IUPAC name
- (8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
- SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34
- InChIKey
- VIKNJXKGJWUCNN-XGXHKTLJSA-N
- XLogP
- 3
- Polar surface area
- 37.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
5,716 papers- Relugolix/Estradiol/Norethisterone Acetate: A Review in Endometriosis-Associated Pain.Drugs · 2024
- Relugolix/Estradiol/Norethisterone (Norethindrone) Acetate: A Review in Symptomatic Uterine Fibroids.Drugs · 2022
- Norethisterone.Report on carcinogens : carcinogen profiles · 2011
- Norethisterone and norethisterone acetate.IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans · 1979
- Norethisterone acetate in combination with estrogen: effects on the skeleton and other organs. A review.American journal of obstetrics and gynecology · 2002
via PubMed
~32 min read
Encyclopedic overview
36 sectionsContents
- Medical uses
- Contraindications
- Side effects
- Androgenic
- Estrogenic
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Progestogenic activity
- Androgenic activity
- Estrogenic activity
- Neurosteroid activity
- Steroidogenesis inhibition
- Other activities
- Antigonadotropic effects
- Pharmacokinetics
- Absorption
- Distribution
- Metabolism
- Elimination
- Chemistry
- Derivatives
- Non-17α-ethynylated
- Synthesis
- Synthesis 1
- Synthesis 2
- History
- Society and culture
- Generic names
- Brand names
- Availability
- United States
- Research
- References
- Further reading
Norethisterone, also known as norethindrone and sold under the brand name Norlutin among others, is a progestin medication used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders. The medication is available in both low-dose and high-dose formulations and both alone and in combination with an estrogen. It is used by mouth or, as norethisterone enanthate, by injection into muscle.
Side effects of norethisterone include menstrual irregularities, headaches, nausea, breast tenderness, mood changes, acne, increased hair growth. Norethisterone 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 weak androgenic and estrogenic activity, mostly at high dosages, and no other important hormonal activity.
Excerpted from Wikipedia’s “norethisterone” article, available under the CC BY-SA 4.0 licence.