Norethisterone acetate
Systematic (IUPAC) name | |
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(8R,9S,10R,13S,14S,17S)-17-ethynyl-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate
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Clinical data | |
AHFS/Drugs.com | International Drug Names |
MedlinePlus | a604034 |
Legal status |
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Routes of administration |
Oral tablet |
Identifiers | |
CAS Number | 38673-38-0 |
PubChem | CID: 63021 |
ChemSpider | 5627 |
ChEBI | CHEBI:7628 |
ChEMBL | CHEMBL1201146 |
Chemical data | |
Formula | C22H28O3 |
Molecular mass | 340.456 g/mol |
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Norethisterone acetate (INN, BAN), also known as norethindrone acetate (USAN), sold under brand names including Aygestin, Gestakadin, Milligynon, Monogest, Norlutate (Canada, USA distributed by ERFA Canada 2012 Inc.[1]), Primolut (Fr., Ger., Swed.), Sovel, Styptin, and others, is a steroidal progestin with additional antigonadotropic (and hence antiandrogen and antiestrogen)[2] effects that is used as a hormonal contraceptive.[3][4] It is an acetate ester of norethisterone.[5] Norethindrone acetate is indicated for abnormal uterine bleedings.[6]
Synthesis
Reaction of norethindrone (1) with acetic anhydride in the presence of p-toluene sulfonic acid, affords norethindrone acetate (2).[7] This in turn affords, on reaction with exess cyclopentanol in the presence of excess phosphorus pentoxide, the 3-cyclopentyl enol ether (3),[8] the progestational component of Riglovic®.
See also
References
- ↑ http://www.eci2012.net/
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- ↑ Norethisterone Acetate @ Drugs.com
- ↑ http://www.drugs.com/ppa/norethindrone-acetate.html
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- Antiandrogens
- Antiestrogens
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