Norethisterone acetate

Norethisterone acetate
Clinical data


Trade names	Primolut-Nor, Aygestin, Gestakadin, Milligynon, Monogest, Norlutate, Primolut N, SH-420, Sovel, Styptin
AHFS/Drugs.com	International Drug Names
MedlinePlus	a604034
Routes of administration	Oral
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name (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
Synonyms	SH-420
CAS Number	38673-38-0^Y
PubChem CID	5832
ChemSpider	5627^N
ChEBI	CHEBI:7628^N
ChEMBL	CHEMBL1201146^N
Chemical and physical data
Formula	C₂₂H₂₈O₃
Molar mass	340.456 g/mol
3D model (Jmol)	Interactive image
SMILES CC(=O)O[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@H]34)C)C#C
InChI InChI=1S/C22H28O3/c1-4-22(25-14(2)23)12-10-20-19-7-5-15-13-16(24)6-8-17(15)18(19)9-11-21(20,22)3/h1,13,17-20H,5-12H2,2-3H3/t17-,18+,19+,20-,21-,22-/m0/s1^N Key:IMONTRJLAWHYGT-ZCPXKWAGSA-N^N
^NY (what is this?)

Norethisterone acetate (NETA) (INN, BAN), also known as norethindrone acetate (USAN), sold under brand names including Primolut-Nor (major), Aygestin (US), Gestakadin, Milligynon, Monogest, Norlutate (US, CA), Primolut N, SH-420 (UK), Sovel, Styptin, and others, is a steroidal progestin of the 19-nortestosterone group with additional weak androgenic and estrogenic activity that is used orally as a hormonal contraceptive, in the treatment of gynecological disorders such as abnormal uterine bleeding, and as a component of hormone replacement therapy for menopause. It is the 17β-acetate ester of norethisterone, and acts as a prodrug to norethisterone in the body.

Upon oral ingestion, NETA is rapidly converted into norethisterone by esterases during intestinal and first-pass hepatic metabolism. Hence, it is a prodrug of norethisterone in the body. As such, NETA is a potent progestogen with additional weak androgenic and estrogenic activity (the latter via its metabolite ethinylestradiol).