Norethisterone acetate

Norethisterone acetate
Clinical data
Trade names	Primolut-Nor, Aygestin, Gestakadin, Milligynon, Monogest, Norlutate, Primolut N, SH-420, Sovel, Styptin, others
Other names	NETA; NETAc; Norethindrone acetate; SH-420; 17α-Ethynyl-19-nortestosterone 17β-acetate; 17α-Ethynylestra-4-en-17β-ol-3-one 17β-acetate
AHFS/Drugs.com	International Drug Names
MedlinePlus	a604034
Routes of; administration	By mouth
Drug class	Progestogen; Progestin; Progestogen ester
ATC code	G03AC01 (WHO) ;
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;
CAS Number	38673-38-0 ;
PubChem CID	5832;
DrugBank	DBSALT000129 ;
ChemSpider	5627 ;
UNII	9S44LIC7OJ;
KEGG	D00953;
ChEBI	CHEBI:7628 ;
ChEMBL	ChEMBL1201146 ;
CompTox Dashboard (EPA)	DTXSID4023381 ;
ECHA InfoCard	100.000.121
Chemical and physical data
Formula	C22H28O3
Molar mass	340.463 g·mol−1
3D model (JSmol)	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 ; Key:IMONTRJLAWHYGT-ZCPXKWAGSA-N ;
	(verify)

Norethisterone acetate (NETA), also known as norethindrone acetate and sold under the brand name Primolut-Nor among others, is a progestin medication which is used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders. The medication available in low-dose and high-dose formulations and is used alone or in combination with an estrogen. It is ingested orally.

Side effects of NETA include menstrual irregularities, headaches, nausea, breast tenderness, mood changes, acne, increased hair growth, and others. NETA 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 and no other important hormonal activity. The medication is a prodrug of norethisterone in the body.

NETA was patented in 1957 and was introduced for medical use in 1964. It is sometimes referred to as a "first-generation" progestin. NETA is marketed widely throughout the world. It is available as a generic medication.

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