Compound: Norethindrone acetate
SMILES: O=C1C=C2[C@@H]([C@@H]3[C@H]([C@H]4[C@]([C@](OC(=O)C)(C#C)CC4)(C)CC3)CC2)CC1
InChIKey: IMONTRJLAWHYGT-ZCPXKWAGSA-N
Synonyms: Norethindrone acetate, Norethisterone acetate, 51-98-9, 19-Norethindrone acetate, Norlutin acetate, ENTA, Norethisteron acetate, 19-Norethisterone acetate, Norethindrone 17-acetate, 19-Norethynyltestosterone acetate, (17-alpha)-Norethindrone acetate, Norethynyltestosterone, 17alpha-Ethynyl-19-nortestosterone acetate, Norethisterone 17-acetate, 17-alpha-Ethinyl-19-nortestosterone acetate, 17-alpha-Ethynyl-19-nortestosterone acetate, 9S44LIC7OJ, Norethindrone acetate [USP], NSC-22844, SH-420, Norethisteroni acetas, 17alpha-Ethinyl-19-nortestosterone 17beta-acetate, 17alpha-Ethinyl-19-nortestosterone-17beta-acetate, DTXSID4023381, 17alpha-Ethynyl-17-hydroxyestr-4-en-3-one acetate, 17-alpha-Ethinyl-19-nortestosterone-17-beta-acetate, 17-alpha-Ethynyl-17-hydroxyestr-4-en-3-one acetate, 17-Acetoxy-19-nor-17alpha-pregn-4-en-20-yn-3-one, 17-Acetoxy-19-nor-17-alpha-pregn-4-en-20-yn-3-one, 17alpha-Ethynyl-17beta-acetoxy-19-norandrost-4-en-3-one, 17beta-Acetoxy-19-nor-17alpha-pregn-4-en-20-yn-3-one, [(8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate, 17-Hydroxy-19-nor-17-alpha-pregn-4-en-20-yn-3-one acetate, 17beta-Hydroxy-19-nor-17alpha-pregn-4-en-20-yn-3-one acetate, Norethindrone acetate (USP), 17-Acetyloxy(17-alpha)-19-norpregn-4-estren-17-beta-ol-acetate-3-one, CHEBI:7628, DTXCID601071, FEMLYV COMPONENT NORETHINDRONE ACETATE, ORIAHNN COMPONENT NORETHINDRONE ACETATE, MYFEMBREE COMPONENT NORETHINDRONE ACETATE, Gallifrey, Ortho Micronor, ((8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta(a)phenanthren-17-yl) acetate, Norethidrone Acetate, RefChem:55726, Estr-4-en-3-one, 17-(acetyloxy)-17-ethynyl-, (17beta)-, 200-132-0, NSC9564, Norlutate, Orlutate, Primolut-Nor, Aygestin, Norethysterone acetate, Norethynyltestosterone acetate, Norlutin A, Norlutine acetate, MFCD00271615, SH 420, Milligynon, Miniphase, Progylut, 17-Hydroxy-19-nor-17alpha-pregn-4-en-20-yn-3-one acetate, Milli-Anovlar, Norlutin-A, (17alpha)-17-(Acetyloxy)-19-Norpregn-4-en-20-yn-3-one, Gestakadin, Monogest, NSC 22844, 17.alpha.-Ethynyl-19-nortestosterone acetate, Norethisterone acetate (JAN), NORETHISTERONE ACETATE [JAN], (1S,11S,15S,2R,10R,14R)-14-ethynyl-15-methyl-5-oxotetracyclo[8.7.0.0<2,7>.0<11 ,15>]heptadec-6-en-14-yl acetate, CCRIS 485, Ethinyl-nortestosterone acetate, EINECS 200-132-0, UNII-9S44LIC7OJ, BRN 2064104, SH-420C, NCGC00183366-01, Aygestin (TN), norethindrone-acetate, 17.alpha.-Ethinyl-19-nortestosterone acetate, 19-nor-17alpha-Pregn-4-en-20-yn-3-one, 17-acetoxy-, Estr-4-en-3-one, 17alpha-ethynyl-17-hydroxy-, acetate, (17-alpha)-17-(Acetyloxy)-19-norpregn-4-en-20-yn-3-one, 17-alpha-Ethynyl-17-beta-acetoxy-19-norandrost-4-en-3-one, 19-Nor-17alpha-ethynyltestosterone Acetate, Norethisterone acetate RS, Norethisterone acetate CRS, Norethisterone acetate (Norethindrone acetate), 17-Acetoxy-19-nor-17.alpha.-pregn-4-en-20-yn-3-one, 17.alpha.-Ethinyl-19-nortestosterone 17.beta.-acetate, 19-nor-17.alpha.-Pregn-4-en-20-yn-3-one, 17-acetoxy-, SCHEMBL37530, 17-Hydroxy-19-nor-17.alpha.-pregn-4-en-20-yn-3-one acetate, 17.beta.-Acetoxy-19-nor-17.alpha.-pregn-4-en-20-yn-3-one, (17beta)-17-ethynyl-3-oxoestr-4-en-17-yl acetate, orb1690485, orb3139940, 17-Acetyloxy(17.alpha.)-19-norpregn-4-estren-17.beta.-ol-acetate-3-one, 17.beta.-Hydroxy-19-nor-17.alpha.-pregn-4-en-20-yn-3-one acetate, CHEMBL1201146, Norethindrone acetate (Standard), HY-B1710R, 19-Nor-17-alpha-pregn-4-en-20-yn-3-one, 17-acetoxy-, MSK2204, WLZ4548, HMS3259A16, NORETHINDRONE ACETATE [MI], 19-Nor-17alpha-pregn-4-en-20-yn-3-one, 17-hydroxy-, acetate, 19-Norpregn-4-en-20-yn-3-one, 17-(acetyloxy)-, (17alpha), HY-B1710, NSC22844, Tox21_113371, MSK2204-100M, NORETHINDRONE ACETATE [VANDF], s5785, AKOS016010517, MSK2204-1000M, NORETHINDRONE ACETATE [USP-RS], NORETHISTERONE ACETATE [MART.], CS-7730, FN26444, NC00575, NORETHISTERONE ACETATE [WHO-DD], NORETHISTERONE ACETATE [WHO-IP], 17?-Ethynyl-19-nortestosterone acetate, CAS-51-98-9, NCGC00159500-02, NCGC00183366-07, AS-13383, CPD001906776, ST075199, SY076006, NORETHINDRONE ACETATE [ORANGE BOOK], FEMHRT COMPONENT NORETHINDRONE ACETATE, N0450, NORETHINDRONE ACETATE [USP MONOGRAPH], NORETHISTERONE ACETATE [EP MONOGRAPH], NORETHISTERONI ACETAS [WHO-IP LATIN], ACTIVELLA COMPONENT NORETHINDRONE ACETATE, C08152, D00953, T72561, COMBIPATCH COMPONENT NORETHINDRONE ACETATE, Norethisterone acetate for system suitability CRS, ESTROSTEP FE COMPONENT NORETHINDRONE ACETATE, TRI-LEGEST FE COMPONENT NORETHINDRONE ACETATE, 17.alpha.-Ethynyl-17-hydroxyestr-4-en-3-one acetate, 19-Nor-17.alpha.-pregn-4-en-20-yn-3-one, acetate, BRD-K96037667-001-01-4, LO LOESTRIN FE COMPONENT NORETHINDRONE ACETATE, Norethisterone acetate Solution in Methanol, 100ug/mL, Q47495694, 17.alpha.-Ethinyl-19-nortestosterone-17.beta.-acetate, 3-Oxo-17alpha-19-norpregn-4-en-20-yn-17-yl acetate, Norethisterone acetate Solution in Methanol, 1000ug/mL, WLN: L E5 B666 OV MUTJ E FOV1 F1UU1 -B&EF, (17?)-17-(Acetyloxy)-19-norpregn-4-en-20-yn-3-one, (17|_)-17-(Acetyloxy)-19-norpregn-4-en-20-yn-3-one, (17alpha)-3-oxo-19-norpregn-4-en-20-yn-17-yl acetate, 17.alpha.-Ethynyl-17.beta.-acetoxy-19-norandrost-4-en-3-one, 19-Norethindrone acetate, VETRANAL(TM), analytical standard, Norethindrone acetate, United States Pharmacopeia (USP) Reference Standard, Norethisterone acetate, European Pharmacopoeia (EP) Reference Standard, Norethisterone acetate for system suitability, European Pharmacopoeia (EP) Reference Standard, (8R,9S,10R,13S,14S,17R)-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
Theoretical properties:
molecular_formula: C22H28O3
molecular_weight: 340.5 g/mol
exact_mass: 340.20384475 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 3
heavy_atom_count: 25
topological_polar_surface_area: 43.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Norethisterone Acetate (Norethindrone Acetate) can cause developmental toxicity according to state or federal government labeling requirements.
chebi: A 3-oxo Δ<small><sup>4</small></sup>-steroid that is norethisterone in which the hydroxy group has been converted to its acetate ester.
chembl: NORETHINDRONE ACETATE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: 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 is 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.