Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00478)
Name
Norethindrone
Synonyms    Click to Show/Hide the Synonyms of This API
norethindrone; Norethisterone; 68-22-4; Micronor; 19-Norethisterone; Norethisteron; Norcolut; Noriday; Norlutin; Primolut-N; Norethynodrone; Conludag; Micronovum; Norluten; Camila; Utovlan; Mini-pill; Mini-Pe; Noresthisterone; Conludaf; Micronett; Noralutin; Norethyndron; Norgestin; Norluton; Proluteasi; Anovule; Gestest; Norfor; Utovlar; Norpregneninlone; 19-Nor-ethindrone; Nor-QD; Ethinylnortestosterone; Norethisteronum; Noretisterona; 17alpha-Ethynyl-19-nortestosterone; Ethynylnortestosterone; 19-Nor-17alpha-ethynyltestosterone; 17alpha-Ethinyl-19-nortestosterone; Anhydrohydroxynorprogesterone; Minovlar; Nor-Q.D.; 19-Norethinyltestosterone; Norpregneninolone; Ethinyl-19-nortestosterone; Normapause; Menzol; 17alpha-Ethynyl-4-estren-17-ol-3-one; 17-alpha-Ethynyl-19-nortestosterone; 19-Nor-17-alpha-ethynyltestosterone; 19-Norethindrone; 19-Nor-17-ethinyltestosterone; 17alpha-Ethinylestra-4-en-17beta-ol-3-one; 17beta-Hydroxy-19-norpregn-4-en-20-yn-3-one; 17-alpha-Ethynyl-4-estren-17-ol-3-one; 19-Nor-17alpha-ethynyl-17beta-hydroxy-4-androsten-3-one; 17alpha-Ethynyl-17-hydroxy-4-estren-3-one; Activella; 19-nor-17alpha-Ethynylandrosten-17beta-ol-3-one; 4-Estren-17alpha-ethynyl-17beta-ol-3-one; NSC-9564; 17alpha-Ethynyl-19-norandrost-4-en-17beta-ol-3-one; 17-Hydroxy-19-nor-17alpha-pregn-4-en-20-yn-3-one; 17-alpha-Ethynyl-17-hydroxy-4-estren-3-one; 17alpha-Ethynyl-17beta-hydroxy-19-norandrost-4-en-3-one; Norethindrone (Norethisterone); UNII-T18F433X4S; 17-beta-Hydroxy-19-norpregn-4-en-20-yn-3-one; Norethindrone (USP); Norethindrone [USP]; Primolut N; 19-Nor-17-alpha-ethynylandrosten-17-beta-ol-3-one; 17-ethynyl-17beta-hydroxyestr-4-en-3-one; 17-alpha-Ethynyl-19-norandrost-4-en-17-beta-ol-3-one; 17-Hydroxy-19-nor-17-alpha-pregn-4-en-20-yn-3-one; Anovulatorio; Ciclovulan; Microneth; Norethadrone; Norethynodron; 19-Nor-17-alpha-ethynyl-17-beta-hydroxy-4-androsten-3-one; Estrinor; Gencept; Norethin; Synphase; Triella; Genora; Nelova; Nodiol; Noraethisteronum; Norpregneninotone; CHEMBL1162; Combipatch; Norcept-E; 17alpha-Ethynyl-19-nor-4-androsten-17beta-ol-3-one; Synphasic 28; (17-alpha)-17-Hydroxy-19-norpregn-4-en-20-yn-3-one; Brevinor 21; Brevinor 28; CHEBI:7627; Trinovum 21; Noriday 28; Jenest-28; Ethynylmortestosterone; Brevinor-1 21; Brevinor-1 28; T18F433X4S; Tri-Norinyl; Ovysmen 1 35; Noretisterone [DCIT]; Ortho-Novum 1 35; Ortho-Novum 1 50; SC 4640; Ortho-Novum 7 7 7; Ovysmen 0.5 35; Ortho 1 35; Ortho 7 7 7; Noretisterone; 19-Nortestosterone, 17-ethynyl-; Norethisteronum [INN-Latin]; Noretisterona [INN-Spanish]; DSSTox_CID_3380; DSSTox_RID_77005; 17alpha-hydroxy-19-norpregn-4-en-20-yn-3-one; DSSTox_GSID_23380; Nora-BE; Norethisterone [Progestins]; 19-Norpregn-4-en-20-yn-3-one, 17-hydroxy-, (17alpha)-; (14beta,17alpha)-17-Ethynyl-17-Hydroxyestr-4-En-3-One; Norethindirone; 17-Ethinyl-19-nortestosterone; (17alpha)-17-ethynyl-17-hydroxyestra-4,8(14),9-trien-3-one; 19-Nor-17alpa-ethynyltestosterone; Micronor (TN); SMR000499579; CCRIS 484; norethisterone (norethindrone); Primolut-N (TN); Camila (TN); N.E.E.; 19-Nor-17-ethinyl testosterone; HSDB 3370; 19-Nor-ethinyl--4,5-testosterone; EINECS 200-681-6; BRN 1915671; AI3-26422; 17-alpha-Ethinylestra-4-en-17-beta-ol-3-one; CAS-68-22-4; Estr-4-en-3-one, 17alpha-ethynyl-17-hydroxy-; NCGC00094738-01; Prestwick_646; Norethisterone [INN]; 17-alpha-19-Norpregn-4-en-20-yn-3-one, 17-hydroxy-; 17alpha-Ethinyl-17beta-hydroxy-delta(sup:4)-estren-3-one; 19-Nor-17alpha-pregn-4-en-20-yn-3-one, 17-hydroxy-; 17-alpha-Ethinyl-17-beta-hydroxy-delta(sup:4)-estren-3-one; 17-alpha-Ethynyl-17-beta-hydroxy-19-norandrost-4-en-3-one; Norethisterone (JP17); Prestwick0_000253; Prestwick1_000253; Prestwick2_000253; Prestwick3_000253; EC 200-681-6; SCHEMBL23390; BSPBio_000066; Levonorgestrel EP Impurity U; MLS001076679; MLS001163874; ARONIS24281; Norethisterone / norethindrone; SPBio_002285; BPBio1_000074; GTPL2880; 17-Ethynyl-19-Nortestosterone; (17alpha)-17-hydroxy-19-norpregn-4-en-20-yn-3-one; DTXSID9023380; 17-Ethinyl-19-nor-testosterone; 19-Nor-17-alpha-pregn-4-en-20-yn-3-one, 17-hydroxy-; HMS1568D08; HMS2090D21; HMS2095D08; HMS2231E18; HMS3259C16; HMS3712D08; BCP28306; HY-B0554; 17alpha-pregn-4-en-20-yn-3-one; Tox21_111322; Tox21_302427; 19-Norethindrone, >=98%, powder; BDBM50148732; LMST02030097; MFCD00067596; ZINC85205451; AKOS005267172; Tox21_111322_1; CCG-220253; DB00717; MCULE-9156628994; NC00576; SC-4640; NCGC00179669-01; NCGC00179669-02; NCGC00179669-04; NCGC00255187-01; AC-11100; AC-33117; AS-56451; CPD000499579; 17alpha-Ethynyl-17-hydroxyest-4-en-3-one; 17alpha-Ethynyl-3-oxo-4-estren-17beta-ol; 17alpha-ethynyl-17-hydroxy-Estr-4-en-3-one; Norethisterone 100 microg/mL in Acetonitrile; C05028; D00182; 17alpha-Ethynyl-17beta-hydroxyestr-4-en-3-one; 17beta-Hydroxy-17alpha-ethynylestr-4-en-3-one; 067N596; 17-alpha-Ethynyl-17-beta-hydroxy-4-estren-3-one; Q421352; SR-01000765382; 17alpha-Ethinyl-17alpha-Ethinyl-19-nortestosterone; SR-01000765382-3; W-104686; 13-methyl-17alpha-ethynyl-17-hydroxygon-4-en-3-one; 17-Hydroxy-17-alpha-19-norpregn-4-en-20-yn-3-one; 17-Hydroxy-19-nor-17alpha-4-pregnen-20-yn-3-one; 17-hydroxy-19-nor-17alpha-pregn-4-en-20yn-3-one; 19-Nor-17alpha-ethynyl-4-androsten-17beta-ol-3-one; 19-Norethindrone, VETRANAL(TM), analytical standard; BRD-K92073408-001-03-3; BRD-K92073408-001-16-5; 17-Hydroxy-(17alpha)-19-Norpregn-4-en-20-yn-3-one; 17-Ethynyl-17-hydroxyestr-4-en-3-one (ACD/Name 4.0); 17alpha-Ethynyl-17beta-hydroxy-19-nor-4-androsten-3-one; Norethisterone, British Pharmacopoeia (BP) Reference Standard; Norethisterone, European Pharmacopoeia (EP) Reference Standard; 19-Nor-17alpha-pregn-4-en-20-yn-3-one, 17-hydroxy- (8CI); Norethindrone, United States Pharmacopeia (USP) Reference Standard
Clinical Status
Approved
Disease Indication Contraception ICD-11: JA65 [1]
PubChem CID
6230
Formula
C20H26O2
Canonical SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34
InChI
1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1
InChIKey
VIKNJXKGJWUCNN-XGXHKTLJSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=6230"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 298.4 Topological Polar Surface Area 37.3
XlogP 3 Complexity 594
Heavy Atom Count 22 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Full List of Drug Formulations (DFMs) Containing This API
          Norethindrone 0.35 mg tablet Click to Show/Hide the Full List of Formulation(s):          2 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Anhydrous lactose; D&c yellow no. 10; Magnesium stearate; Talc; Silicon dioxide; Cellulose, microcrystalline; Ethylcelluloses; Povidones; Starch, corn
                   Dosage Form Oral Tablet
                   Company A-S Medication Solutions
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Fd&c yellow no. 6; Magnesium stearate; Povidones; Starch, corn
                   Dosage Form Oral Tablet
                   Company Central Texas Community Health Centers
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
          Norethindrone 5 mg tablet Click to Show/Hide the Full List of Formulation(s):          5 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Talc; Silicon dioxide; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Avera McKennan Hospital; Glenmark Pharmaceutials; Kaiser Foundation Hospitals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Anhydrous lactose; Magnesium stearate; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Barr Laboratories; Kaiser Foundation Hospitals; Teva Women's Health
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 3 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Anhydrous lactose; Magnesium stearate; Cellulose, microcrystalline; Methylene chloride
                   Dosage Form Oral Tablet
                   Company Aurobindo Pharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 4 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose; Magnesium stearate; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company AvKARE; AvPAK
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 5 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose, unspecified form; Magnesium stearate; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Amneal Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
References
1 FDA label for approved norethindrone from the official website of the U.S. Food and Drug Administration.
2 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
3 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
4 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.

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