Drug Information
| Drug General Information | Top | |||
|---|---|---|---|---|
| Drug ID |
D0GL7U
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| Former ID |
DAP001212
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| Drug Name |
Norethindrone
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| Synonyms |
Activella; Anhydrohydroxynorprogesterone; Anovulatorio; Anovule; Brevicon; Brevinor; Camila; Ciclovulan; Conceplan;Conludaf; Conludag; Demulen; Errin; Estrinor; Ethinylnortestosterone; Ethynylmortestosterone; Ethynylnortestosterone; Gencept; Genora; Gestest; Jenest; Loestrin; Menzol; Microneth; Micronett; Micronor; Micronovum; Milli; Minovlar; Nelova; Nodiol; Noraethisteronum; Noralutin; Norcept; Norcolut; Norcolute; Noresthisterone; Norethadrone; Norethin; Norethindirone; Norethisteron; Norethisterone; Norethisteronum; Norethyndron; Norethynodron; Norethynodrone; Noretisterona; Noretisterone; Norfor; Norgestin; Noriday; Norluten; Norlutin; Norluton; Normapause; Norpregneninlone; Norpregneninolone; Norpregneninotone; Orlest; Proluteasi; Synphase; Triella; Utovlan; Utovlar; Component of Noriday; Norethindrone Norethisterone; Norethindrone [USAN]; Norethisterone [Progestins]; Noretisterone [DCIT]; Primolut N; Brevinor 21; Brevinor 28; Noriday 28; Ortho 1 35; Ortho 7 7 7; Ovysmen 1 35; SC 4640; Synphasic 28; Trinovum 21; Brevinor-1 21; Brevinor-1 28; Camila (TN); Jenest-28; Micronor (TN); Mini-Pe; Mini-pill; Nor-QD; Nora-BE; Norcept-E; Norethin 1/35 E; Norethin 1/50 M; Norethindrone (USP); Norethisterone (JP15); Norethisteronum [INN-Latin]; Noretisterona [INN-Spanish]; Ortho-Novum 1 35; Ortho-Novum 1 50; Ortho-Novum 7 7 7; Ovysmen 0.5 35; Primolut-N; Tri-Norinyl; Ethinyl-19-nortestosterone; Nor-Q.D; Primolut-N (TN); Nor-Q.D.; 17-Ethinyl-19-nortestosterone; 17-Ethynyl-17-hydroxyestr-4-en-3-one; 17-alpha-Ethynyl-19-nortestosterone; 17-alpha-Ethynyl-4-estren-17-ol-3-one; 17-ethynyl-17beta-hydroxyestr-4-en-3-one; 17.alpha.-Ethinyl-19-nortestosterone; 17.alpha.-Ethynyl-19-nortestosterone; 17.alpha.-Ethynyl-4-estren-17-ol-3-one; 17alpha-Ethinyl-19-nortestosterone; 17alpha-Ethynyl-19-nortestosterone; 17alpha-Ethynyl-4-estren-17-ol-3-one; 19-Nor-17-alpha-ethynyltestosterone; 19-Nor-17-ethinyltestosterone; 19-Nor-17.alpha.-ethynyltestosterone; 19-Nor-17alpa-ethynyltestosterone; 19-Nor-17alpha-ethynyltestosterone; 19-Nor-ethindrone; 19-Nor-ethinyl-4,5-testosterone; 19-Norethindrone; 19-Norethinyltestosterone; 19-Norethisterone; 4-Estren-17alpha-ethynyl-17beta-ol-3-one
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| Drug Type |
Small molecular drug
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| Indication | Solid tumour/cancer [ICD-11: 2A00-2F9Z; ICD-10: C76-C80; ICD-9: 140-229] | Approved | [1] | |
| Therapeutic Class |
Contraceptive Agents
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| Company |
Parke Davis Div Warner Lambert Co
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| Structure |
 |
Download2D MOL |
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| Formula |
C20H26O2
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| Canonical SMILES |
CC12CCC3C(C1CCC2(C#C)O)CCC4=CC(=O)CCC34
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| 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
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| InChIKey |
VIKNJXKGJWUCNN-XGXHKTLJSA-N
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| CAS Number |
CAS 68-22-4
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| PubChem Compound ID | ||||
| PubChem Substance ID |
7499, 7847250, 7980169, 8153912, 10321609, 11466281, 11467401, 11486021, 12146103, 14873691, 14873694, 24702322, 24870259, 24897669, 25621785, 29225226, 46504816, 47440543, 47736755, 48185240, 48259494, 48416339, 49647479, 49648521, 49698406, 49998430, 50124391, 50139262, 53788259, 56313695, 57581168, 57650825, 77234545, 85788451, 87573784, 92125032, 92309077, 92710502, 103338617, 103914098, 104036985, 104170074, 104311472, 115354325, 121362406, 121362703, 124799740, 124893626, 126603566, 126631815
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| ChEBI ID |
CHEBI:7627
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| ADReCS Drug ID | BADD_D01585 ; BADD_D02427 | |||
| SuperDrug ATC ID |
G03AC01; G03DC02
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| SuperDrug CAS ID |
cas=000068224
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| Interaction between the Drug and Microbe | Top | |||
|---|---|---|---|---|
| The Metabolism of Drug Affected by Studied Microbe(s) | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacteroidales | ||||
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Studied Microbe: Alistipes indistinctus DSM22520
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Alistipes indistinctus DSM22520 (log2FC = -5.159; p = 0.002). | |||
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Studied Microbe: Bacteroides caccae ATCC 43185
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides caccae ATCC 43185 (log2FC = -7.202; p = 0.002). | |||
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Studied Microbe: Bacteroides cellulosilyticus DSM 14838
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides cellulosilyticus DSM 14838 (log2FC = -5.233; p = 0.005). | |||
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Studied Microbe: Bacteroides coprophilus DSM 18228
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides coprophilus DSM 18228 (log2FC = -2.404; p = 0.001). | |||
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Studied Microbe: Bacteroides dorei DSM 17855
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides dorei DSM 17855 (log2FC = -6.995; p = 0.004). | |||
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Studied Microbe: Bacteroides eggerthii DSM20697
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides eggerthii DSM20697 (log2FC = -3.39; p = 0.002). | |||
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Studied Microbe: Bacteroides finegoldii DSM17565
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides finegoldii DSM17565 (log2FC = -5.38; p = 0.018). | |||
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Studied Microbe: Bacteroides fragilis ATCC43859
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides fragilis ATCC43859 (log2FC = -3.97; p = 0.006). | |||
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Studied Microbe: Bacteroides fragilis HMW 610
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides fragilis HMW 610 (log2FC = -6.161; p = 0.002). | |||
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Studied Microbe: Bacteroides fragilis HMW 615
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides fragilis HMW 615 (log2FC = -2.91; p = 0.0). | |||
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Studied Microbe: Bacteroides fragilis NCTC 9343
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides fragilis NCTC 9343 (log2FC = -5.305; p = 0.002). | |||
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Studied Microbe: Bacteroides fragilis str. 3397 T10
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides fragilis str. 3397 T10 (log2FC = -3.89; p = 0.006). | |||
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Studied Microbe: Bacteroides fragilis str. 3986 T(B)9
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides fragilis str. 3986 T(B)9 (log2FC = -5.799; p = 0.005). | |||
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Studied Microbe: Bacteroides fragilis str. DS-208
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides fragilis str. DS-208 (log2FC = -6.489; p = 0.004). | |||
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Studied Microbe: Bacteroides intestinalis DSM 17393
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides intestinalis DSM 17393 (log2FC = -5.316; p = 0.002). | |||
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Studied Microbe: Bacteroides ovatus ATCC 8483
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides ovatus ATCC 8483 (log2FC = -2.875; p = 0.03). | |||
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Studied Microbe: Bacteroides stercoris ATCC 43183
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides stercoris ATCC 43183 (log2FC = -1.14; p = 0.006). | |||
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Studied Microbe: Bacteroides thetaiotaomicron 3731
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides thetaiotaomicron 3731 (log2FC = -5.981; p = 0.002). | |||
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Studied Microbe: Bacteroides thetaiotaomicron 7330
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides thetaiotaomicron 7330 (log2FC = -5.76; p = 0.001). | |||
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Studied Microbe: Bacteroides thetaiotaomicron VPI-5482
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides thetaiotaomicron VPI-5482 (log2FC = -5.859; p = 0.001). | |||
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Studied Microbe: Bacteroides uniformis ATCC 8492
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides uniformis ATCC 8492 (log2FC = -5.273; p = 0.004). | |||
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Studied Microbe: Bacteroides vulgatus ATCC 8482
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides vulgatus ATCC 8482 (log2FC = -7.173; p = 0.004). | |||
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Studied Microbe: Bacteroides WH2
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides WH2 (log2FC = -6.04; p = 0.009). | |||
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Studied Microbe: Bacteroides xylanisolvens DSM18836
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Bacteroides xylanisolvens DSM18836 (log2FC = -5.537; p = 0.005). | |||
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Studied Microbe: Odoribacter splanchnicus
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Odoribacter splanchnicus (log2FC = -0.74; p = 0.012). | |||
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Studied Microbe: Parabacteroides johnsonii DSM 18315
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Parabacteroides johnsonii DSM 18315 (log2FC = -5.826; p = 0.014). | |||
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Studied Microbe: Parabacteroides merdae ATCC 43184
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Parabacteroides merdae ATCC 43184 (log2FC = -6.369; p = 0.002). | |||
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Studied Microbe: Pretovella copri DSM 18205
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Pretovella copri DSM 18205 (log2FC = -0.429; p = 0.005). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Enterobacterales | ||||
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Studied Microbe: Escherichia coli BW25113
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Escherichia coli BW25113 (log2FC = -0.358; p = 0.028). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Erysipelotrichales | ||||
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Studied Microbe: Eubacterium biforme DSM 3989
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Eubacterium biforme DSM 3989 (log2FC = -7.066; p = 0.002). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Blautia hansenii DSM20583
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Blautia hansenii DSM20583 (log2FC = -0.56; p = 0.006). | |||
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Studied Microbe: Clostridium hathewayi DSM 13479
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Clostridium hathewayi DSM 13479 (log2FC = -6.672; p = 0.007). | |||
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Studied Microbe: Clostridium sp.
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Clostridium sp. (log2FC = -0.573; p = 0.021). | |||
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Studied Microbe: Ruminococcus gnavus ATCC 29149
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Ruminococcus gnavus ATCC 29149 (log2FC = -7.132; p = 0.006). | |||
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Studied Microbe: Ruminococcus torques ATCC 27756
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[2] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norethindrone acetate can be metabolized by Ruminococcus torques ATCC 27756 (log2FC = -0.901; p = 0.015). | |||
| Target and Pathway | Top | |||
|---|---|---|---|---|
| Target(s) | Progesterone receptor (PGR) | Target Info | Agonist | [3] |
| KEGG Pathway | Oocyte meiosis | |||
| Progesterone-mediated oocyte maturation | ||||
| Pathway Interaction Database | Cellular roles of Anthrax toxin | |||
| Reactome | Nuclear signaling by ERBB4 | |||
| Nuclear Receptor transcription pathway | ||||
| WikiPathways | Ovarian Infertility Genes | |||
| Signaling by ERBB4 | ||||
| Nuclear Receptors | ||||
| References | Top | |||
|---|---|---|---|---|
| REF 1 | Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015 | |||
| REF 2 | Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467. | |||
| REF 3 | Progesterone receptor ligand binding pocket flexibility: crystal structures of the norethindrone and mometasone furoate complexes. J Med Chem. 2004 Jun 17;47(13):3381-7. | |||
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