Drug Information
| Drug General Information | Top | |||
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| Drug ID |
D09QZI
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| Former ID |
DAP001210
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| Drug Name |
Norgestimate
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| Synonyms |
Norgestimato; Norgestimatum; Dexnorgestrel acetime; Norgestrel oxime acetate; D 138; ORF 10131; RWJ 10131; Norgestimato [INN-Spanish]; Norgestimatum [INN-Latin]; ORF-10131; Ortho-Prefest; RWJ-10131; Norgestimate (USP/INN); Norgestimate [USAN:INN:BAN]; D-13beta-Ethyl-17alpha-ethynyl-17beta-acetoxygon-4-en-3-oneoxime; D-13-beta-Ethyl-17-alpha-ethynyl-17-beta-acetoxygon-4-en-3-one oxime; [(3E,8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate; (+)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one oxime acetate (ester); (17-alpha)-17-(Acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-oxime; (17alpha)-17-(Acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-oxime; (3E)-17alpha-ethynyl-3-(hydroxyimino)-18a-homoestr-4-en-17beta-yl acetate
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| Drug Type |
Small molecular drug
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| Indication | Contraception [ICD-11: QA21] | Approved | [1], [2] | |
| Therapeutic Class |
Contraceptive Agents
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| Structure |
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Download2D MOL |
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| Formula |
C23H31NO3
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| Canonical SMILES |
CCC12CCC3C(C1CCC2(C#C)OC(=O)C)CCC4=CC(=NO)CCC34
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| InChI |
1S/C23H31NO3/c1-4-22-12-10-19-18-9-7-17(24-26)14-16(18)6-8-20(19)21(22)11-13-23(22,5-2)27-15(3)25/h2,14,18-21,26H,4,6-13H2,1,3H3/b24-17+/t18-,19+,20+,21-,22-,23-/m0/s1
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| InChIKey |
KIQQMECNKUGGKA-NMYWJIRASA-N
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| CAS Number |
CAS 20799-27-3
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| PubChem Compound ID | ||||
| PubChem Substance ID |
12013307, 14828760, 14877333, 23948292, 43185588, 46507381, 47206928, 49963131, 50125945, 50406385, 53787279, 56352967, 57370933, 92712530, 99375924, 103770917, 114617529, 126630090, 126656639, 126670754, 131311636, 134338450, 135000359, 135046943, 137002813, 141484503, 144206364, 152056974, 160964296, 162174921, 170464733, 175267643, 176250054, 179150362, 196110215, 223396532, 223556630, 223668437, 226423899, 226423900, 241064393, 249822572, 252062710, 252355235
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| ChEBI ID |
CHEBI:50815
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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 | ||||
|
Studied Microbe: Bacteroides fragilis NCTC 9343
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norgestimate can be metabolized by Bacteroides fragilis NCTC 9343 (log2FC = -0.486; p = 0.029). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bifidobacteriales | ||||
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Studied Microbe: Bifidobacterium ruminantium
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|
[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norgestimate can be metabolized by Bifidobacterium ruminantium (log2FC = -0.704; p = 0.046). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eggerthellales | ||||
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Studied Microbe: Eggerthella lenta ATCC 25559
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norgestimate can be metabolized by Eggerthella lenta ATCC 25559 (log2FC = -1.287; p = 0.029). | |||
| 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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|
[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norgestimate can be metabolized by Escherichia coli BW25113 (log2FC = -0.713; p = 0.031). | |||
| 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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|
[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norgestimate can be metabolized by Eubacterium biforme DSM 3989 (log2FC = -1.47; p = 0.035). | |||
| 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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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norgestimate can be metabolized by Blautia hansenii DSM20583 (log2FC = -1.162; p = 0.008). | |||
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Studied Microbe: Clostridium sp.
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|
[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norgestimate can be metabolized by Clostridium sp. (log2FC = -1.328; p = 0.042). | |||
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Studied Microbe: Coprococcus comes ATCC 27758
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Norgestimate can be metabolized by Coprococcus comes ATCC 27758 (log2FC = -0.324; p = 0.016). | |||
| The Abundace of Studied Microbe(s) Regulated by Drug | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Roseburia intestinalis
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[4] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Roseburia intestinalis was decreased by Norgestimate (adjusted p-values: 5.43E-03). | |||
| Target and Pathway | Top | |||
|---|---|---|---|---|
| Target(s) | Progesterone receptor (PGR) | Target Info | Agonist | [5], [6] |
| 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 | URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7091). | |||
| REF 2 | Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77. | |||
| REF 3 | Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467. | |||
| REF 4 | Extensive impact of non-antibiotic drugs on human gut bacteria. Nature. 2018 Mar 29;555(7698):623-628. | |||
| REF 5 | Pharmacological profile of progestins. Maturitas. 2008 Sep-Oct;61(1-2):151-7. | |||
| REF 6 | A review of transdermal hormonal contraception : focus on the ethinylestradiol/norelgestromin contraceptive patch. Treat Endocrinol. 2006;5(6):359-65. | |||
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