General Information of Drug (ID: DM82JP0)

Drug Name
Lynestrenol Drug Info
Synonyms
Linestrenol; Linestrenol [INN-Spanish]; Linestrenolo [DCIT]; Lynenol; Lynestrenolum [INN-Latin]; Lynoestrenol; Lynoestrenol [Progestins]; Lynstranol; Endometril; Ethinyl oestrenol; Ethinylestrenol; Ethinyloestranol; Ethynloestrenol; Ethynylestrenol; Exluten; Exlution; Exluton; Exlutona; IND 1006; LYNESTRENOL; Org 485-50; Orgametil; Orgametril; Orgametrol; 17-alpha-Ethynylestrenol; 17-alpha-Ethynyloestrenol; 17alpha-Ethynylestrenol; 3-Desoxynorlutin; 52-76-6; CCRIS 9093; EINECS 200-151-4; NSC 37725; NSC-37725; UNII-N2Z8ALG4U5
Cross-matching ID
PubChem CID
5857
ChEBI ID
CHEBI:31790
CAS Number
CAS 52-76-6
TTD Drug ID
DM82JP0
INTEDE Drug ID
DR0997

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DME
DOT
Drug Status:
Approved Drug(s)
Drug(s) Metabolized By Cytochrome P450 3A4 (CYP3A4)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [3]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [4]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [5]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [6]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [7]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [8]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [9]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [10]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [4]
Verapamil DMA7PEW Angina pectoris BA40 Approved [11]
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Drug(s) Metabolized By Cytochrome P450 2C9 (CYP2C9)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Progesterone DMUY35B Amenorrhea GA20.0 Approved [12]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [13]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [14]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [15]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [16]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [15]
Verapamil DMA7PEW Angina pectoris BA40 Approved [17]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [18]
Estrone DM5T6US Acne vulgaris ED80 Approved [19]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [20]
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Drug(s) Metabolized By Mephenytoin 4-hydroxylase (CYP2C19)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Amoxicillin DMUYNEI Acute otitis media AB00 Approved [21]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [12]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [22]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [23]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [15]
Verapamil DMA7PEW Angina pectoris BA40 Approved [24]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [25]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [20]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [26]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [27]
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Drug(s) Affected By Myb-related protein A (MYBL1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [28]
Spironolactone DM2AQ5N Chronic heart failure BD1Z Approved [2]
Quercetin DM3NC4M Obesity 5B81 Approved [29]
Panobinostat DM58WKG Chronic graft versus host disease Approved [30]
Estrone DM5T6US Acne vulgaris ED80 Approved [28]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [31]
Marinol DM70IK5 Anorexia nervosa cachexia 6B80 Approved [32]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [33]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [34]
Ivermectin DMDBX5F Intestinal strongyloidiasis due to nematode parasite 1F6B Approved [2]
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Drug(s) Affected By Protein GREB1 (GREB1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [35]
Spironolactone DM2AQ5N Chronic heart failure BD1Z Approved [2]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [36]
Testosterone DM7HUNW Hot flushes GA30 Approved [37]
Calcitriol DM8ZVJ7 Congenital alopecia LC30 Approved [38]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [39]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [40]
Ivermectin DMDBX5F Intestinal strongyloidiasis due to nematode parasite 1F6B Approved [2]
Nandrolone DMFWKG1 Osteoporosis FB83.0 Approved [41]
Mestranol DMG3F94 Contraception QA21 Approved [2]
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Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [1]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [1]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Myb-related protein A (MYBL1) OTBJMC2P MYBA_HUMAN Gene/Protein Processing [2]
Protein GREB1 (GREB1) OTU6ZA26 GREB1_HUMAN Gene/Protein Processing [2]

References

1 Identification of the human cytochrome P450 enzymes involved in the in vitro biotransformation of lynestrenol and norethindrone. J Steroid Biochem Mol Biol. 2008 May;110(1-2):56-66.
2 A Gene Expression Biomarker Identifies Chemical Modulators of Estrogen Receptor in an MCF-7 Microarray Compendium. Chem Res Toxicol. 2021 Feb 15;34(2):313-329. doi: 10.1021/acs.chemrestox.0c00243. Epub 2021 Jan 6.
3 Expression levels and activation of a PXR variant are directly related to drug resistance in osteosarcoma cell lines. Cancer. 2007 Mar 1;109(5):957-65.
4 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
5 Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75.
6 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
7 Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
8 Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4 substrates. Br J Pharmacol. 2012 Apr;165(8):2787-98.
9 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
10 The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76.
11 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
12 Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9.
13 Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
14 Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms. Endocrinology. 2003 Aug;144(8):3382-98.
15 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
16 Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
17 Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
18 New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126.
19 A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
20 A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
21 High-dose rabeprazole/amoxicillin therapy as the second-line regimen after failure to eradicate H. pylori by triple therapy with the usual doses of a proton pump inhibitor, clarithromycin and amoxicillin. Hepatogastroenterology. 2003 Nov-Dec;50(54):2274-8.
22 Cytochrome P450 pharmacogenetics and cancer. Oncogene. 2006 Mar 13;25(11):1679-91.
23 CYP2C19*17 is associated with decreased breast cancer risk. Breast Cancer Res Treat. 2009 May;115(2):391-6.
24 Cytochromes of the P450 2C subfamily are the major enzymes involved in the O-demethylation of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1995 Dec;353(1):116-21.
25 Diclofenac and its derivatives as tools for studying human cytochromes P450 active sites: particular efficiency and regioselectivity of P450 2Cs. Biochemistry. 1999 Oct 26;38(43):14264-70.
26 Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33.
27 Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
28 Moving toward integrating gene expression profiling into high-throughput testing: a gene expression biomarker accurately predicts estrogen receptor alpha modulation in a microarray compendium. Toxicol Sci. 2016 May;151(1):88-103.
29 Comparison of phenotypic and transcriptomic effects of false-positive genotoxins, true genotoxins and non-genotoxins using HepG2 cells. Mutagenesis. 2011 Sep;26(5):593-604.
30 Development and validation of the TGx-HDACi transcriptomic biomarker to detect histone deacetylase inhibitors in human TK6 cells. Arch Toxicol. 2021 May;95(5):1631-1645. doi: 10.1007/s00204-021-03014-2. Epub 2021 Mar 26.
31 Changes in gene expression profiles of multiple myeloma cells induced by arsenic trioxide (ATO): possible mechanisms to explain ATO resistance in vivo. Br J Haematol. 2005 Mar;128(5):636-44.
32 Single-cell Transcriptome Mapping Identifies Common and Cell-type Specific Genes Affected by Acute Delta9-tetrahydrocannabinol in Humans. Sci Rep. 2020 Feb 26;10(1):3450. doi: 10.1038/s41598-020-59827-1.
33 Comparison of HepG2 and HepaRG by whole-genome gene expression analysis for the purpose of chemical hazard identification. Toxicol Sci. 2010 May;115(1):66-79.
34 The neuroprotective action of the mood stabilizing drugs lithium chloride and sodium valproate is mediated through the up-regulation of the homeodomain protein Six1. Toxicol Appl Pharmacol. 2009 Feb 15;235(1):124-34.
35 Arsenite and cadmium promote the development of mammary tumors. Carcinogenesis. 2020 Jul 14;41(7):1005-1014. doi: 10.1093/carcin/bgz176.
36 Arsenic induces functional re-expression of estrogen receptor by demethylation of DNA in estrogen receptor-negative human breast cancer. PLoS One. 2012;7(4):e35957. doi: 10.1371/journal.pone.0035957. Epub 2012 Apr 27.
37 The exosome-like vesicles derived from androgen exposed-prostate stromal cells promote epithelial cells proliferation and epithelial-mesenchymal transition. Toxicol Appl Pharmacol. 2021 Jan 15;411:115384. doi: 10.1016/j.taap.2020.115384. Epub 2020 Dec 25.
38 Effects of 1alpha,25 dihydroxyvitamin D3 and testosterone on miRNA and mRNA expression in LNCaP cells. Mol Cancer. 2011 May 18;10:58.
39 Integrating multiple omics to unravel mechanisms of Cyclosporin A induced hepatotoxicity in vitro. Toxicol In Vitro. 2015 Apr;29(3):489-501.
40 Human embryonic stem cell-derived test systems for developmental neurotoxicity: a transcriptomics approach. Arch Toxicol. 2013 Jan;87(1):123-43.
41 Evaluation of an imaging-based in vitro screening platform for estrogenic activity with OECD reference chemicals. Toxicol In Vitro. 2022 Jun;81:105348. doi: 10.1016/j.tiv.2022.105348. Epub 2022 Mar 18.