General Information of Drug (ID: DM6YSG3)

Drug Name
LIQUIRTIGENIN Drug Info
Synonyms
578-86-9; 4',7-Dihydroxyflavanone; (S)-7-Hydroxy-2-(4-hydroxyphenyl)chroman-4-one; (2S)-liquiritigenin; 5-DEOXYFLAVANONE; UNII-T194LKP9W6; 7-hydroxy-2-(4-hydroxy-phenyl)-chroman-4-one; T194LKP9W6; CHEMBL252642; CHEBI:28777; AK121923; (2S)-7-Hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one; (2S)-7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one; (2S)-2-(4-hydroxyphenyl)-7-oxidanyl-2,3-dihydrochromen-4-one
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
114829
ChEBI ID
CHEBI:28777
CAS Number
CAS 578-86-9
TTD Drug ID
DM6YSG3

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DOT
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Patented Agent(s)
Drug(s) Targeting Aromatase (CYP19A1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Anastrozole DMNP60F Breast cancer 2C60-2C65 Approved [6]
Letrozole DMH07Y3 Estrogen-receptor positive breast cancer Approved [7]
Exemestane DM9HPW3 Hormonally-responsive breast cancer 2C60-2C65 Approved [7]
Aminoglutethimide DMWFHMZ Cushing disease 5A70 Approved [8]
FADROZOLE DM3C5GZ Breast cancer 2C60-2C65 Approved [9]
Testolactone DMVY4GN Breast cancer 2C60-2C65 Approved [10]
LIAROZOLE DM4OYXE Dermatological disease DA24.Y Phase 2/3 [11]
Coumate DMVKW0N Breast cancer 2C60-2C65 Phase 2 [12]
BGS-649 DMO4MNQ Endometriosis GA10 Phase 2 [13]
NARINGENIN DMHAZLM N. A. N. A. Phase 1 [11]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Allopurinol DMLPAOB Gout FA25 Approved [14]
Febuxostat DMDEXQ0 Hyperuricaemia 5C55.Y Approved [15]
Fosdenopterin DMR0TYK Molybdenum cofactor deficiency 5B5K.A Approved [16]
Curcumin DMQPH29 Solid tumour/cancer 2A00-2F9Z Phase 3 [17]
Oxypurinol DMURH4X Heart failure BD10-BD13 Phase 2/3 [18]
BAICALEIN DM4C7E6 Influenza virus infection 1E30-1E32 Phase 2 [1]
Topiroxostat DMA04DE Gout FA25 Phase 2 [19]
TMX-049 DME8PFQ Diabetic nephropathy GB61.Z Phase 2 [20]
LC-350189 DMHT3CB Gout FA25 Phase 1 [21]
Azaindole derivative 5 DMD2BL3 N. A. N. A. Patented [22]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Cytochrome P450 2C9 (CYP2C9)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [23]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [24]
Dapsone DM4LT8A Acne vulgaris ED80 Approved [25]
Voriconazole DMAOL2S Aspergillosis 1F20 Approved [26]
Capsaicin DMGMF6V Back pain ME84.Z Approved [27]
Zafirlukast DMHNQOG Asthma CA23 Approved [28]
Niclosamide DMJAGXQ Cestodes infection 1F70-1F76 Approved [25]
Eicosapentaenoic acid/docosa-hexaenoic acid DMMUCG4 Hypertriglyceridemia 5C80.1 Approved [29]
Fluconazole DMOWZ6B Cryptococcal meningitis Approved [26]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [25]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Cytochrome P450 2C19 (CYP2C19)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [23]
Thioridazine DM35M8J Schizophrenia 6A20 Approved [30]
Voriconazole DMAOL2S Aspergillosis 1F20 Approved [26]
Chloramphenicol DMFXEWT Bacterial infection 1A00-1C4Z Approved [31]
Capsaicin DMGMF6V Back pain ME84.Z Approved [27]
Pentamidine DMHZJCG African trypanosomiasis 1F51 Approved [25]
Stiripentol DMMSDOY Dravet syndrome 8A61.11 Approved [32]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [25]
Desipramine DMT2FDC Attention deficit hyperactivity disorder 6A05.Z Approved [30]
Amitriptyline DMK7F9S Depression 6A70-6A7Z Approved [33]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Estrogen receptor (ESR1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [34]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [35]
Gefitinib DM15F0X Colon adenocarcinoma Approved [36]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [37]
Lapatinib DM3BH1Y Breast cancer 2C60-2C65 Approved [38]
Liraglutide DM3FXPS Non-insulin dependent diabetes 5A11 Approved [39]
Quercetin DM3NC4M Obesity 5B81 Approved [40]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [41]
Procaine DM4LSNE Anaesthesia 9A78.6 Approved [37]
Estrone DM5T6US Acne vulgaris ED80 Approved [42]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Beta-carotene DM0RXBT Vitamin deficiency 5B55-5B71 Approved [43]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [44]
Methotrexate DM2TEOL Anterior urethra cancer Approved [45]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [46]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [47]
Panobinostat DM58WKG Chronic graft versus host disease Approved [48]
Estrone DM5T6US Acne vulgaris ED80 Approved [44]
Hydroquinone DM6AVR4 Melasma ED60.1 Approved [49]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [50]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [51]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Estrogen receptor beta (ESR2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [52]
Gefitinib DM15F0X Colon adenocarcinoma Approved [53]
Quercetin DM3NC4M Obesity 5B81 Approved [54]
Estrone DM5T6US Acne vulgaris ED80 Approved [55]
Tibolone DM78XFG Anabolic metabolism 5C50-5C8Z Approved [56]
Testosterone DM7HUNW Hot flushes GA30 Approved [57]
Lindane DMB8CNL Infestations of lice and scabies 1G00.Z Approved [58]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [59]
Mestranol DMG3F94 Contraception QA21 Approved [60]
Flutamide DMK0O7U Prostate cancer 2C82.0 Approved [61]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Aromatase (CYP19A1) TTSZLWK CP19A_HUMAN Inhibitor [2]
Xanthine dehydrogenase/oxidase (XDH) TT7RJY8 XDH_HUMAN Inhibitor [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cytochrome P450 2C19 (CYP2C19) OTFMJYYE CP2CJ_HUMAN Gene/Protein Processing [3]
Cytochrome P450 2C9 (CYP2C9) OTGLBN29 CP2C9_HUMAN Gene/Protein Processing [3]
Estrogen receptor (ESR1) OTKLU61J ESR1_HUMAN Gene/Protein Processing [4]
Estrogen receptor beta (ESR2) OTXNR2WQ ESR2_HUMAN Gene/Protein Processing [5]
Stromal cell-derived factor 1 (CXCL12) OT2QX5LL SDF1_HUMAN Gene/Protein Processing [4]

References

1 Inhibition of cow's milk xanthine oxidase by flavonoids. J Nat Prod. 1988 Mar-Apr;51(2):345-8.
2 Screening of herbal constituents for aromatase inhibitory activity. Bioorg Med Chem. 2008 Sep 15;16(18):8466-70.
3 Drug interaction study of flavonoids toward CYP3A4 and their quantitative structure activity relationship (QSAR) analysis for predicting potential effects. Toxicol Lett. 2018 Sep 15;294:27-36.
4 Assessment of the potential activity of major dietary compounds as selective estrogen receptor modulators in two distinct cell models for proliferation and differentiation. Toxicol Appl Pharmacol. 2017 Jun 15;325:61-70. doi: 10.1016/j.taap.2017.04.005. Epub 2017 Apr 7.
5 Selectivity of natural, synthetic and environmental estrogens for zebrafish estrogen receptors. Toxicol Appl Pharmacol. 2014 Oct 1;280(1):60-9. doi: 10.1016/j.taap.2014.07.020. Epub 2014 Aug 8.
6 Effective aromatase inhibition by anastrozole in a patient with gonadotropin-independent precocious puberty in McCune-Albright syndrome. J Pediatr Endocrinol Metab. 2002;15 Suppl 3:945-8.
7 Aromatase inhibitors--theoretical concept and present experiences in the treatment of endometriosis. Zentralbl Gynakol. 2003 Jul-Aug;125(7-8):247-51.
8 Aminoglutethimide-induced protein free radical formation on myeloperoxidase: a potential mechanism of agranulocytosis. Chem Res Toxicol. 2007 Jul;20(7):1038-45.
9 Enantioselective nonsteroidal aromatase inhibitors identified through a multidisciplinary medicinal chemistry approach. J Med Chem. 2005 Nov 17;48(23):7282-9.
10 Aromatase inhibitors for male infertility. J Urol. 2002 Feb;167(2 Pt 1):624-9.
11 Pharmacophore modeling strategies for the development of novel nonsteroidal inhibitors of human aromatase (CYP19). Bioorg Med Chem Lett. 2010 May 15;20(10):3050-64.
12 Highly potent first examples of dual aromatase-steroid sulfatase inhibitors based on a biphenyl template. J Med Chem. 2010 Mar 11;53(5):2155-70.
13 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800032111)
14 Allopurinol: xanthine oxidase inhibitor. Tex Med. 1966 Jan;62(1):100-1.
15 Clinical pipeline report, company report or official report of Takeda (2009).
16 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2021
17 Inhibition studies of bovine xanthine oxidase by luteolin, silibinin, quercetin, and curcumin. J Nat Prod. 2009 Apr;72(4):725-31.
18 Oxypurinol as an inhibitor of xanthine oxidase-catalyzed production of superoxide radical. Biochem Pharmacol. 1988 Jan 15;37(2):349-52.
19 QT/QTc study conducted in Japanese adult healthy subjects: a novel xanthine oxidase inhibitor topiroxostat was not associated with QT prolongation. J Clin Pharmacol. 2014 Apr;54(4):446-52.
20 Clinical pipeline report, company report or official report of Teijin Pharma.
21 Pharmacokinetics, pharmacodynamics, and tolerability of LC350189, a novel xanthine oxidase inhibitor, in healthy subjects. Drug Des Devel Ther. 2015 Aug 31;9:5033-49.
22 An updated patent review: xanthine oxidase inhibitors for the treatment of hyperuricemia and gout (2011-2015).Expert Opin Ther Pat. 2017 Mar;27(3):311-345.
23 Characterization of the structural determinants required for potent mechanism-based inhibition of human cytochrome P450 1A1 by cannabidiol. Chem Biol Interact. 2014 May 25;215:62-8.
24 Comparative effects of thiazolidinediones on in vitro P450 enzyme induction and inhibition. Drug Metab Dispos. 2003 Apr;31(4):439-46.
25 Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. Drug Metab Dispos. 2001 Jan;29(1):30-5.
26 The novel azole R126638 is a selective inhibitor of ergosterol synthesis in Candida albicans, Trichophyton spp., and Microsporum canis. Antimicrob Agents Chemother. 2004 Sep;48(9):3272-8.
27 Effects of capsaicin and dihydrocapsaicin on human and rat liver microsomal CYP450 enzyme activities in vitro and in vivo. J Asian Nat Prod Res. 2012;14(4):382-95.
28 Potential of pranlukast and zafirlukast in the inhibition of human liver cytochrome P450 enzymes. Xenobiotica. 2004 May;34(5):429-38.
29 The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes. Life Sci. 2006 Nov 25;79(26):2432-40.
30 Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors. Chem Biol Interact. 2004 Apr 15;147(3):331-40.
31 Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class. Toxicol Lett. 2016 Jan 22;241:82-94.
32 Stiripentol. Expert Opin Investig Drugs. 2005 Jul;14(7):905-11.
33 ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
34 Estrogen-like activity of metals in MCF-7 breast cancer cells. Endocrinology. 2003 Jun;144(6):2425-36. doi: 10.1210/en.2002-221054.
35 Cross-talk between non-genomic and genomic signalling pathways--distinct effect profiles of environmental estrogens. Toxicol Appl Pharmacol. 2010 Jun 1;245(2):160-70. doi: 10.1016/j.taap.2010.02.015. Epub 2010 Mar 4.
36 Bidirectional cross talk between ERalpha and EGFR signalling pathways regulates tamoxifen-resistant growth. Breast Cancer Res Treat. 2006 Mar;96(2):131-46. doi: 10.1007/s10549-005-9070-2. Epub 2005 Oct 27.
37 Sensitivity of human dental pulp cells to eighteen chemical agents used for endodontic treatments in dentistry. Odontology. 2013 Jan;101(1):43-51.
38 The dual ErbB1/ErbB2 inhibitor, lapatinib (GW572016), cooperates with tamoxifen to inhibit both cell proliferation- and estrogen-dependent gene expression in antiestrogen-resistant breast cancer. Cancer Res. 2005 Jan 1;65(1):18-25.
39 Antitumoral activity of liraglutide, a new DNMT inhibitor in breast cancer cells in vitro and in vivo. Chem Biol Interact. 2021 Nov 1;349:109641. doi: 10.1016/j.cbi.2021.109641. Epub 2021 Sep 14.
40 Estrogen receptor alpha mediates the proliferative but not the cytotoxic dose-dependent effects of two major phytoestrogens on human breast cancer cells. Mol Pharmacol. 2001 Sep;60(3):595-602.
41 Novel retinoic acid metabolism blocking agents have potent inhibitory activities on human breast cancer cells and tumour growth. Br J Cancer. 2007 Apr 23;96(8):1204-15. doi: 10.1038/sj.bjc.6603705. Epub 2007 Mar 27.
42 Prediction of the combined effects of multiple estrogenic chemicals on MCF-7 human breast cancer cells and a preliminary molecular exploration of the estrogenic proliferative effects and related gene expression. Ecotoxicol Environ Saf. 2018 Sep 30;160:1-9. doi: 10.1016/j.ecoenv.2018.05.025. Epub 2018 May 21.
43 Beta-carotene and apocarotenals promote retinoid signaling in BEAS-2B human bronchioepithelial cells. Arch Biochem Biophys. 2006 Nov 1;455(1):48-60.
44 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.
45 The contribution of methotrexate exposure and host factors on transcriptional variance in human liver. Toxicol Sci. 2007 Jun;97(2):582-94.
46 Chemokine stromal cell-derived factor-1 induction by C/EBPbeta activation is associated with all-trans-retinoic acid-induced leukemic cell differentiation. J Leukoc Biol. 2007 Nov;82(5):1332-9. doi: 10.1189/jlb.1106697. Epub 2007 Jul 26.
47 Temporal changes in gene expression in the skin of patients treated with isotretinoin provide insight into its mechanism of action. Dermatoendocrinol. 2009 May;1(3):177-87.
48 A transcriptome-based classifier to identify developmental toxicants by stem cell testing: design, validation and optimization for histone deacetylase inhibitors. Arch Toxicol. 2015 Sep;89(9):1599-618.
49 How benzene and its metabolites affect human marrow derived mesenchymal stem cells. Toxicol Lett. 2012 Oct 17;214(2):145-53. doi: 10.1016/j.toxlet.2012.08.015. Epub 2012 Aug 30.
50 Integrative "-Omics" analysis in primary human hepatocytes unravels persistent mechanisms of cyclosporine A-induced cholestasis. Chem Res Toxicol. 2016 Dec 19;29(12):2164-2174.
51 Sevoflurane but not propofol enhances ovarian cancer cell biology through regulating cellular metabolic and signaling mechanisms. Cell Biol Toxicol. 2023 Aug;39(4):1395-1411. doi: 10.1007/s10565-022-09766-6. Epub 2022 Oct 8.
52 Arsenite and cadmium promote the development of mammary tumors. Carcinogenesis. 2020 Jul 14;41(7):1005-1014. doi: 10.1093/carcin/bgz176.
53 Combined tamoxifen and gefitinib in non-small cell lung cancer shows antiproliferative effects. Biomed Pharmacother. 2010 Feb;64(2):88-92. doi: 10.1016/j.biopha.2009.06.010. Epub 2009 Oct 23.
54 Quercetin exerts bidirectional regulation effects on the efficacy of tamoxifen in estrogen receptor-positive breast cancer therapy: An in vitro study. Environ Toxicol. 2020 Nov;35(11):1179-1193. doi: 10.1002/tox.22983. Epub 2020 Jun 12.
55 Comparison of an array of in vitro assays for the assessment of the estrogenic potential of natural and synthetic estrogens, phytoestrogens and xenoestrogens. Toxicology. 2001 Sep 14;166(1-2):79-89. doi: 10.1016/s0300-483x(01)00437-1.
56 Estrogenic effects of natural and synthetic compounds including tibolone assessed in Saccharomyces cerevisiae expressing the human estrogen alpha and beta receptors. FASEB J. 2006 Jul;20(9):1552-4. doi: 10.1096/fj.05-5413fje. Epub 2006 May 23.
57 Comparison of relative binding affinities to fish and mammalian estrogen receptors: the regulatory implications. Toxicol Lett. 2010 Feb 15;192(3):298-315. doi: 10.1016/j.toxlet.2009.11.004. Epub 2009 Nov 12.
58 Screening for estrogen and androgen receptor activities in 200 pesticides by in vitro reporter gene assays using Chinese hamster ovary cells. Environ Health Perspect. 2004 Apr;112(5):524-31. doi: 10.1289/ehp.6649.
59 Valproic acid and its derivatives enhanced estrogenic activity but not androgenic activity in a structure dependent manner. Reprod Toxicol. 2013 Dec;42:49-57. doi: 10.1016/j.reprotox.2013.07.019. Epub 2013 Jul 26.
60 Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids. Biosci Biotechnol Biochem. 2002 Jul;66(7):1479-87. doi: 10.1271/bbb.66.1479.
61 Arylpiperazines for management of benign prostatic hyperplasia: design, synthesis, quantitative structure-activity relationships, and pharmacokinetic studies. J Med Chem. 2011 Jan 13;54(1):302-11. doi: 10.1021/jm101163m. Epub 2010 Dec 3.