General Information of Drug (ID: DMASOWP)

Drug Name
ROBINETIN Drug Info
Synonyms
Robinetin; 490-31-3; Norkanugin; 3,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one; 5-Hydroxyfisetin; 5-Deoxymyricetin; 4H-1-Benzopyran-4-one, 3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-; UNII-KJ6DBC4U7E; 3,7,3',4',5'-pentahydroxyflavone; NSC 656274; NSC 407331; CCRIS 7520; EINECS 207-709-6; KJ6DBC4U7E; NSC-407331; BRN 0308905; CHEMBL170405; CHEBI:8876; FLAVONE, 3,3',4',5',7-PENTAHYDROXY-; NSC656274; 3,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-4-benzopyrone
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
5281692
ChEBI ID
CHEBI:8876
CAS Number
CAS 490-31-3
TTD Drug ID
DMASOWP

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 Name Drug ID Indication ICD 11 Highest Status REF
Allopurinol DMLPAOB Gout FA25 Approved [4]
Febuxostat DMDEXQ0 Hyperuricaemia 5C55.Y Approved [5]
Fosdenopterin DMR0TYK Molybdenum cofactor deficiency 5B5K.A Approved [6]
Curcumin DMQPH29 Solid tumour/cancer 2A00-2F9Z Phase 3 [7]
Oxypurinol DMURH4X Heart failure BD10-BD13 Phase 2/3 [8]
BAICALEIN DM4C7E6 Influenza virus infection 1E30-1E32 Phase 2 [1]
Topiroxostat DMA04DE Gout FA25 Phase 2 [9]
TMX-049 DME8PFQ Diabetic nephropathy GB61.Z Phase 2 [10]
LC-350189 DMHT3CB Gout FA25 Phase 1 [11]
Azaindole derivative 5 DMD2BL3 N. A. N. A. Patented [12]
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Drug(s) Affected By Cytochrome P450 1A1 (CYP1A1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Amodiaquine DME4RA8 Malaria 1F40-1F45 Approved [13]
Riluzole DMECBWN Amyotrophic lateral sclerosis 8B60.0 Approved [14]
Flutamide DMK0O7U Prostate cancer 2C82.0 Approved [15]
Menadione DMSJDTY Vitamin K deficiency 5B59 Approved [16]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [17]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [18]
Ethacrynic acid DM60QMR Edema MG29 Approved [19]
Marinol DM70IK5 Anorexia nervosa cachexia 6B80 Approved [20]
Ethinyl Estradiol DMODJ40 Acne vulgaris ED80 Approved [21]
Clofibrate DMPC1J7 Dysbetalipoproteinemia 5C80.2 Approved [22]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Ivermectin DMDBX5F Intestinal strongyloidiasis due to nematode parasite 1F6B Approved [23]
Folic Acid DMEMBJC Colorectal carcinoma Approved [24]
Methotrexate DM2TEOL Anterior urethra cancer Approved [25]
Quercetin DM3NC4M Obesity 5B81 Approved [26]
Docetaxel DMDI269 Advanced cancer 2A00-2F9Z Approved [27]
Irinotecan DMP6SC2 Adenocarcinoma 2D40 Approved [28]
Epirubicin DMPDW6T Solid tumour/cancer 2A00-2F9Z Approved [29]
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [30]
Colchicine DM2POTE Acute gout flare FA25.0 Approved [31]
Dactinomycin DM2YGNW Adult kidney Wilms tumor Approved [31]
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Drug Name Drug ID Indication ICD 11 Highest Status REF
Lopinavir DMITQS0 Human immunodeficiency virus infection 1C62 Approved [32]
Sulfinpyrazone DMEV954 Gout FA25 Approved [33]
Probenecid DMMFWOJ Acute gonococcal cervicitis Approved [34]
Docetaxel DMDI269 Advanced cancer 2A00-2F9Z Approved [35]
Methotrexate DM2TEOL Anterior urethra cancer Approved [25]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [36]
Cholic Acid DM7OKQV Cholelithiasis DC11 Approved [37]
Epirubicin DMPDW6T Solid tumour/cancer 2A00-2F9Z Approved [29]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [38]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [39]
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Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

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

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
ATP-binding cassette sub-family C member 2 (ABCC2) OTJSIGV5 MRP2_HUMAN Gene/Protein Processing [2]
Cytochrome P450 1A1 (CYP1A1) OTE4EFH8 CP1A1_HUMAN Gene/Protein Processing [3]
Multidrug resistance-associated protein 1 (ABCC1) OTGUN89S MRP1_HUMAN Gene/Protein Processing [2]
UDP-glucuronosyltransferase 1A1 OTH1C8OJ UD11_HUMAN Gene/Protein Processing [3]

References

1 Inhibition of cow's milk xanthine oxidase by flavonoids. J Nat Prod. 1988 Mar-Apr;51(2):345-8.
2 Quantitative structure activity relationship studies on the flavonoid mediated inhibition of multidrug resistance proteins 1 and 2. Biochem Pharmacol. 2005 Feb 15;69(4):699-708. doi: 10.1016/j.bcp.2004.11.002. Epub 2004 Dec 23.
3 Structure-dependent modulation of aryl hydrocarbon receptor-mediated activities by flavonoids. Toxicol Sci. 2018 Jul 1;164(1):205-217.
4 Allopurinol: xanthine oxidase inhibitor. Tex Med. 1966 Jan;62(1):100-1.
5 Clinical pipeline report, company report or official report of Takeda (2009).
6 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2021
7 Inhibition studies of bovine xanthine oxidase by luteolin, silibinin, quercetin, and curcumin. J Nat Prod. 2009 Apr;72(4):725-31.
8 Oxypurinol as an inhibitor of xanthine oxidase-catalyzed production of superoxide radical. Biochem Pharmacol. 1988 Jan 15;37(2):349-52.
9 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.
10 Clinical pipeline report, company report or official report of Teijin Pharma.
11 Pharmacokinetics, pharmacodynamics, and tolerability of LC350189, a novel xanthine oxidase inhibitor, in healthy subjects. Drug Des Devel Ther. 2015 Aug 31;9:5033-49.
12 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.
13 Cytochrome P450 1A1/2 induction by antiparasitic drugs: dose-dependent increase in ethoxyresorufin O-deethylase activity and mRNA caused by quinine, primaquine and albendazole in HepG2 cells. Eur J Clin Pharmacol. 2002 Nov;58(8):537-42.
14 Association of CYP1A1 and CYP1B1 inhibition in in vitro assays with drug-induced liver injury. J Toxicol Sci. 2021;46(4):167-176. doi: 10.2131/jts.46.167.
15 Anti-androgenic effect of 6-formylindolo[3,2-b]carbazole (FICZ) in LNCaP cells is mediated by the aryl hydrocarbon-androgen receptors cross-talk. Steroids. 2020 Jan;153:108508. doi: 10.1016/j.steroids.2019.108508. Epub 2019 Oct 3.
16 Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition. Arch Toxicol. 2008 Dec;82(12):909-21.
17 Effect of CYP1A1 gene polymorphisms on estrogen metabolism and bone density. J Bone Miner Res. 2005 Feb;20(2):232-9. doi: 10.1359/JBMR.041110. Epub 2004 Nov 16.
18 Increased sensitivity for troglitazone-induced cytotoxicity using a human in vitro co-culture model. Toxicol In Vitro. 2009 Oct;23(7):1387-95.
19 Isoform-specific induction of a human aldo-keto reductase by polycyclic aromatic hydrocarbons (PAHs), electrophiles, and oxidative stress: implications for the alternative pathway of PAH activation catalyzed by human dihydrodiol dehydrogenase. Cancer Res. 1999 Feb 1;59(3):607-14.
20 Gene expression changes in human small airway epithelial cells exposed to Delta9-tetrahydrocannabinol. Toxicol Lett. 2005 Aug 14;158(2):95-107.
21 The metallohormone cadmium modulates AhR-associated gene expression in the small intestine of rats similar to ethinyl-estradiol. Arch Toxicol. 2013 Apr;87(4):633-43.
22 Evidence for a new human CYP1A1 regulation pathway involving PPAR-alpha and 2 PPRE sites. Gastroenterology. 2004 Nov;127(5):1436-45.
23 Characterization of multidrug transporter-mediated efflux of avermectins in human and mouse neuroblastoma cell lines. Toxicol Lett. 2015 Jun 15;235(3):189-98. doi: 10.1016/j.toxlet.2015.04.005. Epub 2015 Apr 9.
24 Folate concentration dependent transport activity of the Multidrug Resistance Protein 1 (ABCC1). Biochem Pharmacol. 2004 Apr 15;67(8):1541-8.
25 Methotrexate normalizes up-regulated folate pathway genes in rheumatoid arthritis. Arthritis Rheum. 2013 Nov;65(11):2791-802.
26 Influence of redox-active compounds and PXR-activators on human MRP1 and MRP2 gene expression. Toxicology. 2002 Feb 28;171(2-3):137-46.
27 Enhanced in vitro invasiveness and drug resistance with altered gene expression patterns in a human lung carcinoma cell line after pulse selection with anticancer drugs. Int J Cancer. 2004 Sep 10;111(4):484-93. doi: 10.1002/ijc.20230.
28 Clinical determinants of response to irinotecan-based therapy derived from cell line models. Clin Cancer Res. 2008 Oct 15;14(20):6647-55.
29 Co-encapsulation of chrysophsin-1 and epirubicin in PEGylated liposomes circumvents multidrug resistance in HeLa cells. Chem Biol Interact. 2015 Dec 5;242:13-23. doi: 10.1016/j.cbi.2015.08.023. Epub 2015 Sep 1.
30 Upregulation of multi drug resistance genes in doxorubicin resistant human acute myelogeneous leukemia cells and reversal of the resistance. Hematology. 2007 Dec;12(6):511-7. doi: 10.1080/10245330701562535.
31 Functional analysis of MRP1 cloned from bovine. FEBS Lett. 2002 Jun 19;521(1-3):211-3. doi: 10.1016/s0014-5793(02)02816-8.
32 Functional defect caused by the 4544G>A SNP in ABCC2: potential impact for drug cellular disposition. Pharmacogenet Genomics. 2011 Dec;21(12):884-93. doi: 10.1097/FPC.0b013e32834d672b.
33 Role of multidrug resistance protein 2 (MRP2, ABCC2) in alkylating agent detoxification: MRP2 potentiates glutathione S-transferase A1-1-mediated resistance to chlorambucil cytotoxicity. J Pharmacol Exp Ther. 2004 Jan;308(1):260-7. doi: 10.1124/jpet.103.057729. Epub 2003 Oct 20.
34 MRP2 (ABCC2) transports taxanes and confers paclitaxel resistance and both processes are stimulated by probenecid. Int J Cancer. 2005 Sep 20;116(5):824-9. doi: 10.1002/ijc.21013.
35 Association of genetic polymorphisms in SLCO1B3 and ABCC2 with docetaxel-induced leukopenia. Cancer Sci. 2008 May;99(5):967-72.
36 In vitro study of transporters involved in intestinal absorption of inorganic arsenic. Chem Res Toxicol. 2012 Feb 20;25(2):446-53. doi: 10.1021/tx200491f. Epub 2012 Jan 26.
37 Potency of individual bile acids to regulate bile acid synthesis and transport genes in primary human hepatocyte cultures. Toxicol Sci. 2014 Oct;141(2):538-46. doi: 10.1093/toxsci/kfu151. Epub 2014 Jul 23.
38 Evaluation of drug transporters' significance for multidrug resistance in head and neck squamous cell carcinoma. Head Neck. 2011 Jul;33(7):959-68. doi: 10.1002/hed.21559. Epub 2010 Aug 24.
39 Gene expression analysis of precision-cut human liver slices indicates stable expression of ADME-Tox related genes. Toxicol Appl Pharmacol. 2011 May 15;253(1):57-69.