Details of the Drug-Related molecule(s) Interaction Atlas

General Information of Drug (ID: DMAEI51)

• Drug Name: Dichloroindophenol Drug Info
• Synonyms: Dichlorophenolindophenol; Indochlorophenol; Tillmans Reagent; 2,5-Cyclohexadien-1-one, 2,6-dichloro-4-((4-hydroxyphenyl)imino)-; 2,6-Dichlorophenolindophenol; 2,5-cyclohexadien-1-one, 2,6-dichloro-4-[(4-hydroxyphenyl)imino]-; 2,6-DICHLOROINDOPHENOL; 2,6-Dichloro-N-4-hydroxyphenyl-p-benzoquinone monoimine; 4-[(3,5-dichloro-4-hydroxyphenyl)imino]cyclohexa-2,5-dien-1-one; 956-48-9; C35QN2Z58B; CHEBI:27451; CHEBI:945; DCPIP; DPIP; N-3,5-dichloro-4-hydroxyphenyl-1,4-benzoquinone imine; UNII-C35QN2Z58B
• Cross-matching ID:
  PubChem CID: 13726
  ChEBI ID: CHEBI:945
  CAS Number: CAS 956-48-9
  TTD Drug ID: DMAEI51
  INTEDE Drug ID: DR2045

Molecule-Related Drug Atlas

Drug(s) Metabolized By Methionine synthase reductase (MTRR)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Doxorubicin	DMVP5YE	Acute myelogenous leukaemia	2A41	Approved	[1]
Folic Acid	DMEMBJC	Colorectal carcinoma		Approved	[4]
Menadione	DMSJDTY	Vitamin K deficiency	5B59	Approved	[1]
Ferricyanide	DM1TH08	N. A.	N. A.	Investigative	[1]

Drug(s) Affected By Ribosyldihydronicotinamide dehydrogenase (NQO2)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Quercetin	DM3NC4M	Obesity	5B81	Approved	[5]
Tretinoin	DM49DUI	Acne vulgaris	ED80	Approved	[6]
Isotretinoin	DM4QTBN	Acne vulgaris	ED80	Approved	[7]
Tacrine	DM51FY6	Alzheimer disease	8A20	Approved	[3]
Panobinostat	DM58WKG	Chronic graft versus host disease		Approved	[8]
Arsenic trioxide	DM61TA4	Acute lymphoblastic leukaemia	2A85	Approved	[9]
Ciclosporin	DMAZJFX	Graft-versus-host disease	4B24	Approved	[10]
Valproate	DMCFE9I	Epilepsy	8A60-8A68	Approved	[11]
Ivermectin	DMDBX5F	Intestinal strongyloidiasis due to nematode parasite	1F6B	Approved	[12]
Hesperetin	DMKER83	High blood cholesterol level	5C80.00	Approved	[13]

Drug(s) Affected By NAD(P)H dehydrogenase 1 (NQO1)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Cisplatin	DMRHGI9	Adenocarcinoma	2D40	Approved	[14]
Doxorubicin	DMVP5YE	Acute myelogenous leukaemia	2A41	Approved	[15]
Cannabidiol	DM0659E	Dravet syndrome	8A61.11	Approved	[16]
Hydrogen peroxide	DM1NG5W	Infectious disease	1A00-CA43.1	Approved	[17]
TECFIDERA	DM2OVDT	Multiple sclerosis	8A40	Approved	[18]
Sulindac	DM2QHZU	Acute myelogenous leukaemia	2A41	Approved	[19]
Simvastatin	DM30SGU	Arteriosclerosis	BD40	Approved	[20]
Lapatinib	DM3BH1Y	Breast cancer	2C60-2C65	Approved	[21]
Quercetin	DM3NC4M	Obesity	5B81	Approved	[22]
Rofecoxib	DM3P5DA	Osteoarthritis	FA00-FA05	Approved	[23]

Molecular Interaction Atlas of This Drug

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Methionine synthase reductase (MTRR) Main DME	DE6NIY9	MTRR_HUMAN	Substrate	[1]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
NAD(P)H dehydrogenase 1 (NQO1)	OTZGGIVK	NQO1_HUMAN	Drug Response	[2]
Ribosyldihydronicotinamide dehydrogenase (NQO2)	OTGDAJRZ	NQO2_HUMAN	Biotransformations	[3]

References

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• [2] DCPIP (2,6-dichlorophenolindophenol) as a genotype-directed redox chemotherapeutic targeting NQO1*2 breast carcinoma. Free Radic Res. 2011 Mar;45(3):276-92. doi: 10.3109/10715762.2010.526766. Epub 2010 Nov 1.
• [3] Reduction and scavenging of chemically reactive drug metabolites by NAD(P)H:quinone oxidoreductase 1 and NRH:quinone oxidoreductase 2 and variability in hepatic concentrations. Chem Res Toxicol. 2018 Feb 19;31(2):116-126.
• [4] Polymorphisms in genes involved in folate metabolism as maternal risk factors for Down syndrome in China. J Zhejiang Univ Sci B. 2008 Feb;9(2):93-9.
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• [6] Transcriptional and Metabolic Dissection of ATRA-Induced Granulocytic Differentiation in NB4 Acute Promyelocytic Leukemia Cells. Cells. 2020 Nov 5;9(11):2423. doi: 10.3390/cells9112423.
• [7] 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.
• [8] 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.
• [9] Aberrantly expressed genes in HaCaT keratinocytes chronically exposed to arsenic trioxide. Biomark Insights. 2011 Feb 8;6:7-16.
• [10] Integrating multiple omics to unravel mechanisms of Cyclosporin A induced hepatotoxicity in vitro. Toxicol In Vitro. 2015 Apr;29(3):489-501.
• [11] Integrative omics data analyses of repeated dose toxicity of valproic acid in vitro reveal new mechanisms of steatosis induction. Toxicology. 2018 Jan 15;393:160-170.
• [12] Quantitative proteomics reveals a broad-spectrum antiviral property of ivermectin, benefiting for COVID-19 treatment. J Cell Physiol. 2021 Apr;236(4):2959-2975. doi: 10.1002/jcp.30055. Epub 2020 Sep 22.
• [13] Various concentrations of hesperetin induce different types of programmed cell death in human breast cancerous and normal cell lines in a ROS-dependent manner. Chem Biol Interact. 2023 Sep 1;382:110642. doi: 10.1016/j.cbi.2023.110642. Epub 2023 Jul 23.
• [14] Transcriptomics hit the target: monitoring of ligand-activated and stress response pathways for chemical testing. Toxicol In Vitro. 2015 Dec 25;30(1 Pt A):7-18.
• [15] Functional cardiotoxicity assessment of cosmetic compounds using human-induced pluripotent stem cell-derived cardiomyocytes. Arch Toxicol. 2018 Jan;92(1):371-381.
• [16] Cannabidiol induces antioxidant pathways in keratinocytes by targeting BACH1. Redox Biol. 2020 Jan;28:101321. doi: 10.1016/j.redox.2019.101321. Epub 2019 Sep 5.
• [17] Gypenosides protect retinal pigment epithelium cells from oxidative stress. Food Chem Toxicol. 2018 Feb;112:76-85.
• [18] Enhanced cytotoxicity of bioreductive antitumor agents with dimethyl fumarate in human glioblastoma cells. Anticancer Drugs. 2005 Feb;16(2):167-74.
• [19] Growth-suppressive effect of non-steroidal anti-inflammatory drugs on 11 colon-cancer cell lines and fluorescence differential display of genes whose expression is influenced by sulindac. Int J Cancer. 2000 Dec 15;88(6):873-80. doi: 10.1002/1097-0215(20001215)88:6<873::aid-ijc6>3.0.co;2-b.
• [20] Simvastatin protects dopaminergic neurons against MPP+-induced oxidative stress and regulates the endogenous anti-oxidant system through ERK. Cell Physiol Biochem. 2018;51(4):1957-1968.
• [21] P450 3A-catalyzed O-dealkylation of lapatinib induces mitochondrial stress and activates Nrf2. Chem Res Toxicol. 2016 May 16;29(5):784-96.
• [22] Induction of human NAD(P)H:quinone oxidoreductase (NQO1) gene expression by the flavonol quercetin. Toxicol Lett. 2001 Feb 3;119(1):49-57.
• [23] Rofecoxib modulates multiple gene expression pathways in a clinical model of acute inflammatory pain. Pain. 2007 Mar;128(1-2):136-47.