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

General Information of Drug (ID: DMCIM9A)

Drug Name
Citraconic acid Drug Info
Synonyms
Citraconic acid; 2-methylmaleic acid; METHYLMALEIC ACID; 498-23-7; 2-Methyl-2-butenedioic acid; cis-Methylbutenedioic acid; Citraconate; (Z)-2-Methyl-2-butenedioic acid; Maleic acid, methyl-; Citraconsaeure; Methyl-maleinsaeure; Kyselina citrakonova; Kyselina citrakonova [Czech]; citraconsaure; UNII-0RQ6CXO9KD; (2Z)-2-methylbut-2-enedioic acid; BRN 1722679; 2-Butenedioic acid, 2-methyl-, (Z)-; 2-Methylmaleate; alpha-methylmaleic acid; EINECS 207-858-7; NSC 32949; 0RQ6CXO9KD; cis-2-methylbutenedioic acid; 2-methyl-2Z-butenedioic ac
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
643798
ChEBI ID
CHEBI:17626
CAS Number
CAS 498-23-7
TTD Drug ID
DMCIM9A

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DOT
Drug Status:
Approved Drug(s)
Investigative Drug(s)
Download the Complete Related Drug List
Drug(s) Targeting Bacterial Fumarate reductase flavoprotein (Bact frdA)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Thiabendazole DM7YCK3 Ascariasis 1F62 Approved [4]
Oxantel pamoate DMZ30JT Trichuris trichiura infection 1F6G Approved [4]
Morantel tartrate DM560Y3 Mature gastrointestinal nematode infection 1F6Y Approved [4]
Flavin-Adenine Dinucleotide DM5S4GK Discovery agent N.A. Investigative [5]
Heme DMGC287 Discovery agent N.A. Investigative [6]
Fumarate DM9VLS2 Discovery agent N.A. Investigative [5]
2,3-DIMETHYL-1,4-NAPHTHOQUINONE DMGXVBA Discovery agent N.A. Investigative [6]
2-[1-(4-CHLORO-PHENYL)-ETHYL]-4,6-DINITRO-PHENOL DMUZDSC Discovery agent N.A. Investigative [6]
2-HEPTYL-4-HYDROXY QUINOLINE N-OXIDE DMJ3ATL Discovery agent N.A. Investigative [6]
Malate Like Intermediate DM4OQWZ Discovery agent N.A. Investigative [1]
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Drug(s) Affected By Transcription regulator protein BACH1 (BACH1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [7]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [8]
TECFIDERA DM2OVDT Multiple sclerosis 8A40 Approved [3]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [9]
Acetic Acid, Glacial DM4SJ5Y infection in the ear canal AA0Y Approved [10]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [11]
Hydroquinone DM6AVR4 Melasma ED60.1 Approved [12]
Leflunomide DMR8ONJ Arthritis FA20 Approved [13]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [14]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [15]
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Drug(s) Affected By Ferritin light chain (FTL)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [7]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [16]
Selenium DM25CGV N. A. N. A. Approved [17]
TECFIDERA DM2OVDT Multiple sclerosis 8A40 Approved [2]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [18]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [19]
Disulfiram DMCL2OK Alcohol dependence 6C40.2 Approved [20]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [21]
Ivermectin DMDBX5F Intestinal strongyloidiasis due to nematode parasite 1F6B Approved [22]
Ethanol DMDRQZU Chronic pain MG30 Approved [23]
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Drug(s) Affected By Ferritin heavy chain (FTH1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [7]
TECFIDERA DM2OVDT Multiple sclerosis 8A40 Approved [2]
Sulindac DM2QHZU Acute myelogenous leukaemia 2A41 Approved [24]
Methotrexate DM2TEOL Anterior urethra cancer Approved [25]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [26]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [9]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [27]
Hydroquinone DM6AVR4 Melasma ED60.1 Approved [28]
Marinol DM70IK5 Anorexia nervosa cachexia 6B80 Approved [29]
Clodronate DM9Y6X7 Hypercalcaemia 5B91.0 Approved [30]
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Drug(s) Affected By Forkhead box protein M1 (FOXM1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [31]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [16]
Methotrexate DM2TEOL Anterior urethra cancer Approved [32]
Quercetin DM3NC4M Obesity 5B81 Approved [33]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [26]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [9]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [34]
Marinol DM70IK5 Anorexia nervosa cachexia 6B80 Approved [35]
Testosterone DM7HUNW Hot flushes GA30 Approved [36]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [37]
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Drug(s) Affected By Nuclear factor erythroid 2-related factor 2 (NFE2L2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [38]
Verapamil DMA7PEW Angina pectoris BA40 Approved [39]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [40]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [41]
Selenium DM25CGV N. A. N. A. Approved [17]
TECFIDERA DM2OVDT Multiple sclerosis 8A40 Approved [3]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [42]
Lapatinib DM3BH1Y Breast cancer 2C60-2C65 Approved [43]
Quercetin DM3NC4M Obesity 5B81 Approved [33]
Furazolidone DM3P6V7 Diarrhea ME05.1 Approved [44]
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Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas
Download the Complete Interaction Atlas for Visualization in Cytoscape

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial Fumarate reductase flavoprotein (Bact frdA) TTHDSE2 FRDA_HELPY Inhibitor [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Ferritin heavy chain (FTH1) OT6IFS0O FRIH_HUMAN Gene/Protein Processing [2]
Ferritin light chain (FTL) OTYQA8A6 FRIL_HUMAN Gene/Protein Processing [2]
Forkhead box protein M1 (FOXM1) OT5887KR FOXM1_HUMAN Gene/Protein Processing [2]
Nuclear factor erythroid 2-related factor 2 (NFE2L2) OT0HENJ5 NF2L2_HUMAN Protein Interaction/Cellular Processes [3]
Transcription regulator protein BACH1 (BACH1) OTY8004K BACH1_HUMAN Protein Interaction/Cellular Processes [3]

References

1 DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Nucleic Acids Res. 2011 Jan;39(Database issue):D1035-41.
2 Fumarate Mediates a Chronic Proliferative Signal in Fumarate Hydratase-Inactivated Cancer Cells by Increasing Transcription and Translation of Ferritin Genes. Mol Cell Biol. 2017 May 16;37(11):e00079-17. doi: 10.1128/MCB.00079-17. Print 2017 Jun 1.
3 Distinct Nrf2 Signaling Mechanisms of Fumaric Acid Esters and Their Role in Neuroprotection against 1-Methyl-4-Phenyl-1,2,3,6-Tetrahydropyridine-Induced Experimental Parkinson's-Like Disease. J Neurosci. 2016 Jun 8;36(23):6332-51. doi: 10.1523/JNEUROSCI.0426-16.2016.
4 Fumarate reductase is essential for Helicobacter pylori colonization of the mouse stomach. Microb Pathog. 2000 Nov;29(5):279-87.
5 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
6 The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
7 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.
8 Comparison of protective effect of ascorbic acid on redox and endocannabinoid systems interactions in in vitro cultured human skin fibroblasts exposed to UV radiation and hydrogen peroxide. Arch Dermatol Res. 2017 May;309(4):285-303. doi: 10.1007/s00403-017-1729-0. Epub 2017 Mar 11.
9 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.
10 Motexafin gadolinium and zinc induce oxidative stress responses and apoptosis in B-cell lymphoma lines. Cancer Res. 2005 Dec 15;65(24):11676-88.
11 miR-155/BACH1 signaling pathway in human lung adenocarcinoma cell death induced by arsenic trioxide. Sichuan Da Xue Xue Bao Yi Xue Ban. 2017 Nov;48(6):828-833.
12 The electrophilic character of quinones is essential for the suppression of Bach1. Toxicology. 2017 Jul 15;387:17-26.
13 Endoplasmic reticulum stress and MAPK signaling pathway activation underlie leflunomide-induced toxicity in HepG2 Cells. Toxicology. 2017 Dec 1;392:11-21.
14 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.
15 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.
16 Gene expression after treatment with hydrogen peroxide, menadione, or t-butyl hydroperoxide in breast cancer cells. Cancer Res. 2002 Nov 1;62(21):6246-54.
17 Selenium and vitamin E: cell type- and intervention-specific tissue effects in prostate cancer. J Natl Cancer Inst. 2009 Mar 4;101(5):306-20.
18 Systems analysis of transcriptome and proteome in retinoic acid/arsenic trioxide-induced cell differentiation/apoptosis of promyelocytic leukemia. Proc Natl Acad Sci U S A. 2005 May 24;102(21):7653-8.
19 Essential role of cell cycle regulatory genes p21 and p27 expression in inhibition of breast cancer cells by arsenic trioxide. Med Oncol. 2011 Dec;28(4):1225-54.
20 Keratinocyte gene expression profiles discriminate sensitizing and irritating compounds. Toxicol Sci. 2010 Sep;117(1):81-9.
21 Human embryonic stem cell-derived test systems for developmental neurotoxicity: a transcriptomics approach. Arch Toxicol. 2013 Jan;87(1):123-43.
22 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.
23 Comparison of replicative senescence and stress-induced premature senescence combining differential display and low-density DNA arrays. FEBS Lett. 2005 Jul 4;579(17):3651-9. doi: 10.1016/j.febslet.2005.05.056.
24 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.
25 Global molecular effects of tocilizumab therapy in rheumatoid arthritis synovium. Arthritis Rheumatol. 2014 Jan;66(1):15-23.
26 Effects of ciglitazone and troglitazone on the proliferation of human stomach cancer cells. World J Gastroenterol. 2009 Jan 21;15(3):310-20.
27 [Construction of subtracted cDNA library in human Jurkat T cell line induced by arsenic trioxide in vitro]. Zhonghua Yu Fang Yi Xue Za Zhi. 2003 Nov;37(6):403-7.
28 Survival of retinal pigment epithelium after exposure to prolonged oxidative injury: a detailed gene expression and cellular analysis. Invest Ophthalmol Vis Sci. 2004 Oct;45(10):3767-77.
29 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.
30 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.
31 mTOR inhibition reverses acquired endocrine therapy resistance of breast cancer cells at the cell proliferation and gene-expression levels. Cancer Sci. 2008 Oct;99(10):1992-2003. doi: 10.1111/j.1349-7006.2008.00955.x.
32 Methotrexate modulates folate phenotype and inflammatory profile in EA.hy 926 cells. Eur J Pharmacol. 2014 Jun 5;732:60-7.
33 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.
34 Identification of transcriptome signatures and biomarkers specific for potential developmental toxicants inhibiting human neural crest cell migration. Arch Toxicol. 2016 Jan;90(1):159-80.
35 JunD is involved in the antiproliferative effect of Delta9-tetrahydrocannabinol on human breast cancer cells. Oncogene. 2008 Aug 28;27(37):5033-44.
36 Effects of 1alpha,25 dihydroxyvitamin D3 and testosterone on miRNA and mRNA expression in LNCaP cells. Mol Cancer. 2011 May 18;10:58.
37 Anthelmintic Niclosamide Disrupts the Interplay of p65 and FOXM1/-catenin and Eradicates Leukemia Stem Cells in Chronic Myelogenous Leukemia. Clin Cancer Res. 2017 Feb 1;23(3):789-803. doi: 10.1158/1078-0432.CCR-16-0226. Epub 2016 Aug 4.
38 Gingival Stromal Cells as an In Vitro Model: Cannabidiol Modulates Genes Linked With Amyotrophic Lateral Sclerosis. J Cell Biochem. 2017 Apr;118(4):819-828. doi: 10.1002/jcb.25757. Epub 2016 Nov 28.
39 Protective role of HO-1 for alcohol-dependent liver damage. Dig Dis. 2010;28(6):792-8. doi: 10.1159/000324287. Epub 2011 Apr 27.
40 Sertraline induces endoplasmic reticulum stress in hepatic cells. Toxicology. 2014 Aug 1;322:78-88. doi: 10.1016/j.tox.2014.05.007. Epub 2014 May 24.
41 Gypenosides protect retinal pigment epithelium cells from oxidative stress. Food Chem Toxicol. 2018 Feb;112:76-85.
42 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.
43 P450 3A-catalyzed O-dealkylation of lapatinib induces mitochondrial stress and activates Nrf2. Chem Res Toxicol. 2016 May 16;29(5):784-96.
44 P21(Waf1/Cip1) plays a critical role in furazolidone-induced apoptosis in HepG2 cells through influencing the caspase-3 activation and ROS generation. Food Chem Toxicol. 2016 Feb;88:1-12. doi: 10.1016/j.fct.2015.12.004. Epub 2015 Dec 11.