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

General Information of Drug (ID: DMWX3HT)

Drug Name
ACEA Drug Info
Synonyms
Arachidonyl-2-chloroethylamide; arachidonyl-2-chloroethylamide; Arachidonyl-2'-chloroethylamide; CHEMBL151167; (5Z,8Z,11Z,14Z)-N-(2-chloroethyl)icosa-5,8,11,14-tetraenamide; C22H36ClNO; Arachidonoyl-2-chloroethylamide; AC1NSJTE; GTPL738; SCHEMBL1517676; MolPort-003-940-362; HMS3649N11; MFCD02683581; BN0049; BDBM50072769; ZINC13675373; 1595AH; AKOS024456526; Arachidonyl-2'-chloroethylamide hydrate; NCGC00162406-01; LS-63778; ACM273734079; SR-01000946682; L000112; SR-01000946682-1; N-(2-Chloroethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
5311006
CAS Number
CAS 220556-69-4
TTD Drug ID
DMWX3HT

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DOT
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Patented Agent(s)
Investigative Drug(s)
Download the Complete Related Drug List
Drug(s) Targeting Cannabinoid receptor 1 (CB1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Marinol DM70IK5 Anorexia nervosa cachexia 6B80 Approved [6]
NABILONE DMVRYT2 Insomnia 7A00-7A0Z Approved [7]
Orlistat DMRJSP8 Obesity 5B81 Approved [8]
SR141716A DMCO5JZ Obesity 5B81 Approved [9]
Tebipenem DMVSX6O Urinary tract infection GC08 Phase 3 [10]
Conatumumab DM2UOSN Colorectal cancer 2B91.Z Phase 2 [11]
GW-42004 DMY3KSU Lipid metabolism disorder 5C52.Z Phase 2 [12]
SR-147778 DMNAECP Obesity 5B81 Phase 2 [13]
Nimacimab DM21Z68 Diabetic nephropathy GB61.Z Phase 2 [14]
AEF0117 DMQ1GH4 Marijuana use disorder 6C41 Phase 2 [15]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Mitogen-activated protein kinase 3 (MAPK3)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [16]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [17]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [18]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [19]
Beta-carotene DM0RXBT Vitamin deficiency 5B55-5B71 Approved [20]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [21]
Secobarbital DM14RF5 Epilepsy 8A60-8A68 Approved [22]
Gefitinib DM15F0X Colon adenocarcinoma Approved [23]
Fexofenadine DM17ONX Allergic rhinitis CA08.0 Approved [24]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [25]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Mitogen-activated protein kinase 1 (MAPK1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Ethanol DMDRQZU Chronic pain MG30 Approved [26]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [17]
Carvedilol DMHTEAO Chronic heart failure BD1Z Approved [27]
Paclitaxel DMLB81S Breast carcinoma Approved [28]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [29]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [16]
Urokinase DM0GOUD Myocardial infarction BA41-BA43 Approved [30]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [31]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [19]
Beta-carotene DM0RXBT Vitamin deficiency 5B55-5B71 Approved [20]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Estrogen-related receptor gamma (ESRRG)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tretinoin DM49DUI Acne vulgaris ED80 Approved [32]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [33]
Marinol DM70IK5 Anorexia nervosa cachexia 6B80 Approved [34]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [35]
Testosterone enanthate DMB6871 N. A. N. A. Approved [36]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [37]
Rosiglitazone DMILWZR Chronic kidney disease GB61 Approved [38]
Zoledronate DMIXC7G Adenocarcinoma 2D40 Approved [39]
Diethylstilbestrol DMN3UXQ Gonorrheal vaginitis GA02 Approved [40]
Arsenic DMTL2Y1 N. A. N. A. Approved [41]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Diacylglycerol lipase-beta (DAGLB)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [42]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [35]
Ivermectin DMDBX5F Intestinal strongyloidiasis due to nematode parasite 1F6B Approved [43]
Clozapine DMFC71L Schizophrenia 6A20 Approved [44]
Temozolomide DMKECZD Adenocarcinoma 2D40 Approved [45]
Cupric Sulfate DMP0NFQ Fungal infection 1F29-1F2F Approved [46]
Irinotecan DMP6SC2 Adenocarcinoma 2D40 Approved [47]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [48]
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [49]
Carbamazepine DMZOLBI Epilepsy 8A60-8A68 Approved [50]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Fibroblast growth factor 21 (FGF21)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [35]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [37]
Fenofibrate DMFKXDY Coronary atherosclerosis Approved [51]
Rosiglitazone DMILWZR Chronic kidney disease GB61 Approved [52]
Pioglitazone DMKJ485 Amyotrophic lateral sclerosis 8B60.0 Approved [52]
Dexamethasone DMMWZET Acute adrenal insufficiency Approved [53]
Famotidine DMRL3AB Gastric ulcer DA60 Approved [54]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [55]
Lansoprazole DMXYLQ3 Gastric ulcer DA60 Approved [54]
Bezafibrate DMZDCS0 Hypercholesterolaemia 5C80.0 Approved [51]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Diacylglycerol lipase-alpha (DAGLA)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tretinoin DM49DUI Acne vulgaris ED80 Approved [56]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [57]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [37]
Cupric Sulfate DMP0NFQ Fungal infection 1F29-1F2F Approved [46]
Orlistat DMRJSP8 Obesity 5B81 Approved [58]
Phenobarbital DMXZOCG Cluster headache 8A81.0 Approved [59]
Tamibarotene DM3G74J T-cell leukaemia 2A90 Phase 3 [56]
Benzo(a)pyrene DMN7J43 N. A. N. A. Phase 1 [60]
PMID28460551-Compound-2 DM4DOUB N. A. N. A. Patented [61]
KOJIC ACID DMP84CS Discovery agent N.A. Investigative [62]
⏷ Show the Full List of 10 Drug(s)

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
Cannabinoid receptor 1 (CB1) TT6OEDT CNR1_HUMAN Agonist [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Diacylglycerol lipase-alpha (DAGLA) OT8GVKGM DGLA_HUMAN Gene/Protein Processing [3]
Diacylglycerol lipase-beta (DAGLB) OT1S9869 DGLB_HUMAN Gene/Protein Processing [3]
Estrogen-related receptor gamma (ESRRG) OTC3A0KU ERR3_HUMAN Gene/Protein Processing [3]
Fibroblast growth factor 21 (FGF21) OT3RXVRD FGF21_HUMAN Gene/Protein Processing [4]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [5]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [5]

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 738).
2 Synthesis and characterization of potent and selective agonists of the neuronal cannabinoid receptor (CB1). J Pharmacol Exp Ther. 1999 Jun;289(3):1427-33.
3 An inverse agonist of estrogen-related receptor regulates 2-arachidonoylglycerol synthesis by modulating diacylglycerol lipase expression in alcohol-intoxicated mice. Arch Toxicol. 2020 Feb;94(2):427-438. doi: 10.1007/s00204-019-02648-7. Epub 2020 Jan 7.
4 The Orphan Nuclear Receptor ERR Regulates Hepatic CB1 Receptor-Mediated Fibroblast Growth Factor 21 Gene Expression. PLoS One. 2016 Jul 25;11(7):e0159425. doi: 10.1371/journal.pone.0159425. eCollection 2016.
5 Human lung-resident macrophages express CB1 and CB2 receptors whose activation inhibits the release of angiogenic and lymphangiogenic factors. J Leukoc Biol. 2016 Apr;99(4):531-40. doi: 10.1189/jlb.3HI1214-584R. Epub 2015 Oct 14.
6 Emerging strategies for exploiting cannabinoid receptor agonists as medicines. Br J Pharmacol. 2009 Feb;156(3):397-411.
7 Novel 1',1'-chain substituted hexahydrocannabinols: 9-hydroxy-3-(1-hexyl-cyclobut-1-yl)-hexahydrocannabinol (AM2389) a highly potent cannabinoid r... J Med Chem. 2010 Oct 14;53(19):6996-7010.
8 Tetrahydrolipstatin analogues as modulators of endocannabinoid 2-arachidonoylglycerol metabolism. J Med Chem. 2008 Nov 13;51(21):6970-9.
9 Anti-obesity drugs. Expert Opin Pharmacother. 2008 Jun;9(8):1339-50.
10 Emerging drugs for obesity: linking novel biological mechanisms to pharmaceutical pipelines. Expert Opin Emerg Drugs. 2005 Aug;10(3):643-60.
11 Clinical pipeline report, company report or official report of AstraZeneca (2009).
12 Company report (Gwpharm)
13 Surinabant, a selective cannabinoid receptor type 1 antagonist, inhibits 9-tetrahydrocannabinol-induced central nervous system and heart rate effects in humans.Br J Clin Pharmacol.2013 Jul;76(1):65-77.
14 Clinical pipeline report, company report or official report of Bird Rock Bio.
15 Clinical pipeline report, company report or official report of Affimed Therapeutics.
16 Treatment with anticancer agents induces dysregulation of specific Wnt signaling pathways in human ovarian luteinized granulosa cells in vitro. Toxicol Sci. 2013 Nov;136(1):183-92. doi: 10.1093/toxsci/kft175. Epub 2013 Aug 16.
17 Progesterone increases csk homologous kinase in HMC-1560 human mast cells and reduces cell proliferation. J Cell Biochem. 2007 Dec 1;102(5):1271-80. doi: 10.1002/jcb.21357.
18 Cannabidiol upregulates melanogenesis through CB1 dependent pathway by activating p38 MAPK and p42/44 MAPK. Chem Biol Interact. 2017 Aug 1;273:107-114. doi: 10.1016/j.cbi.2017.06.005. Epub 2017 Jun 7.
19 Sertraline, an antidepressant, induces apoptosis in hepatic cells through the mitogen-activated protein kinase pathway. Toxicol Sci. 2014 Feb;137(2):404-15. doi: 10.1093/toxsci/kft254. Epub 2013 Nov 5.
20 Growth stimulation of human pulmonary adenocarcinoma cells and small airway epithelial cells by beta-carotene via activation of cAMP, PKA, CREB and ERK1/2. Int J Cancer. 2006 Mar 15;118(6):1370-80. doi: 10.1002/ijc.21537.
21 Estrogen and pure antiestrogen fulvestrant (ICI 182 780) augment cell-matrigel adhesion of MCF-7 breast cancer cells through a novel G protein coupled estrogen receptor (GPR30)-to-calpain signaling axis. Toxicol Appl Pharmacol. 2014 Mar 1;275(2):176-81. doi: 10.1016/j.taap.2014.01.005. Epub 2014 Jan 17.
22 Inhibition of activator protein 1 by barbiturates is mediated by differential effects on mitogen-activated protein kinases and the small G proteins ras and rac-1. J Pharmacol Exp Ther. 2004 Dec;311(3):1232-40. doi: 10.1124/jpet.104.071332. Epub 2004 Jul 19.
23 Growth of hormone-dependent MCF-7 breast cancer cells is promoted by constitutive caveolin-1 whose expression is lost in an EGF-R-mediated manner during development of tamoxifen resistance. Breast Cancer Res Treat. 2010 Feb;119(3):575-91. doi: 10.1007/s10549-009-0355-8. Epub 2009 Mar 15.
24 Effect of histamine H1 receptor antagonists on TARC/CCL17 and MDC/CCL22 production from CD14+ cells induced by antigenic stimulation in vitro. Int Arch Allergy Immunol. 2011;155(1):38-51. doi: 10.1159/000318720. Epub 2010 Nov 25.
25 SIRT3 Mediates the Antioxidant Effect of Hydrogen Sulfide in Endothelial Cells. Antioxid Redox Signal. 2016 Feb 20;24(6):329-43. doi: 10.1089/ars.2015.6331. Epub 2015 Nov 10.
26 Downregulation of mitogen-activated protein kinases (MAPKs) in chronic ethanol-induced fatty liver. Toxicol Mech Methods. 2020 Jul;30(6):407-416. doi: 10.1080/15376516.2020.1747126. Epub 2020 Apr 1.
27 A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling. Proc Natl Acad Sci U S A. 2007 Oct 16;104(42):16657-62. doi: 10.1073/pnas.0707936104. Epub 2007 Oct 9.
28 The stent-eluting drugs sirolimus and paclitaxel suppress healing of the endothelium by induction of autophagy. Am J Pathol. 2009 Nov;175(5):2226-34.
29 Modulation of apoptosis in HaCaT keratinocytes via differential regulation of ERK signaling pathway by flavonoids. J Biol Chem. 2005 Sep 9;280(36):31498-507. doi: 10.1074/jbc.M505537200. Epub 2005 Jul 13.
30 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.
31 Cannabidiol Modulates the Immunophenotype and Inhibits the Activation of the Inflammasome in Human Gingival Mesenchymal Stem Cells. Front Physiol. 2016 Nov 24;7:559. doi: 10.3389/fphys.2016.00559. eCollection 2016.
32 Phenotypic characterization of retinoic acid differentiated SH-SY5Y cells by transcriptional profiling. PLoS One. 2013 May 28;8(5):e63862.
33 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.
34 9-Tetrahydrocannabinol leads to endoplasmic reticulum stress and mitochondrial dysfunction in human BeWo trophoblasts. Reprod Toxicol. 2019 Aug;87:21-31. doi: 10.1016/j.reprotox.2019.04.008. Epub 2019 May 1.
35 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.
36 Transcriptional profiling of testosterone-regulated genes in the skeletal muscle of human immunodeficiency virus-infected men experiencing weight loss. J Clin Endocrinol Metab. 2007 Jul;92(7):2793-802. doi: 10.1210/jc.2006-2722. Epub 2007 Apr 17.
37 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.
38 Transcriptomic analysis of untreated and drug-treated differentiated HepaRG cells over a 2-week period. Toxicol In Vitro. 2015 Dec 25;30(1 Pt A):27-35.
39 Interleukin-19 as a translational indicator of renal injury. Arch Toxicol. 2015 Jan;89(1):101-6.
40 4-Hydroxytamoxifen binds to and deactivates the estrogen-related receptor gamma. Proc Natl Acad Sci U S A. 2001 Jul 17;98(15):8880-4. doi: 10.1073/pnas.151244398. Epub 2001 Jul 10.
41 Prenatal arsenic exposure and the epigenome: identifying sites of 5-methylcytosine alterations that predict functional changes in gene expression in newborn cord blood and subsequent birth outcomes. Toxicol Sci. 2015 Jan;143(1):97-106. doi: 10.1093/toxsci/kfu210. Epub 2014 Oct 10.
42 Cannabidiol Activates Neuronal Precursor Genes in Human Gingival Mesenchymal Stromal Cells. J Cell Biochem. 2017 Jun;118(6):1531-1546. doi: 10.1002/jcb.25815. Epub 2016 Dec 29.
43 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.
44 Toxicoproteomics reveals an effect of clozapine on autophagy in human liver spheroids. Toxicol Mech Methods. 2023 Jun;33(5):401-410. doi: 10.1080/15376516.2022.2156005. Epub 2022 Dec 19.
45 Temozolomide induces activation of Wnt/-catenin signaling in glioma cells via PI3K/Akt pathway: implications in glioma therapy. Cell Biol Toxicol. 2020 Jun;36(3):273-278. doi: 10.1007/s10565-019-09502-7. Epub 2019 Nov 22.
46 Physiological and toxicological transcriptome changes in HepG2 cells exposed to copper. Physiol Genomics. 2009 Aug 7;38(3):386-401.
47 Clinical determinants of response to irinotecan-based therapy derived from cell line models. Clin Cancer Res. 2008 Oct 15;14(20):6647-55.
48 Multiple microRNAs function as self-protective modules in acetaminophen-induced hepatotoxicity in humans. Arch Toxicol. 2018 Feb;92(2):845-858.
49 Bringing in vitro analysis closer to in vivo: studying doxorubicin toxicity and associated mechanisms in 3D human microtissues with PBPK-based dose modelling. Toxicol Lett. 2018 Sep 15;294:184-192.
50 Gene Expression Regulation and Pathway Analysis After Valproic Acid and Carbamazepine Exposure in a Human Embryonic Stem Cell-Based Neurodevelopmental Toxicity Assay. Toxicol Sci. 2015 Aug;146(2):311-20. doi: 10.1093/toxsci/kfv094. Epub 2015 May 15.
51 Sodium butyrate stimulates expression of fibroblast growth factor 21 in liver by inhibition of histone deacetylase 3. Diabetes. 2012 Apr;61(4):797-806. doi: 10.2337/db11-0846. Epub 2012 Feb 14.
52 Thiazolidinediones are potent inducers of fibroblast growth factor 21 expression in the liver. Biol Pharm Bull. 2011;34(7):1120-1. doi: 10.1248/bpb.34.1120.
53 Activation of GR but not PXR by dexamethasone attenuated acetaminophen hepatotoxicities via Fgf21 induction. Toxicology. 2017 Mar 1;378:95-106. doi: 10.1016/j.tox.2017.01.009. Epub 2017 Jan 11.
54 Increased immunoreactivity and concentration of basic fibroblast growth factor in lansoprazole-treated gastric mucosa. J Clin Gastroenterol. 1995;21 Suppl 1:S24-9.
55 Predictive toxicology using systemic biology and liver microfluidic "on chip" approaches: application to acetaminophen injury. Toxicol Appl Pharmacol. 2012 Mar 15;259(3):270-80.
56 Differential modulation of PI3-kinase/Akt pathway during all-trans retinoic acid- and Am80-induced HL-60 cell differentiation revealed by DNA microarray analysis. Biochem Pharmacol. 2004 Dec 1;68(11):2177-86.
57 Integrating multiple omics to unravel mechanisms of Cyclosporin A induced hepatotoxicity in vitro. Toxicol In Vitro. 2015 Apr;29(3):489-501.
58 Development of the first potent and specific inhibitors of endocannabinoid biosynthesis. Biochim Biophys Acta. 2006 Feb;1761(2):205-12. doi: 10.1016/j.bbalip.2005.12.009. Epub 2006 Jan 23.
59 Reproducible chemical-induced changes in gene expression profiles in human hepatoma HepaRG cells under various experimental conditions. Toxicol In Vitro. 2009 Apr;23(3):466-75. doi: 10.1016/j.tiv.2008.12.018. Epub 2008 Dec 30.
60 Air pollution and DNA methylation alterations in lung cancer: A systematic and comparative study. Oncotarget. 2017 Jan 3;8(1):1369-1391. doi: 10.18632/oncotarget.13622.
61 Cell-based two-dimensional morphological assessment system to predict cancer drug-induced cardiotoxicity using human induced pluripotent stem cell-derived cardiomyocytes. Toxicol Appl Pharmacol. 2019 Nov 15;383:114761. doi: 10.1016/j.taap.2019.114761. Epub 2019 Sep 15.
62 Toxicogenomics of kojic acid on gene expression profiling of a375 human malignant melanoma cells. Biol Pharm Bull. 2006 Apr;29(4):655-69.