General Information of Drug (ID: DM1DEYU)

Drug Name
JWH-133 Drug Info
Synonyms
JWH-133; 259869-55-1; JWH 133; JWH133; CHEMBL371214; (6AR,10AR)-3-(1,1-DIMETHYLBUTYL)-6A,7,10,10A-TETRAHYDRO-6,6,9-TRIMETHYL-6H-DIBENZO[B,D]PYRAN; JW-133/JW133; (6aR,10aR)-6,6,9-trimethyl-3-(2-methylpentan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromene; (6aR,10aR)-6,6,9-trimethyl-3-(2-methylpentan-2-yl)-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene; (6aR,10aR)-6,6,9-Trimethyl-3-(2-methyl-2-pentanyl)-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene; YSBFLLZNALVODA-RBUKOAKNSA-N; JW 133; AC1OCFIJ
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
6918505
ChEBI ID
CHEBI:146243
CAS Number
CAS 259869-55-1
TTD Drug ID
DM1DEYU

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DOT
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Investigative Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Guanfacine extended release DMB1CZ8 Attention deficit hyperactivity disorder 6A05.Z Approved [6]
NABILONE DMVRYT2 Insomnia 7A00-7A0Z Approved [7]
GW-42004 DMY3KSU Lipid metabolism disorder 5C52.Z Phase 2 [8]
KHK-6188 DMF6CTI Neuropathic pain 8E43.0 Phase 2 [9]
LY-2828360 DMO8IEZ Pain MG30-MG3Z Phase 2 [9]
APD371 DM3XT5V Crohn disease DD70 Phase 2 [10]
S-777469 DMZGNOJ Atopic dermatitis EA80 Phase 2 [11]
842166X DMOV0AP Pain MG30-MG3Z Phase 2 [12]
Beta-caryophyllene DM7583A Pain MG30-MG3Z Phase 2 [13]
Vicasinabin DMF16CU Diabetic retinopathy 9B71.0 Phase 2 [14]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Marinol DM70IK5 Anorexia nervosa cachexia 6B80 Approved [15]
NABILONE DMVRYT2 Insomnia 7A00-7A0Z Approved [7]
Orlistat DMRJSP8 Obesity 5B81 Approved [16]
SR141716A DMCO5JZ Obesity 5B81 Approved [17]
Tebipenem DMVSX6O Urinary tract infection GC08 Phase 3 [18]
Conatumumab DM2UOSN Colorectal cancer 2B91.Z Phase 2 [19]
GW-42004 DMY3KSU Lipid metabolism disorder 5C52.Z Phase 2 [8]
SR-147778 DMNAECP Obesity 5B81 Phase 2 [20]
Nimacimab DM21Z68 Diabetic nephropathy GB61.Z Phase 2 [21]
AEF0117 DMQ1GH4 Marijuana use disorder 6C41 Phase 2 [22]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Claudin-5 (CLDN5)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [23]
Guanfacine extended release DMB1CZ8 Attention deficit hyperactivity disorder 6A05.Z Approved [24]
Sanguinarine DMDINFS Dental plaque DA08.4 Approved [25]
Glycine DMIOZ29 Allergic rhinitis CA08.0 Approved [26]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [27]
Urethane DM7NSI0 N. A. N. A. Phase 4 [28]
CS-600G DM1PV4Y N. A. N. A. Phase 3 [29]
Benzo(a)pyrene DMN7J43 N. A. N. A. Phase 1 [30]
LY294002 DMY1AFS Neuroblastoma 2D11.2 Phase 1 [31]
Glyphosate DM0AFY7 Malaria 1F40-1F45 Investigative [26]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [32]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [33]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [34]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [35]
Beta-carotene DM0RXBT Vitamin deficiency 5B55-5B71 Approved [36]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [37]
Secobarbital DM14RF5 Epilepsy 8A60-8A68 Approved [38]
Gefitinib DM15F0X Colon adenocarcinoma Approved [39]
Fexofenadine DM17ONX Allergic rhinitis CA08.0 Approved [40]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [41]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Ethanol DMDRQZU Chronic pain MG30 Approved [42]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [33]
Carvedilol DMHTEAO Chronic heart failure BD1Z Approved [43]
Paclitaxel DMLB81S Breast carcinoma Approved [44]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [45]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [32]
Urokinase DM0GOUD Myocardial infarction BA41-BA43 Approved [46]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [47]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [35]
Beta-carotene DM0RXBT Vitamin deficiency 5B55-5B71 Approved [36]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Occludin (OCLN)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [48]
Methotrexate DM2TEOL Anterior urethra cancer Approved [49]
Quercetin DM3NC4M Obesity 5B81 Approved [50]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [51]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [52]
Testosterone DM7HUNW Hot flushes GA30 Approved [53]
Thioguanine DM7NKEV Acute lymphocytic leukaemia 2B33.3 Approved [54]
Calcitriol DM8ZVJ7 Congenital alopecia LC30 Approved [55]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [56]
Ethanol DMDRQZU Chronic pain MG30 Approved [57]
⏷ 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
Cannabinoid receptor 1 (CB1) TT6OEDT CNR1_HUMAN Inhibitor [2]
Cannabinoid receptor 2 (CB2) TTMSFAW CNR2_HUMAN Inhibitor [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Claudin-5 (CLDN5) OTUX60YO CLD5_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]
Occludin (OCLN) OTSUTVWL OCLN_HUMAN Gene/Protein Processing [4]

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: 747).
2 1-Bromo-3-(1',1'-dimethylalkyl)-1-deoxy-(8)-tetrahydrocannabinols: New selective ligands for the cannabinoid CB(2) receptor. Bioorg Med Chem. 2010 Nov 15;18(22):7809-15.
3 Design, synthesis, and biological evaluation of new 1,8-naphthyridin-4(1H)-on-3-carboxamide and quinolin-4(1H)-on-3-carboxamide derivatives as CB2 ... J Med Chem. 2006 Oct 5;49(20):5947-57.
4 Activation of cannabinoid receptor 2 attenuates leukocyte-endothelial cell interactions and blood-brain barrier dysfunction under inflammatory conditions. J Neurosci. 2012 Mar 21;32(12):4004-16. doi: 10.1523/JNEUROSCI.4628-11.2012.
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 Posttraining activation of CB1 cannabinoid receptors in the CA1 region of the dorsal hippocampus impairs object recognition long-term memory. Neurobiol Learn Mem. 2008 Sep;90(2):374-81.
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 Company report (Gwpharm)
9 Recent Development of CB2 Selective and Peripheral CB1/CB2 Cannabinoid Receptor Ligands. Current Medicinal Chemistry . 10/2013; 21(2).
10 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
11 Emerging drugs for atopic dermatitis. Expert Opin Emerg Drugs. 2009 Mar;14(1):165-79.
12 The agonist binding mechanism of human CB2 receptor studied by molecular dynamics simulation, free energy calculation and 3D-QSAR studies. Yao Xue Xue Bao. 2013 Sep;48(9):1436-49.
13 The cannabinoid CB1 receptor-selective phytocannabinoid beta-caryophyllene exerts analgesic effects in mouse models of inflammatory and neuropathic pain. Eur Neuropsychopharmacol. 2014 Apr;24(4):608-20.
14 Clinical pipeline report, company report or official report of Roche
15 Emerging strategies for exploiting cannabinoid receptor agonists as medicines. Br J Pharmacol. 2009 Feb;156(3):397-411.
16 Tetrahydrolipstatin analogues as modulators of endocannabinoid 2-arachidonoylglycerol metabolism. J Med Chem. 2008 Nov 13;51(21):6970-9.
17 Anti-obesity drugs. Expert Opin Pharmacother. 2008 Jun;9(8):1339-50.
18 Emerging drugs for obesity: linking novel biological mechanisms to pharmaceutical pipelines. Expert Opin Emerg Drugs. 2005 Aug;10(3):643-60.
19 Clinical pipeline report, company report or official report of AstraZeneca (2009).
20 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.
21 Clinical pipeline report, company report or official report of Bird Rock Bio.
22 Clinical pipeline report, company report or official report of Affimed Therapeutics.
23 Arsenic downregulates tight junction claudin proteins through p38 and NF-B in intestinal epithelial cell line, HT-29. Toxicology. 2017 Mar 15;379:31-39. doi: 10.1016/j.tox.2017.01.011. Epub 2017 Jan 20.
24 Palmitoylethanolamide and Cannabidiol Prevent Inflammation-induced Hyperpermeability of the Human Gut In Vitro and In Vivo-A Randomized, Placebo-controlled, Double-blind Controlled Trial. Inflamm Bowel Dis. 2019 May 4;25(6):1006-1018. doi: 10.1093/ibd/izz017.
25 Anti-invasive activity of sanguinarine through modulation of tight junctions and matrix metalloproteinase activities in MDA-MB-231 human breast carcinoma cells. Chem Biol Interact. 2009 May 15;179(2-3):185-91. doi: 10.1016/j.cbi.2008.11.009. Epub 2008 Nov 21.
26 Effects of glyphosate and aminomethylphosphonic acid on an isogeneic model of the human blood-brain barrier. Toxicol Lett. 2019 Apr;304:39-49. doi: 10.1016/j.toxlet.2018.12.013. Epub 2018 Dec 31.
27 Progesterone regulation of implantation-related genes: new insights into the role of oestrogen. Cell Mol Life Sci. 2007 Apr;64(7-8):1009-32.
28 Ethyl carbamate induces cell death through its effects on multiple metabolic pathways. Chem Biol Interact. 2017 Nov 1;277:21-32.
29 Loxoprofen enhances intestinal barrier function via generation of its active metabolite by carbonyl reductase 1 in differentiated Caco-2?cells. Chem Biol Interact. 2021 Oct 1;348:109634. doi: 10.1016/j.cbi.2021.109634. Epub 2021 Sep 8.
30 Transcriptional signature of human macrophages exposed to the environmental contaminant benzo(a)pyrene. Toxicol Sci. 2010 Apr;114(2):247-59.
31 Involvement of claudin-5 in H(2)S-induced acute lung injury. J Toxicol Sci. 2020;45(5):293-304. doi: 10.2131/jts.45.293.
32 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.
33 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.
34 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.
35 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.
36 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.
37 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.
38 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.
39 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.
40 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.
41 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.
42 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.
43 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.
44 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.
45 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.
46 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.
47 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.
48 Protective effect of quercetin on hydrogen peroxide-induced tight junction disruption. Int J Toxicol. 2010 Jul;29(4):418-24. doi: 10.1177/1091581810366487. Epub 2010 May 5.
49 Development of an alternative zebrafish model for drug-induced intestinal toxicity. J Appl Toxicol. 2018 Feb;38(2):259-273. doi: 10.1002/jat.3520. Epub 2017 Oct 13.
50 Quercetin enhances intestinal barrier function through the assembly of zonula [corrected] occludens-2, occludin, and claudin-1 and the expression of claudin-4 in Caco-2 cells. J Nutr. 2009 May;139(5):965-74. doi: 10.3945/jn.108.100867. Epub 2009 Mar 18.
51 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.
52 Arsenite-induced downregulation of occludin in mouse lungs and BEAS-2B cells via the ROS/ERK/ELK1/MLCK and ROS/p38 MAPK signaling pathways. Toxicol Lett. 2020 Oct 10;332:146-154. doi: 10.1016/j.toxlet.2020.07.010. Epub 2020 Jul 16.
53 The exosome-like vesicles derived from androgen exposed-prostate stromal cells promote epithelial cells proliferation and epithelial-mesenchymal transition. Toxicol Appl Pharmacol. 2021 Jan 15;411:115384. doi: 10.1016/j.taap.2020.115384. Epub 2020 Dec 25.
54 The thiopurine methyltransferase genetic polymorphism is associated with thioguanine-related veno-occlusive disease of the liver in children with acute lymphoblastic leukemia. Clin Pharmacol Ther. 2006 Oct;80(4):375-83. doi: 10.1016/j.clpt.2006.07.002.
55 Identification of vitamin D3 target genes in human breast cancer tissue. J Steroid Biochem Mol Biol. 2016 Nov;164:90-97.
56 Human embryonic stem cell-derived test systems for developmental neurotoxicity: a transcriptomics approach. Arch Toxicol. 2013 Jan;87(1):123-43.
57 Ethanol impairs intestinal barrier function in humans through mitogen activated protein kinase signaling: a combined in vivo and in vitro approach. PLoS One. 2014 Sep 16;9(9):e107421. doi: 10.1371/journal.pone.0107421. eCollection 2014.