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

General Information of Drug (ID: DMM6A7P)

Drug Name

cannabinol Drug Info

Synonyms

cannabinol; 521-35-7; Cannabinolo [DCIT]; Cannabinolum [INN-Latin]; Cannabinol [INN:BAN]; UNII-7UYP6MC9GH; 6H-Dibenzo(b,d)pyran-1-ol, 6,6,9-trimethyl-3-pentyl-; NSC 134455; 3-Amyl-1-hydroxy-6,6,9-trimethyl-6H-dibenzo(b,d)pyran; 7UYP6MC9GH; BRN 0237145; 6,6,9-Trimethyl-3-pentyl-6H-dibenzo(b,d)pyran-1-ol; CHEMBL74415; CHEBI:3360; VBGLYOIFKLUMQG-UHFFFAOYSA-N; 6,6,9-trimethyl-3-pentylbenzo[c]chromen-1-ol; 6,6,9-Trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol; 6H-Dibenzo[b,d]pyran-1-ol, 6,6,9-trimethyl-3-pentyl-

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]

Cross-matching ID

PubChem CID: 2543
ChEBI ID: CHEBI:3360
CAS Number: CAS 521-35-7
TTD Drug ID: DMM6A7P

Molecule-Related Drug Atlas

Molecule Type:

DTT

DOT

Drug Status:

Approved Drug(s)

Clinical Trial Drug(s)

Investigative Drug(s)

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Drug(s) Targeting Cannabinoid receptor 1 (CB1)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Marinol	DM70IK5	Anorexia nervosa cachexia	6B80	Approved	[7]
NABILONE	DMVRYT2	Insomnia	7A00-7A0Z	Approved	[8]
Orlistat	DMRJSP8	Obesity	5B81	Approved	[9]
SR141716A	DMCO5JZ	Obesity	5B81	Approved	[10]
Tebipenem	DMVSX6O	Urinary tract infection	GC08	Phase 3	[11]
Conatumumab	DM2UOSN	Colorectal cancer	2B91.Z	Phase 2	[12]
GW-42004	DMY3KSU	Lipid metabolism disorder	5C52.Z	Phase 2	[13]
SR-147778	DMNAECP	Obesity	5B81	Phase 2	[14]
Nimacimab	DM21Z68	Diabetic nephropathy	GB61.Z	Phase 2	[15]
AEF0117	DMQ1GH4	Marijuana use disorder	6C41	Phase 2	[16]
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Drug(s) Targeting Transient receptor potential cation channel V2 (TRPV2)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
[14C]TEA	DM6SFYH	Discovery agent	N.A.	Investigative	[17]
2-APB	DM9AKVR	Discovery agent	N.A.	Investigative	[17]
lysophosphatidylcholine	DMOGFVH	Discovery agent	N.A.	Investigative	[18]
diphenylboronic anhydride	DMRQZTS	Discovery agent	N.A.	Investigative	[17]
lysophosphatidylinositol	DMETM3R	Discovery agent	N.A.	Investigative	[18]
citral	DM53ZGY	Discovery agent	N.A.	Investigative	[19]
TRIM	DMNHU4M	Discovery agent	N.A.	Investigative	[17]
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Drug(s) Affected By Multidrug resistance-associated protein 1 (ABCC1)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Ivermectin	DMDBX5F	Intestinal strongyloidiasis due to nematode parasite	1F6B	Approved	[20]
Folic Acid	DMEMBJC	Colorectal carcinoma		Approved	[21]
Methotrexate	DM2TEOL	Anterior urethra cancer		Approved	[22]
Quercetin	DM3NC4M	Obesity	5B81	Approved	[23]
Docetaxel	DMDI269	Advanced cancer	2A00-2F9Z	Approved	[24]
Irinotecan	DMP6SC2	Adenocarcinoma	2D40	Approved	[25]
Epirubicin	DMPDW6T	Solid tumour/cancer	2A00-2F9Z	Approved	[26]
Doxorubicin	DMVP5YE	Acute myelogenous leukaemia	2A41	Approved	[27]
Colchicine	DM2POTE	Acute gout flare	FA25.0	Approved	[28]
Dactinomycin	DM2YGNW	Adult kidney Wilms tumor		Approved	[28]
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Drug(s) Affected By Transient receptor potential cation channel subfamily A member 1 (TRPA1)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Cannabidiol	DM0659E	Dravet syndrome	8A61.11	Approved	[29]
Hydroquinone	DM6AVR4	Melasma	ED60.1	Approved	[30]
Valproate	DMCFE9I	Epilepsy	8A60-8A68	Approved	[31]
Capsaicin	DMGMF6V	Back pain	ME84.Z	Approved	[32]
Dasatinib	DMJV2EK	Blast phase chronic myelogenous leukemia, BCR-ABL1 positive		Approved	[33]
Menadione	DMSJDTY	Vitamin K deficiency	5B59	Approved	[30]
Mechlorethamine	DM0CVXA	Chronic myelogenous leukaemia	2A20.0	Approved	[34]
SNDX-275	DMH7W9X	Breast cancer	2C60-2C65	Phase 3	[35]
phorbol 12-myristate 13-acetate	DMJWD62	Acute myeloid leukaemia	2A60	Phase 2	[36]
(+)-JQ1	DM1CZSJ	Testicular cancer	2C80	Phase 1	[37]
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Drug(s) Affected By Cytochrome P450 2J2 (CYP2J2)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Nitrendipine	DM21C09	Hypertension	BA00-BA04	Approved	[38]
Quercetin	DM3NC4M	Obesity	5B81	Approved	[39]
Troglitazone	DM3VFPD	Diabetic complication	5A2Y	Approved	[40]
Tretinoin	DM49DUI	Acne vulgaris	ED80	Approved	[41]
Rifampicin	DM5DSFZ	Non-insulin dependent diabetes	5A11	Approved	[42]
Nisoldipine	DM7ISKJ	Hypertension	BA00-BA04	Approved	[38]
Ciclosporin	DMAZJFX	Graft-versus-host disease	4B24	Approved	[43]
Amlodipine	DMBDAZV	Angina pectoris	BA40	Approved	[38]
Valproate	DMCFE9I	Epilepsy	8A60-8A68	Approved	[44]
Gemfibrozil	DMD8Q3J	Hyperlipidaemia	5C80	Approved	[45]
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Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

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Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Cannabinoid receptor 1 (CB1)	TT6OEDT	CNR1_HUMAN	Agonist	[2]
Transient receptor potential cation channel V2 (TRPV2)	TTBECWA	TRPV2_HUMAN	Activator	[3]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Cytochrome P450 2J2 (CYP2J2)	OTJBTEH8	CP2J2_HUMAN	Regulation of Drug Effects	[4]
Multidrug resistance-associated protein 1 (ABCC1)	OTGUN89S	MRP1_HUMAN	Gene/Protein Processing	[5]
Transient receptor potential cation channel subfamily A member 1 (TRPA1)	OTRDIR5M	TRPA1_HUMAN	Gene/Protein Processing	[6]

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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: 740).
2	Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): identification of cannabinoid receptor subtype selective ligands. J Pharmacol Exp Ther. 1996 Sep;278(3):989-99.
3	TRPV2 is activated by cannabidiol and mediates CGRP release in cultured rat dorsal root ganglion neurons. J Neurosci. 2008 Jun 11;28(24):6231-8.
4	Cross-talk of cannabinoid and endocannabinoid metabolism is mediated via human cardiac CYP2J2. J Inorg Biochem. 2018 Jul;184:88-99. doi: 10.1016/j.jinorgbio.2018.03.016. Epub 2018 Apr 7.
5	Interaction of plant cannabinoids with the multidrug transporter ABCC1 (MRP1). Eur J Pharmacol. 2008 Sep 4;591(1-3):128-31.
6	Diverse TRPV1 responses to cannabinoids. Channels (Austin). 2019 Dec;13(1):172-191. doi: 10.1080/19336950.2019.1619436.
7	Emerging strategies for exploiting cannabinoid receptor agonists as medicines. Br J Pharmacol. 2009 Feb;156(3):397-411.
8	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.
9	Tetrahydrolipstatin analogues as modulators of endocannabinoid 2-arachidonoylglycerol metabolism. J Med Chem. 2008 Nov 13;51(21):6970-9.
10	Anti-obesity drugs. Expert Opin Pharmacother. 2008 Jun;9(8):1339-50.
11	Emerging drugs for obesity: linking novel biological mechanisms to pharmaceutical pipelines. Expert Opin Emerg Drugs. 2005 Aug;10(3):643-60.
12	Clinical pipeline report, company report or official report of AstraZeneca (2009).
13	Company report (Gwpharm)
14	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.
15	Clinical pipeline report, company report or official report of Bird Rock Bio.
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17	Pharmacological characterization and molecular determinants of the activation of transient receptor potential V2 channel orthologs by 2-aminoethoxy... Mol Pharmacol. 2007 Nov;72(5):1258-68.
18	Lysophospholipids stimulate prostate cancer cell migration via TRPV2 channel activation. Biochim Biophys Acta. 2009 Mar;1793(3):528-39.
19	Citral sensing by Transient [corrected] receptor potential channels in dorsal root ganglion neurons. PLoS One. 2008 May 7;3(5):e2082.
20	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.
21	Folate concentration dependent transport activity of the Multidrug Resistance Protein 1 (ABCC1). Biochem Pharmacol. 2004 Apr 15;67(8):1541-8.
22	Methotrexate normalizes up-regulated folate pathway genes in rheumatoid arthritis. Arthritis Rheum. 2013 Nov;65(11):2791-802.
23	Influence of redox-active compounds and PXR-activators on human MRP1 and MRP2 gene expression. Toxicology. 2002 Feb 28;171(2-3):137-46.
24	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.
25	Clinical determinants of response to irinotecan-based therapy derived from cell line models. Clin Cancer Res. 2008 Oct 15;14(20):6647-55.
26	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.
27	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.
28	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.
29	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.
30	Electrophilic components of diesel exhaust particles (DEP) activate transient receptor potential ankyrin-1 (TRPA1): a probable mechanism of acute pulmonary toxicity for DEP. Chem Res Toxicol. 2011 Jun 20;24(6):950-9. doi: 10.1021/tx200123z. Epub 2011 May 25.
31	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.
32	The anthelminthic drug praziquantel is a selective agonist of the sensory transient receptor potential melastatin type 8 channel. Toxicol Appl Pharmacol. 2017 Dec 1;336:55-65. doi: 10.1016/j.taap.2017.10.012. Epub 2017 Oct 18.
33	Dasatinib reverses cancer-associated fibroblasts (CAFs) from primary lung carcinomas to a phenotype comparable to that of normal fibroblasts. Mol Cancer. 2010 Jun 27;9:168.
34	Activation of the human TRPA1 channel by different alkylating sulfur and nitrogen mustards and structurally related chemotherapeutic drugs. Toxicol Lett. 2023 Mar 1;376:51-59. doi: 10.1016/j.toxlet.2023.01.007. Epub 2023 Jan 21.
35	Definition of transcriptome-based indices for quantitative characterization of chemically disturbed stem cell development: introduction of the STOP-Toxukn and STOP-Toxukk tests. Arch Toxicol. 2017 Feb;91(2):839-864.
36	Mechanisms and Consequences of Variable TRPA1 Expression by Airway Epithelial Cells: Effects of TRPV1 Genotype and Environmental Agonists on Cellular Responses to Pollutants in Vitro and Asthma. Environ Health Perspect. 2023 Feb;131(2):27009. doi: 10.1289/EHP11076. Epub 2023 Feb 27.
37	Inhibition of BRD4 attenuates tumor cell self-renewal and suppresses stem cell signaling in MYC driven medulloblastoma. Oncotarget. 2014 May 15;5(9):2355-71.
38	Inhibitory effects of antihypertensive drugs on human cytochrome P450 2J2 activity: Potent inhibition by azelnidipine and manidipine. Chem Biol Interact. 2019 Jun 1;306:1-9.
39	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.
40	In vitro inhibition of human small intestinal and liver microsomal astemizole O-demethylation: different contribution of CYP2J2 in the small intestine and liver. Xenobiotica. 2003 Jun;33(6):615-23.
41	Differentiation-specific factors modulate epidermal CYP1-4 gene expression in human skin in response to retinoic acid and classic aryl hydrocarbon receptor ligands. J Pharmacol Exp Ther. 2006 Dec;319(3):1162-71.
42	Cytochrome P450 expression, induction and activity in human induced pluripotent stem cell-derived intestinal organoids and comparison with primary human intestinal epithelial cells and Caco-2 cells. Arch Toxicol. 2021 Mar;95(3):907-922. doi: 10.1007/s00204-020-02953-6. Epub 2020 Dec 2.
43	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.
44	Stem cell transcriptome responses and corresponding biomarkers that indicate the transition from adaptive responses to cytotoxicity. Chem Res Toxicol. 2017 Apr 17;30(4):905-922.
45	Expression of cytochrome P450 epoxygenases and soluble epoxide hydrolase is regulated by hypolipidemic drugs in dose-dependent manner. Toxicol Appl Pharmacol. 2018 Sep 15;355:156-163.