General Information of Drug (ID: DMJQ4L7)

Drug Name
N-oleoylethanolamide Drug Info
Synonyms
n-Oleoylethanolamine; n-oleoylethanolamine; oleoylethanolamide; N-(2-Hydroxyethyl)oleamide; 111-58-0; Oleylethanolamide; N-oleoyl ethanolamine; Oleamide MEA; Oleoyl monoethanolamide; Oleoyl Ethanolamide; N-(2-Hydroxyethyl)-9-octadecenamide; N-(Hydroxyethyl)oleamide; UNII-1HI5J9N8E6; (Z)-N-(2-hydroxyethyl)octadec-9-enamide; Oleic acid ethanolamide; N-(9Z-octadecenoyl)-ethanolamine; EINECS 203-884-8; OEA; MLS002153155; CHEMBL280065; 1HI5J9N8E6; (9Z)-N-(2-hydroxyethyl)octadec-9-enamide; Monoethanolamine oleic acid amide; CHEBI:71466; N-oleoylethanolamine; oleylethanolamide; NOE; OLEOYLETHANOLAMIDE
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
5283454
ChEBI ID
CHEBI:71466
CAS Number
CAS 111-58-0
TTD Drug ID
DMJQ4L7

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DOT
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Investigative Drug(s)
Discontinued Drug(s)
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 Name Drug ID Indication ICD 11 Highest Status REF
Lobeglitazone DMHY3IP Type-2 diabetes 5A11 Approved [16]
Fenofibrate DMFKXDY Coronary atherosclerosis Approved [17]
Bezafibrate DMZDCS0 Hypercholesterolaemia 5C80.0 Approved [18]
Ciprofibrate DMGC5DB Hyperlipoproteinemia 5C80 Approved [17]
Pemafibrate DMD1VZL Hyperlipidemia 5C80.Z Approved [19]
MURAGLITAZAR DMG3NFZ N. A. N. A. Phase 3 [20]
Ragaglitazar DMFSHEM Type-1 diabetes 5A10 Phase 3 [21]
CS-038 DM67P0F Type-2 diabetes 5A11 Phase 3 [22]
TESAGLITAZAR DMGRBN5 Type-1 diabetes 5A10 Phase 3 [23]
GFT-505 DM7ZOAE Non-alcoholic steatohepatitis DB92.1 Phase 3 [24]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Guanfacine extended release DMB1CZ8 Attention deficit hyperactivity disorder 6A05.Z Approved [2]
BIO-017 DMYHK3Y Angelman syndrome LD90.0 Phase 1 [25]
[3H]CP55940 DMU7FC5 Discovery agent N.A. Investigative [2]
lysophosphatidylinositol DMETM3R Discovery agent N.A. Investigative [3]
O-1602 DM9VISB Discovery agent N.A. Investigative [26]
abnormal cannabidiol DMV6DAO Discovery agent N.A. Investigative [2]
O-arachidonoyl ethanolamine DML0P72 Discovery agent N.A. Investigative [2]
CID1172084 DMK6YOP Discovery agent N.A. Investigative [27]
CID16020046 DMLWZRT Discovery agent N.A. Investigative [28]
2-arachidonyl glyceryl ether DM2H8TV Discovery agent N.A. Investigative [2]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Guanfacine extended release DMB1CZ8 Attention deficit hyperactivity disorder 6A05.Z Approved [29]
DS-8500 DMUXIRM Diabetic complication 5A2Y Phase 2 [30]
SAR-260093 DMBJU2G Type-2 diabetes 5A11 Phase 2 [31]
GSK1292263 DMDMXKQ Gastric adenocarcinoma 2B72 Phase 2 [32]
BMS-903452 DM7JW0B Type-2 diabetes 5A11 Phase 1 [33]
APD-597 DM36FOG Type-2 diabetes 5A11 Phase 1 [34]
DA-1241 DMPJA64 Type 2 diabetes 5A11 Phase 1 [35]
APD668 DMN8R2U Type-2 diabetes 5A11 Discontinued in Phase 1 [36]
PSN821 DMGEWUS Type-2 diabetes 5A11 Terminated [37]
lysophosphatidylinositol DMETM3R Discovery agent N.A. Investigative [38]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Flupentixol DM0DJ9O Schizophrenia 6A20 Approved [39]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [40]
Crizotinib DM4F29C Non-small-cell lung cancer 2C25.Y Approved [41]
Lamotrigine DM8SXYG Bipolar disorder 6A60 Approved [42]
Cepharanthine DM9Y5JB N. A. N. A. Approved [43]
Itraconazole DMCR1MV Aspergillosis 1F20 Approved [44]
Clozapine DMFC71L Schizophrenia 6A20 Approved [45]
Midostaurin DMI6E0R Acute myeloid leukaemia 2A60 Approved [46]
Trifluoperazine DMKBYWI Anxiety Approved [47]
Olanzapine DMPFN6Y Bipolar depression Approved [45]
⏷ 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 [1]
G-protein coupled receptor 55 (GPR55) TTNET8J GPR55_HUMAN Agonist [2]
Glucose-dependent insulinotropic receptor (GPR119) TT7QNVC GP119_HUMAN Agonist [3]
Peroxisome proliferator-activated receptor alpha (PPARA) TTJ584C PPARA_HUMAN Agonist [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Regulation of Drug Effects [5]

References

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2 The orphan receptor GPR55 is a novel cannabinoid receptor. Br J Pharmacol. 2007 Dec;152(7):1092-101.
3 Screening beta-arrestin recruitment for the identification of natural ligands for orphan G-protein-coupled receptors. J Biomol Screen. 2013 Jun;18(5):599-609.
4 Oleoylethanolamide, an endogenous PPAR-alpha agonist, lowers body weight and hyperlipidemia in obese rats. Neuropharmacology. 2005 Jun;48(8):1147-53.
5 Intestinal P-glycoprotein exports endocannabinoids to prevent inflammation and maintain homeostasis. J Clin Invest. 2018 Aug 31;128(9):4044-4056. doi: 10.1172/JCI96817. Epub 2018 Aug 13.
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 Tolerability and pharmacokinetics of lobeglitazone, a novel peroxisome proliferator-activated receptor-gamma agonist, after a single oral administration in healthy female subjects. Clin Drug Investig. 2014 Jul;34(7):467-74.
17 Peroxisome proliferator-activated receptor alpha activators improve insulin sensitivity and reduce adiposity. J Biol Chem. 2000 Jun 2;275(22):16638-42.
18 Bezafibrate at clinically relevant doses decreases serum/liver triglycerides via down-regulation of sterol regulatory element-binding protein-1c in... Mol Pharmacol. 2009 Apr;75(4):782-92.
19 Pemafibrate: First Global Approval. Drugs. 2017 Oct;77(16):1805-1810.
20 Muraglitazar, a dual (alpha/gamma) PPAR activator: a randomized, double-blind, placebo-controlled, 24-week monotherapy trial in adult patients with... Clin Ther. 2005 Aug;27(8):1181-95.
21 Ragaglitazar: the pharmacokinetics, pharmacodynamics, and tolerability of a novel dual PPAR alpha and gamma agonist in healthy subjects and patients with type 2 diabetes. J Clin Pharmacol. 2003 Nov;43(11):1244-56.
22 Determination of chiglitazar, a dual alpha/gamma peroxisome proliferator-activated receptor (PPAR) agonist, in human plasma by liquid chromatograph... Pharmazie. 2007 Nov;62(11):825-9.
23 Tesaglitazar, a dual PPAR-/ agonist, hamster carcinogenicity, investigative animal and clinical studies.Toxicol Pathol.2012;40(1):18-32.
24 Dual peroxisome proliferator-activated receptor / agonist GFT505 improves hepatic and peripheral insulin sensitivity in abdominally obese subjects.Diabetes Care.2013 Oct;36(10):2923-30.
25 Clinical pipeline report, company report or official report of Biom Therapeutics
26 International Union of Basic and Clinical Pharmacology. LXXIX. Cannabinoid receptors and their ligands: beyond CB and CB Pharmacol Rev. 2010 Dec;62(4):588-631.
27 Identification of the GPR55 agonist binding site using a novel set of high-potency GPR55 selective ligands. Biochemistry. 2011 Jun 28;50(25):5633-47.
28 A selective antagonist reveals a potential role of G protein-coupled receptor 55 in platelet and endothelial cell function. J Pharmacol Exp Ther. 2013 Jul;346(1):54-66.
29 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. (Target id: 126).
30 Addressing Unmet Medical Needs in Type 2 Diabetes: A Narrative Review of Drugs under Development. Curr Diabetes Rev. 2015 March; 11(1): 17-31.
31 GPR119 agonists for the treatment of type 2 diabetes. Expert Opin Ther Pat. 2009 Oct;19(10):1339-59.
32 Gut hormone pharmacology of a novel GPR119 agonist (GSK1292263), metformin, and sitagliptin in type 2 diabetes mellitus: results from two randomized studies.PLoS One.2014 Apr 3;9(4):e92494.
33 Discovery of 5-chloro-4-((1-(5-chloropyrimidin-2-yl)piperidin-4-yl)oxy)-1-(2-fluoro-4-(methylsulfonyl)phenyl)pyridin-2(1H)-one (BMS-903452), an antidiabetic clinical candidate targeting GPR119. J MedChem. 2014 Sep 25;57(18):7499-508.
34 Discovery of a second generation agonist of the orphan G-protein coupled receptor GPR119 with an improved profile. Bioorg Med Chem Lett. 2012 Feb 15;22(4):1750-5.
35 ClinicalTrials.gov (NCT03646721) A Study to Evaluate the Safety, Tolerability, PK and PD of DA-1241 in Healthy Male Subjects and Subjects With T2DM. U.S. National Institutes of Health.
36 Announces Initiation of Phase 1 Clinical Trial of Arena Type 2 Diabetes Drug Candidate in Collaboration With Ortho-McNeil. Arena Pharmaceuticals, Inc. FEBRUARY 07, 2006.
37 Clinical pipeline report, company report or official report of Astellas Pharma (2011).
38 Lysophosphatidylcholine enhances glucose-dependent insulin secretion via an orphan G-protein-coupled receptor. Biochem Biophys Res Commun. 2005 Jan 28;326(4):744-51.
39 Characteristics of P388/VMDRC.04, a simple, sensitive model for studying P-glycoprotein antagonists. Cancer Res. 1994 Feb 1;54(3):730-7.
40 Michaelis-Menten kinetic analysis of drugs of abuse to estimate their affinity to human P-glycoprotein. Toxicol Lett. 2013 Feb 27;217(2):137-42. doi: 10.1016/j.toxlet.2012.12.012. Epub 2012 Dec 27.
41 Editor's Highlight: PlacentalDisposition and Effects of Crizotinib: An Ex Vivo Study in the Isolated Dual-Side Perfused Human Cotyledon. Toxicol Sci. 2017 Jun 1;157(2):500-509. doi: 10.1093/toxsci/kfx063.
42 Functional evaluation of polymorphisms in the human ABCB1 gene and the impact on clinical responses of antiepileptic drugs. Pharmacogenet Genomics. 2008 May;18(5):390-402. doi: 10.1097/FPC.0b013e3282f85e36.
43 Cepharanthine potently enhances the sensitivity of anticancer agents in K562 cells. Cancer Sci. 2005 Jun;96(6):372-6. doi: 10.1111/j.1349-7006.2005.00057.x.
44 Clinical pharmacokinetic monitoring of itraconazole is warranted in only a subset of patients. Ther Drug Monit. 2005 Jun;27(3):322-33. doi: 10.1097/01.ftd.0000150135.22645.ea.
45 Evaluation of antipsychotic drugs as inhibitors of multidrug resistance transporter P-glycoprotein. Psychopharmacology (Berl). 2006 Sep;187(4):415-23. doi: 10.1007/s00213-006-0437-9. Epub 2006 Jun 30.
46 Actions of the selective protein kinase C inhibitor PKC412 on B-chronic lymphocytic leukemia cells in vitro. Haematologica. 2002 Feb;87(2):167-76.
47 Characterization of the ATPase activity of the Mr 170,000 to 180,000 membrane glycoprotein (P-glycoprotein) associated with multidrug resistance in K562/ADM cells. Cancer Res. 1988 Sep 1;48(17):4926-32.