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Article ; Online: Molecular Mechanisms for the Inflammation-Resolving Actions of Lenabasum.

Burstein, Sumner

2020 Volume 99, Issue 2, Page(s) 125–132

Abstract: A first-in-class cannabinoid analog called lenabasum that is a CB2 agonist is being developed as an inflammation-resolving drug candidate. Thus far, specific therapeutic targets include scleroderma, cystic fibrosis, dermatomyositis, and lupus, all of ... ...

Abstract	A first-in-class cannabinoid analog called lenabasum that is a CB2 agonist is being developed as an inflammation-resolving drug candidate. Thus far, specific therapeutic targets include scleroderma, cystic fibrosis, dermatomyositis, and lupus, all of which represent unmet medical needs. Two somewhat-independent molecular mechanisms for this type of action are here proposed. Both pathways initially involve the release of free arachidonic acid after activation of the CB2 receptor and phospholipase A2 by lenabasum. The pathways then diverge into a cyclooxygenase 2-mediated and a lipoxygenase-mediated route. The former leads to increased levels of the cyclopentenone prostaglandin 15-deoxy-Δ
MeSH term(s)	Animals ; Anti-Inflammatory Agents/pharmacology ; Arachidonic Acid/metabolism ; Cannabinoid Receptor Agonists/pharmacology ; Dronabinol/analogs & derivatives ; Dronabinol/pharmacology ; Gene Expression Regulation/drug effects ; Humans ; Phospholipases A2/metabolism ; Receptor, Cannabinoid, CB2/metabolism ; Receptors, Formyl Peptide/metabolism ; Receptors, Lipoxin/metabolism
Chemical Substances	Anti-Inflammatory Agents ; CNR2 protein, human ; Cannabinoid Receptor Agonists ; FPR2 protein, human ; Receptor, Cannabinoid, CB2 ; Receptors, Formyl Peptide ; Receptors, Lipoxin ; Arachidonic Acid (27YG812J1I) ; Dronabinol (7J8897W37S) ; Phospholipases A2 (EC 3.1.1.4) ; lenabasum (OGN7X90BT8)
Language	English
Publishing date	2020-11-25
Publishing country	United States
Document type	Journal Article ; Review
ZDB-ID	124034-1
ISSN	1521-0111 ; 0026-895X
ISSN (online)	1521-0111
ISSN	0026-895X
DOI	10.1124/molpharm.120.000083
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Article: The chemistry, biology and pharmacology of the cyclopentenone prostaglandins.

Burstein, Sumner H

Prostaglandins & other lipid mediators

2020 Volume 148, Page(s) 106408

Abstract: The cyclopentenone prostaglandins (CyPGs) are a small group compounds that are a subset of the eicosanoid superfamily, which are metabolites of arachidonic acid as well as other polyunsaturated fatty acids. The CyPGs are defined by a structural feature, ... ...

Abstract	The cyclopentenone prostaglandins (CyPGs) are a small group compounds that are a subset of the eicosanoid superfamily, which are metabolites of arachidonic acid as well as other polyunsaturated fatty acids. The CyPGs are defined by a structural feature, namely, a five-membered carbocyclic ring containing an alfa-beta unsaturated keto group. The two most studied members are PGA
MeSH term(s)	Animals ; Humans ; Inflammation/metabolism ; Inflammation/pathology ; Inflammation/prevention & control ; Neoplasms/metabolism ; Neoplasms/pathology ; Neoplasms/prevention & control ; Prostaglandins/chemistry ; Prostaglandins/pharmacology
Chemical Substances	Prostaglandins
Language	English
Publishing date	2020-01-10
Publishing country	United States
Document type	Journal Article ; Review
ZDB-ID	1426962-4
ISSN	2212-196X ; 1098-8823 ; 0090-6980
ISSN (online)	2212-196X
ISSN	1098-8823 ; 0090-6980
DOI	10.1016/j.prostaglandins.2020.106408
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Article ; Online: Eicosanoid mediation of cannabinoid actions.

Burstein, Sumner H

Bioorganic & medicinal chemistry

2019 Volume 27, Issue 13, Page(s) 2718–2728

Abstract: Interactions between cannabinoids and eicosanoids have been observed for the last several decades and account for a variety of cannabinoid actions. These were seen both in vitro and in vivo and may provide a molecular basis for these actions. Some of the ...

Abstract	Interactions between cannabinoids and eicosanoids have been observed for the last several decades and account for a variety of cannabinoid actions. These were seen both in vitro and in vivo and may provide a molecular basis for these actions. Some of the topics included in this review are; effects on adenylate cyclase activity, alteration of behavioral responses, reduction of pain sensation, reduction and resolution of inflammation, hypotensive and vasorelaxant responses, anti-cancer and anti-metastatic activities, reduction of intraocular pressure and others. The most widely studied cannabinoids so far are tetrahydrocannabinol and cannabidiol. However, synthetic agents such as CP55,940, ajulemic acid, JWH-133 and WIN-55,212-2 were also investigated for interaction with eicosanoids. The endocannabinoids anandamide and 2-arachidonoylglycerol have been examined as well. Among the eicosanoids mediating cannabinoid actions are PGE
MeSH term(s)	Cannabinoids/chemistry ; Cannabinoids/pharmacology ; Cannabinoids/therapeutic use ; Eicosanoids/pharmacology ; Eicosanoids/therapeutic use ; Humans
Chemical Substances	Cannabinoids ; Eicosanoids
Language	English
Publishing date	2019-05-13
Publishing country	England
Document type	Journal Article ; Review
ZDB-ID	1161284-8
ISSN	1464-3391 ; 0968-0896
ISSN (online)	1464-3391
ISSN	0968-0896
DOI	10.1016/j.bmc.2019.05.018
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Article ; Online: Ajulemic acid: potential treatment for chronic inflammation.

Burstein, Sumner H

Pharmacology research & perspectives

2018 Volume 6, Issue 2, Page(s) e00394

Abstract: Ajulemic acid (AJA, CT-3, IP-751, JBT-101, anabasum) is a first-in-class, synthetic, orally active, cannabinoid-derived drug that preferentially binds to the CB2 receptor and is nonpsychoactive. In preclinical studies, and in Phase 1 and 2 clinical ... ...

Abstract	Ajulemic acid (AJA, CT-3, IP-751, JBT-101, anabasum) is a first-in-class, synthetic, orally active, cannabinoid-derived drug that preferentially binds to the CB2 receptor and is nonpsychoactive. In preclinical studies, and in Phase 1 and 2 clinical trials, AJA showed a favorable safety, tolerability, and pharmacokinetic profile. It also demonstrated significant efficacy in preclinical models of inflammation and fibrosis. It suppresses tissue scarring and stimulates endogenous eicosanoids that resolve chronic inflammation and fibrosis without causing immunosuppression. AJA is currently being developed for use in 4 separate but related indications including systemic sclerosis (SSc), cystic fibrosis, dermatomyositis (DM), and systemic lupus erythematosus. Phase 2 clinical trials in the first 3 targets demonstrated that it is safe, is a potential treatment for these orphan diseases and appears to be a potent inflammation-resolving drug with a unique mechanism of action, distinct from the nonsteroidal anti-inflammatory drug (NSAID), and will be useful for treating a wide range of chronic inflammatory diseases. It may be considered to be a disease-modifying drug unlike most NSAIDs that only provide symptomatic relief. AJA is currently being evaluated in 24-month open-label extension studies in SSc and in skin-predominant DM. A Phase 3 multicenter trial to demonstrate safety and efficacy in SSc has recently been initiated.
MeSH term(s)	Animals ; Chronic Disease ; Clinical Trials as Topic ; Dronabinol/administration & dosage ; Dronabinol/analogs & derivatives ; Dronabinol/pharmacokinetics ; Dronabinol/therapeutic use ; Drug Evaluation, Preclinical ; Humans ; Inflammation/drug therapy ; Inflammation/etiology ; Treatment Outcome
Chemical Substances	Dronabinol (7J8897W37S) ; lenabasum (OGN7X90BT8)
Language	English
Publishing date	2018-04-07
Publishing country	United States
Document type	Journal Article ; Review
ZDB-ID	2740389-0
ISSN	2052-1707 ; 2052-1707
ISSN (online)	2052-1707
ISSN	2052-1707
DOI	10.1002/prp2.394
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Article ; Online: N-

Burstein, Sumner H

Molecular pharmacology

2017 Volume 93, Issue 3, Page(s) 228–238

Abstract: The subject ... ...

Abstract	The subject of
MeSH term(s)	Analgesics/chemistry ; Analgesics/metabolism ; Animals ; Anti-Inflammatory Agents/chemistry ; Anti-Inflammatory Agents/metabolism ; Arachidonic Acids/chemistry ; Arachidonic Acids/metabolism ; Biosynthetic Pathways ; Endocannabinoids/chemistry ; Endocannabinoids/metabolism ; Glycine/analogs & derivatives ; Glycine/chemistry ; Glycine/metabolism ; Humans ; Polyunsaturated Alkamides/chemistry ; Polyunsaturated Alkamides/metabolism ; Receptors, G-Protein-Coupled/metabolism
Chemical Substances	Analgesics ; Anti-Inflammatory Agents ; Arachidonic Acids ; Endocannabinoids ; N-arachidonylglycine ; Polyunsaturated Alkamides ; Receptors, G-Protein-Coupled ; Glycine (TE7660XO1C) ; anandamide (UR5G69TJKH)
Language	English
Publishing date	2017-11-14
Publishing country	United States
Document type	Journal Article ; Review
ZDB-ID	124034-1
ISSN	1521-0111 ; 0026-895X
ISSN (online)	1521-0111
ISSN	0026-895X
DOI	10.1124/mol.117.110841
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Article ; Online: Cannabidiol (CBD) and its analogs: a review of their effects on inflammation.

Burstein, Sumner

Bioorganic & medicinal chemistry

2015 Volume 23, Issue 7, Page(s) 1377–1385

Abstract: First isolated from Cannabis in 1940 by Roger Adams, the structure of CBD was not completely elucidated until 1963. Subsequent studies resulted in the pronouncement that THC was the 'active' principle of Cannabis and research then focused primarily on it ...

Abstract	First isolated from Cannabis in 1940 by Roger Adams, the structure of CBD was not completely elucidated until 1963. Subsequent studies resulted in the pronouncement that THC was the 'active' principle of Cannabis and research then focused primarily on it to the virtual exclusion of CBD. This was no doubt due to the belief that activity meant psychoactivity that was shown by THC and not by CBD. In retrospect this must be seen as unfortunate since a number of actions of CBD with potential therapeutic benefit were downplayed for many years. In this review, attention will be focused on the effects of CBD in the broad area of inflammation where such benefits seem likely to be developed. Topics covered in this review are; the medicinal chemistry of CBD, CBD receptor binding involved in controlling Inflammation, signaling events generated by CBD, downstream events affected by CBD (gene expression and transcription), functional effects reported for CBD and combined THC plus CBD treatment.
MeSH term(s)	Animals ; Cannabidiol/analogs & derivatives ; Cannabidiol/chemistry ; Cannabidiol/therapeutic use ; Humans ; Inflammation/drug therapy ; Inflammation/metabolism ; Inflammation/pathology ; Inflammation Mediators/antagonists & inhibitors ; Inflammation Mediators/metabolism ; Protein Structure, Tertiary ; Treatment Outcome
Chemical Substances	Inflammation Mediators ; Cannabidiol (19GBJ60SN5)
Language	English
Publishing date	2015-04-01
Publishing country	England
Document type	Journal Article ; Review
ZDB-ID	1161284-8
ISSN	1464-3391 ; 0968-0896
ISSN (online)	1464-3391
ISSN	0968-0896
DOI	10.1016/j.bmc.2015.01.059
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Article ; Online: The cannabinoid acids, analogs and endogenous counterparts.

Burstein, Sumner H

Bioorganic & medicinal chemistry

2014 Volume 22, Issue 10, Page(s) 2830–2843

Abstract: The cannabinoid acids are a structurally heterogeneous group of compounds some of which are endogenous molecules and others that are metabolites of phytocannabinoids. The prototypic endogenous substance is N-arachidonoyl glycine (NAgly) that is closely ... ...

Abstract	The cannabinoid acids are a structurally heterogeneous group of compounds some of which are endogenous molecules and others that are metabolites of phytocannabinoids. The prototypic endogenous substance is N-arachidonoyl glycine (NAgly) that is closely related in structure to the cannabinoid agonist anandamide. The most studied phytocannabinoid is Δ(9)-THC-11-oic acid, the principal metabolite of Δ(9)-THC. Both types of acids have in common several biological actions such as low affinity for CB1 anti-inflammatory activity and analgesic properties. This suggests that there may be similarities in their mechanism of action, a point that is discussed in this review. Also presented are reports on analogs of the acids that provide opportunities for the development of novel therapeutic agents, such as ajulemic acid.
MeSH term(s)	Analgesics/chemistry ; Analgesics/metabolism ; Analgesics/pharmacology ; Animals ; Cannabinoids/chemistry ; Cannabinoids/metabolism ; Cannabinoids/pharmacology ; Dronabinol/analogs & derivatives ; Dronabinol/pharmacology ; Endocannabinoids/chemistry ; Endocannabinoids/metabolism ; Endocannabinoids/pharmacology ; Humans ; Molecular Structure
Chemical Substances	Analgesics ; Cannabinoids ; Endocannabinoids ; Dronabinol (7J8897W37S) ; lenabasum (OGN7X90BT8)
Language	English
Publishing date	2014-04-01
Publishing country	England
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Review
ZDB-ID	1161284-8
ISSN	1464-3391 ; 0968-0896
ISSN (online)	1464-3391
ISSN	0968-0896
DOI	10.1016/j.bmc.2014.03.038
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Article ; Online: Cannabinoids, inflammation, and fibrosis.

Zurier, Robert B / Burstein, Sumner H

FASEB journal : official publication of the Federation of American Societies for Experimental Biology

2016 Volume 30, Issue 11, Page(s) 3682–3689

Abstract: Cannabinoids apparently act on inflammation through mechanisms different from those of agents such as nonsteroidal anti-inflammatory drugs (NSAIDs). As a class, the cannabinoids are generally free from the adverse effects associated with NSAIDs. Their ... ...

Abstract	Cannabinoids apparently act on inflammation through mechanisms different from those of agents such as nonsteroidal anti-inflammatory drugs (NSAIDs). As a class, the cannabinoids are generally free from the adverse effects associated with NSAIDs. Their clinical development thus provides a new approach to treatment of diseases characterized by acute and chronic inflammation and fibrosis. A concise survey of the anti-inflammatory actions of the phytocannabinoids Δ
MeSH term(s)	Animals ; Anti-Inflammatory Agents/therapeutic use ; Anti-Inflammatory Agents, Non-Steroidal/therapeutic use ; Cannabinoids/therapeutic use ; Endocannabinoids/metabolism ; Fibrosis/drug therapy ; Humans ; Inflammation/drug therapy ; Inflammation/metabolism
Chemical Substances	Anti-Inflammatory Agents ; Anti-Inflammatory Agents, Non-Steroidal ; Cannabinoids ; Endocannabinoids
Language	English
Publishing date	2016-11
Publishing country	United States
Document type	Journal Article ; Review
ZDB-ID	639186-2
ISSN	1530-6860 ; 0892-6638
ISSN (online)	1530-6860
ISSN	0892-6638
DOI	10.1096/fj.201600646R
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Article ; Online: Comparison of Symptoms Associated With SARS-CoV-2 Variants Among Children in Canada.

Sumner, Madeleine W / Xie, Jianling / Zemek, Roger / Winston, Kathleen / Freire, Gabrielle / Burstein, Brett / Kam, April / Emsley, Jason / Gravel, Jocelyn / Porter, Robert / Sabhaney, Vikram / Mater, Ahmed / Salvadori, Marina I / Berthelot, Simon / Beer, Darcy / Poonai, Naveen / Moffatt, Anne / Wright, Bruce / Freedman, Stephen B

JAMA network open

2023 Volume 6, Issue 3, Page(s) e232328

Abstract: Importance: Clinical manifestations of SARS-CoV-2 variants have not been systematically compared in children.: Objective: To compare symptoms, emergency department (ED) chest radiography, treatments, and outcomes among children with different SARS- ... ...

Abstract	Importance: Clinical manifestations of SARS-CoV-2 variants have not been systematically compared in children. Objective: To compare symptoms, emergency department (ED) chest radiography, treatments, and outcomes among children with different SARS-CoV-2 variants. Design, setting, and participants: This multicenter cohort study was performed at 14 Canadian pediatric EDs. Participants included children and adolescents younger than 18 years (hereinafter referred to as children) tested for SARS-CoV-2 infection in an ED between August 4, 2020, and February 22, 2022, with 14 days of follow-up. Exposure(s): SARS-CoV-2 variants detected on a specimen collected from the nasopharynx, nares, or throat. Main outcomes and measures: The primary outcome was presence and number of presenting symptoms. The secondary outcomes were presence of core COVID-19 symptoms, chest radiography findings, treatments, and 14-day outcomes. Results: Among 7272 participants presenting to an ED, 1440 (19.8%) had test results positive for SARS-CoV-2 infection. Of these, 801 (55.6%) were boys, with a median age of 2.0 (IQR, 0.6-7.0) years. Children with the Alpha variant reported the fewest core COVID-19 symptoms (195 of 237 [82.3%]), which were most often reported by participants with Omicron variant infection (434 of 468 [92.7%]; difference, 10.5% [95% CI, 5.1%-15.9%]). In a multivariable model with the original type as the referent, the Omicron and Delta variants were associated with fever (odds ratios [ORs], 2.00 [95% CI, 1.43-2.80] and 1.93 [95% CI, 1.33-2.78], respectively) and cough (ORs, 1.42 [95% CI, 1.06-1.91] and 1.57 [95% CI, 1.13-2.17], respectively). Upper respiratory tract symptoms were associated with Delta infection (OR, 1.96 [95% CI, 1.38-2.79]); lower respiratory tract and systemic symptoms were associated with Omicron variant infection (ORs, 1.42 [95% CI, 1.04-1.92] and 1.77 [95% CI, 1.24-2.52], respectively). Children with Omicron infection most often had chest radiography performed and received treatments; compared with those who had Delta infection, they were more likely to have chest radiography performed (difference, 9.7% [95% CI, 4.7%-14.8%]), to receive intravenous fluids (difference, 5.6% [95% CI, 1.0%-10.2%]) and corticosteroids (difference, 7.9% [95% CI, 3.2%-12.7%]), and to have an ED revisit (difference, 8.8% [95% CI, 3.5%-14.1%]). The proportions of children admitted to the hospital and intensive care unit did not differ between variants. Conclusions and relevance: The findings of this cohort study of SARS-CoV-2 variants suggest that the Omicron and Delta variants were more strongly associated with fever and cough than the original-type virus and the Alpha variant. Children with Omicron variant infection were more likely to report lower respiratory tract symptoms and systemic manifestations, undergo chest radiography, and receive interventions. No differences were found in undesirable outcomes (ie, hospitalization, intensive care unit admission) across variants.
MeSH term(s)	Adolescent ; Male ; Humans ; Child ; Infant ; Child, Preschool ; Female ; SARS-CoV-2 ; COVID-19/epidemiology ; Canada/epidemiology ; Cohort Studies ; Cough/etiology ; Fever/etiology ; Hepatitis D
Language	English
Publishing date	2023-03-01
Publishing country	United States
Document type	Multicenter Study ; Journal Article ; Research Support, Non-U.S. Gov't
ISSN	2574-3805
ISSN (online)	2574-3805
DOI	10.1001/jamanetworkopen.2023.2328
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Article: The elmiric acids: biologically active anandamide analogs.

Burstein, Sumner

Neuropharmacology

2008 Volume 55, Issue 8, Page(s) 1259–1264

Abstract: As chemical entities, lipoamino acids have been known for some time. However, more recently their occurrence and importance in mammalian species has been discovered. They appear to have close relationships with the endocannabinoids not only structurally ... ...

Abstract	As chemical entities, lipoamino acids have been known for some time. However, more recently their occurrence and importance in mammalian species has been discovered. They appear to have close relationships with the endocannabinoids not only structurally but also in terms of biological actions. The latter include analgesia, anti-inflammatory effects, inhibition of cell proliferation and calcium ion mobilization. To date about 40 naturally occurring members of this family have been identified and, additionally, several synthetic analogs have been prepared and studied. To facilitate their identity, a nomenclature system has been suggested based on the name elmiric acid (EMA). The prototypic example, N-arachidonoyl glycine, does not bind to CB1, however it does inhibit the glycine transporter GLYT2a and also appears to be a ligand for the orphan G-protein-coupled receptor GPR18. It may also have a role in regulating tissue levels of anandamide by virtue of its inhibitory effect on FAAH the enzyme that mediates inactivation of anandamide. Its concentration in rat brain is several-fold higher than anandamide supporting its possible role as a physiological mediator. Future studies should be aimed at elucidating the actions of all of the members of this interesting family of molecules.
MeSH term(s)	Analgesics ; Animals ; Arachidonic Acids/chemistry ; Arachidonic Acids/classification ; Arachidonic Acids/pharmacology ; Calcium/metabolism ; Cannabinoid Receptor Modulators/classification ; Cannabinoid Receptor Modulators/pharmacology ; Cell Proliferation/drug effects ; Endocannabinoids ; Ganglia, Spinal/drug effects ; Neurons/drug effects ; Neurons/metabolism ; Polyunsaturated Alkamides/chemistry ; Polyunsaturated Alkamides/classification ; Polyunsaturated Alkamides/pharmacology
Chemical Substances	Analgesics ; Arachidonic Acids ; Cannabinoid Receptor Modulators ; Endocannabinoids ; Polyunsaturated Alkamides ; Calcium (SY7Q814VUP) ; anandamide (UR5G69TJKH)
Language	English
Publishing date	2008-12
Publishing country	England
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Review
ZDB-ID	218272-5
ISSN	1873-7064 ; 0028-3908
ISSN (online)	1873-7064
ISSN	0028-3908
DOI	10.1016/j.neuropharm.2007.11.011
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