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  1. 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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  2. 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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  3. 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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  4. 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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    Zs.A 525: Show issues Location:
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  5. 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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  6. 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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    Zs.A 2266: Show issues Location:
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    Zs.MO 296: Show issues

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  7. Book: Marijuana

    Burstein, Sumner H. / Mechoulam, Raphael

    chemistry, pharmacology, metabolism and clinical effects

    1973  

    Author's details ed. by Raphael Mechoulam. [Contributors: Sumner H. Burstein ...]
    Language English
    Size IX, 409 S. : Ill., graph. Darst.
    Publisher Acad. Press
    Publishing place New York u.a.
    Publishing country United States
    Document type Book
    HBZ-ID HT004475174
    Database Catalogue ZB MED Medicine, Health

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    Shelf markLoan statusLocation
    1975 A 1830 order for loan Magazin

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  8. Article: In vitro metabolism and metabolic effects of ajulemic acid, a synthetic cannabinoid agonist.

    Burstein, Sumner H / Tepper, Mark A

    Pharmacology research & perspectives

    2013  Volume 1, Issue 2, Page(s) e00017

    Abstract: ... detected after the 2-h incubation were 103%, 90%, 86%, and 83% for rat, dog, monkey, and human hepatocytes ...

    Abstract Ajulemic acid is a synthetic analog of Δ(8)-THC-11-oic acid, the terminal metabolite of Δ(8)-THC. Unlike Δ(9)-THC, the psychoactive principle of Cannabis, it shows potent anti-inflammatory action and has minimal CNS cannabimimetic activity. Its in vitro metabolism by hepatocytes from rats, dogs, cynomolgus monkeys and humans was studied and the results are reported here. Five metabolites, M1 to M5, were observed in human hepatocyte incubations. One metabolite, M5, a glucuronide, was observed in the chromatogram of canine hepatocyte incubations. In monkey hepatocyte incubations, M5 was observed in the chromatograms of both the 120 and 240 min samples, trace metabolite M1 (side-chain hydroxyl) was observed in the 120 min samples, and trace metabolite M4 (side-chain dehydrogenation) was observed in the 240 min samples. No metabolites were found in the rat hepatocyte incubations. Unchanged amounts of ajulemic acid detected after the 2-h incubation were 103%, 90%, 86%, and 83% for rat, dog, monkey, and human hepatocytes, respectively. Additional studies were done to ascertain if ajulemic acid can inhibit the activities of five principal human cytochrome P450 isozymes; CYP1A2, CYP2C9, CYP2C19, CYP2D6, and CYP3A4/5. In contrast to the phytocannabinoids Δ(9)-THC and CBD, no significant inhibition of cytochrome activity was observed. These data further support the conclusions reached in earlier reports on ajulemic acid's high margin of safety and suggest that it undergoes minimal metabolism and is not likely to interfere with the normal metabolism of drugs or endogenous substances.
    Language English
    Publishing date 2013-12
    Publishing country United States
    Document type Journal Article
    ZDB-ID 2740389-0
    ISSN 2052-1707
    ISSN 2052-1707
    DOI 10.1002/prp2.17
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  9. Article ; Online: Ultrapure ajulemic acid has improved CB2 selectivity with reduced CB1 activity.

    Tepper, Mark A / Zurier, Robert B / Burstein, Sumner H

    Bioorganic & medicinal chemistry

    2014  Volume 22, Issue 13, Page(s) 3245–3251

    Abstract: Ajulemic acid, a side-chain analog of Δ(8)-THC-11-oic acid, was designed as a potent therapeutic agent free of the psychotropic adverse effects typical of most cannabinoids. Subsequent studies of ajulemic acid have yielded widely divergent findings on ... ...

    Abstract Ajulemic acid, a side-chain analog of Δ(8)-THC-11-oic acid, was designed as a potent therapeutic agent free of the psychotropic adverse effects typical of most cannabinoids. Subsequent studies of ajulemic acid have yielded widely divergent findings on the occurrence of these adverse effects. To help resolve these discrepancies, we have prepared highly purified ajulemic acid using a different synthetic method than previously reported in the literature and compared its cannabinoid receptor binding constants with those obtained using several other preparations from different sources. Whereas CB2 binding did not vary greatly among all of the samples, the CB1 binding showed a wide range of affinities. The highly purified product (JBT-101) reported here had the weakest affinity for CB1 while the original preparation (HU-239) showed the strongest affinity for CB1. The CB1/CB2 ratio of affinities was 12.3 for JBT-101 whereas that for HU-239 was 0.19, a 65-fold difference. Functional responses such as catalepsy and hypothermia using JBT-101 versus HU-239 displayed reduced CB1 activity in keeping with the receptor binding data. Thus, earlier conclusions on the limited therapeutic index for ajulemic acid need to be reconsidered in the light of the data now obtained using JBT-101.
    MeSH term(s) Animals ; Behavior, Animal/drug effects ; Binding Sites/drug effects ; Dose-Response Relationship, Drug ; Dronabinol/administration & dosage ; Dronabinol/analogs & derivatives ; Dronabinol/chemistry ; Dronabinol/pharmacology ; Female ; HL-60 Cells ; Humans ; Mice ; Molecular Conformation ; Pain Measurement/drug effects ; Receptor, Cannabinoid, CB1/agonists ; Receptor, Cannabinoid, CB1/metabolism ; Receptor, Cannabinoid, CB2/agonists ; Receptor, Cannabinoid, CB2/metabolism ; Structure-Activity Relationship
    Chemical Substances Receptor, Cannabinoid, CB1 ; Receptor, Cannabinoid, CB2 ; Dronabinol (7J8897W37S) ; lenabasum (OGN7X90BT8)
    Language English
    Publishing date 2014-05-09
    Publishing country England
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 1161284-8
    ISSN 1464-3391 ; 0968-0896
    ISSN (online) 1464-3391
    ISSN 0968-0896
    DOI 10.1016/j.bmc.2014.04.062
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  10. Book: Molecular endocrinology of the steroid hormones

    Schulster, Dennis / Burstein, Sumner H. / Cooke, Brian A.

    1976  

    Author's details Dennis Schulster ; Sumner Bursteiin ; Brian A. Cooke
    Keywords Endokrinologie ; Sexualhormon ; Steroidhormon
    Subject Geschlechtshormon
    Language English
    Size 321 S.
    Publisher Wiley
    Publishing place London
    Publishing country Great Britain
    Document type Book
    HBZ-ID HT000364012
    ISBN 0-471-76582-1 ; 978-0-471-76582-0
    Database Catalogue ZB MED Medicine, Health

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    Shelf markLoan statusLocation
    1977 A 1249 order for loan Magazin

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