Rimonabant (BioDeep_00000009827)
Secondary id: BioDeep_00000858382
human metabolite blood metabolite Chemicals and Drugs Volatile Flavor Compounds
代谢物信息卡片
化学式: C22H21Cl3N4O (462.0780866)
中文名称: 利莫纳班
谱图信息:
最多检出来源 Homo sapiens(blood) 98.46%
分子结构信息
SMILES: CC1=C(N(N=C1C(=O)NN1CCCCC1)C1=C(Cl)C=C(Cl)C=C1)C1=CC=C(Cl)C=C1
InChI: InChI=1S/C22H21Cl3N4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-9-17(24)13-18(19)25)21(14)15-5-7-16(23)8-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30)
描述信息
Rimonabant is an anorectic anti-obesity drug produced and marketed by Sanofi-Aventis. It is an inverse agonist for the cannabinoid receptor CB1. Its main avenue of effect is reduction in appetite. Rimonabant is the first selective CB1 receptor blocker to be approved for use anywhere in the world. Rimonabant is approved in 38 countries including the E.U., Mexico, and Brazil. It was rejected for approval for use in the United States. This decision was made after a U.S. advisory panel recommended the medicine not be approved because it may increase suicidal thinking and depression.
A - Alimentary tract and metabolism > A08 - Antiobesity preparations, excl. diet products > A08A - Antiobesity preparations, excl. diet products
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D063385 - Cannabinoid Receptor Modulators
D018377 - Neurotransmitter Agents > D063385 - Cannabinoid Receptor Modulators > D063387 - Cannabinoid Receptor Antagonists
C78272 - Agent Affecting Nervous System > C28197 - Antianxiety Agent
D019440 - Anti-Obesity Agents
Same as: D05731
同义名列表
15 个代谢物同义名
N-(Piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide hydrochloride; 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide; N-(1-Piperidinyl)-1-(2,4-dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carboxamide; 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl-1H-pyrazole-3-carboxamide; Rimonabant hydrochloride; Rimonabantum; SR 141716A; Rimonabant; SR141716a; SR 141716; SR141716; Acomplia; Zimulti; a 281; SR 141716
数据库引用编号
17 个数据库交叉引用编号
- ChEBI: CHEBI:34967
- KEGG: C14319
- PubChem: 104850
- HMDB: HMDB0015623
- Metlin: METLIN63002
- DrugBank: DB06155
- ChEMBL: CHEMBL111
- Wikipedia: Rimonabant
- MeSH: Rimonabant
- KNApSAcK: C00053749
- chemspider: 94641
- CAS: 168273-06-1
- PMhub: MS000023646
- PubChem: 17395319
- PDB-CCD: AY6
- NIKKAJI: J649.754C
- KNApSAcK: 34967
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:
- PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。
文献列表
- Abigail L Brewer, Claire E Felter, Anna R Sternitzky, Sade M Spencer. Somatic and anxiety-like behaviors in male and female rats during withdrawal from the non-selective cannabinoid agonist WIN 55,212-2.
Pharmacology, biochemistry, and behavior.
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American journal of physiology. Endocrinology and metabolism.
2023 02; 324(2):E176-E184. doi:
10.1152/ajpendo.00258.2022
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Drug and alcohol dependence.
2022 11; 240(?):109640. doi:
10.1016/j.drugalcdep.2022.109640
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Cell death & disease.
2022 09; 13(9):808. doi:
10.1038/s41419-022-05242-5
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Toxicological sciences : an official journal of the Society of Toxicology.
2022 04; 187(1):175-185. doi:
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. [PMID: 35201352] - Erkan Kilinc, Seyit Ankarali, Ibrahim Ethem Torun, Yasar Dagistan. Receptor mechanisms mediating the anti-neuroinflammatory effects of endocannabinoid system modulation in a rat model of migraine.
The European journal of neuroscience.
2022 02; 55(4):1015-1031. doi:
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Cellular and molecular gastroenterology and hepatology.
2022; 13(4):1041-1055. doi:
10.1016/j.jcmgh.2021.12.013
. [PMID: 34954190] - Nicolas Hoertel, Marina Sánchez-Rico, Céline Cougoule, Erich Gulbins, Johannes Kornhuber, Alexander Carpinteiro, Katrin Anne Becker, Angela M Reiersen, Eric J Lenze, David Seftel, Cédric Lemogne, Frédéric Limosin. Repurposing antidepressants inhibiting the sphingomyelinase acid/ceramide system against COVID-19: current evidence and potential mechanisms.
Molecular psychiatry.
2021 12; 26(12):7098-7099. doi:
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. [PMID: 34385600] - Juliette Salles, Fabienne Briand-Mésange, Stéphanie Trudel, Jérôme Ausseil, Jean-Pierre Salles, Hugues Chap. Can antidepressants unlock prescription of rimonabant in the fight against COVID-19?.
Molecular psychiatry.
2021 12; 26(12):7091-7092. doi:
10.1038/s41380-021-01221-y
. [PMID: 34282263] - Samar Rezq, Reham Hassan, Mona F Mahmoud. Rimonabant ameliorates hepatic ischemia/reperfusion injury in rats: Involvement of autophagy via modulating ERK- and PI3K/AKT-mTOR pathways.
International immunopharmacology.
2021 Nov; 100(?):108140. doi:
10.1016/j.intimp.2021.108140
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Neuropharmacology.
2021 06; 190(?):108554. doi:
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. [PMID: 33845073] - Li Zhao, Tao Liu, Zhan-Jun Dou, Mei-Ting Wang, Zi-Xuan Hu, Bei Wang. CB1 receptor antagonist rimonabant protects against chronic intermittent hypoxia-induced renal injury in rats.
BMC nephrology.
2021 04; 22(1):153. doi:
10.1186/s12882-021-02362-6
. [PMID: 33902473] - Olivier Le Bacquer, Kassandra Lanchais, Kristell Combe, Loïc Van Den Berghe, Stéphane Walrand. Acute rimonabant treatment promotes protein synthesis in C2C12 myotubes through a CB1-independent mechanism.
Journal of cellular physiology.
2021 04; 236(4):2669-2683. doi:
10.1002/jcp.30034
. [PMID: 32885412] - Alba Huerga-Gómez, Tania Aguado, Aníbal Sánchez-de la Torre, Ana Bernal-Chico, Carlos Matute, Susana Mato, Manuel Guzmán, Ismael Galve-Roperh, Javier Palazuelos. Δ9 -Tetrahydrocannabinol promotes oligodendrocyte development and CNS myelination in vivo.
Glia.
2021 03; 69(3):532-545. doi:
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The Journal of pharmacology and experimental therapeutics.
2021 01; 376(1):1-11. doi:
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. [PMID: 33087396] - Yue-Mei Zhang, Michael Greco, Tonya Le Blanc, Wensheng Lang, Jack Kauffman, John Masucci, William V Murray, Keith Demarest, Mark Joseph Macielag. Discovery of PEGylated 6-Benzhydryl-4-amino-quinazolines as Peripherally Restricted CB1R Inverse Agonists.
ACS medicinal chemistry letters.
2020 Dec; 11(12):2504-2509. doi:
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Sleep & breathing = Schlaf & Atmung.
2020 Dec; 24(4):1441-1449. doi:
10.1007/s11325-019-02009-9
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Cellular and molecular life sciences : CMLS.
2020 Nov; 77(22):4709-4723. doi:
10.1007/s00018-019-03433-6
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Obesity (Silver Spring, Md.).
2020 09; 28(9):1580-1581. doi:
10.1002/oby.22916
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British journal of pharmacology.
2020 09; 177(17):4034-4054. doi:
10.1111/bph.15155
. [PMID: 32510591] - Jérémie Joffre, Che-Chung Yeh, Erika Wong, Mayuri Thete, Fengyun Xu, Ivana Zlatanova, Elliot Lloyd, Lester Kobzik, Matthieu Legrand, Judith Hellman. Activation of CB1R Promotes Lipopolysaccharide-Induced IL-10 Secretion by Monocytic Myeloid-Derived Suppressive Cells and Reduces Acute Inflammation and Organ Injury.
Journal of immunology (Baltimore, Md. : 1950).
2020 06; 204(12):3339-3350. doi:
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Behavioural brain research.
2020 03; 381(?):112311. doi:
10.1016/j.bbr.2019.112311
. [PMID: 31711896] - Karuna Irungbam, Yuri Churin, Tomomitsu Matono, Jakob Weglage, Matthias Ocker, Dieter Glebe, Martin Hardt, Alica Koeppel, Martin Roderfeld, Elke Roeb. Cannabinoid receptor 1 knockout alleviates hepatic steatosis by downregulating perilipin 2.
Laboratory investigation; a journal of technical methods and pathology.
2020 03; 100(3):454-465. doi:
10.1038/s41374-019-0327-5
. [PMID: 31570772] - Günter A Müller, Andreas W Herling, Susanne Wied, Timo D Müller. CB1 Receptor-Dependent and Independent Induction of Lipolysis in Primary Rat Adipocytes by the Inverse Agonist Rimonabant (SR141716A).
Molecules (Basel, Switzerland).
2020 Feb; 25(4):. doi:
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. [PMID: 32085406] - G A Müller, S Wied, A W Herling. Analysis of Direct Effects of the CB1 Receptor Antagonist Rimonabant on Fatty Acid Oxidation and Glycogenolysis in Liver and Muscle Cells in vitro.
Biochemistry. Biokhimiia.
2019 Aug; 84(8):954-962. doi:
10.1134/s000629791908011x
. [PMID: 31522677] - Ester Aso, Víctor Fernández-Dueñas, Marc López-Cano, Jaume Taura, Masahiko Watanabe, Isidre Ferrer, Rafael Luján, Francisco Ciruela. Adenosine A2A-Cannabinoid CB1 Receptor Heteromers in the Hippocampus: Cannabidiol Blunts Δ9-Tetrahydrocannabinol-Induced Cognitive Impairment.
Molecular neurobiology.
2019 Aug; 56(8):5382-5391. doi:
10.1007/s12035-018-1456-3
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Neurochemistry international.
2019 05; 125(?):57-66. doi:
10.1016/j.neuint.2019.02.008
. [PMID: 30769029] - Julieta Lazarte, Robert A Hegele. Cannabis effects on lipoproteins.
Current opinion in lipidology.
2019 04; 30(2):140-146. doi:
10.1097/mol.0000000000000575
. [PMID: 30649023] - M C G Leite-Avalca, F T Staats, D Verona, P de Souza, M C Almeida, J E Silva-Santos, A R Zampronio. Cannabinoid CB1 Receptor Antagonist Rimonabant Decreases Levels of Markers of Organ Dysfunction and Alters Vascular Reactivity in Aortic Vessels in Late Sepsis in Rats.
Inflammation.
2019 Apr; 42(2):618-627. doi:
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FASEB journal : official publication of the Federation of American Societies for Experimental Biology.
2019 03; 33(3):4314-4326. doi:
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Canadian journal of physiology and pharmacology.
2019 Feb; 97(2):120-129. doi:
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. [PMID: 30673308] - Caitlin A D Jagla, Caitlin E Scott, Yaliang Tang, Changjiang Qiao, Gabriel E Mateo-Semidey, Guillermo A Yudowski, Dai Lu, Debra A Kendall. Pyrimidinyl Biphenylureas Act as Allosteric Modulators to Activate Cannabinoid Receptor 1 and Initiate β-Arrestin-Dependent Responses.
Molecular pharmacology.
2019 01; 95(1):1-10. doi:
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. [PMID: 30322873] - Yue-Mei Zhang, Michael N Greco, Mark J Macielag, Christopher A Teleha, Renee L DesJarlais, Yuting Tang, George Ho, Cuifen Hou, Cailin Chen, Shuyuan Zhao, Jack Kauffman, Raul Camacho, Jenson Qi, William Murray, Keith Demarest, James Leonard. 6-Benzhydryl-4-amino-quinolin-2-ones as Potent Cannabinoid Type 1 (CB1) Receptor Inverse Agonists and Chemical Modifications for Peripheral Selectivity.
Journal of medicinal chemistry.
2018 11; 61(22):10276-10298. doi:
10.1021/acs.jmedchem.8b01467
. [PMID: 30339387] - Abhigyan Ravula, Hardik Chandasana, Barry Setlow, Marcelo Febo, Adriaan W Bruijnzeel, Hartmut Derendorf. Simultaneous quantification of cannabinoids tetrahydrocannabinol, cannabidiol and CB1 receptor antagonist in rat plasma: An application to characterize pharmacokinetics after passive cannabis smoke inhalation and co-administration of rimonabant.
Journal of pharmaceutical and biomedical analysis.
2018 Oct; 160(?):119-125. doi:
10.1016/j.jpba.2018.07.004
. [PMID: 30077950] - L W Wei, Z Q Yuan, M D Zhao, C W Gu, J H Han, L Fu. Inhibition of Cannabinoid Receptor 1 Can Influence the Lipid Metabolism in Mice with Diet-Induced Obesity.
Biochemistry. Biokhimiia.
2018 Oct; 83(10):1279-1287. doi:
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Drug and alcohol dependence.
2018 Oct; 191(?):14-24. doi:
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Diabetes, obesity & metabolism.
2018 09; 20(9):2179-2189. doi:
10.1111/dom.13350
. [PMID: 29740969] - George S Amato, Amruta Manke, Vineetha Vasukuttan, Robert W Wiethe, Rodney W Snyder, Scott P Runyon, Rangan Maitra. Synthesis and pharmacological characterization of functionalized 6-piperazin-1-yl-purines as cannabinoid receptor 1 (CB1) inverse agonists.
Bioorganic & medicinal chemistry.
2018 08; 26(15):4518-4531. doi:
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The Journal of pharmacy and pharmacology.
2018 Aug; 70(8):1031-1039. doi:
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2018 May; 287(?):59-69. doi:
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The Journal of pharmacology and experimental therapeutics.
2018 05; 365(2):437-446. doi:
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Neuropharmacology.
2018 05; 133(?):107-120. doi:
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PloS one.
2018; 13(10):e0206152. doi:
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British journal of pharmacology.
2017 Dec; 174(23):4523-4539. doi:
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. [PMID: 28963716] - Noha I Hussien, Hanan I El-Kerdasy, Mohammad El-Tantawy Ibrahim. Protective effect of rimonabant, a canabinoid receptor 1 antagonist, on nonalcoholic fatty liver disease in a rat model through modulation of the hepatic expression of activin A and follistatin.
Canadian journal of physiology and pharmacology.
2017 Dec; 95(12):1433-1441. doi:
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Scientific reports.
2017 11; 7(1):15645. doi:
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. [PMID: 29142285] - Cintia Folgueira, Silvia Barja-Fernandez, Laura Prado, Omar Al-Massadi, Cecilia Castelao, Veronica Pena-Leon, Patricia Gonzalez-Saenz, Javier Baltar, Ivan Baamonde, Rosaura Leis, Carlos Dieguez, Uberto Pagotto, Felipe F Casanueva, Sulay A Tovar, Ruben Nogueiras, Luisa M Seoane. Pharmacological inhibition of cannabinoid receptor 1 stimulates gastric release of nesfatin-1 via the mTOR pathway.
World journal of gastroenterology.
2017 Sep; 23(35):6403-6411. doi:
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BMC endocrine disorders.
2017 Jul; 17(1):41. doi:
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The Journal of pharmacology and experimental therapeutics.
2017 07; 362(1):210-218. doi:
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Free radical biology & medicine.
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