Nabilone (BioDeep_00000026930)

   

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6H,6aH,7H,8H,9H,10H,10aH-benzo[c]isochromen-9-one

化学式: C24H36O3 (372.26643060000004)
中文名称: 大麻隆
谱图信息: 最多检出来源 Homo sapiens(blood) 0.43%

分子结构信息

SMILES: CCCCCCC(C)(C)C1=CC(=C2C3CC(=O)CCC3C(OC2=C1)(C)C)O
InChI: InChI=1S/C24H36O3/c1-6-7-8-9-12-23(2,3)16-13-20(26)22-18-15-17(25)10-11-19(18)24(4,5)27-21(22)14-16/h13-14,18-19,26H,6-12,15H2,1-5H3/t18-,19-/m1/s1

描述信息

Nabilone is a synthetic cannabinoid with therapeutic use as an antiemetic and as an adjunct analgesic for neuropathic pain. It is a synthetic cannabinoid, which mimics the main ingredient of marijuana (THC) but it has more predictable side effects and causes no or minimal euphoria. Nabilone is not derived from the cannabis plant as is dronabinol. In Canada, the United States, the United Kingdom and Mexico, nabilone is marketed as Cesamet. It was approved in 1985 by the United States FDA for treatment of chemotherapy-induced nausea and vomiting that has not responded to conventional antiemetics. Though it was approved by the FDA in 1985, the drug only began marketing in the United States in 2006. It is also approved for use in treatment of anorexia and weight loss in patients with AIDS. Although it doesnt have the official indication (except in Mexico), nabilone is widely used as an adjunct therapy for chronic pain management. Numerous trials and case studies have demonstrate various benefits for condition such as fibromyalgia and multiple scerosis. Nabilone is a racemate consisting of the (S,S) and the (R,R) isomers (trans).
A - Alimentary tract and metabolism > A04 - Antiemetics and antinauseants > A04A - Antiemetics and antinauseants
D002492 - Central Nervous System Depressants > D014149 - Tranquilizing Agents > D014151 - Anti-Anxiety Agents
D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D014149 - Tranquilizing Agents
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants
D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents
C78272 - Agent Affecting Nervous System > C267 - Antiemetic Agent
D005765 - Gastrointestinal Agents > D000932 - Antiemetics

同义名列表

10 个代谢物同义名

(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6H,6aH,7H,8H,9H,10H,10aH-benzo[c]isochromen-9-one; Nabilone, (trans-(+-))-isomer; Nabilone, (6ar-trans)-isomer; Nabilone, (6as-trans)-isomer; Nabilone, (cis-(+-))-isomer; Lilly brand OF nabilone; (−)-nabilone; LY-109514; Nabilone; Cesamet



数据库引用编号

11 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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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

  • Winfried Häuser, Patrick Welsch, Lukas Radbruch, Emma Fisher, Rae Frances Bell, R Andrew Moore. Cannabis-based medicines and medical cannabis for adults with cancer pain. The Cochrane database of systematic reviews. 2023 06; 6(?):CD014915. doi: 10.1002/14651858.cd014915.pub2. [PMID: 37283486]
  • Myuri Ruthirakuhan, Nathan Herrmann, Ana C Andreazza, Nicolaas Paul L G Verhoeff, Damien Gallagher, Sandra E Black, Alex Kiss, Krista L Lanctôt. 24S-Hydroxycholesterol Is Associated with Agitation Severity in Patients with Moderate-to-Severe Alzheimer's Disease: Analyses from a Clinical Trial with Nabilone. Journal of Alzheimer's disease : JAD. 2019; 71(1):21-31. doi: 10.3233/jad-190202. [PMID: 31322567]
  • Martin Mücke, Tudor Phillips, Lukas Radbruch, Frank Petzke, Winfried Häuser. Cannabis-based medicines for chronic neuropathic pain in adults. The Cochrane database of systematic reviews. 2018 03; 3(?):CD012182. doi: 10.1002/14651858.cd012182.pub2. [PMID: 29513392]
  • N Krcevski-Skvarc, C Wells, W Häuser. Availability and approval of cannabis-based medicines for chronic pain management and palliative/supportive care in Europe: A survey of the status in the chapters of the European Pain Federation. European journal of pain (London, England). 2018 03; 22(3):440-454. doi: 10.1002/ejp.1147. [PMID: 29134767]
  • Suzanne Nielsen, Rada Germanos, Megan Weier, John Pollard, Louisa Degenhardt, Wayne Hall, Nicholas Buckley, Michael Farrell. The Use of Cannabis and Cannabinoids in Treating Symptoms of Multiple Sclerosis: a Systematic Review of Reviews. Current neurology and neuroscience reports. 2018 02; 18(2):8. doi: 10.1007/s11910-018-0814-x. [PMID: 29442178]
  • Jørgen G Bramness, Geert Dom, Antoni Gual, Karl Mann, Friedrich Martin Wurst. A Survey on the Medical Use of Cannabis in Europe: A Position Paper. European addiction research. 2018; 24(4):201-205. doi: 10.1159/000492757. [PMID: 30134238]
  • Kevin P Hill, Matthew D Palastro, Staci A Gruber, Garrett M Fitzmaurice, Shelly F Greenfield, Scott E Lukas, Roger D Weiss. Nabilone pharmacotherapy for cannabis dependence: A randomized, controlled pilot study. The American journal on addictions. 2017 Dec; 26(8):795-801. doi: 10.1111/ajad.12622. [PMID: 28921814]
  • Chee W Chia, Olga D Carlson, David D Liu, Isabel González-Mariscal, Sara Santa-Cruz Calvo, Josephine M Egan. Incretin secretion in humans is under the influence of cannabinoid receptors. American journal of physiology. Endocrinology and metabolism. 2017 09; 313(3):E359-E366. doi: 10.1152/ajpendo.00080.2017. [PMID: 28655715]
  • ". Cannabis and cannabinoids. The Medical letter on drugs and therapeutics. 2016 Aug; 58(1500):97-8. doi: ". [PMID: 27466748]
  • Brian Walitt, Petra Klose, Mary-Ann Fitzcharles, Tudor Phillips, Winfried Häuser. Cannabinoids for fibromyalgia. The Cochrane database of systematic reviews. 2016 Jul; 7(?):CD011694. doi: 10.1002/14651858.cd011694.pub2. [PMID: 27428009]
  • Brian Owens. Drug development: The treasure chest. Nature. 2015 Sep; 525(7570):S6-8. doi: 10.1038/525s6a. [PMID: 26398738]
  • Eric P Baron. Comprehensive Review of Medicinal Marijuana, Cannabinoids, and Therapeutic Implications in Medicine and Headache: What a Long Strange Trip It's Been …. Headache. 2015 Jun; 55(6):885-916. doi: 10.1111/head.12570. [PMID: 26015168]
  • Philip W Lam, David W Frost. Nabilone therapy for cannabis withdrawal presenting as protracted nausea and vomiting. BMJ case reports. 2014 Sep; 2014(?):. doi: 10.1136/bcr-2014-205287. [PMID: 25246463]
  • Kevin P Hill. Medical marijuana: more questions than answers. Journal of psychiatric practice. 2014 Sep; 20(5):389-91. doi: 10.1097/01.pra.0000454786.97976.96. [PMID: 25226202]
  • Amine Benyamina, Michel Reynaud. [Therapeutic use of cannabis derivatives]. La Revue du praticien. 2014 Feb; 64(2):165-8. doi: ". [PMID: 24701869]
  • Franjo Grotenhermen, Kirsten Müller-Vahl. The therapeutic potential of cannabis and cannabinoids. Deutsches Arzteblatt international. 2012 Jul; 109(29-30):495-501. doi: 10.3238/arztebl.2012.0495. [PMID: 23008748]
  • Linda E Klumpers, Tim L Beumer, Johan G C van Hasselt, Astrid Lipplaa, Lennard B Karger, H Daniël Kleinloog, Jan I Freijer, Marieke L de Kam, Joop M A van Gerven. Novel Δ(9) -tetrahydrocannabinol formulation Namisol® has beneficial pharmacokinetics and promising pharmacodynamic effects. British journal of clinical pharmacology. 2012 Jul; 74(1):42-53. doi: 10.1111/j.1365-2125.2012.04164.x. [PMID: 22680341]
  • Javier Fernández-Ruiz. [Cannabinoid drugs for neurological diseases: what is behind?]. Revista de neurologia. 2012 May; 54(10):613-28. doi: ". [PMID: 22573509]
  • Jarkko Kalliomäki, Andrew Philipp, Jane Baxendale, Peter Annas, Rolf Karlsten, Märta Segerdahl. Lack of effect of central nervous system-active doses of nabilone on capsaicin-induced pain and hyperalgesia. Clinical and experimental pharmacology & physiology. 2012 Apr; 39(4):336-42. doi: 10.1111/j.1440-1681.2012.05674.x. [PMID: 22233155]
  • J Michael Bostwick. Blurred boundaries: the therapeutics and politics of medical marijuana. Mayo Clinic proceedings. 2012 Feb; 87(2):172-86. doi: 10.1016/j.mayocp.2011.10.003. [PMID: 22305029]
  • Marek Tkaczyk, Ewa Florek, Wojciech Piekoszewski. [Marihuana and cannobinoids as medicaments]. Przeglad lekarski. 2012; 69(10):1095-7. doi: . [PMID: 23421098]
  • Albert Tuca. Use of granisetron transdermal system in the prevention of chemotherapy-induced nausea and vomiting: a review. Cancer management and research. 2009 Dec; 2(?):1-12. doi: 10.2147/cmar.s4953. [PMID: 21188092]
  • Shaheen E Lakhan, Marie Rowland. Whole plant cannabis extracts in the treatment of spasticity in multiple sclerosis: a systematic review. BMC neurology. 2009 Dec; 9(?):59. doi: 10.1186/1471-2377-9-59. [PMID: 19961570]
  • Sanjai Saxena. Fungal biotransformation of cannabinoids: potential for new effective drugs. Current opinion in drug discovery & development. 2009 Mar; 12(2):305-12. doi: ". [PMID: 19333876]
  • Sumner H Burstein, Robert B Zurier. Cannabinoids, endocannabinoids, and related analogs in inflammation. The AAPS journal. 2009 Mar; 11(1):109-19. doi: 10.1208/s12248-009-9084-5. [PMID: 19199042]
  • Roger G Pertwee. Emerging strategies for exploiting cannabinoid receptor agonists as medicines. British journal of pharmacology. 2009 Feb; 156(3):397-411. doi: 10.1111/j.1476-5381.2008.00048.x. [PMID: 19226257]
  • M David Marks, Li Tian, Jonathan P Wenger, Stephanie N Omburo, Wilfredo Soto-Fuentes, Ji He, David R Gang, George D Weiblen, Richard A Dixon. Identification of candidate genes affecting Delta9-tetrahydrocannabinol biosynthesis in Cannabis sativa. Journal of experimental botany. 2009; 60(13):3715-26. doi: 10.1093/jxb/erp210. [PMID: 19581347]
  • Mahmoud A Elsohly, Desmond Slade. Chemical constituents of marijuana: the complex mixture of natural cannabinoids. Life sciences. 2005 Dec; 78(5):539-48. doi: 10.1016/j.lfs.2005.09.011. [PMID: 16199061]
  • C H Ashton, P B Moore, P Gallagher, A H Young. Cannabinoids in bipolar affective disorder: a review and discussion of their therapeutic potential. Journal of psychopharmacology (Oxford, England). 2005 May; 19(3):293-300. doi: 10.1177/0269881105051541. [PMID: 15888515]
  • Iain J McGilveray. Pharmacokinetics of cannabinoids. Pain research & management. 2005; 10 Suppl A(?):15A-22A. doi: 10.1155/2005/242516. [PMID: 16237477]
  • Wayne Hall, Louisa Degenhardt. Medical marijuana initiatives : are they justified? How successful are they likely to be?. CNS drugs. 2003; 17(10):689-97. doi: 10.2165/00023210-200317100-00001. [PMID: 12873153]
  • M Campbell, D N Bateman. Pharmacokinetic optimisation of antiemetic therapy. Clinical pharmacokinetics. 1992 Aug; 23(2):147-60. doi: 10.2165/00003088-199223020-00006. [PMID: 1355018]
  • A D Fraser, R Meatherall. Lack of interference by nabilone in the EMIT d.a.u. cannabinoid assay, Abbott TDx cannabinoid assay, and a sensitive TLC assay for delta 9-THC-carboxylic acid. Journal of analytical toxicology. 1989 Jul; 13(4):240. doi: 10.1093/jat/13.4.240. [PMID: 2550703]
  • G K Hanasono, H R Sullivan, C L Gries, W H Jordan, J L Emmerson. A species comparison of the toxicity of nabilone, a new synthetic cannabinoid. Fundamental and applied toxicology : official journal of the Society of Toxicology. 1987 Aug; 9(2):185-97. doi: 10.1016/0272-0590(87)90042-x. [PMID: 2888699]
  • H R Sullivan, G K Hanasono, W M Miller, P G Wood. Species specificity in the metabolism of nabilone. Relationship between toxicity and metabolic routes. Xenobiotica; the fate of foreign compounds in biological systems. 1987 Apr; 17(4):459-68. doi: 10.3109/00498258709043952. [PMID: 3037806]
  • J H Mendelson, J Ellingboe, N K Mello. Acute effects of natural and synthetic cannabis compounds on prolactin levels in human males. Pharmacology, biochemistry, and behavior. 1984 Jan; 20(1):103-6. doi: 10.1016/0091-3057(84)90109-6. [PMID: 6320226]
  • L Lemberger, A Rubin, R Wolen, K DeSante, H Rowe, R Forney, P Pence. Pharmacokinetics, metabolism and drug-abuse potential of nabilone. Cancer treatment reviews. 1982 Dec; 9 Suppl B(?):17-23. doi: 10.1016/s0305-7372(82)80031-5. [PMID: 6299550]
  • H R Sullivan, D L Kau, P G Wood. Pharmacokinetics of nabilone, a psychotropically active 9-ketocannabinoid, in the dog. Utilization of quantitative selected ion monitoring and deuterium labeling. Biomedical mass spectrometry. 1978 Apr; 5(4):296-301. doi: 10.1002/bms.1200050405. [PMID: 638236]
  • A Rubin, L Lemberger, P Warrick, R E Crabtree, H Sullivan, H Rowe, B D Obermeyer. Physiologic disposition of nabilone, a cannabinol derivative, in man. Clinical pharmacology and therapeutics. 1977 Jul; 22(1):85-91. doi: 10.1002/cpt197722185. [PMID: 872500]