Levomethorphan (BioDeep_00001873671)
代谢物信息卡片
Levomethorphan
化学式: C18H25NO (271.193604)
中文名称: 左美沙芬
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CN1CCC23CCCCC2C1CC4=C3C=C(C=C4)OC
InChI: InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3/t15-,17+,18+/m0/s1
描述信息
A 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene in which the stereocenters at positions 4a, 10 and 10a have R-configuration. It is a prodrug of levorphanol and a strong narcotic analgesic, and listed as a schedule II controlled substance.
D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018691 - Excitatory Amino Acid Antagonists
D002492 - Central Nervous System Depressants > D009294 - Narcotics > D053610 - Opiate Alkaloids
C78272 - Agent Affecting Nervous System > C67413 - Opioid Receptor Agonist
D019141 - Respiratory System Agents > D000996 - Antitussive Agents
C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent
D002491 - Central Nervous System Agents
同义名列表
1 个代谢物同义名
数据库引用编号
7 个数据库交叉引用编号
- ChEBI: CHEBI:146176
- PubChem: 5362449
- ChEMBL: CHEMBL1908323
- MeSH: Dextromethorphan
- CAS: 510-53-2
- CAS: 125-70-2
- MetaboLights: MTBLC146176
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)
0 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
- Seok Hwee Koo, Gaik Hong Soon, Alain Pruvost, Henri Benech, Tiing Leong Ang, Edmund Jon Deoon Lee, Daphne Shih Wen Ang. Evaluation of a six-probe cocktail (caffeine, tolbutamide, omeprazole, dextromethorphan, midazolam, and digoxin) approach to estimate hepatic drug detoxification capability and dosage requirements after a single oral dosing in healthy Chinese volunteers.
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2022 07; 395(7):815-826. doi:
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Journal of clinical pharmacology.
2022 06; 62(6):747-755. doi:
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2022 05; 40(8):3706-3710. doi:
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International journal of molecular sciences.
2021 Nov; 22(22):. doi:
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Clinical pharmacology in drug development.
2021 08; 10(8):824-839. doi:
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British journal of pharmacology.
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2019 08; 106(2):432-440. doi:
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2019 Jul; 15(3):192-197. doi:
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Clinical and translational science.
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Supportive care in cancer : official journal of the Multinational Association of Supportive Care in Cancer.
2019 Mar; 27(3):819-827. doi:
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2019 Jan; 108(1):268-278. doi:
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British journal of clinical pharmacology.
2017 Oct; 83(10):2214-2224. doi:
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2017 09; 47(4):59-63. doi:
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Scientific reports.
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Pharmacogenomics.
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Life sciences.
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European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.
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European journal of clinical pharmacology.
2016 Jun; 72(6):689-95. doi:
10.1007/s00228-016-2048-7. [PMID: 27023460] - Amar K Durgannavar, Manjanath B Patgar, Sharanappa T Nandibewoor, Shivamurti A Chimatadar. Fluorescent bovine serum albumin interacting with the antitussive quencher dextromethorphan: a spectroscopic insight.
Luminescence : the journal of biological and chemical luminescence.
2016 May; 31(3):843-50. doi:
10.1002/bio.3040. [PMID: 26387777] - Rui Chen, Haotian Wang, Jun Shi, Pei Hu. Alternative methods for CYP2D6 phenotyping: comparison of dextromethorphan metabolic ratios from AUC, single point plasma, and urine.
International journal of clinical pharmacology and therapeutics.
2016 May; 54(5):330-6. doi:
10.5414/cp202387. [PMID: 26902503] - Muhammad Farooq, Edward J Kelly, Jashvant D Unadkat. CYP2D6 Is Inducible by Endogenous and Exogenous Corticosteroids.
Drug metabolism and disposition: the biological fate of chemicals.
2016 May; 44(5):750-7. doi:
10.1124/dmd.115.069229. [PMID: 26965986] - Na Zhang. Letter to the editor regarding 'Development and validation of a sensitive UHPLC-MS/MS method for simultaneous analysis of tramadol, dextromethorphan chlorpheniramine and their major metabolites in human plasma in forensic context: application to pharmacokinetics'.
Biomedical chromatography : BMC.
2016 Apr; 30(4):663-4. doi:
10.1002/bmc.3603. [PMID: 26332009] - Wei-Hsian Yin, Pei Chen, Hung-I Yeh, Kuo-Yang Wang, Yi-Jen Hung, Wei-Kung Tseng, Ming-Shien Wen, Tao-Cheng Wu, Chau-Chung Wu, Shu-Meng Cheng, Jaw-Wen Chen. Combination With Low-dose Dextromethorphan Improves the Effect of Amlodipine Monotherapy in Clinical Hypertension: A First-in-human, Concept-proven, Prospective, Dose-escalation, Multicenter Study.
Medicine.
2016 Mar; 95(12):e3234. doi:
10.1097/md.0000000000003234. [PMID: 27015224] - Ole Kristian Thu, Olav Spigset, Odd Georg Nilsen, Bent Hellum. Effect of commercial Rhodiola rosea on CYP enzyme activity in humans.
European journal of clinical pharmacology.
2016 Mar; 72(3):295-300. doi:
10.1007/s00228-015-1988-7. [PMID: 26613955] - Kendra J Bjoraker, Michael A Swanson, Curtis R Coughlin, John Christodoulou, Ee S Tan, Mark Fergeson, Sarah Dyack, Ayesha Ahmad, Marisa W Friederich, Elaine B Spector, Geralyn Creadon-Swindell, M Antoinette Hodge, Sommer Gaughan, Casey Burns, Johan L K Van Hove. Neurodevelopmental Outcome and Treatment Efficacy of Benzoate and Dextromethorphan in Siblings with Attenuated Nonketotic Hyperglycinemia.
The Journal of pediatrics.
2016 Mar; 170(?):234-9. doi:
10.1016/j.jpeds.2015.12.027. [PMID: 26749113] - Fernando de Andrés, Santiago Terán, Marcela Bovera, Humberto Fariñas, Enrique Terán, Adrián LLerena. Multiplex Phenotyping for Systems Medicine: A One-Point Optimized Practical Sampling Strategy for Simultaneous Estimation of CYP1A2, CYP2C9, CYP2C19, and CYP2D6 Activities Using a Cocktail Approach.
Omics : a journal of integrative biology.
2016 Feb; 20(2):88-96. doi:
10.1089/omi.2015.0131. [PMID: 26600202] - Hiromi Soraoka, Kentaro Oniki, Kazuki Matsuda, Tatsumasa Ono, Kosuke Taharazako, Yoshihiro Uchiyashiki, Ryoko Kamihashi, Ayana Kita, Ayaka Takashima, Kazuko Nakagawa, Norio Yasui-Furukori, Daisuke Kadowaki, Keishi Miyata, Junji Saruwatari. The Effect of Yokukansan, a Traditional Herbal Preparation Used for the Behavioral and Psychological Symptoms of Dementia, on the Drug-Metabolizing Enzyme Activities in Healthy Male Volunteers.
Biological & pharmaceutical bulletin.
2016; 39(9):1468-74. doi:
10.1248/bpb.b16-00248. [PMID: 27582327] - J Marquard, A Stirban, F Schliess, F Sievers, A Welters, S Otter, A Fischer, S Wnendt, T Meissner, T Heise, E Lammert. Effects of dextromethorphan as add-on to sitagliptin on blood glucose and serum insulin concentrations in individuals with type 2 diabetes mellitus: a randomized, placebo-controlled, double-blinded, multiple crossover, single-dose clinical trial.
Diabetes, obesity & metabolism.
2016 Jan; 18(1):100-3. doi:
10.1111/dom.12576. [PMID: 26362564] - F L Opdam, A S Modak, S P Mooijaart, M Louwerens, M W M de Waal, H Gelderblom, H-J Guchelaar. CYP2D6 Metabolism in Frail Elderly Compared to Non-Frail Elderly: A Pilot Feasibility Study.
Drugs & aging.
2015 Dec; 32(12):1019-27. doi:
10.1007/s40266-015-0319-0. [PMID: 26597400] - Worku Bedada, Fernando de Andrés, Ephrem Engidawork, Anton Pohanka, Olof Beck, Leif Bertilsson, Adrián Llerena, Eleni Aklillu. The Psychostimulant Khat (Catha edulis) Inhibits CYP2D6 Enzyme Activity in Humans.
Journal of clinical psychopharmacology.
2015 Dec; 35(6):694-9. doi:
10.1097/jcp.0000000000000413. [PMID: 26444948] - Pao-Pao Yang, Geng-Chang Yeh, Eagle Yi-Kung Huang, Ping-Yee Law, Horace H Loh, Pao-Luh Tao. Effects of dextromethorphan and oxycodone on treatment of neuropathic pain in mice.
Journal of biomedical science.
2015 Sep; 22(?):81. doi:
10.1186/s12929-015-0186-3. [PMID: 26391752] - Eman H El-Naby, Ayman H Kamel. Potential transducers based man-tailored biomimetic sensors for selective recognition of dextromethorphan as an antitussive drug.
Materials science & engineering. C, Materials for biological applications.
2015 Sep; 54(?):217-24. doi:
10.1016/j.msec.2015.05.044. [PMID: 26046285] - Naomi Finn, John Wolf, June Louie, Bing Su. High concentrations of dextromethorphan result in false-positive in opiate immunoassay test.
Clinica chimica acta; international journal of clinical chemistry.
2015 Aug; 448(?):247. doi:
10.1016/j.cca.2015.07.015. [PMID: 26192219] - Hala M Heneedak, Ismail Salama, Samia Mostafa, Ehab El-Kady, Mohamed El-Sadek. Development and validation of a sensitive UHPLC-MS/MS method for the simultaneous analysis of tramadol, dextromethorphan chlorpheniramine and their major metabolites in human plasma in forensic context: application to pharmacokinetics.
Biomedical chromatography : BMC.
2015 Jul; 29(7):998-1007. doi:
10.1002/bmc.3384. [PMID: 25417559] - James Ermer, Mary Corcoran, Patrick Martin. Lisdexamfetamine Dimesylate Effects on the Pharmacokinetics of Cytochrome P450 Substrates in Healthy Adults in an Open-Label, Randomized, Crossover Study.
Drugs in R&D.
2015 Jun; 15(2):175-85. doi:
10.1007/s40268-015-0090-z. [PMID: 25862215] - Jianguo Sun, Ying Peng, Hui Wu, Xueyuan Zhang, Yunxi Zhong, Yanan Xiao, Fengyi Zhang, Huanhuan Qi, Lili Shang, Jianping Zhu, Yue Sun, Ke Liu, Jinghan Liu, Jiye A, Rodney J Y Ho, Guangji Wang. Guanfu base A, an antiarrhythmic alkaloid of Aconitum coreanum, Is a CYP2D6 inhibitor of human, monkey, and dog isoforms.
Drug metabolism and disposition: the biological fate of chemicals.
2015 May; 43(5):713-24. doi:
10.1124/dmd.114.060905. [PMID: 25681130] - Fahad Ibrahim Al-Jenoobi, Areej A Al-Thukair, Mohd Aftab Alam, Fawkeya A Abbas, Abdullah M Al-Mohizea, Khalid M Alkharfy, Saleh A Al-Suwayeh. Effect of Curcuma longa on CYP2D6- and CYP3A4-mediated metabolism of dextromethorphan in human liver microsomes and healthy human subjects.
European journal of drug metabolism and pharmacokinetics.
2015 Mar; 40(1):61-6. doi:
10.1007/s13318-014-0180-2. [PMID: 24510399] - Yu-xin Zang, Bing-ting Sun, Wen-zhu Zhao, Na Rong, Guo-liang Dai, Wen-zheng Ju, Heng-shan Tan. [Study of change in activity of hepatic drug metabolism enzymes in rat model of chronic unpredictable mild stress].
Yao xue xue bao = Acta pharmaceutica Sinica.
2015 Mar; 50(3):319-25. doi:
. [PMID: 26118111] - Sheng-Yu Lee, Shiou-Lan Chen, Yun-Hsuan Chang, Chun-Hsien Chu, Shih-Heng Chen, Po See Chen, San-Yuan Huang, Nian-Sheng Tzeng, Liang-Jen Wang, I Hui Lee, Tzu-Yun Wang, Kao Chin Chen, Yen Kuang Yang, Jau-Shyong Hong, Ru-Band Lu. A placebo-controlled trial of dextromethorphan as an adjunct in opioid-dependent patients undergoing methadone maintenance treatment.
The international journal of neuropsychopharmacology.
2015 Feb; 18(7):pyv008. doi:
10.1093/ijnp/pyv008. [PMID: 25716777] - Jessica L Knittel, Shawn P Vorce, Barry Levine, Rhome L Hughes, Thomas Z Bosy. Multidrug toxicity involving sumatriptan.
Journal of analytical toxicology.
2015 Jan; 39(1):75-9. doi:
10.1093/jat/bku120. [PMID: 25324526] - Satomi Shida, Masahiro Utoh, Norie Murayama, Makiko Shimizu, Yasuhiro Uno, Hiroshi Yamazaki. Human plasma concentrations of cytochrome P450 probes extrapolated from pharmacokinetics in cynomolgus monkeys using physiologically based pharmacokinetic modeling.
Xenobiotica; the fate of foreign compounds in biological systems.
2015; 45(10):881-6. doi:
10.3109/00498254.2015.1028511. [PMID: 26075833] - Lily P H Yang, Emma D Deeks. Dextromethorphan/quinidine: a review of its use in adults with pseudobulbar affect.
Drugs.
2015 Jan; 75(1):83-90. doi:
10.1007/s40265-014-0328-z. [PMID: 25420446] - Bogna Badyra, Bartosz Lisowski, Sebastian Polak, John Kudolo, Barbara Wiśniowska. How in vitro influences in silico utilized for the prediction of in vivo - pilot study of the drug-induced pro-arrhythmic potency prediction.
Folia medica Cracoviensia.
2015; 55(4):5-19. doi:
. [PMID: 26867116] - Fahad I Al-Jenoobi, Areej A Al-Thukair, Mohd Aftab Alam, Fawkeya A Abbas, Abdullah M Al-Mohizea, Khalid M Alkharfy, Saleh A Al-Suwayeh. Effect of Trigonella foenum-graecum L. on Metabolic Activity of CYP2D6 and CYP3A4.
Forschende Komplementarmedizin (2006).
2015; 22(3):180-4. doi:
10.1159/000432412. [PMID: 26335391] - Jessica Tay-Sontheimer, Laura M Shireman, Richard P Beyer, Taurence Senn, Daniela Witten, Robin E Pearce, Andrea Gaedigk, Cletus L Gana Fomban, Justin D Lutz, Nina Isoherranen, Kenneth E Thummel, Oliver Fiehn, J Steven Leeder, Yvonne S Lin. Detection of an endogenous urinary biomarker associated with CYP2D6 activity using global metabolomics.
Pharmacogenomics.
2014 Dec; 15(16):1947-62. doi:
10.2217/pgs.14.155. [PMID: 25521354] - Shoaib Faruqi, Caroline Wright, Rachel Thompson, Alyn H Morice. A randomized placebo controlled trial to evaluate the effects of butamirate and dextromethorphan on capsaicin induced cough in healthy volunteers.
British journal of clinical pharmacology.
2014 Dec; 78(6):1272-80. doi:
10.1111/bcp.12458. [PMID: 24995954] - Shiou-Lan Chen, Sheng-Yu Lee, Yun-Hsuan Chang, Po-See Chen, I-Hui Lee, Tzu-Yun Wang, Kao-Ching Chen, Yen-Kuang Yang, Jau-Shyong Hong, Ru-Band Lu. Therapeutic effects of add-on low-dose dextromethorphan plus valproic acid in bipolar disorder.
European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology.
2014 Nov; 24(11):1753-9. doi:
10.1016/j.euroneuro.2014.09.001. [PMID: 25262178] - Marina Kawaguchi-Suzuki, Reginald F Frye, Hao-Jie Zhu, Bryan J Brinda, Kenneth D Chavin, Hilary J Bernstein, John S Markowitz. The effects of milk thistle (Silybum marianum) on human cytochrome P450 activity.
Drug metabolism and disposition: the biological fate of chemicals.
2014 Oct; 42(10):1611-6. doi:
10.1124/dmd.114.057232. [PMID: 25028567] - Junji Saruwatari, Ayaka Takashima, Kousuke Yoshida, Hiromi Soraoka, Tong-Bin Ding, Yoshihiro Uchiyashiki, Yoshiyuki Tsuda, Motoki Imamura, Kentaro Oniki, Keishi Miyata, Kazuko Nakagawa. Effects of Seijo-bofu-to, a traditional Japanese herbal medicine containing furanocoumarin derivatives, on the drug-metabolizing enzyme activities in healthy male volunteers.
Basic & clinical pharmacology & toxicology.
2014 Oct; 115(4):360-5. doi:
10.1111/bcpt.12224. [PMID: 24612940] - Marek Smoluch, Przemyslaw Mielczarek, Edward Reszke, Gary M Hieftje, Jerzy Silberring. Determination of psychostimulants and their metabolites by electrochemistry linked on-line to flowing atmospheric pressure afterglow mass spectrometry.
The Analyst.
2014 Sep; 139(17):4350-5. doi:
10.1039/c3an02067c. [PMID: 25010982] - Ben D Snyder, Andrew Rowland, Thomas M Polasek, John O Miners, Matthew P Doogue. Evaluation of felodipine as a potential perpetrator of pharmacokinetic drug-drug interactions.
European journal of clinical pharmacology.
2014 Sep; 70(9):1115-22. doi:
10.1007/s00228-014-1716-8. [PMID: 25028073] - Rüdiger Kaspera, Brian J Kirby, Tariku Sahele, Ann C Collier, Evan D Kharasch, Jashvant D Unadkat, Rheem A Totah. Investigating the contribution of CYP2J2 to ritonavir metabolism in vitro and in vivo.
Biochemical pharmacology.
2014 Sep; 91(1):109-18. doi:
10.1016/j.bcp.2014.06.020. [PMID: 24973543] - M Bosilkovska, C F Samer, J Déglon, M Rebsamen, C Staub, P Dayer, B Walder, J A Desmeules, Y Daali. Geneva cocktail for cytochrome p450 and P-glycoprotein activity assessment using dried blood spots.
Clinical pharmacology and therapeutics.
2014 Sep; 96(3):349-59. doi:
10.1038/clpt.2014.83. [PMID: 24722393] - Evan Small, Benjamin J Sandefur. Acute renal failure after ingestion of guaifenesin and dextromethorphan.
The Journal of emergency medicine.
2014 Jul; 47(1):26-9. doi:
10.1016/j.jemermed.2014.01.022. [PMID: 24630853] - Maryam Afshar, Daniel Birnbaum, Carla Golden. Review of dextromethorphan administration in 18 patients with subacute methotrexate central nervous system toxicity.
Pediatric neurology.
2014 Jun; 50(6):625-9. doi:
10.1016/j.pediatrneurol.2014.01.048. [PMID: 24742799] - Nithya J Gogtay, Nitin B Mali, Krishna Iyer, Prashant P Kadam, Kannan Sridharan, Divya Shrimal, Urmila M Thatte. Evaluation of cytochrome P450 2D6 phenotyping in healthy adult Western Indians.
Indian journal of pharmacology.
2014 May; 46(3):266-9. doi:
10.4103/0253-7613.132154. [PMID: 24987171] - Shinya Uchida, Shimako Tanaka, Noriyuki Namiki. Simultaneous and comprehensive in vivo analysis of cytochrome P450 activity by using a cocktail approach in rats.
Biopharmaceutics & drug disposition.
2014 May; 35(4):228-36. doi:
10.1002/bdd.1888. [PMID: 24395703] - Ying Ding, Kai Huang, Lan Chen, Jie Yang, Wen-Yan Xu, Xue-Jiao Xu, Ru Duan, Jing Zhang, Qing He. Simultaneous quantitative analysis of dextromethorphan, dextrorphan and chlorphenamine in human plasma by liquid chromatography-electrospray tandem mass spectrometry.
Biomedical chromatography : BMC.
2014 Mar; 28(3):446-52. doi:
10.1002/bmc.3054. [PMID: 24254834]