Sibutramine (BioDeep_00000003176)
Secondary id: BioDeep_00000406021
human metabolite blood metabolite Chemicals and Drugs
代谢物信息卡片
化学式: C17H26ClN (279.1753666)
中文名称: 盐酸西布曲明, 西布曲明
谱图信息:
最多检出来源 Homo sapiens(blood) 0.55%
分子结构信息
SMILES: CC(C)CC(C1(CCC1)c1ccc(cc1)Cl)N(C)C
InChI: InChI=1S/C17H26ClN/c1-13(2)12-16(19(3)4)17(10-5-11-17)14-6-8-15(18)9-7-14/h6-9,13,16H,5,10-12H2,1-4H3
描述信息
Sibutramine (trade name Meridia in the USA, Reductil in Europe and other countries), usually as sibutramide hydrochloride monohydrate, is an orally administered agent for the treatment of obesity. It is a centrally acting stimulant chemically related to amphetamines. Sibutramine is classified as a Schedule IV controlled substance in the United States. In October 2010, Sibutramine was withdrawn from Canadian and U.S. markets due to concerns that the drug increases the risk of heart attack and stroke in patients with a history of heart disease.
A - Alimentary tract and metabolism > A08 - Antiobesity preparations, excl. diet products > A08A - Antiobesity preparations, excl. diet products > A08AA - Centrally acting antiobesity products
D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D000928 - Antidepressive Agents
D019440 - Anti-Obesity Agents > D001067 - Appetite Depressants
C78272 - Agent Affecting Nervous System > C29728 - Anorexiant
同义名列表
数据库引用编号
16 个数据库交叉引用编号
- ChEBI: CHEBI:9137
- KEGG: C07247
- KEGGdrug: D08513
- PubChem: 5210
- HMDB: HMDB0015237
- Metlin: METLIN44427
- DrugBank: DB01105
- ChEMBL: CHEMBL1419
- Wikipedia: Sibutramine
- chemspider: 5021
- CAS: 106650-56-0
- CAS: 84485-00-7
- PMhub: MS000008396
- PubChem: 9456
- NIKKAJI: J247.963J
- RefMet: Sibutramine
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
- Paola Dos Santos da Rocha, Sarah Lam Orué, Daniel Ferreira Leite, Priscilla Pereira de Toledo Espindola, Nadla Soares Cassemiro, Denise Brentan da Silva, Carlos Alexandre Carollo, Valéria Nunes-Souza, Luiza Antas Rabelo, Jaqueline Ferreira Campos, Letícia Miranda Fernandes Estevinho, Edson Lucas Dos Santos, Kely de Picoli Souza. Beneficial Effects of Bauhinia rufa Leaves on Oxidative Stress, Prevention, and Treatment of Obesity in High-Fat Diet-Fed C57BL/6 Mice.
Oxidative medicine and cellular longevity.
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Cell reports.
2021 04; 35(4):109040. doi:
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Voprosy pitaniia.
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Ultrastructural pathology.
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Clinica chimica acta; international journal of clinical chemistry.
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Hormones (Athens, Greece).
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Minerva endocrinologica.
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"
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Journal of cardiovascular electrophysiology.
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Microscopy research and technique.
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Xenobiotica; the fate of foreign compounds in biological systems.
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Bratislavske lekarske listy.
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Biological trace element research.
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Diabetes, obesity & metabolism.
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Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment.
2010 Jul; 27(7):903-16. doi:
10.1080/19440041003705821
. [PMID: 20437283] - Henrik H Hansen, Gitte Hansen, Mads Tang-Christensen, Philip J Larsen, Anne Marie D Axel, Anne Raben, Jens D Mikkelsen. The novel triple monoamine reuptake inhibitor tesofensine induces sustained weight loss and improves glycemic control in the diet-induced obese rat: comparison to sibutramine and rimonabant.
European journal of pharmacology.
2010 Jun; 636(1-3):88-95. doi:
10.1016/j.ejphar.2010.03.026
. [PMID: 20385125] - Sefa Saraç, Fulden Saraç. Cardiac valve evaluation and adipokine levels in obese women treated with sibutramine.
Anadolu kardiyoloji dergisi : AKD = the Anatolian journal of cardiology.
2010 Jun; 10(3):226-32. doi:
10.5152/akd.2010.062
. [PMID: 20538557] - Stergios A Polyzos, Jannis Kountouras, Christos Zavos, Eleni Tsiaousi. The role of adiponectin in the pathogenesis and treatment of non-alcoholic fatty liver disease.
Diabetes, obesity & metabolism.
2010 May; 12(5):365-83. doi:
10.1111/j.1463-1326.2009.01176.x
. [PMID: 20415685] - Janine Pöss, M Böhm, A Link. [32-year-old patient with acute myocardial infarction possibly induced by the appetite suppressant sibutramine].
Deutsche medizinische Wochenschrift (1946).
2010 May; 135(19):965-8. doi:
10.1055/s-0030-1253684
. [PMID: 20446231] - Célio L de Melo, Maria Goretti R Queiroz, Said G C Fonseca, Ayla M C Bizerra, Telma L G Lemos, Tiago S Melo, Flavia A Santos, Vietla S Rao. Oleanolic acid, a natural triterpenoid improves blood glucose tolerance in normal mice and ameliorates visceral obesity in mice fed a high-fat diet.
Chemico-biological interactions.
2010 Apr; 185(1):59-65. doi:
10.1016/j.cbi.2010.02.028
. [PMID: 20188082] - M Reiser, S Eickmann, T Haverkamp, U Finckh. Variegate porphyria in a 46-year-old patient taking sibutramine for weight loss.
Obesity reviews : an official journal of the International Association for the Study of Obesity.
2010 Apr; 11(4):329-31. doi:
10.1111/j.1467-789x.2009.00670.x
. [PMID: 19845869] - D Taner Ertugrul, B Yavuz, K Okhan Akin, A Arif Yalcin, N Ata, M Kucukazman, B Algul, K Dal, O Sinan Deveci, E Tutal. An obesity drug sibutramine reduces brain natriuretic peptide (BNP) levels in severely obese patients.
International journal of clinical practice.
2010 Mar; 64(4):518-22. doi:
10.1111/j.1742-1241.2009.02197.x
. [PMID: 20456197] - Peter S Talbot, Stefan Bradley, Cyril P Clarke, Kola O Babalola, Andrew W Philipp, Gavin Brown, Adam W McMahon, Julian C Matthews. Brain serotonin transporter occupancy by oral sibutramine dosed to steady state: a PET study using (11)C-DASB in healthy humans.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology.
2010 Feb; 35(3):741-51. doi:
10.1038/npp.2009.182
. [PMID: 19890256] - Keumhan Noh, Kyoungjin Bae, Bokyoung Min, Eunyoung Kim, Kwang-il Kwon, Taecheon Jeong, Wonku Kang. Enantioselective pharmacokinetics of sibutramine in rat.
Archives of pharmacal research.
2010 Feb; 33(2):267-73. doi:
10.1007/s12272-010-0212-7
. [PMID: 20195828] - Wonku Kang, Kyoungjin Bae, Keumhan Noh. Enantioselective determination of sibutramine and its active metabolites in human plasma.
Journal of pharmaceutical and biomedical analysis.
2010 Jan; 51(1):264-7. doi:
10.1016/j.jpba.2009.07.023
. [PMID: 19683887] - Giuseppe Derosa, Pamela Maffioli, Sibilla A T Salvadeo, Ilaria Ferrari, Alessia Gravina, Roberto Mereu, Angela D'Angelo, Ilaria Palumbo, Sabrina Randazzo, Arrigo F G Cicero. Sibutramine and L-carnitine compared to sibutramine alone on insulin resistance in diabetic patients.
Internal medicine (Tokyo, Japan).
2010; 49(16):1717-25. doi:
10.2169/internalmedicine.49.3401
. [PMID: 20720348] - Giuseppe Derosa, Pamela Maffioli, Ilaria Ferrari, Ilaria Palumbo, Sabrina Randazzo, Angela D'Angelo, Arrigo F G Cicero. Effects of one year treatment of sibutramine on insulin resistance parameters in type 2 diabetic patients.
Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques.
2010; 13(3):378-90. doi:
10.18433/j3388p
. [PMID: 21092710] - Dong Xun Li, Ki-Young Jang, Wonku Kang, Kyoungjin Bae, Mann Hyung Lee, Yu-Kyoung Oh, Jun-Pil Jee, Young-Joon Park, Dong Hoon Oh, Youn Gee Seo, Young Ran Kim, Jong Oh Kim, Jong Soo Woo, Chul Soon Yong, Han-Gon Choi. Enhanced solubility and bioavailability of sibutramine base by solid dispersion system with aqueous medium.
Biological & pharmaceutical bulletin.
2010; 33(2):279-84. doi:
10.1248/bpb.33.279
. [PMID: 20118553] - Iu Iu Vlasova, A S Ametov. [Effect of sibutramine (meridia) on body composition, peptide YY3-36 and serotonin levels in patients with exogenous constitutional obesity].
Terapevticheskii arkhiv.
2010; 82(8):44-7. doi:
NULL
. [PMID: 20873245] - K A Kim, W K Song, J Y Park. Association of CYP2B6, CYP3A5, and CYP2C19 genetic polymorphisms with sibutramine pharmacokinetics in healthy Korean subjects.
Clinical pharmacology and therapeutics.
2009 Nov; 86(5):511-8. doi:
10.1038/clpt.2009.145
. [PMID: 19693007] - A C Franco Spínola, S Almeida, A Filipe, R Neves, Z Abolfathi, M Yritia, D Anctil. Comparative bioavailability of two formulations of sibutramine.
International journal of clinical pharmacology and therapeutics.
2009 Oct; 47(10):627-37. doi:
10.5414/cpp47627
. [PMID: 19825326] - V F Sardela, M T R Motta, M C Padilha, H M G Pereira, F R Aquino Neto. Analysis of sibutramine metabolites as N-trifluoroacetamide and O-trimethylsilyl derivatives by gas chromatography-mass spectrometry in urine.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2009 Oct; 877(27):3003-11. doi:
10.1016/j.jchromb.2009.07.013
. [PMID: 19660994] - Kyoungjin Bae, Kyeumhan Noh, Kiyoung Jang, Sohee Kim, Chul Soon Yong, Han-Gon Choi, Jong Seong Kang, Jianbo Chen, Eunsook Ma, Manhyung Lee, Beom Soo Shin, Kwang-Il Kwon, Wonku Kang. Analysis of enantiomers of sibutramine and its metabolites in rat plasma by liquid chromatography-mass spectrometry using a chiral stationary-phase column.
Journal of pharmaceutical and biomedical analysis.
2009 Sep; 50(2):267-70. doi:
10.1016/j.jpba.2009.04.024
. [PMID: 19473801] - Carlo Cifani, Alessandro Zanoncelli, Michela Tessari, Claudio Righetti, Carla Di Francesco, Roberto Ciccocioppo, Maurizio Massi, Sergio Melotto. Pre-exposure to environmental cues predictive of food availability elicits hypothalamic-pituitary-adrenal axis activation and increases operant responding for food in female rats.
Addiction biology.
2009 Sep; 14(4):397-407. doi:
10.1111/j.1369-1600.2009.00152.x
. [PMID: 19413564] - Fábio Bucaretchi, Eduardo Mello de Capitani, Sueli Moreira Mello, Rafael Lanaro, Roberta F Barros, Luciane C R Fernandes, José Luiz da Costa, Stephen Hyslop. Serotonin syndrome following sibutramine poisoning in a child, with sequential quantification of sibutramine and its primary and secondary amine metabolites in plasma.
Clinical toxicology (Philadelphia, Pa.).
2009 Jul; 47(6):598-601. doi:
10.1080/15563650903018603
. [PMID: 19586360] - D C Guzmán, N L Ruíz, E H García, G B Mejía, P P Téllez, G E Jimenez, M De la Rosa Apreza, H J Olguín. Effect of sibutramine on Na+, K+ ATPase activity and tryptophan levels on male and female rat brain.
Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme.
2009 May; 41(5):363-7. doi:
10.1055/s-0028-1128145
. [PMID: 19194834] - Th Stroubini, A Perelas, C Liapi, D Perrea, I Dontas, Ch Tzavara, P Galanopoulou. Serum adiponectin and resistin in rats under three isocaloric diets: The effect of sibutramine.
Cytokine.
2009 May; 46(2):171-5. doi:
10.1016/j.cyto.2009.01.003
. [PMID: 19251435] - Kwang-Seok Oh, Shi Yong Ryu, Sunghou Lee, Ho Won Seo, Byung Koo Oh, Young Sup Kim, Byung Ho Lee. Melanin-concentrating hormone-1 receptor antagonism and anti-obesity effects of ethanolic extract from Morus alba leaves in diet-induced obese mice.
Journal of ethnopharmacology.
2009 Mar; 122(2):216-20. doi:
10.1016/j.jep.2009.01.020
. [PMID: 19330910] - Dieter Müller, Wolfgang Weinmann, Maren Hermanns-Clausen. Chinese slimming capsules containing sibutramine sold over the Internet: a case series.
Deutsches Arzteblatt international.
2009 Mar; 106(13):218-22. doi:
10.3238/arztebl.2009.0218
. [PMID: 19471631] - Andres G Digenio, James P Mancuso, Robert A Gerber, Roman V Dvorak. Comparison of methods for delivering a lifestyle modification program for obese patients: a randomized trial.
Annals of internal medicine.
2009 Feb; 150(4):255-62. doi:
10.7326/0003-4819-150-4-200902170-00006
. [PMID: 19221377] - Konstantinos Tziomalos, Gerasimos E Krassas, Themistoklis Tzotzas. The use of sibutramine in the management of obesity and related disorders: an update.
Vascular health and risk management.
2009; 5(1):441-52. doi:
10.2147/vhrm.s4027
. [PMID: 19475780] - Giuseppe Derosa, Roberto Mereu, Sibilla A T Salvadeo, Angela D'Angelo, Leonardina Ciccarelli, Mario N Piccinni, Ilaria Ferrari, Alessia Gravina, Pamela Maffioli, Arrigo F G Cicero. Pioglitazone metabolic effect in metformin-intolerant obese patients treated with sibutramine.
Internal medicine (Tokyo, Japan).
2009; 48(5):265-71. doi:
10.2169/internalmedicine.48.1670
. [PMID: 19252346] - Antonio José Magaldi, Antonio Carlos Seguro. A possible mechanism for severe symptomatic hyponatremia during sibutramine therapy.
American journal of kidney diseases : the official journal of the National Kidney Foundation.
2008 Dec; 52(6):1197-8; author reply 1198. doi:
10.1053/j.ajkd.2008.07.046
. [PMID: 19026358] - Giuseppe Derosa, Angela D'Angelo, Sibilla A T Salvadeo, Ilaria Ferrari, Alessia Gravina, Elena Fogari, Pamela Maffioli, Arrigo F G Cicero. Sibutramine effect on metabolic control of obese patients with type 2 diabetes mellitus treated with pioglitazone.
Metabolism: clinical and experimental.
2008 Nov; 57(11):1552-7. doi:
10.1016/j.metabol.2008.06.010
. [PMID: 18940393] - Kin-Ming Anfernee Yim, Hon Wah Ng, Chi-Kin Chan, Gabriel Yip, Fei Lung Lau. Sibutramine-induced acute myocardial infarction in a young lady.
Clinical toxicology (Philadelphia, Pa.).
2008 Nov; 46(9):877-9. doi:
10.1080/15563650802136258
. [PMID: 18788006] - April B M Grudell, Seth Sweetser, Michael Camilleri, Deborah J Eckert, Maria I Vazquez-Roque, Paula J Carlson, Duane D Burton, Autumn E Braddock, Matthew M Clark, Karen M Graszer, Sarah A Kalsy, Alan R Zinsmeister. A controlled pharmacogenetic trial of sibutramine on weight loss and body composition in obese or overweight adults.
Gastroenterology.
2008 Oct; 135(4):1142-54. doi:
10.1053/j.gastro.2008.07.009
. [PMID: 18725220] - Ji-Won Lee, Hye-Ree Lee, Jae-Yong Shim, Jee-Aee Im, Duk-Chul Lee. Abdominal visceral fat reduction is associated with favorable changes of serum retinol binding protein-4 in nondiabetic subjects.
Endocrine journal.
2008 Oct; 55(5):811-8. doi:
10.1507/endocrj.k08e-030
. [PMID: 18493106] - Theodora Stroubini, Despoina Perrea, Apostolos Perelas, Charis Liapi, Ismini Dontas, Maria Trapali, Nikolaos Katsilambros, Panagiota Galanopoulou. Effect of sibutramine on regional fat pads and leptin levels in rats fed with three isocaloric diets.
European cytokine network.
2008 Sep; 19(3):149-55. doi:
10.1684/ecn.2008.0130
. [PMID: 18775804] - So Young Um, Kyu-Bong Kim, Seon Hwa Kim, Young Cheol Ju, Hye Sang Lee, Hye young Oh, Ki Hwan Choi, Myeon Woo Chung. Determination of the active metabolites of sibutramine in rat serum using column-switching HPLC.
Journal of separation science.
2008 Aug; 31(15):2820-6. doi:
10.1002/jssc.200800041
. [PMID: 18666167] - E Nakou, T D Filippatos, E N Liberopoulos, A D Tselepis, D N Kiortsis, D P Mikhailidis, M S Elisaf. Effects of sibutramine plus verapamil sustained release/trandolapril combination on blood pressure and metabolic variables in obese hypertensive patients.
Expert opinion on pharmacotherapy.
2008 Jul; 9(10):1629-39. doi:
10.1517/14656566.9.10.1629
. [PMID: 18570597] - Satoshi Mashiko, Akane Ishihara, Hisashi Iwaasa, Ryuichi Moriya, Hidefumi Kitazawa, Yuko Mitobe, Junko Ito, Akira Gomori, Hiroko Matsushita, Toshiyuki Takahashi, Douglas J MacNeil, Lex H T Van der Ploeg, Takehiro Fukami, Akio Kanatani. Effects of a novel Y5 antagonist in obese mice: combination with food restriction or sibutramine.
Obesity (Silver Spring, Md.).
2008 Jul; 16(7):1510-5. doi:
10.1038/oby.2008.223
. [PMID: 18421274] - Pasquale Esposito, Teresa Rampino, Marilena Gregorini, Grazia Soccio, Giovanni Piotti, Giulia Bedino, Chiara Teresa Balenzano, Elisabetta Roscini, Laura Cosmai, Valentina Portalupi, Carmelo Libetta, Antonio Dal Canton. Severe symptomatic hyponatremia during sibutramine therapy: a case report.
American journal of kidney diseases : the official journal of the National Kidney Foundation.
2008 Jul; 52(1):137-9. doi:
10.1053/j.ajkd.2008.02.361
. [PMID: 18487000] - Edoardo Mannucci, Ilaria Dicembrini, Francesco Rotella, Carlo Maria Rotella. Orlistat and sibutramine beyond weight loss.
Nutrition, metabolism, and cardiovascular diseases : NMCD.
2008 Jun; 18(5):342-8. doi:
10.1016/j.numecd.2007.03.010
. [PMID: 17928208] - Didier Quilliot, Philip Böhme, Faiez Zannad, Olivier Ziegler. Sympathetic-leptin relationship in obesity: effect of weight loss.
Metabolism: clinical and experimental.
2008 Apr; 57(4):555-62. doi:
10.1016/j.metabol.2007.11.020
. [PMID: 18328360] - Ulrich H Frey, Hans Hauner, Karl-Heinz Jöckel, Iris Manthey, Norbert Brockmeyer, Winfried Siffert. A novel promoter polymorphism in the human gene GNAS affects binding of transcription factor upstream stimulatory factor 1, Galphas protein expression and body weight regulation.
Pharmacogenetics and genomics.
2008 Feb; 18(2):141-51. doi:
10.1097/fpc.0b013e3282f49964
. [PMID: 18192900] - M Trapali, C Liapi, A Perelas, D Perrea, T Stroubini, I Dontas, E Couvari, M Mavri, P Galanopoulou. Effect of isocaloric diets and sibutramine on food intake, body mass variation and serum TNF-alpha levels in rats.
Pharmacology.
2008; 82(1):15-21. doi:
10.1159/000127363
. [PMID: 18434760] - Rui Huang, Zhi-Ning Xia, Ping Gong. [Study on the interaction of serum albumin and micromolecule compounds by modified fluorescence spectra].
Guang pu xue yu guang pu fen xi = Guang pu.
2008 Jan; 28(1):161-4. doi:
NULL
. [PMID: 18422143]