Nateglinide (BioDeep_00000002471)
human metabolite blood metabolite
代谢物信息卡片
(2R)-3-phenyl-2-[(4-propan-2-ylcyclohexanecarbonyl)amino]propanoic acid
化学式: C19H27NO3 (317.1991)
中文名称: 那格列奈
谱图信息:
最多检出来源 Mentha canadensis(plant) 62.07%
分子结构信息
SMILES: CC(C)C1CCC(C(=O)NC(Cc2ccccc2)C(=O)O)CC1
InChI: InChI=1S/C19H27NO3/c1-13(2)15-8-10-16(11-9-15)18(21)20-17(19(22)23)12-14-6-4-3-5-7-14/h3-7,13,15-17H,8-12H2,1-2H3,(H,20,21)(H,22,23)/t15?,16-,17-/m1/s1
描述信息
Nateglinide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It belongs to the meglitinide class of short-acting insulin secretagogues, which act by binding to cells of the pancreas to stimulate insulin release. Nateglinide is an amino acid derivative that induces an early insulin response to meals decreasing postprandial blood glucose levels. It should only be taken with meals and meal-time doses should be skipped with any skipped meal. Approximately one month of therapy is required before a decrease in fasting blood glucose is seen. Meglitnides may have a neutral effect on weight or cause a slight increase in weight. The average weight gain caused by meglitinides appears to be lower than that caused by sulfonylureas and insulin and appears to occur only in those naive to oral antidiabetic agents. Due to their mechanism of action, meglitinides may cause hypoglycemia although the risk is thought to be lower than that of sulfonylureas since their action is dependent on the presence of glucose. In addition to reducing postprandial and fasting blood glucose, meglitnides have been shown to decrease glycosylated hemoglobin (HbA1c) levels, which are reflective of the last 8-10 weeks of glucose control. Meglitinides appear to be more effective at lowering postprandial blood glucose than metformin, sulfonylureas and thiazolidinediones. Nateglinide is extensively metabolized in the liver and excreted in urine (83\\%) and feces (10\\%). The major metabolites possess less activity than the parent compound. One minor metabolite, the isoprene, has the same potency as its parent compound.
C78276 - Agent Affecting Digestive System or Metabolism > C29711 - Anti-diabetic Agent > C98079 - Meglitinide Antidiabetic Agent
A - Alimentary tract and metabolism > A10 - Drugs used in diabetes > A10B - Blood glucose lowering drugs, excl. insulins
D007004 - Hypoglycemic Agents
同义名列表
数据库引用编号
20 个数据库交叉引用编号
- ChEBI: CHEBI:31897
- ChEBI: CHEBI:94617
- KEGG: C12508
- PubChem: 5311309
- PubChem: 4443
- HMDB: HMDB0014869
- Metlin: METLIN44419
- DrugBank: DB00731
- ChEMBL: CHEMBL2114389
- ChEMBL: CHEMBL783
- Wikipedia: Nateglinide
- MeSH: Nateglinide
- chemspider: 26329508
- CAS: 105746-37-0
- CAS: 105816-04-4
- CAS: 105816-06-6
- PMhub: MS000002748
- PubChem: 582898
- NIKKAJI: J259.863I
- KNApSAcK: 31897
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
- Koji Nishi, Ayana Yano, Kenji Tsukigawa, Victor Tg Chuang, Masaki Otagiri, Keishi Yamasaki. Effect of Fatty Acids and Uremic Toxins on the Binding of Nateglinide, an Insulin Secretagogue, to Site II on Human Serum Albumin.
Biological & pharmaceutical bulletin.
2022; 45(6):803-805. doi:
10.1248/bpb.b22-00116. [PMID: 35650107] - Tao Wang, Jin-Fang Song, Xue-Yan Zhou, Cheng-Lin Li, Xiao-Xing Yin, Qian Lu. PPARD rs2016520 (T/C) and NOS1AP rs12742393 (A/C) polymorphisms affect therapeutic efficacy of nateglinide in Chinese patients with type 2 diabetes mellitus.
BMC medical genomics.
2021 11; 14(1):267. doi:
10.1186/s12920-021-01108-5. [PMID: 34772419] - Susan T Ovbude, Pingyang Tao, Zhao Li, David S Hage. High-Performance affinity chromatographic studies of repaglinide and nateglinide interactions with normal and glyoxal- or methylglyoxal-modified human albumin serum.
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2021 Jul; 201(?):114097. doi:
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Journal of chromatographic science.
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10.1093/chromsci/bmaa096. [PMID: 33275653] - Ming Yu, Xiaobin Li, Hao Jin, Lu Chen, Nan Wang, Huawei Wang, Ying Cao, Xin Sui, Xue Gao, Hanyue Yang, Wenping Wang. Bioequivalence of a Generic Nateglinide Formulation in Healthy Chinese Volunteers under Fasting and Fed Conditions: A Randomized, Open-Label, Double-Cycle, Double-Crossover Study.
Pharmacology.
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10.1186/1758-5996-3-4. [PMID: 21450068] - Konstantinos Tziomalos, Vasilios G Athyros, Asterios Karagiannis, Dimitri P Mikhailidis. Dyslipidemia induced by drugs used for the prevention and treatment of vascular diseases.
The open cardiovascular medicine journal.
2011; 5(?):85-9. doi:
10.2174/1874192401105010085. [PMID: 21769302] - Tae Sasakabe, Hajime Haimoto, Hiroyuki Umegaki, Kenji Wakai. Effects of a moderate low-carbohydrate diet on preferential abdominal fat loss and cardiovascular risk factors in patients with type 2 diabetes.
Diabetes, metabolic syndrome and obesity : targets and therapy.
2011; 4(?):167-74. doi:
10.2147/dmso.s19635. [PMID: 21779148] - Zeinab A Issa, Mira S Zantout, Sami T Azar. Multiple myeloma and diabetes.
ISRN endocrinology.
2011; 2011(?):815013. doi:
10.5402/2011/815013. [PMID: 22363889] - Srinivas Maddi, Gerhard Scriba, Madhusudan Rao Yamsani. Stereoselective binding of chiral anti-diabetic drug nateglinide to plasma proteins.
Drug metabolism and drug interactions.
2011; 26(2):81-6. doi:
10.1515/dmdi.2011.004. [PMID: 21732706] - Karunanidhi S Lakshmi, Tirumala Rajesh. Separation and quantification of eight antidiabetic drugs on a high-performance liquid chromatography: its application to human plasma assay.
ISRN pharmaceutics.
2011; 2011(?):521353. doi:
10.5402/2011/521353. [PMID: 22389851] - S Yoshida, T Ohishi, T Matsui, H Tanaka, H Oshima, Y Yonetoku, M Shibasaki. The role of small molecule GPR119 agonist, AS1535907, in glucose-stimulated insulin secretion and pancreatic β-cell function.
Diabetes, obesity & metabolism.
2011 Jan; 13(1):34-41. doi:
10.1111/j.1463-1326.2010.01315.x. [PMID: 21114601] - Richard Kones. Primary prevention of coronary heart disease: integration of new data, evolving views, revised goals, and role of rosuvastatin in management. A comprehensive survey.
Drug design, development and therapy.
2011; 5(?):325-80. doi:
10.2147/dddt.s14934. [PMID: 21792295] - Youngmin Kim, Kyemyung Park, Wonku Kang. Effect of fluvastatin, lovastatin, nifedipine and verapamil on the systemic exposure of nateglinide in rabbits.
Biopharmaceutics & drug disposition.
2010 Nov; 31(8-9):443-9. doi:
10.1002/bdd.724. [PMID: 20809476] - A Ceriello. The glucose triad and its role in comprehensive glycaemic control: current status, future management.
International journal of clinical practice.
2010 Nov; 64(12):1705-11. doi:
10.1111/j.1742-1241.2010.02517.x. [PMID: 20860758] - Kristen Kulasa, Steven Edelman. Saxagliptin: the evidence for its place in the treatment of type 2 diabetes mellitus.
Core evidence.
2010 Oct; 5(?):23-37. doi:
10.2147/ce.s8006. [PMID: 21042540] - Annikka Kalliokoski, Pertti J Neuvonen, Mikko Niemi. SLCO1B1 polymorphism and oral antidiabetic drugs.
Basic & clinical pharmacology & toxicology.
2010 Oct; 107(4):775-81. doi:
10.1111/j.1742-7843.2010.00581.x. [PMID: 20406215] - Curtis Triplitt, Eugenio Cersosimo, Ralph A DeFronzo. Pioglitazone and alogliptin combination therapy in type 2 diabetes: a pathophysiologically sound treatment.
Vascular health and risk management.
2010 Sep; 6(?):671-90. doi:
10.2147/vhrm.s4852. [PMID: 20859539] - L Romayne Kurukulasuriya, James R Sowers. Therapies for type 2 diabetes: lowering HbA1c and associated cardiovascular risk factors.
Cardiovascular diabetology.
2010 Aug; 9(?):45. doi:
10.1186/1475-2840-9-45. [PMID: 20804556] - François Normand-Lauzière, Frédérique Frisch, Sébastien M Labbé, Patrick Bherer, René Gagnon, Stephen C Cunnane, André C Carpentier. Increased postprandial nonesterified fatty acid appearance and oxidation in type 2 diabetes is not fully established in offspring of diabetic subjects.
PloS one.
2010 Jun; 5(6):e10956. doi:
10.1371/journal.pone.0010956. [PMID: 20532041] - S S Engel, D E Williams-Herman, G T Golm, R J Clay, S V Machotka, K D Kaufman, B J Goldstein. Sitagliptin: review of preclinical and clinical data regarding incidence of pancreatitis.
International journal of clinical practice.
2010 Jun; 64(7):984-90. doi:
10.1111/j.1742-1241.2010.02382.x. [PMID: 20412332] - Robert G Moses. Repaglinide/metformin fixed-dose combination to improve glycemic control in patients with type 2 diabetes: an update.
Diabetes, metabolic syndrome and obesity : targets and therapy.
2010 May; 3(?):145-54. doi:
10.2147/dmsott.s6621. [PMID: 21437084] - Henry Krum, John J V McMurray, Edward Horton, Teresa Gerlock, Bjoern Holzhauer, Lineke Zuurman, Steven M Haffner, M Angelyn Bethel, Rury R Holman, Robert M Califf. Baseline characteristics of the Nateglinide and Valsartan Impaired Glucose Tolerance Outcomes Research (NAVIGATOR) trial population: comparison with other diabetes prevention trials.
Cardiovascular therapeutics.
2010 Apr; 28(2):124-32. doi:
10.1111/j.1755-5922.2010.00146.x. [PMID: 20184589] - Stefanie Geissler, Michael Hellwig, Madlen Zwarg, Fritz Markwardt, Thomas Henle, Matthias Brandsch. Transport of the advanced glycation end products alanylpyrraline and pyrralylalanine by the human proton-coupled peptide transporter hPEPT1.
Journal of agricultural and food chemistry.
2010 Feb; 58(4):2543-7. doi:
10.1021/jf903791u. [PMID: 20104847] - Masafumi Tamura, Sachiko Shiba, Naomi Kudo, Yoichi Kawashima. Pharmacokinetics of nateglinide enantiomers and their metabolites in Goto-Kakizaki rats, a model for type 2 diabetes mellitus.
Chirality.
2010 Jan; 22(1):92-8. doi:
10.1002/chir.20711. [PMID: 19387990] - Jian Cang, Jian Zhang, Changyuan Wang, Qi Liu, Qiang Meng, Desheng Wang, Yuichi Sugiyama, Akira Tsuji, Taiichi Kaku, Kexin Liu. Pharmacokinetics and mechanism of intestinal absorption of JBP485 in rats.
Drug metabolism and pharmacokinetics.
2010; 25(5):500-7. doi:
10.2133/dmpk.dmpk-10-rg-045. [PMID: 20877133] - R B Singh, Fabien Demeester, Agnieska Wilczynska. The tsim tsoum approaches for prevention of cardiovascular disease.
Cardiology research and practice.
2010; 2010(?):824938. doi:
10.4061/2010/824938. [PMID: 20671994] - Hajime Haimoto, Tae Sasakabe, Hiroyuki Umegaki, Kenji Wakai. Acute metabolic responses to a high-carbohydrate meal in outpatients with type 2 diabetes treated with a low-carbohydrate diet: a crossover meal tolerance study.
Nutrition & metabolism.
2009 Dec; 6(?):52. doi:
10.1186/1743-7075-6-52. [PMID: 20040075] - A Mori, P Lee, T Yamashita, Y Nishimaki, H Oda, K Saeki, Y Miki, H Mizutani, K Ishioka, T Honjo, T Arai, T Sako. Effect of glimepiride and nateglinide on serum insulin and glucose concentration in healthy cats.
Veterinary research communications.
2009 Dec; 33(8):957-70. doi:
10.1007/s11259-009-9314-4. [PMID: 19728131] - Aine M McKillop, Nicola A Duffy, John R Lindsay, Brian D Green, S Patterson, Finbarr P M O'Harte, Patrick M Bell, Peter R Flatt. Insulinotropic actions of nateglinide in type 2 diabetic patients and effects on dipeptidyl peptidase-IV activity and glucose-dependent insulinotropic polypeptide degradation.
European journal of endocrinology.
2009 Dec; 161(6):877-85. doi:
10.1530/eje-09-0547. [PMID: 19755410] - M A Bethel, P Deedwania, N S Levitt, O Schmitz, A Huntsman-Labed, R M Califf, S M Haffner, P Diem. Metabolic syndrome and alanine aminotransferase: a global perspective from the NAVIGATOR screening population.
Diabetic medicine : a journal of the British Diabetic Association.
2009 Dec; 26(12):1204-11. doi:
10.1111/j.1464-5491.2009.02864.x. [PMID: 20002471] - Themis Zelmanovitz, Fernando Gerchman, Amely Ps Balthazar, Fúlvio Cs Thomazelli, Jorge D Matos, Luís H Canani. Diabetic nephropathy.
Diabetology & metabolic syndrome.
2009 Sep; 1(1):10. doi:
10.1186/1758-5996-1-10. [PMID: 19825147] - Manthena V S Varma, Bo Feng, R Scott Obach, Matthew D Troutman, Jonathan Chupka, Howard R Miller, Ayman El-Kattan. Physicochemical determinants of human renal clearance.
Journal of medicinal chemistry.
2009 Aug; 52(15):4844-52. doi:
10.1021/jm900403j. [PMID: 19445515] - Tomoko Asakawa, Yusuke Moritoh, Osamu Kataoka, Nobuhiro Suzuki, Koji Takeuchi, Hiroyuki Odaka. A novel dipeptidyl peptidase-4 inhibitor, alogliptin (SYR-322), is effective in diabetic rats with sulfonylurea-induced secondary failure.
Life sciences.
2009 Jul; 85(3-4):122-6. doi:
10.1016/j.lfs.2009.04.024. [PMID: 19427871] - Sayeeda Rahman, Aziz Al-Shafi Ismail, Abdul Rashid A Rahman. Treatment of diabetic vasculopathy with rosiglitazone and ramipril: Hype or hope?.
International journal of diabetes in developing countries.
2009 Jul; 29(3):110-7. doi:
10.4103/0973-3930.54287. [PMID: 20165647] - Robert Moses. Fixed combination of repaglinide and metformin in the management of type 2 diabetes.
Diabetes, metabolic syndrome and obesity : targets and therapy.
2009 Jun; 2(?):101-9. doi:
10.2147/dmsott.s4436. [PMID: 21437123] - Chang-Yu Pan, Yan Gao, Guang-Wei Li, Xi-Xing Zhu, Xin Gao, Xin Liu. [A comparison of efficacy and tolerance of nateglinide and acarbose monotherapy in type 2 diabetes mellitus].
Zhonghua nei ke za zhi.
2009 Apr; 48(4):304-7. doi:
NULL. [PMID: 19576120] - J N Basile. Antihypertensive therapy, new-onset diabetes, and cardiovascular disease.
International journal of clinical practice.
2009 Apr; 63(4):656-66. doi:
10.1111/j.1742-1241.2009.02009.x. [PMID: 19220522] - G Derosa, A D'Angelo, E Fogari, S Salvadeo, A Gravina, I Ferrari, A F G Cicero. Nateglinide and glibenclamide metabolic effects in naïve type 2 diabetic patients treated with metformin.
Journal of clinical pharmacy and therapeutics.
2009 Feb; 34(1):13-23. doi:
10.1111/j.1365-2710.2008.00984.x. [PMID: 19125899] - N Papanas, E Maltezos. Oral antidiabetic agents: anti-atherosclerotic properties beyond glucose lowering?.
Current pharmaceutical design.
2009; 15(27):3179-92. doi:
10.2174/138161209789057995. [PMID: 19754390] - Kyota Aoyagi, Mica Ohara-Imaizumi, Chiyono Nishiwaki, Yoko Nakamichi, Shinya Nagamatsu. Glinide, but not sulfonylurea, can evoke insulin exocytosis by repetitive stimulation: imaging analysis of insulin exocytosis by secretagogue-induced repetitive stimulations.
Experimental diabetes research.
2009; 2009(?):278762. doi:
10.1155/2009/278762. [PMID: 20069052] - Masanori Iwase, Kenzo Iino, Yasufumi Doi, Tamotsu Asano, Mitsuo Iida. Nateglinide may increase high-molecular weight adiponectin in type 2 diabetic patients with hypoadiponectinemia.
Diabetes research and clinical practice.
2008 Dec; 82(3):e19-22. doi:
10.1016/j.diabres.2008.09.001. [PMID: 18849086] - Annikka Kalliokoski, Janne T Backman, Pertti J Neuvonen, Mikko Niemi. Effects of the SLCO1B1*1B haplotype on the pharmacokinetics and pharmacodynamics of repaglinide and nateglinide.
Pharmacogenetics and genomics.
2008 Nov; 18(11):937-42. doi:
10.1097/fpc.0b013e32830d733e. [PMID: 18854776] - Morten A Karsdal, Inger Byrjalsen, Bente J Riis, Claus Christiansen. Optimizing bioavailability of oral administration of small peptides through pharmacokinetic and pharmacodynamic parameters: the effect of water and timing of meal intake on oral delivery of Salmon Calcitonin.
BMC clinical pharmacology.
2008 Sep; 8(?):5. doi:
10.1186/1472-6904-8-5. [PMID: 18782439] - Vivian A Fonseca, Julio Rosenstock, Antonia C Wang, Kenneth E Truitt, Michael R Jones. Colesevelam HCl improves glycemic control and reduces LDL cholesterol in patients with inadequately controlled type 2 diabetes on sulfonylurea-based therapy.
Diabetes care.
2008 Aug; 31(8):1479-84. doi:
10.2337/dc08-0283. [PMID: 18458145] - R Scott Obach, Franco Lombardo, Nigel J Waters. Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
Drug metabolism and disposition: the biological fate of chemicals.
2008 Jul; 36(7):1385-405. doi:
10.1124/dmd.108.020479. [PMID: 18426954] - Shuang Cai, Taoguang Huo, Wanyu Feng, Lingyun Chen, Feng Qin, Famei Li. Quantitative determination of mitiglinide in human plasma by ultra-performance liquid chromatography/electrospray ionization tandem mass spectrometry.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2008 Jun; 868(1-2):83-7. doi:
10.1016/j.jchromb.2008.04.037. [PMID: 18486570] - Kanthi Kiran V S Varanasi, V Sridhar, Suresh Potharaju, R Shraddha, S P N Sivakumar, S Kanaga Sabapathi, T R S Satheeshmanikandan, V V S Swaroop Kumar. Development and validation of a liquid chromatography/tandem mass spectrometry assay for the simultaneous determination of nateglinide, cilostazol and its active metabolite 3,4-dehydro-cilostazol in Wistar rat plasma and its application to pharmacokinetic study.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2008 Apr; 865(1-2):91-8. doi:
10.1016/j.jchromb.2008.02.013. [PMID: 18342586] - Annikka Kalliokoski, Mikko Neuvonen, Pertti J Neuvonen, Mikko Niemi. Different effects of SLCO1B1 polymorphism on the pharmacokinetics and pharmacodynamics of repaglinide and nateglinide.
Journal of clinical pharmacology.
2008 Mar; 48(3):311-21. doi:
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