Tolbutamide (BioDeep_00000001520)

 

Secondary id: BioDeep_00000408956

human metabolite blood metabolite


代谢物信息卡片


N-(Sulphonyl-p-methylbenzene)-n-N-butylurea

化学式: C12H18N2O3S (270.1038)
中文名称: 甲苯磺丁脲
谱图信息: 最多检出来源 Homo sapiens(blood) 36.88%

分子结构信息

SMILES: CCCCN=C(O)NS(=O)(=O)c1ccc(C)cc1
InChI: InChI=1S/C12H18N2O3S/c1-3-4-9-13-12(15)14-18(16,17)11-7-5-10(2)6-8-11/h5-8H,3-4,9H2,1-2H3,(H2,13,14,15)

描述信息

Tolbutamide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It is structurally similar to acetohexamide, chlorpropamide and tolazamide and belongs to the sulfonylurea class of insulin secretagogues, which act by stimulating cells of the pancreas to release insulin. Sulfonylureas increase both basal insulin secretion and meal-stimulated insulin release. Medications in this class differ in their dose, rate of absorption, duration of action, route of elimination and binding site on their target pancreatic cell receptor. Sulfonylureas also increase peripheral glucose utilization, decrease hepatic gluconeogenesis and may increase the number and sensitivity of insulin receptors. Sulfonylureas are associated with weight gain, though less so than insulin. Due to their mechanism of action, sulfonylureas may cause hypoglycemia and require consistent food intake to decrease this risk. The risk of hypoglycemia is increased in elderly, debilitated and malnourished individuals. Tolbutamide appears to be metabolized in the liver. Tolbutamide and its metabolites are excreted in urine (75-85\\%) and feces.
CONFIDENCE standard compound; INTERNAL_ID 693; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4159; ORIGINAL_PRECURSOR_SCAN_NO 4157
CONFIDENCE standard compound; INTERNAL_ID 693; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8370; ORIGINAL_PRECURSOR_SCAN_NO 8367
CONFIDENCE standard compound; INTERNAL_ID 693; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8423; ORIGINAL_PRECURSOR_SCAN_NO 8420
CONFIDENCE standard compound; INTERNAL_ID 693; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8415; ORIGINAL_PRECURSOR_SCAN_NO 8413
CONFIDENCE standard compound; INTERNAL_ID 693; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4159; ORIGINAL_PRECURSOR_SCAN_NO 4156
CONFIDENCE standard compound; INTERNAL_ID 693; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4203; ORIGINAL_PRECURSOR_SCAN_NO 4202
ORIGINAL_ACQUISITION_NO 8354; CONFIDENCE standard compound; INTERNAL_ID 693; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_PRECURSOR_SCAN_NO 8351
CONFIDENCE standard compound; INTERNAL_ID 693; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8415; ORIGINAL_PRECURSOR_SCAN_NO 8412
CONFIDENCE standard compound; INTERNAL_ID 693; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4133; ORIGINAL_PRECURSOR_SCAN_NO 4130
CONFIDENCE standard compound; INTERNAL_ID 693; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8326; ORIGINAL_PRECURSOR_SCAN_NO 8324
CONFIDENCE standard compound; INTERNAL_ID 693; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8354; ORIGINAL_PRECURSOR_SCAN_NO 8351
CONFIDENCE standard compound; INTERNAL_ID 693; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4161; ORIGINAL_PRECURSOR_SCAN_NO 4157
A - Alimentary tract and metabolism > A10 - Drugs used in diabetes > A10B - Blood glucose lowering drugs, excl. insulins > A10BB - Sulfonylureas
C78276 - Agent Affecting Digestive System or Metabolism > C29711 - Anti-diabetic Agent > C97936 - Sulfonylurea Antidiabetic Agent
V - Various > V04 - Diagnostic agents > V04C - Other diagnostic agents > V04CA - Tests for diabetes
D007004 - Hypoglycemic Agents

同义名列表

54 个代谢物同义名

N-(Sulphonyl-p-methylbenzene)-n-N-butylurea; N-(Sulfonyl-p-methylbenzene)-n-N-butylurea; N-(p-Methylbenzenesulphonyl)-n-butylurea; N-(4-Methylbenzenesulphonyl)-n-butylurea; N-Butyl-n-(4-methylphenylsulphonyl)urea; N-(4-Methylbenzenesulfonyl)-n-butylurea; 1-Butyl-3-(p-methylphenylsulphonyl)urea; N-(4-Methylphenylsulphonyl)-n-butylurea; 3-butyl-1-(4-methylbenzenesulfonyl)urea; N-(p-Methylbenzenesulfonyl)-n-butylurea; N-(4-Methylphenylsulfonyl)-n-butylurea; N-Butyl-n-(4-methylphenylsulfonyl)urea; 1-Butyl-3-(p-methylphenylsulfonyl)urea; 3-(p-Tolyl-4-sulphonyl)-1-butylurea; 3-(p-Tolyl-4-sulfonyl)-1-butylurea; Berlin-chemie brand OF tolbutamide; Berlin chemie brand OF tolbutamide; 1-Butyl-3-(p-tolylsulphonyl)urea; N-Butyl-n-(p-tolylsulphonyl)urea; N-Butyl-n-p-toluenesulphonylurea; 1-p-Toluenesulphonyl-3-butylurea; 1-Butyl-3-(p-tolylsulfonyl)urea; N-Butyl-n-p-toluenesulfonylurea; N-Butyl-n-(p-tolylsulfonyl)urea; Yamanouchi brand OF tolbutamide; 1-p-Toluenesulfonyl-3-butylurea; Valdecasas brand OF tolbutamide; Butamide brand OF tolbutamide; Hoechst brand OF tolbutamide; Aventis brand OF tolbutamide; Pfizer brand OF tolbutamide; Apotex brand OF tolbutamide; R.A.N. brand OF tolbutamide; Tolbutamide butamide brand; Tolbutamide aventis brand; Tolbutamide hoechst brand; Tolbutamide pfizer brand; Tolylsulphonylbutylurea; Tolylsulfonylbutylurea; N-N-Butyl-n-tosylurea; 1-Butyl-3-tosylurea; Tolbutamid r.a.n.; Apo-tolbutamide; Tolbutamidum; tolbutamide; Tolbutamida; Rastinon; Diabetol; Artosin; Dolipol; Orinase; Orabet; Diaval; Tolbutamide



数据库引用编号

30 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(5)

BioCyc(0)

PlantCyc(0)

代谢反应

50 个相关的代谢反应过程信息。

Reactome(50)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

2 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。

亚细胞结构定位 关联基因列表
Cytoplasm 11 ABCB1, ALB, CA1, CYP2B6, CYP2C19, CYP2C8, CYP2C9, CYP2D6, CYP2E1, CYP3A4, PRKX
Peripheral membrane protein 3 CYP1B1, CYP2B6, CYP2E1
Endoplasmic reticulum membrane 9 CYP1A2, CYP1B1, CYP2B6, CYP2C19, CYP2C8, CYP2C9, CYP2D6, CYP2E1, CYP3A4
Nucleus 2 ALB, PRKX
cytosol 4 ALB, CA1, PRKCQ, SST
centrosome 1 ALB
nucleoplasm 1 PRKX
Cell membrane 1 ABCB1
Multi-pass membrane protein 4 ABCB1, CACNA1I, KCNA3, KCNJ11
cell surface 1 ABCB1
glutamatergic synapse 2 KCNA3, KCNJ11
Golgi apparatus 1 ALB
Golgi membrane 1 INS
mitochondrial inner membrane 1 CYP2E1
neuronal cell body 2 KCNJ11, SST
presynaptic membrane 2 KCNA3, KCNJ11
acrosomal vesicle 1 KCNJ11
endosome 1 KCNJ11
plasma membrane 9 ABCB1, CACNA1I, CYP2C19, CYP2C8, CYP2C9, GCG, KCNA3, KCNJ11, PRKCQ
Membrane 7 ABCB1, CACNA1I, CYP1B1, CYP2D6, CYP3A4, KCNA3, KCNJ11
apical plasma membrane 1 ABCB1
axon 1 KCNA3
extracellular exosome 3 ABCB1, ALB, CA1
endoplasmic reticulum 2 ALB, CYP2D6
extracellular space 4 ALB, GCG, INS, SST
perinuclear region of cytoplasm 1 KCNA3
intercalated disc 1 KCNJ11
mitochondrion 2 CYP1B1, CYP2D6
protein-containing complex 1 ALB
intracellular membrane-bounded organelle 9 CYP1A2, CYP1B1, CYP2B6, CYP2C19, CYP2C8, CYP2C9, CYP2D6, CYP2E1, CYP3A4
Microsome membrane 7 CYP1A2, CYP1B1, CYP2B6, CYP2C9, CYP2D6, CYP2E1, CYP3A4
Secreted 4 ALB, GCG, INS, SST
extracellular region 4 ALB, GCG, INS, SST
Single-pass membrane protein 1 CYP2D6
anchoring junction 1 ALB
centriolar satellite 1 PRKCQ
T-tubule 1 KCNJ11
postsynaptic membrane 1 KCNA3
Apical cell membrane 1 ABCB1
Mitochondrion inner membrane 1 CYP2E1
Membrane raft 1 KCNA3
axolemma 1 KCNJ11
GABA-ergic synapse 1 SST
ciliary basal body 1 ALB
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 1 ALB
[Isoform 2]: Cell membrane 1 KCNA3
nuclear envelope 1 KCNJ11
endosome lumen 1 INS
monoatomic ion channel complex 1 KCNJ11
cell body fiber 1 KCNJ11
inward rectifying potassium channel 1 KCNJ11
voltage-gated potassium channel complex 1 KCNA3
secretory granule lumen 2 GCG, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 ALB, GCG, INS
platelet alpha granule lumen 1 ALB
voltage-gated calcium channel complex 1 CACNA1I
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
immunological synapse 1 PRKCQ
neuronal dense core vesicle 1 SST
aggresome 1 PRKCQ
calyx of Held 1 KCNA3
external side of apical plasma membrane 1 ABCB1
[Isoform 1]: Cell membrane 1 KCNA3
[Glucagon-like peptide 1]: Secreted 1 GCG
[Isoform 3]: Cytoplasm, perinuclear region 1 KCNA3
ciliary transition fiber 1 ALB


文献列表

  • Hui-Lin Yang, Ying Li, Yi Chen, Si-Ying Chen, Yue-Ting Li, Yong Huang, Lin Zheng, Jing Huang, Yong-Lin Wang, Zi-Peng Gong. [Effect of Laportea bulbifera extract on CYP450 enzyme activities in rats by Cocktail probe drug method]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2022 Dec; 47(23):6320-6332. doi: 10.19540/j.cnki.cjcmm.20220623.204. [PMID: 36604876]
  • Xizi Liu, Shiyi Han, Qian Yang, Siyang Fan. Beneficial herb-drug interaction of Gnaphalium affine extract on benzbromarone: A pharmacokinetic and pharmacodynamic study in rats. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2022 Jul; 102(?):154203. doi: 10.1016/j.phymed.2022.154203. [PMID: 35660349]
  • 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. Naunyn-Schmiedeberg's archives of pharmacology. 2022 07; 395(7):815-826. doi: 10.1007/s00210-022-02235-1. [PMID: 35394133]
  • Shotaro Uehara, Nao Yoneda, Yuichiro Higuchi, Hiroshi Yamazaki, Hiroshi Suemizu. Methyl-hydroxylation and subsequent oxidation to produce carboxylic acid is the major metabolic pathway of tolbutamide in chimeric TK-NOG mice transplanted with human hepatocytes. Xenobiotica; the fate of foreign compounds in biological systems. 2021 May; 51(5):582-589. doi: 10.1080/00498254.2021.1875515. [PMID: 33455497]
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  • Richard B van Breemen, Luying Chen, Alyssa Tonsing-Carter, Suzanne Banuvar, Elena Barengolts, Marlos Viana, Shao-Nong Chen, Guido F Pauli, Judy L Bolton. Pharmacokinetic Interactions of a Hop Dietary Supplement with Drug Metabolism in Perimenopausal and Postmenopausal Women. Journal of agricultural and food chemistry. 2020 May; 68(18):5212-5220. doi: 10.1021/acs.jafc.0c01077. [PMID: 32285669]
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  • Abhinav Sharma, Neha J Pagidipati, Robert M Califf, Darren K McGuire, Jennifer B Green, Dave Demets, Jyothis Thomas George, Hertzel C Gerstein, Todd Hobbs, Rury R Holman, Francesca C Lawson, Lawrence A Leiter, Marc A Pfeffer, Jane Reusch, Jeffrey S Riesmeyer, Matthew T Roe, Yves Rosenberg, Robert Temple, Stephen Wiviott, John McMurray, Christopher Granger. Impact of Regulatory Guidance on Evaluating Cardiovascular Risk of New Glucose-Lowering Therapies to Treat Type 2 Diabetes Mellitus: Lessons Learned and Future Directions. Circulation. 2020 03; 141(10):843-862. doi: 10.1161/circulationaha.119.041022. [PMID: 31992065]
  • Luying Chen, Richard B van Breemen. Validation of a sensitive UHPLC-MS/MS method for cytochrome P450 probe substrates caffeine, tolbutamide, dextromethorphan, and alprazolam in human serum reveals drug contamination of serum used for research. Journal of pharmaceutical and biomedical analysis. 2020 Feb; 179(?):112983. doi: 10.1016/j.jpba.2019.112983. [PMID: 31744669]
  • Mei-Ling Wu, Yi-Ping Lin, Yan-Li Wei, Hong-Jian Du, Xiao-Qian Ying, Wen-Zhuang Tan, Bi-E Tang. Calycosin Influences the Metabolism of Five Probe Drugs in Rats. Drug design, development and therapy. 2020; 14(?):429-434. doi: 10.2147/dddt.s236221. [PMID: 32099327]
  • Imocha Rajkumar Singh, Sivaprasad Mitra. Modulated Protein Binding Ability of Anti-Diabetic Drugs in Presence of Monodispersed Gold Nanoparticles and its Inhibitory Potential towards Advanced Glycated End (AGE) Product Formation. Journal of fluorescence. 2020 Jan; 30(1):193-204. doi: 10.1007/s10895-019-02485-y. [PMID: 31925653]
  • Jing Li, Ming-Rui Li, Bao Sun, Cheng-Ming Liu, Jing Ren, Wen-Qian Zhi, Pei-Yu Zhang, Hai-Ling Qiao, Na Gao. Inhibition of Rat CYP1A2 and CYP2C11 by Honokiol, a Component of Traditional Chinese Medicine. European journal of drug metabolism and pharmacokinetics. 2019 Dec; 44(6):787-796. doi: 10.1007/s13318-019-00565-9. [PMID: 31175627]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Shuhei Fukuno, Katsuhito Nagai, Kohei Yamamoto, Takehiro Tanimura, Takeshi Nabe, Hiroki Konishi. Pharmacokinetic interference of doxorubicin with tolbutamide due to reduced metabolic clearance with increased serum unbound fraction in rats. Biopharmaceutics & drug disposition. 2019 Jul; 40(7):225-233. doi: 10.1002/bdd.2195. [PMID: 31215040]
  • Luiz F Barella, Mario Rossi, Lu Zhu, Yinghong Cui, Fang C Mei, Xiaodong Cheng, Wei Chen, Vsevolod V Gurevich, Jürgen Wess. β-Cell-intrinsic β-arrestin 1 signaling enhances sulfonylurea-induced insulin secretion. The Journal of clinical investigation. 2019 06; 129(9):3732-3737. doi: 10.1172/jci126309. [PMID: 31184597]
  • Satoshi Endo, Namiki Miyagi, Toshiyuki Matsunaga, Akira Ikari. Rabbit dehydrogenase/reductase SDR family member 11 (DHRS11): Its identity with acetohexamide reductase with broad substrate specificity and inhibitor sensitivity, different from human DHRS11. Chemico-biological interactions. 2019 May; 305(?):12-20. doi: 10.1016/j.cbi.2019.03.026. [PMID: 30926317]
  • Zafar Iqbal, Grant Morahan, Mahreen Arooj, Alexandre N Sobolev, Shahid Hameed. Synthesis of new arylsulfonylspiroimidazolidine-2',4'-diones and study of their effect on stimulation of insulin release from MIN6 cell line, inhibition of human aldose reductase, sorbitol accumulations in various tissues and oxidative stress. European journal of medicinal chemistry. 2019 Apr; 168(?):154-175. doi: 10.1016/j.ejmech.2019.02.036. [PMID: 30818176]
  • Jing Wang, Zhi-Yi Zhang, Sharon Lu, Dan Powers, Vikram Kansra, Xiaodong Wang. Effects of rolapitant administered orally on the pharmacokinetics of dextromethorphan (CYP2D6), tolbutamide (CYP2C9), omeprazole (CYP2C19), efavirenz (CYP2B6), and repaglinide (CYP2C8) in healthy subjects. Supportive care in cancer : official journal of the Multinational Association of Supportive Care in Cancer. 2019 Mar; 27(3):819-827. doi: 10.1007/s00520-018-4331-x. [PMID: 30084103]
  • Chen Cheng, Jianchang Qian, Zhe Wang, Wanshu Li, Chengke Huang, Mengchun Chen, Yaoyao Dong, Lejing Lian, Wei Sun. Influences of Corydalis decumbens on the Activities of CYP450 Enzymes in Rats with a Cocktail Approach. BioMed research international. 2019; 2019(?):9614781. doi: 10.1155/2019/9614781. [PMID: 30800683]
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