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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.
Term:tolbutamide
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Accession:CHEBI:27999 term browser browse the term
Definition:An N-sulfonylurea that consists of 1-butylurea having a tosyl group attached at the 3-position.
Synonyms:exact_synonym: N-[(butylamino)carbonyl]-4-methylbenzenesulfonamide
 related_synonym: 1-Butyl-3-(p-methylphenylsulfonyl)urea;   1-Butyl-3-(p-tolylsulfonyl)urea;   1-Butyl-3-tosylurea;   1-p-Toluenesulfonyl-3-butylurea;   3-(p-Tolyl-4-sulfonyl)-1-butylurea;   Formula=C12H18N2O3S;   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);   InChIKey=JLRGJRBPOGGCBT-UHFFFAOYSA-N;   N-(4-Methylbenzenesulfonyl)-N'-butylurea;   N-(4-Methylphenylsulfonyl)-N'-butylurea;   N-(Sulfonyl-p-methylbenzene)-N'-N-butylurea;   N-(p-Methylbenzenesulfonyl)-N'-butylurea;   N-Butyl-N'-(4-methylphenylsulfonyl)urea;   N-Butyl-N'-(p-tolylsulfonyl)urea;   N-Butyl-N'-p-toluenesulfonylurea;   N-n-Butyl-N'-tosylurea;   Orinase (TN);   SMILES=CCCCNC(=O)NS(=O)(=O)c1ccc(C)cc1;   Tolylsulfonylbutylurea;   tolbutamida;   tolbutamidum
 alt_id: CHEBI:27019;   CHEBI:9616
 xref: CAS:64-77-7;   DrugBank:DB01124;   Drug_Central:2696;   KEGG:C07148;   KEGG:D00380;   LINCS:LSM-3907
 xref_mesh: MESH:D014044
 xref: PMID:11835228;   PMID:11840346;   PMID:11911494;   PMID:12042355;   PMID:12355256;   PMID:15207658;   PMID:15317941;   PMID:15620874;   PMID:15655519;   PMID:16290322;   PMID:16426753;   PMID:19059420;   PMID:20880646;   PMID:21178111;   PMID:21193530;   PMID:21471135;   PMID:21535124;   PMID:21712613;   PMID:21757329;   PMID:21827497;   PMID:21831467;   PMID:22028182;   PMID:22079696;   Patent:DE1066575;   Patent:GB808071;   Patent:US2968158;   Reaxys:1984428;   Wikipedia:Tolbutamide


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tolbutamide term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb1a ATP binding cassette subfamily B member 1A multiple interactions
decreases activity		 ISO Tolbutamide inhibits the reaction [ABCB1 protein results in increased uptake of quinidinium]
Tolbutamide results in decreased activity of ABCB1 protein		 CTD PMID:32305507 NCBI chr 4:25,357,467...25,529,941
Ensembl chr 4:25,158,362...25,442,709 		JBrowse link
G Abcc8 ATP binding cassette subfamily C member 8 multiple interactions ISO [KCNJ11 mutant form co-treated with ABCC8 mutant form] results in decreased susceptibility to Tolbutamide; ABCC8 gene SNP inhibits the reaction [Tolbutamide results in increased secretion of INS protein]; Tolbutamide inhibits the reaction [ABCC8 protein mutant form results in increased activity of KCNJ11 protein] CTD PMID:9568693 PMID:18025464 PMID:22209866 NCBI chr 1:96,598,568...96,679,563
Ensembl chr 1:96,598,647...96,679,510 		JBrowse link
G Alb albumin affects binding ISO Tolbutamide binds to ALB protein CTD PMID:19596536 PMID:20435530 PMID:20956006 PMID:20974553 NCBI chr14:17,607,397...17,622,814
Ensembl chr14:17,607,381...17,622,836 		JBrowse link
G Ccnd1 cyclin D1 increases expression EXP Tolbutamide results in increased expression of CCND1 protein CTD PMID:16718685 NCBI chr 1:200,089,002...200,098,524
Ensembl chr 1:200,089,002...200,098,602 		JBrowse link
G Ccnd3 cyclin D3 increases expression EXP Tolbutamide results in increased expression of CCND3 protein CTD PMID:16718685 NCBI chr 9:13,394,161...13,400,341
Ensembl chr 9:13,394,169...13,489,371 		JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A multiple interactions
increases expression		 EXP GJA1 promotes the reaction [Tolbutamide results in increased expression of CDKN1A protein] CTD PMID:16718685 NCBI chr20:7,149,177...7,159,727
Ensembl chr20:7,149,217...7,159,585 		JBrowse link
G Cdkn1b cyclin-dependent kinase inhibitor 1B increases expression EXP Tolbutamide results in increased expression of CDKN1B protein CTD PMID:16718685 NCBI chr 4:167,760,067...167,765,177
Ensembl chr 4:167,760,181...167,764,982 		JBrowse link
G Cyp2c11 cytochrome P450, subfamily 2, polypeptide 11 increases metabolic processing ISO CYP2C18 results in increased metabolism of Tolbutamide CTD PMID:15301741 NCBI chr 1:236,762,719...236,799,069
Ensembl chr 1:236,762,842...236,799,066 		JBrowse link
G Cyp2c24 cytochrome P450, family 2, subfamily c, polypeptide 24 increases metabolic processing
multiple interactions		 ISO CYP2C55 protein results in increased metabolism of Tolbutamide
[CYP2C55 protein results in increased metabolism of Tolbutamide] which results in increased chemical synthesis of 4'-hydroxytolbutamide		 CTD PMID:30503582 NCBI chr 1:236,873,967...236,936,238
Ensembl chr 1:236,873,967...236,936,238 		JBrowse link
G Cyp2c6 cytochrome P450, family 2, subfamily C, polypeptide 6 increases metabolic processing
increases hydroxylation
multiple interactions		 ISO CYP2C19 protein results in increased metabolism of Tolbutamide
CYP2C19 protein results in increased hydroxylation of Tolbutamide
[CYP2C19 protein results in increased hydroxylation of Tolbutamide] which results in increased chemical synthesis of 4'-hydroxytolbutamide		 CTD PMID:18511451 PMID:30500380 NCBI chr 1:237,938,521...237,976,238
Ensembl chr 1:237,693,094...238,057,596 		JBrowse link
G Cyp2c66 cytochrome P450, family 2, subfamily c, polypeptide 66 multiple interactions
increases metabolic processing		 ISO [CYP2C66 protein results in increased metabolism of Tolbutamide] which results in increased chemical synthesis of 4'-hydroxytolbutamide CTD PMID:30503582 NCBI chr 1:237,078,517...237,169,841
Ensembl chr 1:237,078,517...237,169,650 		JBrowse link
G Cyp2c79 cytochrome P450, family 2, subfamily c, polypeptide 79 increases hydroxylation ISO CYP2C8 protein results in increased hydroxylation of Tolbutamide CTD PMID:15843491
G Gcg glucagon increases secretion EXP Tolbutamide results in increased secretion of GCG protein CTD PMID:15919803 NCBI chr 3:47,113,914...47,122,958
Ensembl chr 3:47,113,914...47,122,929 		JBrowse link
G Gja1 gap junction protein, alpha 1 multiple interactions
increases expression		 EXP GJA1 promotes the reaction [Tolbutamide results in increased expression of CDKN1A protein]; Tolbutamide promotes the reaction [Bucladesine results in increased expression of GJA1 protein]
Tolbutamide results in increased expression of GJA1 protein		 CTD PMID:11741589 PMID:16718685 NCBI chr20:35,756,007...35,768,481
Ensembl chr20:35,755,991...35,768,582 		JBrowse link
G Hk1 hexokinase 1 increases expression ISO Tolbutamide results in increased expression of HK1 protein CTD PMID:11835228 NCBI chr20:30,230,488...30,332,099
Ensembl chr20:30,230,486...30,332,131 		JBrowse link
G Ins1 insulin 1 affects secretion
multiple interactions		 ISO Tolbutamide affects the secretion of INS1 protein
[Tolbutamide co-treated with FR900359] inhibits the reaction [Glucose results in increased secretion of INS1 protein]; Tolbutamide inhibits the reaction [arsenite inhibits the reaction [Glucose results in increased secretion of INS1 protein]]; Tolbutamide inhibits the reaction [dimethylarsinous acid inhibits the reaction [Glucose results in increased secretion of INS1 protein]]; Tolbutamide inhibits the reaction [methylarsonite inhibits the reaction [Glucose results in increased secretion of INS1 protein]]; Tolbutamide promotes the reaction [Glucose results in increased secretion of INS1 protein]		 CTD PMID:9366569 PMID:31332465 PMID:37217659 NCBI chr 1:251,244,973...251,245,540
Ensembl chr 1:251,244,973...251,245,536 		JBrowse link
G Ins2 insulin 2 multiple interactions
increases secretion		 ISO ABCC8 gene SNP inhibits the reaction [Tolbutamide results in increased secretion of INS protein] CTD PMID:9032110 PMID:9568693 NCBI chr 1:197,843,277...197,992,522
Ensembl chr 1:197,843,281...197,864,775 		JBrowse link
G Kcnj11 potassium inwardly-rectifying channel, subfamily J, member 11 multiple interactions
decreases activity		 ISO [KCNJ11 mutant form co-treated with ABCC8 mutant form] results in decreased susceptibility to Tolbutamide; Tolbutamide inhibits the reaction [ABCC8 protein mutant form results in increased activity of KCNJ11 protein]
Tolbutamide results in decreased activity of KCNJ11 protein		 CTD PMID:18025464 PMID:22209866 NCBI chr 1:96,591,048...96,594,574
Ensembl chr 1:96,591,049...96,594,082 		JBrowse link
G Mki67 marker of proliferation Ki-67 decreases expression EXP Tolbutamide results in decreased expression of MKI67 protein CTD PMID:16718685 NCBI chr 1:190,496,319...190,522,983
Ensembl chr 1:190,496,319...190,522,762 		JBrowse link
G Pdcd4 programmed cell death 4 decreases expression
increases expression		 ISO Tolbutamide results in decreased expression of PDCD4 mRNA
Tolbutamide results in increased expression of PDCD4 mRNA		 CTD PMID:21873647 NCBI chr 1:252,921,342...252,944,278
Ensembl chr 1:252,921,392...252,944,275 		JBrowse link
G Rb1 RB transcriptional corepressor 1 decreases phosphorylation EXP Tolbutamide results in decreased phosphorylation of RB1 protein CTD PMID:16718685 NCBI chr15:48,371,295...48,502,473
Ensembl chr15:48,371,296...48,502,302 		JBrowse link
G Slc2a1 solute carrier family 2 member 1 increases expression ISO Tolbutamide results in increased expression of SLC2A1 mRNA; Tolbutamide results in increased expression of SLC2A1 protein CTD PMID:2682625 PMID:11835228 NCBI chr 5:132,717,196...132,745,416
Ensembl chr 5:132,717,196...132,745,416 		JBrowse link
G Tnfaip3 TNF alpha induced protein 3 decreases expression ISO Tolbutamide results in decreased expression of TNFAIP3 mRNA CTD PMID:21873647 NCBI chr 1:13,709,211...13,724,291
Ensembl chr 1:13,709,206...13,725,282 		JBrowse link
G Tp53 tumor protein p53 increases expression EXP Tolbutamide results in increased expression of TP53 mRNA CTD PMID:16426753 NCBI chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524 		JBrowse link
G Tpd52 tumor protein D52 decreases expression
increases expression		 ISO Tolbutamide results in decreased expression of TPD52 mRNA
Tolbutamide results in increased expression of TPD52 mRNA		 CTD PMID:21873647 NCBI chr 2:92,735,365...92,816,079
Ensembl chr 2:92,735,620...92,816,622 		JBrowse link
G Ugdh UDP-glucose 6-dehydrogenase decreases expression EXP Tolbutamide results in decreased expression of UGDH protein CTD PMID:4270849 NCBI chr14:42,848,704...42,872,351
Ensembl chr14:42,848,854...42,872,354 		JBrowse link
Term paths to the root
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Term Annotations click to browse term
  CHEBI ontology 19921
    role 19893
      application 19734
        pharmaceutical 19573
          drug 19573
            hypoglycemic agent 4214
              tolbutamide 26
Path 2
Term Annotations click to browse term
  CHEBI ontology 19921
    subatomic particle 19919
      composite particle 19919
        hadron 19919
          baryon 19919
            nucleon 19919
              atomic nucleus 19919
                atom 19919
                  main group element atom 19865
                    p-block element atom 19865
                      carbon group element atom 19804
                        carbon atom 19801
                          organic molecular entity 19801
                            heteroorganic entity 19558
                              organochalcogen compound 19317
                                organooxygen compound 19233
                                  carbon oxoacid 18695
                                    carboxylic acid 18692
                                      carboacyl group 17724
                                        univalent carboacyl group 17724
                                          carbamoyl group 17577
                                            carboxamide 17577
                                              monocarboxylic acid amide 15748
                                                urea 6225
                                                  ureas 6223
                                                    N-sulfonylurea 148
                                                      tolbutamide 26
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