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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 4:22,339,829...22,517,642
Ensembl chr 4:22,133,521...22,425,515
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 1:102,110,708...102,191,287
Ensembl chr 1:102,110,708...102,191,287
JBrowse link
G Alb albumin affects binding ISO Tolbutamide binds to ALB protein CTD PMID:19596536, PMID:20435530, PMID:20956006, PMID:20974553 NCBI chr14:19,176,275...19,191,793
Ensembl chr14:19,176,277...19,191,863
JBrowse link
G Ccnd1 cyclin D1 increases expression EXP Tolbutamide results in increased expression of CCND1 protein CTD PMID:16718685 NCBI chr 1:218,090,750...218,100,447
Ensembl chr 1:218,090,750...218,100,325
JBrowse link
G Ccnd3 cyclin D3 increases expression EXP Tolbutamide results in increased expression of CCND3 protein CTD PMID:16718685 NCBI chr 9:15,404,816...15,410,905
Ensembl chr 9:15,404,822...15,410,943
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 chr20:6,348,422...6,358,864
Ensembl chr20:6,351,458...6,358,864
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 4:168,689,043...168,694,159
Ensembl chr 4:168,689,163...168,693,964
JBrowse link
G Cyp2c24 cytochrome P450, family 2, subfamily c, polypeptide 24 increases metabolic processing
multiple interactions
ISO CYP2C18 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:15301741, PMID:30503582 NCBI chr 1:258,074,797...258,139,176
Ensembl chr 1:258,074,860...258,139,176
JBrowse link
G Cyp2c6v1 cytochrome P450, family 2, subfamily C, polypeptide 6, variant 1 increases metabolic processing
multiple interactions
increases hydroxylation
ISO CYP2C19 protein results in increased metabolism 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 1:147,713,879...147,814,410
Ensembl chr 1:147,713,892...147,888,007
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 NCBI chr 1:147,236,480...147,307,988 JBrowse link
G Gcg glucagon increases secretion EXP Tolbutamide results in increased secretion of GCG protein CTD PMID:15919803 NCBI chr 3:48,442,635...48,451,650
Ensembl chr 3:48,442,635...48,451,650
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 chr20:37,876,650...37,889,097
Ensembl chr20:37,876,650...37,889,089
JBrowse link
G Hk1 hexokinase 1 increases expression ISO Tolbutamide results in increased expression of HK1 protein CTD PMID:11835228 NCBI chr20:31,911,460...31,979,780
Ensembl chr20:31,912,262...31,956,649
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 1:215,856,967...215,858,034
Ensembl chr 1:215,856,971...215,858,034
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 1:102,103,093...102,107,134
Ensembl chr 1:102,103,094...102,106,127
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 1:207,993,895...208,020,454
Ensembl chr 1:207,993,895...208,020,454
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 1:274,616,625...274,648,204
Ensembl chr 1:274,625,224...274,648,204
JBrowse link
G Rb1 RB transcriptional corepressor 1 decreases phosphorylation EXP Tolbutamide results in decreased phosphorylation of RB1 protein CTD PMID:16718685 NCBI chr15:55,081,582...55,209,060
Ensembl chr15:55,083,140...55,209,342
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 5:138,154,677...138,182,897
Ensembl chr 5:138,154,673...138,182,897
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 1:14,401,103...14,416,369
Ensembl chr 1:14,402,913...14,412,807
JBrowse link
G Tp53 tumor protein p53 increases expression EXP Tolbutamide results in increased expression of TP53 mRNA CTD PMID:16426753 NCBI chr10:56,186,299...56,198,449
Ensembl chr10:56,187,020...56,198,449
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 2:94,959,732...95,041,277
Ensembl chr 2:95,008,311...95,040,514
JBrowse link
G Ugdh UDP-glucose 6-dehydrogenase decreases expression EXP Tolbutamide results in decreased expression of UGDH protein CTD PMID:4270849 NCBI chr14:44,479,614...44,502,845
Ensembl chr14:44,479,614...44,502,845
JBrowse link

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Term Annotations click to browse term
  CHEBI ontology 19816
    role 19764
      application 19426
        pharmaceutical 19301
          drug 19301
            hypoglycemic agent 4037
              tolbutamide 23
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Term Annotations click to browse term
  CHEBI ontology 19816
    subatomic particle 19814
      composite particle 19814
        hadron 19814
          baryon 19814
            nucleon 19814
              atomic nucleus 19814
                atom 19814
                  main group element atom 19702
                    p-block element atom 19702
                      carbon group element atom 19608
                        carbon atom 19597
                          organic molecular entity 19597
                            organic group 18537
                              organic divalent group 18530
                                organodiyl group 18530
                                  carbonyl group 18436
                                    carbonyl compound 18436
                                      carboxylic acid 18114
                                        carboacyl group 17372
                                          univalent carboacyl group 17372
                                            carbamoyl group 17158
                                              carboxamide 17158
                                                monocarboxylic acid amide 14569
                                                  urea 4989
                                                    ureas 4987
                                                      N-sulfonylurea 115
                                                        tolbutamide 23
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