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: phenylbutazone
Accession: CHEBI:48574
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Definition: A member of the class of pyrazolidines that is 1,2-diphenylpyrazolidine-3,5-dione carrying a butyl group at the 4-position.
Synonyms: related_synonym: 3,5-Dioxo-1,2-diphenyl-4-n-butylpyrazolidine; 4-BUTYL-1,2-DIPHENYL-PYRAZOLIDINE-3,5-DIONE; 4-butyl-1,2-diphenylpyrazolidine-3,5-dione; 4-n-Butyl-1,2-diphenyl-3,5-pyrazolidinedione; Formula=C19H20N2O2; InChI=1S/C19H20N2O2/c1-2-3-14-17-18(22)20(15-10-6-4-7-11-15)21(19(17)23)16-12-8-5-9-13-16/h4-13,17H,2-3,14H2,1H3; InChIKey=VYMDGNCVAMGZFE-UHFFFAOYSA-N; Phenbutazone; Phenylbutazon; SMILES=CCCCC1C(=O)N(N(C1=O)c1ccccc1)c1ccccc1; fenilbutazona; phenylbutazonum
alt_id: CHEBI:44635; CHEBI:8091
xref: Beilstein:290080; CAS:50-33-9; DrugBank:DB00812; Drug_Central:2145; HMDB:HMDB0014950; KEGG:C07440; KEGG:D00510; LINCS:LSM-2219
xref_mesh: MESH:D010653
xref: PDBeChem:P1Z; PMID:11264893; PMID:12692637; PMID:13010905; PMID:13048452; PMID:13747451; PMID:19614844; PMID:20176071; PMID:21668837; PMID:22082440; PMID:22180948; PMID:22245664; PMID:23369749; PMID:23525812; PMID:25287371; PMID:26090772; PMID:26808199; PMID:3425858; PMID:7655439; Reaxys:290080; VSDB:1775; Wikipedia:Phenylbutazone
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Bcat1
branched chain amino acid transaminase 1
increases expression
EXP
Phenylbutazone results in increased expression of BCAT1 mRNA
CTD
PMID:23558518
NCBI chr 4:177,964,834...178,046,573
Ensembl chr 4:177,964,834...178,046,597
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Ccnd1
cyclin D1
multiple interactions
ISO
Phenylbutazone inhibits the reaction [TNF protein results in increased expression of CCND1 protein]
CTD
PMID:15489888
NCBI chr 1:200,089,002...200,098,524
Ensembl chr 1:200,089,002...200,098,602
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Chuk
component of inhibitor of nuclear factor kappa B kinase complex
multiple interactions
ISO
Phenylbutazone inhibits the reaction [TNF protein results in increased activity of CHUK protein]
CTD
PMID:15489888
NCBI chr 1:242,959,539...242,995,066
Ensembl chr 1:242,959,760...242,995,065
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Cyp3a2
cytochrome P450, family 3, subfamily a, polypeptide 2
increases expression increases activity multiple interactions
ISO
Phenylbutazone results in increased expression of CYP3A4 mRNA Phenylbutazone results in increased activity of CYP3A4 protein NR3C1 protein promotes the reaction [Phenylbutazone results in increased expression of CYP3A4 mRNA]
CTD
PMID:9512926 PMID:10219967
NCBI chr12:9,207,978...9,230,064
Ensembl chr12:9,015,383...9,285,008
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Gstp1
glutathione S-transferase pi 1
multiple interactions
ISO
Phenylbutazone inhibits the reaction [GSTP1 protein results in increased metabolism of 1-chloro-2,4-dinitrobenzene-glutathione conjugate]
CTD
PMID:23769903
NCBI chr 1:201,337,762...201,340,230
Ensembl chr 1:201,321,672...201,340,226
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Havcr1
hepatitis A virus cellular receptor 1
increases expression
EXP
Phenylbutazone results in increased expression of HAVCR1 mRNA
CTD
PMID:23142791
NCBI chr10:31,118,667...31,151,730
Ensembl chr10:31,119,088...31,151,698
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Krt14
keratin 14
increases expression
EXP
Phenylbutazone results in increased expression of KRT14 mRNA
CTD
PMID:23142791
NCBI chr10:85,137,786...85,142,054
Ensembl chr10:85,066,802...85,171,799
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Lmcd1
LIM and cysteine-rich domains 1
increases expression
EXP
Phenylbutazone results in increased expression of LMCD1 mRNA
CTD
PMID:23558518
NCBI chr 4:145,393,153...145,452,049
Ensembl chr 4:145,393,145...145,452,046
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Nfkb1
nuclear factor kappa B subunit 1
multiple interactions
ISO
Phenylbutazone inhibits the reaction [TNF protein results in increased activity of [NFKB1 protein binds to RELA protein]]; Phenylbutazone inhibits the reaction [TNF protein results in increased activity of NFKB1 protein]
CTD
PMID:15489888
NCBI chr 2:224,016,214...224,132,135
Ensembl chr 2:224,016,214...224,110,404
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Nfkbia
NFKB inhibitor alpha
multiple interactions
ISO
Phenylbutazone inhibits the reaction [TNF protein results in increased degradation of NFKBIA protein]
CTD
PMID:15489888
NCBI chr 6:72,858,713...72,861,941
Ensembl chr 6:72,858,712...72,861,941
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Nr3c1
nuclear receptor subfamily 3, group C, member 1
multiple interactions
ISO
NR3C1 protein promotes the reaction [Phenylbutazone results in increased expression of CYP3A4 mRNA]
CTD
PMID:10219967
NCBI chr18:31,271,681...31,393,320
Ensembl chr18:31,271,681...31,393,375
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Ptgs2
prostaglandin-endoperoxide synthase 2
multiple interactions
ISO
Phenylbutazone inhibits the reaction [TNF protein results in increased expression of PTGS2 protein]
CTD
PMID:15489888
NCBI chr13:62,163,936...62,172,193
Ensembl chr13:62,163,932...62,172,188
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Rela
RELA proto-oncogene, NF-kB subunit
multiple interactions
ISO
Phenylbutazone inhibits the reaction [TNF protein results in increased activity of [NFKB1 protein binds to RELA protein]]; Phenylbutazone inhibits the reaction [TNF protein results in increased activity of RELA protein]
CTD
PMID:15489888
NCBI chr 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484
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Rnd1
Rho family GTPase 1
increases expression
EXP
Phenylbutazone results in increased expression of RND1 mRNA
CTD
PMID:23558518
NCBI chr 7:129,821,311...129,828,385
Ensembl chr 7:129,821,311...129,828,399
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Sell
selectin L
affects expression
ISO
Phenylbutazone affects the expression of SELL protein
CTD
PMID:12147693
NCBI chr13:76,416,969...76,436,444
Ensembl chr13:76,416,915...76,436,456
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Slc22a12
solute carrier family 22 member 12
multiple interactions
ISO
Phenylbutazone inhibits the reaction [SLC22A12 protein results in increased uptake of Uric Acid]
CTD
PMID:21272127
NCBI chr 1:203,845,039...203,852,496
Ensembl chr 1:203,845,048...203,853,555
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Tgfb2
transforming growth factor, beta 2
increases expression
EXP
Phenylbutazone results in increased expression of TGFB2 mRNA
CTD
PMID:23558518
NCBI chr13:98,160,075...98,261,771
Ensembl chr13:98,160,087...98,261,405
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Tnf
tumor necrosis factor
multiple interactions
ISO
Phenylbutazone inhibits the reaction [Lipopolysaccharides results in increased expression of TNF protein]; Phenylbutazone inhibits the reaction [TNF protein results in increased activity of [NFKB1 protein binds to RELA protein]]; Phenylbutazone inhibits the reaction [TNF protein results in increased activity of CHUK protein]; Phenylbutazone inhibits the reaction [TNF protein results in increased activity of NFKB1 protein]; Phenylbutazone inhibits the reaction [TNF protein results in increased activity of RELA protein]; Phenylbutazone inhibits the reaction [TNF protein results in increased degradation of NFKBIA protein]; Phenylbutazone inhibits the reaction [TNF protein results in increased expression of CCND1 protein]; Phenylbutazone inhibits the reaction [TNF protein results in increased expression of PTGS2 protein] [Phenylbutazone co-treated with Lipopolysaccharides] results in increased secretion of TNF protein
CTD
PMID:10328874 PMID:15489888 PMID:17328244
NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
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Ugt1a1
UDP glucuronosyltransferase family 1 member A1
multiple interactions
ISO
Phenylbutazone inhibits the reaction [UGT1A1 protein results in increased glucuronidation of Diethylstilbestrol]
CTD
PMID:23126256
NCBI chr 9:88,801,344...88,808,465
Ensembl chr 9:88,713,184...88,808,465
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Ugt1a2
UDP glucuronosyltransferase 1 family, polypeptide A2
multiple interactions
ISO
Phenylbutazone inhibits the reaction [UGT1A3 protein results in increased glucuronidation of Diethylstilbestrol]
CTD
PMID:23126256
NCBI chr 9:88,791,216...88,808,465
Ensembl chr 9:88,713,184...88,808,465
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Gstp1
glutathione S-transferase pi 1
multiple interactions
ISO
Oxyphenbutazone inhibits the reaction [GSTP1 protein results in increased metabolism of 1-chloro-2,4-dinitrobenzene-glutathione conjugate]
CTD
PMID:23769903
NCBI chr 1:201,337,762...201,340,230
Ensembl chr 1:201,321,672...201,340,226
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Hsf1
heat shock transcription factor 1
increases activity
ISO
Oxyphenbutazone results in increased activity of HSF1 protein
CTD
PMID:34170685
NCBI chr 7:108,196,040...108,223,011
Ensembl chr 7:108,196,056...108,223,011
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