CHEBI:76258 - oxyphenbutazone

ChEBI IDCHEBI:76258
ChEBI Nameoxyphenbutazone
Stars
DefinitionA metabolite of phenylbutazone obtained by hydroxylation at position 4 of one of the phenyl rings. Commonly used (as its hydrate) to treat pain, swelling and stiffness associated with arthritis and gout, it was withdrawn from the market 1984 following association with blood dyscrasis and Stevens-Johnson syndrome.
Last Modified22 February 2017
SubmitterSteve
DownloadsMolfile
FormulaC19H20N2O3
Net Charge0
Average Mass324.380
Monoisotopic Mass324.14739
SMILESCCCCC1C(=O)N(c2ccccc2)N(c2ccc(O)cc2)C1=O
InChIInChI=1S/C19H20N2O3/c1-2-3-9-17-18(23)20(14-7-5-4-6-8-14)21(19(17)24)15-10-12-16(22)13-11-15/h4-8,10-13,17,22H,2-3,9H2,1H3
InChIKeyHFHZKZSRXITVMK-UHFFFAOYSA-N
Wikipedia
Roles Classification
Biological Roles:
xenobiotic metabolite  Any metabolite produced by metabolism of a xenobiotic compound.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
non-narcotic analgesic  A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
non-steroidal anti-inflammatory drug  An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
gout suppressant  A drug that increases uric acid excretion by the kidney (uricosuric drug), decreases uric acid production (antihyperuricemic), or alleviates the pain and inflammation of acute attacks of gout.
antipyretic  A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.
non-narcotic analgesic  A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
ChEBI Ontology
Outgoing Relation(s)
oxyphenbutazone (CHEBI:76258) has functional parent phenylbutazone (CHEBI:48574)
oxyphenbutazone (CHEBI:76258) has role antimicrobial agent (CHEBI:33281)
oxyphenbutazone (CHEBI:76258) has role antineoplastic agent (CHEBI:35610)
oxyphenbutazone (CHEBI:76258) has role antipyretic (CHEBI:35493)
oxyphenbutazone (CHEBI:76258) has role drug metabolite (CHEBI:49103)
oxyphenbutazone (CHEBI:76258) has role gout suppressant (CHEBI:35845)
oxyphenbutazone (CHEBI:76258) has role non-narcotic analgesic (CHEBI:35481)
oxyphenbutazone (CHEBI:76258) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
oxyphenbutazone (CHEBI:76258) has role xenobiotic metabolite (CHEBI:76206)
oxyphenbutazone (CHEBI:76258) is a phenols (CHEBI:33853)
oxyphenbutazone (CHEBI:76258) is a pyrazolidines (CHEBI:38312)
Incoming Relation(s)
oxyphenbutazone hydrate (CHEBI:76259) has part oxyphenbutazone (CHEBI:76258)
INNs  Source
oxyphenbutazoneKEGG DRUG
oxyphenbutazonumChemIDplus
oxifenbutazonaChemIDplus
oxyphenbutazoneWHO MedNet
Synonyms  Source
4-Butyl-2-(4-hydroxyphenyl)-1-phenyl-3,5-dioxopyrazolidineDrugBank
4-Butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedioneDrugBank
4-Butyl-1-(p-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedioneDrugBank
1-(p-Hydroxyphenyl)-2-phenyl-4-butyl-3,5-pyrazolidinedioneDrugBank
HydroxyphenylbutazonDrugBank
1-Phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-butylpyrazolidineNIST Chemistry WebBook
Manual XrefsDatabases
C19494KEGG COMPOUND
D08324KEGG DRUG
DB03585DrugBank
US2008014272Patent
WO2005107748Patent
EP642336Patent
OxyphenbutazoneWikipedia
LSM-5029LINCS
2036DrugCentral
Registry NumbersSources
Reaxys:307474Reaxys
CAS:129-20-4KEGG DRUG
CAS:129-20-4ChemIDplus
CAS:129-20-4NIST Chemistry WebBook
CAS:129-20-4KEGG COMPOUND
Citations