CHEBI:76258 - oxyphenbutazone

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ChEBI Name oxyphenbutazone
ChEBI ID CHEBI:76258
Definition A 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 Commonly used (as its hydrate) to treat pain, swelling and stiffness associated with arthritis and gout, it was withdrawn from the market 1984 following association with blood dyscrasis and Stevens-Johnson syndrome.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C19H20N2O3
Net Charge 0
Average Mass 324.37370
Monoisotopic Mass 324.147
InChI InChI=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
InChIKey HFHZKZSRXITVMK-UHFFFAOYSA-N
SMILES CCCCC1C(=O)N(N(C1=O)c1ccc(O)cc1)c1ccccc1
Roles Classification
Biological Role(s): non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
drug metabolite

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.
Application(s): 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.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
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.
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.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 oxyphenbutazone hydrate (CHEBI:76259) has part oxyphenbutazone (CHEBI:76258)
INNs Sources
oxifenbutazona ChemIDplus
oxyphenbutazone WHO MedNet
oxyphenbutazone KEGG DRUG
oxyphenbutazonum ChemIDplus
Synonyms Sources
1-(p-Hydroxyphenyl)-2-phenyl-4-butyl-3,5-pyrazolidinedione DrugBank
1-Phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-butylpyrazolidine NIST Chemistry WebBook
1-Phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-n-butylpyrazolidine NIST Chemistry WebBook
3,5-Dioxo-1-phenyl-2-(p-hydroxyphenyl)-4-N-butylpyrazolidene ChemIDplus
4-Butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione DrugBank
4-Butyl-1-(p-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione DrugBank
4-Butyl-2-(4-hydroxyphenyl)-1-phenyl-3,5-dioxopyrazolidine DrugBank
4-Butyl-2-(p-hydroxyphenyl)-1-phenyl-3,5-pyrazolidinedione DrugBank
Hydroxyphenylbutazon DrugBank
Oxi-fenibutol ChemIDplus
Oxifenylbutazon ChemIDplus
Oxiphenbutazonum ChemIDplus
Oxyphenylbutazone ChemIDplus
p-Hydroxyphenylbutazone ChemIDplus
p-Oxyphenylbutazone NIST Chemistry WebBook
Manual Xrefs Databases
2036 DrugCentral
C19494 KEGG COMPOUND
D08324 KEGG DRUG
DB03585 DrugBank
EP642336 Patent
LSM-5029 LINCS
Oxyphenbutazone Wikipedia
US2008014272 Patent
WO2005107748 Patent
View more database links
Registry Numbers Types Sources
129-20-4 CAS Registry Number NIST Chemistry WebBook
129-20-4 CAS Registry Number ChemIDplus
129-20-4 CAS Registry Number KEGG DRUG
307474 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017