Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H20N2O2 |
Molecular Weight | 308.3743 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC1C(=O)N(N(C1=O)C2=CC=CC=C2)C3=CC=CC=C3
InChI
InChIKey=VYMDGNCVAMGZFE-UHFFFAOYSA-N
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
Molecular Formula | C19H20N2O2 |
Molecular Weight | 308.3743 |
Charge | 0 |
Count |
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Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Phenylbutazone is an anti-inflammatory drug, which binds to and inactivates cyclooxygenases and prostacyclin synthase through peroxide (H2O2) mediated deactivation. The reduced production of prostaglandin leads to reduced inflammation of the surrounding tissues. Phenylbutazone was marked under the brand name butazolidin for the treatment rheumatoid arthritis and gout, but then this usage was discontinued. In addition, phenylbutazone is used in UK for the treatment of ankylosing spondylitis, but only in those cases, when other therapies are unsuitable.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Q16647 Gene ID: 5740.0 Gene Symbol: PTGIS Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/3917545 |
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Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/809810 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Sources: https://www.ncbi.nlm.nih.gov/pubmed/14927431 |
Palliative | BUTAZOLIDIN Approved UseUnknown |
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Palliative | BUTAZOLIDIN Approved UseUnknown |
Doses
Dose | Population | Adverse events |
---|---|---|
8 g single, oral Overdose |
healthy, 17 years n = 1 Health Status: healthy Age Group: 17 years Sex: F Population Size: 1 Sources: |
Other AEs: Renal disorder NOS, Jaundice... |
800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
unhealthy, 52.8 years (range: 24-89 years) Health Status: unhealthy Condition: acute gouty arthritis Age Group: 52.8 years (range: 24-89 years) Sources: |
Other AEs: Rash, Dyspepsia... Other AEs: Rash (1 patient) Sources: Dyspepsia (1 patient) Constipation (2 patients) Sleepiness (1 patient) Irritability (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Jaundice | 8 g single, oral Overdose |
healthy, 17 years n = 1 Health Status: healthy Age Group: 17 years Sex: F Population Size: 1 Sources: |
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Renal disorder NOS | 8 g single, oral Overdose |
healthy, 17 years n = 1 Health Status: healthy Age Group: 17 years Sex: F Population Size: 1 Sources: |
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Dyspepsia | 1 patient | 800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
unhealthy, 52.8 years (range: 24-89 years) Health Status: unhealthy Condition: acute gouty arthritis Age Group: 52.8 years (range: 24-89 years) Sources: |
Irritability | 1 patient | 800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
unhealthy, 52.8 years (range: 24-89 years) Health Status: unhealthy Condition: acute gouty arthritis Age Group: 52.8 years (range: 24-89 years) Sources: |
Rash | 1 patient | 800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
unhealthy, 52.8 years (range: 24-89 years) Health Status: unhealthy Condition: acute gouty arthritis Age Group: 52.8 years (range: 24-89 years) Sources: |
Sleepiness | 1 patient | 800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
unhealthy, 52.8 years (range: 24-89 years) Health Status: unhealthy Condition: acute gouty arthritis Age Group: 52.8 years (range: 24-89 years) Sources: |
Constipation | 2 patients | 800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
unhealthy, 52.8 years (range: 24-89 years) Health Status: unhealthy Condition: acute gouty arthritis Age Group: 52.8 years (range: 24-89 years) Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/17578901/ Page: 5.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/17578901/ Page: 5.0 |
partial | |||
yes [Ki 11 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/17578901/ Page: 5.0 |
yes [Ki 354 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/17578901/ Page: 5.0 |
yes [Ki 6.82 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/17578901/ Page: 5.0 |
yes [Ki 71.6 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/10219967/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12130730/ Page: 1.0 |
yes | |||
yes |
PubMed
Title | Date | PubMed |
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Phenylbutazone-induced pericarditis. | 1965 Oct 2 |
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[Vasculitis allergica cutis caused by phenylbutazone]. | 1966 |
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[The renal incidents of phenylbutazone]. | 1966 Dec 3 |
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Phenylbutazone anuria. | 1967 Dec |
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Nephrotic syndrome caused by probenecid. | 1967 Jan 2 |
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Probenecid, nephrotic syndrome, and renal failure. | 1968 May |
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[A fatal pathological condition with hyperglobulinemic purpura and polymyositis after phenylbutazone]. | 1968 Nov 15 |
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Rheumatoid arthritis: comparison of treatment with monophenylbutazone and phenylbutazone. | 1969 Dec 27 |
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Treatment of aplastic anemia with nandrolone decanoate. | 1970 Dec |
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Mefanamic acid-induced haemolytic anaemia. | 1970 May 2 |
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[Allergo-toxic disturbances of the heart muscle with congestive heart failure as a result of parenteral treatment with phenylbutazone]. | 1971 Feb |
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Papillary necrosis following phenylbutazone ingestion. | 1971 Sep |
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[Acute renal insufficiency following butapyrazole treatment in the course of plasmatic cell leukemia (author's transl)]. | 1973 |
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Femoral neuropathy due to retroperitoneal bleeding. An unusual complication of heparin therapy. | 1973 Jul |
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Acetanilide oxidation in phenylbutazone-associated hypoplastic anaemia. | 1974 Aug 3 |
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[Primary cardiac involvement and painful salivary gland enlargement due to phenylbutazone]. | 1974 Mar 1 |
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Aspirin and the kidney. New Zealand Rheumatism Association Study. | 1974 Mar 30 |
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Double-bind cross-over tiral of flurbiprofen and phenylbutazone in ankylosing spondylitis. | 1974 Nov 30 |
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Renal and gastric lesions after phenylbutazone and indomethacin in the rat. | 1974 Oct |
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Letter: Idiosyncrasy to phenothiazines in phenylbutazone-associated aplastic anaemia. | 1974 Oct 5 |
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Proceedings: A pharmacokinetic study of phenylbutazone-associated hypoplastic anaemia. | 1974 Sep |
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Further studies of the acute effects of phenylbutazone, oxyphenbutazone and indomethacin on the rat kidney. | 1976 Apr |
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Aplastic anemia from veterinary phenylbutazone. | 1976 Aug 30 |
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Polycythaemia in androgen-dependent aplastic anaemia. | 1976 Jan 24 |
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[Evaluation of the effects of some non-steroid anti-inflammatory agents on the gastric mucosa]. | 1976 Jul 7 |
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Granulomas and cholestatic--hepatocellular injury associated with phenylbutazone. Report of two cases. | 1977 Jul |
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Development of a lymphocytic lymphoma during immunosuppressive therapy with azathioprine for systemic lupus erythematosus with renal involvement induced by phenylbutazone. | 1977 Jul |
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Phenylbutazone and the horse--a review. | 1977 Jul |
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[Macroscopic hematuria during treatment with phenylbutazone derivatives. Positive lymphocyte transformation test for these drugs. Two cases in children]. | 1977 Oct |
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Renal papillary necrosis associated with indomethacin and phenylbutazone treated rheumatoid arthritis. | 1978 Apr |
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Drug-related gustatory disorders. | 1978 Jan-Feb |
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Sialadenitis and systemic reaction associated with phenylbutazone. | 1982 Jun |
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Drug-induced hepatitis associated with anticytoplasmic organelle autoantibodies. | 1985 Sep-Oct |
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Strain-related susceptibility to nephrotoxicity induced by aspirin and phenylbutazone in rats. | 1986 |
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Risks of agranulocytosis and aplastic anemia. A first report of their relation to drug use with special reference to analgesics. The International Agranulocytosis and Aplastic Anemia Study. | 1986 Oct 3 |
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Dermatomyositis-like syndrome associated with phenylbutazone therapy. | 1987 Apr |
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Differential effects of non-steroidal anti-inflammatory drugs on seizures produced by pilocarpine in rats. | 1988 Oct 18 |
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Anti-inflammatory activity and sub-acute toxicity of artemetin. | 1990 Feb |
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Inhibition of tolbutamide 4-methylhydroxylation by a series of non-steroidal anti-inflammatory drugs in V79-NH cells expressing human cytochrome P4502C10. | 1996 Dec |
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Efficacy of anticancer alkylphosphocholines in Trypanosoma brucei subspecies. | 1997 Apr 15 |
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Development of an in vitro reporter gene assay to assess xenobiotic induction of the human CYP3A4 gene. | 1997 Oct-Dec |
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Non-steroidal anti-inflammatory drugs inhibit the expression of cytokines and induce HSP70 in human monocytes. | 1999 May |
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Structure-function relationship and role of tumor necrosis factor-alpha-converting enzyme in the down-regulation of L-selectin by non-steroidal anti-inflammatory drugs. | 2002 Oct 11 |
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Nonsteroidal anti-inflammatory agents differ in their ability to suppress NF-kappaB activation, inhibition of expression of cyclooxygenase-2 and cyclin D1, and abrogation of tumor cell proliferation. | 2004 Dec 9 |
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Immunomodulatory effect of nonsteroidal anti-inflammatory drugs (NSAIDs) at the clinically available doses. | 2007 Jan |
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Characterization of UDP-glucuronosyltransferases involved in glucuronidation of diethylstilbestrol in human liver and intestine. | 2012 Dec 17 |
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Nonsteroidal anti-inflammatory drug sensitizes Mycobacterium tuberculosis to endogenous and exogenous antimicrobials. | 2012 Oct 2 |
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Toxicogenomic biomarkers for renal papillary injury in rats. | 2013 Jan 7 |
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Use of micropatterned cocultures to detect compounds that cause drug-induced liver injury in humans. | 2013 Mar |
|
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1. | 2013 Sep 5 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/796939
300 mg daily for 4 weeks
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3698130
Unknown
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:16:04 GMT 2023
by
admin
on
Fri Dec 15 15:16:04 GMT 2023
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Record UNII |
GN5P7K3T8S
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 522.1720
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CFR |
21 CFR 520.1720D
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CFR |
21 CFR 520.1720
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CFR |
21 CFR 520.1720B
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CFR |
21 CFR 520.1720C
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CFR |
21 CFR 520.1720A
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NCI_THESAURUS |
C257
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WHO-VATC |
QM02AA01
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CFR |
21 CFR 520.1720E
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WHO-VATC |
QM01BA01
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WHO-ATC |
M02AA01
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IARC | Phenylbutazone | ||
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WHO-VATC |
QM01AA01
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WHO-ATC |
M01BA01
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WHO-ATC |
M01AA01
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m8660
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1531007
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CHEMBL101
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GN5P7K3T8S
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PHENYLBUTAZONE
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8160
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C66377
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200-029-0
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DTXSID9021136
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SUB09787MIG
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50-33-9
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4781
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100000092182
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7270
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3159
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DB00812
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48574
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2145
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D010653
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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SALT/SOLVATE -> PARENT | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PARENT |
Metabolite to parent drug ratio in non-uraemic human plasma.
METABOLITE TO PARENT DRUG RATIO
PLASMA; URINE
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METABOLITE ACTIVE -> PARENT |
Oxyphenbutazone, having the same antirheumatic and sodium retaining activities as phenylbutazone, is in clinical use.
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METABOLITE ACTIVE -> PARENT |
Percent of dose excreted in urine as metabolite.
AMOUNT ADMINISTERED
URINE
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 0.55
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |