Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C19H20N2O2.C4H11NO2 |
| Molecular Weight | 413.5099 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OCCNCCO.CCCCC1C(=O)N(N(C1=O)C2=CC=CC=C2)C3=CC=CC=C3
InChI
InChIKey=RZQGMINQPCEZCE-UHFFFAOYSA-N
InChI=1S/C19H20N2O2.C4H11NO2/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;6-3-1-5-2-4-7/h4-13,17H,2-3,14H2,1H3;5-7H,1-4H2
| Molecular Formula | C19H20N2O2 |
| Molecular Weight | 308.3743 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C4H11NO2 |
| Molecular Weight | 105.1356 |
| Charge | 0 |
| Count |
|
| 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) |
|||
Target ID: CHEMBL2094253 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Palliative | BUTAZOLIDIN Approved UseUnknown |
|||
| Palliative | BUTAZOLIDIN Approved UseUnknown |
Doses
| Dose | Population | Adverse events |
|---|---|---|
8 g single, oral Overdose |
healthy, 17 years |
Other AEs: Jaundice, Renal disorder NOS... |
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 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 |
|
| Renal disorder NOS | 8 g single, oral Overdose |
healthy, 17 years |
|
| 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 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 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 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 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 Age Group: 52.8 years (range: 24-89 years) Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Development of an in vitro reporter gene assay to assess xenobiotic induction of the human CYP3A4 gene. | 1998-03-26 |
|
| Efficacy of anticancer alkylphosphocholines in Trypanosoma brucei subspecies. | 1997-04-15 |
|
| Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. | 1997-01-10 |
|
| Inhibition of tolbutamide 4-methylhydroxylation by a series of non-steroidal anti-inflammatory drugs in V79-NH cells expressing human cytochrome P4502C10. | 1996-12 |
|
| Antiinflammatory 4,5-diarylpyrroles. 2. Activity as a function of cyclooxygenase-2 inhibition. | 1995-09-29 |
|
| Misuse of veterinary phenylbutazone. | 1995-06-12 |
|
| Long-term exposure to the anti-inflammatory agent phenylbutazone induces kidney tumors in rats and liver tumors in mice. | 1995-03 |
|
| Aplastic anemia induced by an adulterated herbal medication. | 1995 |
|
| Antrafenine: anti-inflammatory activity with respect to oedema and leucocyte infiltration in the rat. | 1984-02 |
|
| Phenylbutazone nephrotoxicity--a light and electron microscopic study. | 1983-12 |
|
| [Kidney damage after treatment with butapyrazole]. | 1983-11-15 |
|
| Renal medullary crest necrosis associated with phenylbutazone therapy in horses. | 1983-11 |
|
| Effects of large doses of phenylbutazone administration to horses. | 1983-05 |
|
| Phenylbutazone associated glomerulonephritis. Glomerulonephritis and fever. | 1982-12 |
|
| Sialadenitis and systemic reaction associated with phenylbutazone. | 1982-06 |
|
| Animal experiments on the safety pharmacology of lofexidine. | 1982 |
|
| Phenylbutazone liver injury: a clinical-pathologic survey of 23 cases and review of the literature. | 1981-05-01 |
|
| Acute nephrotic syndrome with reversible renal failure after phenylbutazone. | 1981-03-21 |
|
| Intrahepatic cholestasis induced by phenylbutazone. | 1981 |
|
| Phenylbutazone-induced blood dyscrasias suspected in three dogs. | 1980-09-13 |
|
| Use of phenylbutazone in sports medicine: understanding the risks. | 1980-07-01 |
|
| Exacerbation of phenylbutazone-related renal failure by indomethacin. | 1978-11 |
|
| Interstitial nephritis in a case of phenylbutazone hypersensitivity. | 1978-05-20 |
|
| Drug-related gustatory disorders. | 1978-01-01 |
|
| Granulomas and cholestatic--hepatocellular injury associated with phenylbutazone. Report of two cases. | 1977-07 |
|
| Development of a lymphocytic lymphoma during immunosuppressive therapy with azathioprine for systemic lupus erythematosus with renal involvement induced by phenylbutazone. | 1977-07 |
|
| Association of renal papillary necrosis and ankylosing spondylitis. | 1977-05 |
|
| Aplastic anemia from veterinary phenylbutazone. | 1976-08-30 |
|
| Further studies of the acute effects of phenylbutazone, oxyphenbutazone and indomethacin on the rat kidney. | 1976-04 |
|
| Clinical evaluation of ketoprofen (Orudis) in rheumatoid arthritis. Results of a multi-centre, double-blind, cross-over trial against phenylbutazone. | 1976 |
|
| Double-bind cross-over tiral of flurbiprofen and phenylbutazone in ankylosing spondylitis. | 1974-11-30 |
|
| Letter: Idiosyncrasy to phenothiazines in phenylbutazone-associated aplastic anaemia. | 1974-10-05 |
|
| Renal and gastric lesions after phenylbutazone and indomethacin in the rat. | 1974-10 |
|
| Proceedings: A pharmacokinetic study of phenylbutazone-associated hypoplastic anaemia. | 1974-09 |
|
| Aspirin and the kidney. New Zealand Rheumatism Association Study. | 1974-03-30 |
|
| [Primary cardiac involvement and painful salivary gland enlargement due to phenylbutazone]. | 1974-03-01 |
|
| [Acute renal insufficiency following butapyrazole treatment in the course of plasmatic cell leukemia (author's transl)]. | 1973 |
|
| Papillary necrosis following phenylbutazone ingestion. | 1971-09 |
|
| [Allergo-toxic disturbances of the heart muscle with congestive heart failure as a result of parenteral treatment with phenylbutazone]. | 1971-02 |
|
| Treatment of aplastic anemia with nandrolone decanoate. | 1970-12 |
|
| Mefanamic acid-induced haemolytic anaemia. | 1970-05-02 |
|
| Rheumatoid arthritis: comparison of treatment with monophenylbutazone and phenylbutazone. | 1969-12-27 |
|
| [A fatal pathological condition with hyperglobulinemic purpura and polymyositis after phenylbutazone]. | 1968-11-15 |
|
| Probenecid, nephrotic syndrome, and renal failure. | 1968-05 |
|
| Phenylbutazone anuria. | 1967-12 |
|
| Bone marrow depression induced by chloramphenicol or phenylbutazone. Leukemia and other sequelae. | 1967-09-11 |
|
| Nephrotic syndrome caused by probenecid. | 1967-01-02 |
|
| [The renal incidents of phenylbutazone]. | 1966-12-03 |
|
| [Renal complications following phenylbutazone treatment]. | 1966-05-19 |
|
| Phenylbutazone-induced pericarditis. | 1965-10-02 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:00:50 GMT 2025
by
admin
on
Mon Mar 31 18:00:50 GMT 2025
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| Record UNII |
A09K6UG6UJ
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| Record Status |
Validated (UNII)
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| Record Version |
|
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109374152
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36551-68-5
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