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
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) |
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Target ID: CHEMBL2094253 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| 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: |
|
| 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: |
|
| 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: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Vasculitis allergica cutis caused by phenylbutazone]. | 1966 |
|
| Rheumatoid arthritis: comparison of treatment with monophenylbutazone and phenylbutazone. | 1969 Dec 27 |
|
| Treatment of aplastic anemia with nandrolone decanoate. | 1970 Dec |
|
| Mefanamic acid-induced haemolytic anaemia. | 1970 May 2 |
|
| [Allergo-toxic disturbances of the heart muscle with congestive heart failure as a result of parenteral treatment with phenylbutazone]. | 1971 Feb |
|
| Papillary necrosis following phenylbutazone ingestion. | 1971 Sep |
|
| [Acute renal insufficiency following butapyrazole treatment in the course of plasmatic cell leukemia (author's transl)]. | 1973 |
|
| 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 |
|
| 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 |
|
| Proceedings: A pharmacokinetic study of phenylbutazone-associated hypoplastic anaemia. | 1974 Sep |
|
| Clinical evaluation of ketoprofen (Orudis) in rheumatoid arthritis. Results of a multi-centre, double-blind, cross-over trial against phenylbutazone. | 1976 |
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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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| Development of a lymphocytic lymphoma during immunosuppressive therapy with azathioprine for systemic lupus erythematosus with renal involvement induced by phenylbutazone. | 1977 Jul |
|
| Drug-related gustatory disorders. | 1978 Jan-Feb |
|
| Interstitial nephritis in a case of phenylbutazone hypersensitivity. | 1978 May 20 |
|
| Exacerbation of phenylbutazone-related renal failure by indomethacin. | 1978 Nov |
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| Confusion associated with cimetidine. | 1979 Dec 1 |
|
| Use of phenylbutazone in sports medicine: understanding the risks. | 1980 Jul-Aug |
|
| Phenylbutazone-induced blood dyscrasias suspected in three dogs. | 1980 Sep 13 |
|
| Intrahepatic cholestasis induced by phenylbutazone. | 1981 |
|
| Acute nephrotic syndrome with reversible renal failure after phenylbutazone. | 1981 Mar 21 |
|
| Phenylbutazone liver injury: a clinical-pathologic survey of 23 cases and review of the literature. | 1981 May-Jun |
|
| Animal experiments on the safety pharmacology of lofexidine. | 1982 |
|
| Phenylbutazone associated glomerulonephritis. Glomerulonephritis and fever. | 1982 Dec |
|
| Sialadenitis and systemic reaction associated with phenylbutazone. | 1982 Jun |
|
| Phenylbutazone nephrotoxicity--a light and electron microscopic study. | 1983 Dec |
|
| Effects of large doses of phenylbutazone administration to horses. | 1983 May |
|
| Renal medullary crest necrosis associated with phenylbutazone therapy in horses. | 1983 Nov |
|
| [Kidney damage after treatment with butapyrazole]. | 1983 Nov 15 |
|
| Antrafenine: anti-inflammatory activity with respect to oedema and leucocyte infiltration in the rat. | 1984 Feb |
|
| Phenylbutazone-induced systemic vasculitis with crescentic glomerulonephritis. | 1985 Apr |
|
| Drug-induced hepatitis associated with anticytoplasmic organelle autoantibodies. | 1985 Sep-Oct |
|
| Strain-related susceptibility to nephrotoxicity induced by aspirin and phenylbutazone in rats. | 1986 |
|
| 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 |
|
| Diagnosis of antibody-mediated drug allergy. Pyrazolinone and pyrazolidinedione cross-reactivity relationships. | 1987 Nov |
|
| Differential effects of non-steroidal anti-inflammatory drugs on seizures produced by pilocarpine in rats. | 1988 Oct 18 |
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| Aplastic anemia induced by an adulterated herbal medication. | 1995 |
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| Misuse of veterinary phenylbutazone. | 1995 Jun 12 |
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| Long-term exposure to the anti-inflammatory agent phenylbutazone induces kidney tumors in rats and liver tumors in mice. | 1995 Mar |
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| Antiinflammatory 4,5-diarylpyrroles. 2. Activity as a function of cyclooxygenase-2 inhibition. | 1995 Sep 29 |
|
| 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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| Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. | 1997 Jan 10 |
|
| Development of an in vitro reporter gene assay to assess xenobiotic induction of the human CYP3A4 gene. | 1997 Oct-Dec |
Patents
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109374152
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36551-68-5
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A09K6UG6UJ
Created by
admin on Fri Dec 15 15:33:00 GMT 2023 , Edited by admin on Fri Dec 15 15:33:00 GMT 2023
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PARENT (SALT/SOLVATE)
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
