Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C19H19N2O2.Na |
| Molecular Weight | 330.3561 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CCCC[C-]1C(=O)N(N(C1=O)C2=CC=CC=C2)C3=CC=CC=C3
InChI
InChIKey=VYOUHDLOIRJOSW-UHFFFAOYSA-N
InChI=1S/C19H19N2O2.Na/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;/h4-13H,2-3,14H2,1H3;/q-1;+1
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 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 |
|---|---|---|
| Phenylbutazone-induced pericarditis. | 1965 Oct 2 |
|
| [The renal incidents of phenylbutazone]. | 1966 Dec 3 |
|
| Nephrotic syndrome caused by probenecid. | 1967 Jan 2 |
|
| Bone marrow depression induced by chloramphenicol or phenylbutazone. Leukemia and other sequelae. | 1967 Sep 11 |
|
| Probenecid, nephrotic syndrome, and renal failure. | 1968 May |
|
| [A fatal pathological condition with hyperglobulinemic purpura and polymyositis after phenylbutazone]. | 1968 Nov 15 |
|
| Mefanamic acid-induced haemolytic anaemia. | 1970 May 2 |
|
| Papillary necrosis following phenylbutazone ingestion. | 1971 Sep |
|
| Acetanilide oxidation in phenylbutazone-associated hypoplastic anaemia. | 1974 Aug 3 |
|
| [Primary cardiac involvement and painful salivary gland enlargement due to phenylbutazone]. | 1974 Mar 1 |
|
| Renal and gastric lesions after phenylbutazone and indomethacin in the rat. | 1974 Oct |
|
| Letter: Idiosyncrasy to phenothiazines in phenylbutazone-associated aplastic anaemia. | 1974 Oct 5 |
|
| Proceedings: A pharmacokinetic study of phenylbutazone-associated hypoplastic anaemia. | 1974 Sep |
|
| Phenylbutazone and hepatitis. | 1975 May |
|
| Further studies of the acute effects of phenylbutazone, oxyphenbutazone and indomethacin on the rat kidney. | 1976 Apr |
|
| Aplastic anemia from veterinary phenylbutazone. | 1976 Aug 30 |
|
| Polycythaemia in androgen-dependent aplastic anaemia. | 1976 Jan 24 |
|
| [Evaluation of the effects of some non-steroid anti-inflammatory agents on the gastric mucosa]. | 1976 Jul 7 |
|
| Granulomas and cholestatic--hepatocellular injury associated with phenylbutazone. Report of two cases. | 1977 Jul |
|
| Development of a lymphocytic lymphoma during immunosuppressive therapy with azathioprine for systemic lupus erythematosus with renal involvement induced by phenylbutazone. | 1977 Jul |
|
| Association of renal papillary necrosis and ankylosing spondylitis. | 1977 May |
|
| [Macroscopic hematuria during treatment with phenylbutazone derivatives. Positive lymphocyte transformation test for these drugs. Two cases in children]. | 1977 Oct |
|
| Renal papillary necrosis associated with indomethacin and phenylbutazone treated rheumatoid arthritis. | 1978 Apr |
|
| Drug-related gustatory disorders. | 1978 Jan-Feb |
|
| Confusion associated with cimetidine. | 1979 Dec 1 |
|
| Phenylbutazone-induced blood dyscrasias suspected in three dogs. | 1980 Sep 13 |
|
| 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 |
|
| Effects of large doses of phenylbutazone administration to horses. | 1983 May |
|
| Phenylbutazone-induced systemic vasculitis with crescentic glomerulonephritis. | 1985 Apr |
|
| 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 |
|
| [Hepatic lesions induced by drugs. Report of 26 cases]. | 1987 |
|
| 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 |
|
| Neurosensory adverse effects after phenylbutazone and misoprostol combined treatment. | 1989 Nov 25 |
|
| Anti-inflammatory activity and sub-acute toxicity of artemetin. | 1990 Feb |
|
| Aplastic anemia induced by an adulterated herbal medication. | 1995 |
|
| Misuse of veterinary phenylbutazone. | 1995 Jun 12 |
|
| Antiinflammatory 4,5-diarylpyrroles. 2. Activity as a function of cyclooxygenase-2 inhibition. | 1995 Sep 29 |
|
| Efficacy of anticancer alkylphosphocholines in Trypanosoma brucei subspecies. | 1997 Apr 15 |
|
| Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. | 1997 Jan 10 |
|
| [Phenylbutazone-induced sialadenitis fever simulating angioedema]. | 2002 Jan |
|
| Renal papillary necrosis. | 2002 Nov-Dec |
|
| Synthesis of biologically active N-methyl derivatives of amidines and cyclized five-membered products of amidines with oxalyl chloride. | 2008 Dec |
|
| Characterization of UDP-glucuronosyltransferases involved in glucuronidation of diethylstilbestrol in human liver and intestine. | 2012 Dec 17 |
|
| Use of micropatterned cocultures to detect compounds that cause drug-induced liver injury in humans. | 2013 Mar |
|
| Genomic biomarkers for cardiotoxicity in rats as a sensitive tool in preclinical studies. | 2013 Oct |
|
| FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1. | 2013 Sep 5 |
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| Code System | Code | Type | Description | ||
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SUB03773MIG
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46174103
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236529
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m8660
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204-935-7
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189M850I32
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DTXSID70926268
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129-18-0
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100000085296
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ACTIVE MOIETY
SUBSTANCE RECORD
