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 | C4H11NO2 |
Molecular Weight | 105.1356 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
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 |
|||
Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/809810 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14927431 |
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: |
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 |
---|---|---|
[The renal incidents of phenylbutazone]. | 1966 Dec 3 |
|
[Renal complications following phenylbutazone treatment]. | 1966 May 19 |
|
Rheumatoid arthritis: comparison of treatment with monophenylbutazone and phenylbutazone. | 1969 Dec 27 |
|
Mefanamic acid-induced haemolytic anaemia. | 1970 May 2 |
|
Papillary necrosis following phenylbutazone ingestion. | 1971 Sep |
|
Double-bind cross-over tiral of flurbiprofen and phenylbutazone in ankylosing spondylitis. | 1974 Nov 30 |
|
Proceedings: A pharmacokinetic study of phenylbutazone-associated hypoplastic anaemia. | 1974 Sep |
|
Phenylbutazone and hepatitis. | 1975 May |
|
Clinical evaluation of ketoprofen (Orudis) in rheumatoid arthritis. Results of a multi-centre, double-blind, cross-over trial against phenylbutazone. | 1976 |
|
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 |
|
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 |
|
Phenylbutazone and the horse--a review. | 1977 Jul |
|
Association of renal papillary necrosis and ankylosing spondylitis. | 1977 May |
|
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 |
|
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 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 |
|
Diagnosis of antibody-mediated drug allergy. Pyrazolinone and pyrazolidinedione cross-reactivity relationships. | 1987 Nov |
|
Neurosensory adverse effects after phenylbutazone and misoprostol combined treatment. | 1989 Nov 25 |
|
Aplastic anemia induced by an adulterated herbal medication. | 1995 |
|
Misuse of veterinary phenylbutazone. | 1995 Jun 12 |
|
Long-term exposure to the anti-inflammatory agent phenylbutazone induces kidney tumors in rats and liver tumors in mice. | 1995 Mar |
|
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 |
|
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 |
|
Development of an in vitro reporter gene assay to assess xenobiotic induction of the human CYP3A4 gene. | 1997 Oct-Dec |
|
Renal papillary necrosis. | 2002 Nov-Dec |
|
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 |
|
Identification of genomic biomarkers for concurrent diagnosis of drug-induced renal tubular injury using a large-scale toxicogenomics database. | 2009 Nov 9 |
|
Toxicogenomic biomarkers for renal papillary injury in rats. | 2013 Jan 7 |
|
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1. | 2013 Sep 5 |
|
Phenylbutazone Oxidation via Cu,Zn-SOD Peroxidase Activity: An EPR Study. | 2015 Jul 20 |
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 15:33:00 GMT 2023
by
admin
on
Fri Dec 15 15:33:00 GMT 2023
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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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Created by
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