Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H20N2O2.C4H10N2 |
Molecular Weight | 394.5099 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C1CNCCN1.CCCCC2C(=O)N(N(C2=O)C3=CC=CC=C3)C4=CC=CC=C4
InChI
InChIKey=HWGAOXKGTHUMFZ-UHFFFAOYSA-N
InChI=1S/C19H20N2O2.C4H10N2/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;1-2-6-4-3-5-1/h4-13,17H,2-3,14H2,1H3;5-6H,1-4H2
Molecular Formula | C4H10N2 |
Molecular Weight | 86.1356 |
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 |
---|---|---|
Phenylbutazone-induced pericarditis. | 1965 Oct 2 |
|
[Vasculitis allergica cutis caused by phenylbutazone]. | 1966 |
|
Nephrotic syndrome caused by probenecid. | 1967 Jan 2 |
|
Rheumatoid arthritis: comparison of treatment with monophenylbutazone and phenylbutazone. | 1969 Dec 27 |
|
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 |
|
[Acute renal insufficiency following butapyrazole treatment in the course of plasmatic cell leukemia (author's transl)]. | 1973 |
|
[Primary cardiac involvement and painful salivary gland enlargement due to phenylbutazone]. | 1974 Mar 1 |
|
Aspirin and the kidney. New Zealand Rheumatism Association Study. | 1974 Mar 30 |
|
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 |
|
Granulomas and cholestatic--hepatocellular injury associated with phenylbutazone. Report of two cases. | 1977 Jul |
|
Phenylbutazone and the horse--a review. | 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 |
|
Interstitial nephritis in a case of phenylbutazone hypersensitivity. | 1978 May 20 |
|
Confusion associated with cimetidine. | 1979 Dec 1 |
|
Use of phenylbutazone in sports medicine: understanding the risks. | 1980 Jul-Aug |
|
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 |
|
[Nephrotic syndrome and acute interstitial nephritis after phenylbutazone]. | 1985 Nov 2 |
|
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 |
|
[Hepatic lesions induced by drugs. Report of 26 cases]. | 1987 |
|
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 |
|
Anti-inflammatory activity and sub-acute toxicity of artemetin. | 1990 Feb |
|
Misuse of veterinary phenylbutazone. | 1995 Jun 12 |
|
Efficacy of anticancer alkylphosphocholines in Trypanosoma brucei subspecies. | 1997 Apr 15 |
|
Development of an in vitro reporter gene assay to assess xenobiotic induction of the human CYP3A4 gene. | 1997 Oct-Dec |
|
Non-steroidal anti-inflammatory drugs inhibit the expression of cytokines and induce HSP70 in human monocytes. | 1999 May |
|
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 |
|
Synthesis of biologically active N-methyl derivatives of amidines and cyclized five-membered products of amidines with oxalyl chloride. | 2008 Dec |
|
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 |
|
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 |
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
Sat Dec 17 01:54:00 UTC 2022
by
admin
on
Sat Dec 17 01:54:00 UTC 2022
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Record UNII |
0J1026H8UB
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Record Status |
Validated (UNII)
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Record Version |
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-
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SUB37106
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225-639-4
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SUB03774MIG
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236354
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M8660
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C100279
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78682
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