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 |
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: |
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 |
---|---|---|
[Renal complications following phenylbutazone treatment]. | 1966 May 19 |
|
Nephrotic syndrome caused by probenecid. | 1967 Jan 2 |
|
Probenecid, nephrotic syndrome, and renal failure. | 1968 May |
|
Rheumatoid arthritis: comparison of treatment with monophenylbutazone and phenylbutazone. | 1969 Dec 27 |
|
Papillary necrosis following phenylbutazone ingestion. | 1971 Sep |
|
[Acute renal insufficiency following butapyrazole treatment in the course of plasmatic cell leukemia (author's transl)]. | 1973 |
|
Acetanilide oxidation in phenylbutazone-associated hypoplastic anaemia. | 1974 Aug 3 |
|
Aspirin and the kidney. New Zealand Rheumatism Association Study. | 1974 Mar 30 |
|
Proceedings: A pharmacokinetic study of phenylbutazone-associated hypoplastic anaemia. | 1974 Sep |
|
[Evaluation of the effects of some non-steroid anti-inflammatory agents on the gastric mucosa]. | 1976 Jul 7 |
|
Renal papillary necrosis associated with indomethacin and phenylbutazone treated rheumatoid arthritis. | 1978 Apr |
|
Drug-related gustatory disorders. | 1978 Jan-Feb |
|
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 |
|
Intrahepatic cholestasis induced by phenylbutazone. | 1981 |
|
Acute nephrotic syndrome with reversible renal failure after phenylbutazone. | 1981 Mar 21 |
|
Sialadenitis and systemic reaction associated with phenylbutazone. | 1982 Jun |
|
Phenylbutazone nephrotoxicity--a light and electron microscopic study. | 1983 Dec |
|
Drug-induced hepatitis associated with anticytoplasmic organelle autoantibodies. | 1985 Sep-Oct |
|
[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 |
|
Long-term exposure to the anti-inflammatory agent phenylbutazone induces kidney tumors in rats and liver tumors in mice. | 1995 Mar |
|
Non-steroidal anti-inflammatory drugs inhibit the expression of cytokines and induce HSP70 in human monocytes. | 1999 May |
|
Interactions of urate transporter URAT1 in human kidney with uricosuric drugs. | 2011 Feb |
|
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 |
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
Mon Mar 31 19:31:30 GMT 2025
by
admin
on
Mon Mar 31 19:31:30 GMT 2025
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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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0J1026H8UB
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SUB37106
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m8660
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C100279
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ACTIVE MOIETY |