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 |
---|---|---|
[Vasculitis allergica cutis caused by phenylbutazone]. | 1966 |
|
Phenylbutazone anuria. | 1967 Dec |
|
Bone marrow depression induced by chloramphenicol or phenylbutazone. Leukemia and other sequelae. | 1967 Sep 11 |
|
Rheumatoid arthritis: comparison of treatment with monophenylbutazone and phenylbutazone. | 1969 Dec 27 |
|
Treatment of aplastic anemia with nandrolone decanoate. | 1970 Dec |
|
[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 |
|
Femoral neuropathy due to retroperitoneal bleeding. An unusual complication of heparin therapy. | 1973 Jul |
|
Acetanilide oxidation in phenylbutazone-associated hypoplastic anaemia. | 1974 Aug 3 |
|
Letter: Idiosyncrasy to phenothiazines in phenylbutazone-associated aplastic anaemia. | 1974 Oct 5 |
|
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 |
|
Phenylbutazone and the horse--a review. | 1977 Jul |
|
Association of renal papillary necrosis and ankylosing spondylitis. | 1977 May |
|
Phenylbutazone-induced blood dyscrasias suspected in three dogs. | 1980 Sep 13 |
|
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 |
|
Sialadenitis and systemic reaction associated with phenylbutazone. | 1982 Jun |
|
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 |
|
Dermatomyositis-like syndrome associated with phenylbutazone therapy. | 1987 Apr |
|
Anti-inflammatory activity and sub-acute toxicity of artemetin. | 1990 Feb |
|
Aplastic anemia induced by an adulterated herbal medication. | 1995 |
|
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 |
|
Interactions of urate transporter URAT1 in human kidney with uricosuric drugs. | 2011 Feb |
|
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 19:02:51 UTC 2023
by
admin
on
Fri Dec 15 19:02:51 UTC 2023
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Record UNII |
0J1026H8UB
|
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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