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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
Structure of PHENYLBUTAZONE PIPERAZINE

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

HIDE SMILES / InChI

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q16647
Gene ID: 5740.0
Gene Symbol: PTGIS
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Palliative
BUTAZOLIDIN

Approved Use

Unknown
Palliative
BUTAZOLIDIN

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
8 g single, oral
Overdose
Dose: 8 g
Route: oral
Route: single
Dose: 8 g
Sources:
healthy, 17 years
n = 1
Health Status: healthy
Age Group: 17 years
Sex: F
Population Size: 1
Sources:
Other AEs: Renal disorder NOS, Jaundice...
Other AEs:
Renal disorder NOS
Jaundice
Sources:
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)
Dyspepsia (1 patient)
Constipation (2 patients)
Sleepiness (1 patient)
Irritability (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Jaundice
8 g single, oral
Overdose
Dose: 8 g
Route: oral
Route: single
Dose: 8 g
Sources:
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
Dose: 8 g
Route: oral
Route: single
Dose: 8 g
Sources:
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

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​
PubMed

PubMed

TitleDatePubMed
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

Patents

Sample Use Guides

In Vivo Use Guide
300 mg daily for 4 weeks
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 17 01:54:00 UTC 2022
Edited
by admin
on Sat Dec 17 01:54:00 UTC 2022
Record UNII
0J1026H8UB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENYLBUTAZONE PIPERAZINE
Common Name English
PYRASANONE
Common Name English
PHENYLBUTAZONE-PIPERAZINE
WHO-DD  
Common Name English
PHENYLBUTAZONE PIPERAZINE SALT [MI]
Common Name English
3,5-PYRAZOLIDINEDIONE, 4-BUTYL-1,2-DIPHENYL-, COMPD. WITH PIPERAZINE (1:1)
Systematic Name English
PYRAZINOBUTAZONE
Common Name English
Phenylbutazone-piperazine [WHO-DD]
Common Name English
CARUDOL
Brand Name English
Code System Code Type Description
FDA UNII
0J1026H8UB
Created by admin on Sat Dec 17 01:54:00 UTC 2022 , Edited by admin on Sat Dec 17 01:54:00 UTC 2022
PRIMARY
EVMPD
SUB37106
Created by admin on Sat Dec 17 01:54:00 UTC 2022 , Edited by admin on Sat Dec 17 01:54:00 UTC 2022
PRIMARY
ECHA (EC/EINECS)
225-639-4
Created by admin on Sat Dec 17 01:54:00 UTC 2022 , Edited by admin on Sat Dec 17 01:54:00 UTC 2022
PRIMARY
EVMPD
SUB03774MIG
Created by admin on Sat Dec 17 01:54:00 UTC 2022 , Edited by admin on Sat Dec 17 01:54:00 UTC 2022
PRIMARY
CAS
4985-25-5
Created by admin on Sat Dec 17 01:54:00 UTC 2022 , Edited by admin on Sat Dec 17 01:54:00 UTC 2022
PRIMARY
RXCUI
236354
Created by admin on Sat Dec 17 01:54:00 UTC 2022 , Edited by admin on Sat Dec 17 01:54:00 UTC 2022
PRIMARY RxNorm
MERCK INDEX
M8660
Created by admin on Sat Dec 17 01:54:00 UTC 2022 , Edited by admin on Sat Dec 17 01:54:00 UTC 2022
PRIMARY Merck Index
MESH
C100279
Created by admin on Sat Dec 17 01:54:00 UTC 2022 , Edited by admin on Sat Dec 17 01:54:00 UTC 2022
PRIMARY
EPA CompTox
DTXSID60198119
Created by admin on Sat Dec 17 01:54:00 UTC 2022 , Edited by admin on Sat Dec 17 01:54:00 UTC 2022
PRIMARY
PUBCHEM
78682
Created by admin on Sat Dec 17 01:54:00 UTC 2022 , Edited by admin on Sat Dec 17 01:54:00 UTC 2022
PRIMARY
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ACTIVE MOIETY