U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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

Description

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

1952
114
Targets

Targets

Primary TargetPharmacologyConditionPotency
Prostacyclin synthase
4
Target ID: Q16647
Gene ID: 5740.0
Gene Symbol: PTGIS
Target Organism: Homo sapiens (Human)
Inhibitor
8504
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Unknown

Approved Use

Unknown
Palliative
Approved
8583
BUTAZOLIDIN

Approved Use

Unknown
Palliative
Approved
8583
BUTAZOLIDIN

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
8 g single, oral
Overdose
Dose: 8 g
Route: oral
Route: single
Dose: 8 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/7427601
healthy, 17 years
Health Status: healthy
Age Group: 17 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/7427601
Other AEs: Jaundice, Renal disorder NOS...
Other AEs:
Jaundice
Renal disorder NOS
Sources:
https://pubmed.ncbi.nlm.nih.gov/7427601
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:
https://pubmed.ncbi.nlm.nih.gov/3907678
unhealthy, 52.8 years (range: 24-89 years)
Health Status: unhealthy
Age Group: 52.8 years (range: 24-89 years)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907678
Other AEs: Rash, Dyspepsia...
Other AEs:
Rash (1 patient)
Dyspepsia (1 patient)
Constipation (2 patients)
Sleepiness (1 patient)
Irritability (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907678
AEs

AEs

AESignificanceDosePopulation
Jaundice
8 g single, oral
Overdose
Dose: 8 g
Route: oral
Route: single
Dose: 8 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/7427601
healthy, 17 years
Health Status: healthy
Age Group: 17 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/7427601
Renal disorder NOS
8 g single, oral
Overdose
Dose: 8 g
Route: oral
Route: single
Dose: 8 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/7427601
healthy, 17 years
Health Status: healthy
Age Group: 17 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/7427601
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:
https://pubmed.ncbi.nlm.nih.gov/3907678
unhealthy, 52.8 years (range: 24-89 years)
Health Status: unhealthy
Age Group: 52.8 years (range: 24-89 years)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907678
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:
https://pubmed.ncbi.nlm.nih.gov/3907678
unhealthy, 52.8 years (range: 24-89 years)
Health Status: unhealthy
Age Group: 52.8 years (range: 24-89 years)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907678
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:
https://pubmed.ncbi.nlm.nih.gov/3907678
unhealthy, 52.8 years (range: 24-89 years)
Health Status: unhealthy
Age Group: 52.8 years (range: 24-89 years)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907678
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:
https://pubmed.ncbi.nlm.nih.gov/3907678
unhealthy, 52.8 years (range: 24-89 years)
Health Status: unhealthy
Age Group: 52.8 years (range: 24-89 years)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907678
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:
https://pubmed.ncbi.nlm.nih.gov/3907678
unhealthy, 52.8 years (range: 24-89 years)
Health Status: unhealthy
Age Group: 52.8 years (range: 24-89 years)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907678
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inducer
1087
inhibitor
2438

OverviewOther

Other InhibitorOther SubstrateOther Inducer
OAT1
725

OAT3
747

OAT4
150

MRP4
290

BCRP
910

MRP2
499

UGT1A6
136
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
MRP2
625
 no
BCRP
985
 partial
CYP2C9
2497
 yes [Ki 11 uM]
MRP4
345
 yes [Ki 354 uM]
OAT3
749
 yes [Ki 6.82 uM]
OAT1
730
 yes [Ki 71.6 uM]
CYP3A4
2633
 yes
OAT4
150
 yes
UGT1A6
171
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:48574
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:48574
ChemicalBook
CB0370134
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0370134
eMolecules
27523332
https://www.emolecules.com/cgi-bin/more?vid=27523332
eMolecules
593834
https://www.emolecules.com/cgi-bin/more?vid=593834
MolPort
MolPort-001-783-564
https://www.molport.com/shop/molecule-link/MolPort-001-783-564
Selleck Chemicals
Phenylbutazone(Butazolidin)
http://www.selleckchem.com/products/Phenylbutazone(Butazolidin).html
ZINC
ZINC000100004227
http://zinc15.docking.org/substances/ZINC000100004227
PubMed

PubMed

TitleDatePubMed
[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

Patents

JPS5815912A
4

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 Mon Mar 31 19:31:30 GMT 2025
Edited
by admin
on Mon Mar 31 19:31:30 GMT 2025
Record UNII
0J1026H8UB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENYLBUTAZONE-PIPERAZINE
WHO-DD  
Preferred Name English
PHENYLBUTAZONE PIPERAZINE
Common Name English
PYRASANONE
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 Mon Mar 31 19:31:30 GMT 2025 , Edited by admin on Mon Mar 31 19:31:30 GMT 2025
PRIMARY
EVMPD
SUB37106
Created by admin on Mon Mar 31 19:31:30 GMT 2025 , Edited by admin on Mon Mar 31 19:31:30 GMT 2025
PRIMARY
ECHA (EC/EINECS)
225-639-4
Created by admin on Mon Mar 31 19:31:30 GMT 2025 , Edited by admin on Mon Mar 31 19:31:30 GMT 2025
PRIMARY
EVMPD
SUB03774MIG
Created by admin on Mon Mar 31 19:31:30 GMT 2025 , Edited by admin on Mon Mar 31 19:31:30 GMT 2025
PRIMARY
CAS
4985-25-5
Created by admin on Mon Mar 31 19:31:30 GMT 2025 , Edited by admin on Mon Mar 31 19:31:30 GMT 2025
PRIMARY
RXCUI
236354
Created by admin on Mon Mar 31 19:31:30 GMT 2025 , Edited by admin on Mon Mar 31 19:31:30 GMT 2025
PRIMARY RxNorm
MERCK INDEX
m8660
Created by admin on Mon Mar 31 19:31:30 GMT 2025 , Edited by admin on Mon Mar 31 19:31:30 GMT 2025
PRIMARY Merck Index
MESH
C100279
Created by admin on Mon Mar 31 19:31:30 GMT 2025 , Edited by admin on Mon Mar 31 19:31:30 GMT 2025
PRIMARY
EPA CompTox
DTXSID60198119
Created by admin on Mon Mar 31 19:31:30 GMT 2025 , Edited by admin on Mon Mar 31 19:31:30 GMT 2025
PRIMARY
SMS_ID
100000085278
Created by admin on Mon Mar 31 19:31:30 GMT 2025 , Edited by admin on Mon Mar 31 19:31:30 GMT 2025
PRIMARY
PUBCHEM
78682
Created by admin on Mon Mar 31 19:31:30 GMT 2025 , Edited by admin on Mon Mar 31 19:31:30 GMT 2025
PRIMARY
Related Record Type Details
Structure of Piperazine
PARENT -> SALT/SOLVATE
Structure of PHENYLBUTAZONE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of PHENYLBUTAZONE
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966