U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C19H20N2O2
Molecular Weight 308.375
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENYLBUTAZONE

SMILES

CCCCC1C(=O)N(c2ccccc2)N(c3ccccc3)C1=O

InChI

InChIKey=VYMDGNCVAMGZFE-UHFFFAOYSA-N
InChI=1S/C19H20N2O2/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/h4-13,17H,2-3,14H2,1H3

HIDE SMILES / InChI
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
[The renal incidents of phenylbutazone].
1966 Dec 3
[Acute renal insufficiency following butapyrazole treatment in the course of plasmatic cell leukemia (author's transl)].
1973
Aspirin and the kidney. New Zealand Rheumatism Association Study.
1974 Mar 30
Renal and gastric lesions after phenylbutazone and indomethacin in the rat.
1974 Oct
Letter: Idiosyncrasy to phenothiazines in phenylbutazone-associated aplastic anaemia.
1974 Oct 5
Proceedings: A pharmacokinetic study of phenylbutazone-associated hypoplastic anaemia.
1974 Sep
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
Polycythaemia in androgen-dependent aplastic anaemia.
1976 Jan 24
Development of a lymphocytic lymphoma during immunosuppressive therapy with azathioprine for systemic lupus erythematosus with renal involvement induced by phenylbutazone.
1977 Jul
[Macroscopic hematuria during treatment with phenylbutazone derivatives. Positive lymphocyte transformation test for these drugs. Two cases in children].
1977 Oct
Drug-related gustatory disorders.
1978 Jan-Feb
Confusion associated with cimetidine.
1979 Dec 1
Intrahepatic cholestasis induced by phenylbutazone.
1981
Phenylbutazone liver injury: a clinical-pathologic survey of 23 cases and review of the literature.
1981 May-Jun
Effects of large doses of phenylbutazone administration to horses.
1983 May
Renal medullary crest necrosis associated with phenylbutazone therapy in horses.
1983 Nov
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
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
Antiinflammatory 4,5-diarylpyrroles. 2. Activity as a function of cyclooxygenase-2 inhibition.
1995 Sep 29
Efficacy of anticancer alkylphosphocholines in Trypanosoma brucei subspecies.
1997 Apr 15
Cancer chemopreventive activity of resveratrol, a natural product derived from grapes.
1997 Jan 10
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
Renal papillary necrosis.
2002 Nov-Dec
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
Name Type Language
PHENYLBUTAZONE
EP   GREEN BOOK   HSDB   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
SHIGRODIN
Common Name English
AMBENE
Brand Name English
PHEBUZINE
Common Name English
FLEXAZONE
Common Name English
BUTAPIRAZOL
Brand Name English
DIPHENYLBUTAZONE
Common Name English
3,5-PYRAZOLIDINEDIONE, 4-BUTYL-1,2-DIPHENYL-
Systematic Name English
ROBIZONE-V
Brand Name English
3,5-DIOXO-1,2-DIPHENYL-4-N-BUTYLPYRAZOLIDINE
Common Name English
PHENYLBUTAZONE [MART.]
Common Name English
EXRHEUDON N
Brand Name English
FENYLBUTAZON
Common Name English
PHENYLBUTAZONE [USP-RS]
Common Name English
BUTACOTE
Brand Name English
FENIBUTAZONA
Common Name English
PHENYLBUTAZONE [INN]
Common Name English
BUTAZOLIDIN
Brand Name English
PHENYLBUTAZONE [WHO-DD]
Common Name English
4-BUTYL-1,2-DIPHENYL-3,5-PYRAZOLIDINEDIONE
Systematic Name English
ARTRIZIN
Brand Name English
NSC-25134
Code English
INTRABUTAZONE
Brand Name English
BUTADIONA
Brand Name English
ZOLAPHEN
Common Name English
FENIBUTOL
Brand Name English
MEPHA-BUTAZON
Brand Name English
BUZON
Brand Name English
PHENYLBUTAZONE [MI]
Common Name English
PHENYLBUTAZONE [USP MONOGRAPH]
Common Name English
AZOLID
Systematic Name English
PHENYZENE
Brand Name English
INTRAZONE
Brand Name English
UZONE
Brand Name English
EQUIPALAZONE
Brand Name English
BUTATRON
Brand Name English
PHENYLBUTAZONE [JAN]
Common Name English
PHENYLBUTAZONE [GREEN BOOK]
Common Name English
PHENYLBUTAZONE [ORANGE BOOK]
Common Name English
PHENYLBUTAZONE [VANDF]
Common Name English
R-3-ZON
Code English
PHENYLBUTAZONE [IARC]
Common Name English
DIPHEBUZOL
Common Name English
PHENYLBUTAZONE [HSDB]
Common Name English
4-BUTYL-1,2-DIPHENYL-3,5-DIOXOPYRAZOLIDINE
Systematic Name English
BUTOZ
Brand Name English
BUTADION
Brand Name English
SUXIBUZONE IMPURITY A [EP]
Common Name English
BIZOLIN
Brand Name English
PHENYLBUTAZONE [EP MONOGRAPH]
Common Name English
ECOBUTAZONE
Brand Name English
TEVCODYNE
Brand Name English
G-13871
Code English
Classification Tree Code System Code
CFR 21 CFR 522.1720
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
CFR 21 CFR 520.1720D
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
CFR 21 CFR 520.1720
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
CFR 21 CFR 520.1720B
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
CFR 21 CFR 520.1720C
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
CFR 21 CFR 520.1720A
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
NCI_THESAURUS C257
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
WHO-VATC QM02AA01
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
CFR 21 CFR 520.1720E
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
WHO-VATC QM01BA01
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
WHO-ATC M02AA01
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
IARC Phenylbutazone
WHO-VATC QM01AA01
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
WHO-ATC M01BA01
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
WHO-ATC M01AA01
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
Code System Code Type Description
MERCK INDEX
M8660
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL101
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
PRIMARY
FDA UNII
GN5P7K3T8S
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
PRIMARY
WIKIPEDIA
PHENYLBUTAZONE
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
PRIMARY
RXCUI
8160
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C66377
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-029-0
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
PRIMARY
EPA CompTox
50-33-9
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
PRIMARY
EVMPD
SUB09787MIG
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
PRIMARY
CAS
50-33-9
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
PRIMARY
PUBCHEM
4781
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
PRIMARY
IUPHAR
7270
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
PRIMARY
HSDB
3159
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
PRIMARY
DRUG BANK
DB00812
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
PRIMARY
INN
4
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
PRIMARY
USP_CATALOG
1531007
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
PRIMARY USP-RS
DRUG CENTRAL
2145
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
PRIMARY
MESH
D010653
Created by admin on Fri Jun 25 20:58:52 UTC 2021 , Edited by admin on Fri Jun 25 20:58:52 UTC 2021
PRIMARY