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Details

Stereochemistry ACHIRAL
Molecular Formula C19H20N2O2
Molecular Weight 308.3743
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENYLBUTAZONE

SMILES

CCCCC1C(=O)N(N(C1=O)C2=CC=CC=C2)C3=CC=CC=C3

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
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
Development of an in vitro reporter gene assay to assess xenobiotic induction of the human CYP3A4 gene.
1998-03-26
Efficacy of anticancer alkylphosphocholines in Trypanosoma brucei subspecies.
1997-04-15
Cancer chemopreventive activity of resveratrol, a natural product derived from grapes.
1997-01-10
Inhibition of tolbutamide 4-methylhydroxylation by a series of non-steroidal anti-inflammatory drugs in V79-NH cells expressing human cytochrome P4502C10.
1996-12
Antiinflammatory 4,5-diarylpyrroles. 2. Activity as a function of cyclooxygenase-2 inhibition.
1995-09-29
Misuse of veterinary phenylbutazone.
1995-06-12
Long-term exposure to the anti-inflammatory agent phenylbutazone induces kidney tumors in rats and liver tumors in mice.
1995-03
Aplastic anemia induced by an adulterated herbal medication.
1995
Antrafenine: anti-inflammatory activity with respect to oedema and leucocyte infiltration in the rat.
1984-02
Phenylbutazone nephrotoxicity--a light and electron microscopic study.
1983-12
[Kidney damage after treatment with butapyrazole].
1983-11-15
Renal medullary crest necrosis associated with phenylbutazone therapy in horses.
1983-11
Effects of large doses of phenylbutazone administration to horses.
1983-05
Phenylbutazone associated glomerulonephritis. Glomerulonephritis and fever.
1982-12
Sialadenitis and systemic reaction associated with phenylbutazone.
1982-06
Animal experiments on the safety pharmacology of lofexidine.
1982
Phenylbutazone liver injury: a clinical-pathologic survey of 23 cases and review of the literature.
1981-05-01
Acute nephrotic syndrome with reversible renal failure after phenylbutazone.
1981-03-21
Intrahepatic cholestasis induced by phenylbutazone.
1981
Phenylbutazone-induced blood dyscrasias suspected in three dogs.
1980-09-13
Use of phenylbutazone in sports medicine: understanding the risks.
1980-07-01
Exacerbation of phenylbutazone-related renal failure by indomethacin.
1978-11
Interstitial nephritis in a case of phenylbutazone hypersensitivity.
1978-05-20
Drug-related gustatory disorders.
1978-01-01
Granulomas and cholestatic--hepatocellular injury associated with phenylbutazone. Report of two cases.
1977-07
Development of a lymphocytic lymphoma during immunosuppressive therapy with azathioprine for systemic lupus erythematosus with renal involvement induced by phenylbutazone.
1977-07
Association of renal papillary necrosis and ankylosing spondylitis.
1977-05
Aplastic anemia from veterinary phenylbutazone.
1976-08-30
Further studies of the acute effects of phenylbutazone, oxyphenbutazone and indomethacin on the rat kidney.
1976-04
Clinical evaluation of ketoprofen (Orudis) in rheumatoid arthritis. Results of a multi-centre, double-blind, cross-over trial against phenylbutazone.
1976
Double-bind cross-over tiral of flurbiprofen and phenylbutazone in ankylosing spondylitis.
1974-11-30
Letter: Idiosyncrasy to phenothiazines in phenylbutazone-associated aplastic anaemia.
1974-10-05
Renal and gastric lesions after phenylbutazone and indomethacin in the rat.
1974-10
Proceedings: A pharmacokinetic study of phenylbutazone-associated hypoplastic anaemia.
1974-09
Aspirin and the kidney. New Zealand Rheumatism Association Study.
1974-03-30
[Primary cardiac involvement and painful salivary gland enlargement due to phenylbutazone].
1974-03-01
[Acute renal insufficiency following butapyrazole treatment in the course of plasmatic cell leukemia (author's transl)].
1973
Papillary necrosis following phenylbutazone ingestion.
1971-09
[Allergo-toxic disturbances of the heart muscle with congestive heart failure as a result of parenteral treatment with phenylbutazone].
1971-02
Treatment of aplastic anemia with nandrolone decanoate.
1970-12
Mefanamic acid-induced haemolytic anaemia.
1970-05-02
Rheumatoid arthritis: comparison of treatment with monophenylbutazone and phenylbutazone.
1969-12-27
[A fatal pathological condition with hyperglobulinemic purpura and polymyositis after phenylbutazone].
1968-11-15
Probenecid, nephrotic syndrome, and renal failure.
1968-05
Phenylbutazone anuria.
1967-12
Bone marrow depression induced by chloramphenicol or phenylbutazone. Leukemia and other sequelae.
1967-09-11
Nephrotic syndrome caused by probenecid.
1967-01-02
[The renal incidents of phenylbutazone].
1966-12-03
[Renal complications following phenylbutazone treatment].
1966-05-19
Phenylbutazone-induced pericarditis.
1965-10-02
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 17:52:12 GMT 2025
Edited
by admin
on Mon Mar 31 17:52:12 GMT 2025
Record UNII
GN5P7K3T8S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENYLBUTAZONE
EP   GREEN BOOK   HSDB   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
AMBENE
Preferred Name English
SHIGRODIN
Common 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
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
SUXIBUZONE IMPURITY A [EP IMPURITY]
Common Name English
Phenylbutazone [WHO-DD]
Common 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
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 Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
CFR 21 CFR 520.1720D
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
CFR 21 CFR 520.1720
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
CFR 21 CFR 520.1720B
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
CFR 21 CFR 520.1720C
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
CFR 21 CFR 520.1720A
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
NCI_THESAURUS C257
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
WHO-VATC QM02AA01
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
CFR 21 CFR 520.1720E
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
WHO-VATC QM01BA01
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
WHO-ATC M02AA01
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
IARC Phenylbutazone
WHO-VATC QM01AA01
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
WHO-ATC M01BA01
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
WHO-ATC M01AA01
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
Code System Code Type Description
MERCK INDEX
m8660
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY Merck Index
RS_ITEM_NUM
1531007
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY
ChEMBL
CHEMBL101
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY
FDA UNII
GN5P7K3T8S
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY
WIKIPEDIA
PHENYLBUTAZONE
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY
RXCUI
8160
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY RxNorm
NCI_THESAURUS
C66377
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-029-0
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY
EPA CompTox
DTXSID9021136
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY
EVMPD
SUB09787MIG
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY
CAS
50-33-9
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY
PUBCHEM
4781
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY
SMS_ID
100000092182
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY
IUPHAR
7270
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY
HSDB
3159
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY
DRUG BANK
DB00812
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY
INN
4
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY
NSC
25134
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY
DAILYMED
GN5P7K3T8S
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY
CHEBI
48574
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY
DRUG CENTRAL
2145
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY
MESH
D010653
Created by admin on Mon Mar 31 17:52:12 GMT 2025 , Edited by admin on Mon Mar 31 17:52:12 GMT 2025
PRIMARY
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Structure of PHENYLBUTAZONE PIPERAZINE
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Structure of CLOFEZONE
SALT/SOLVATE -> PARENT
Structure of PHENYLBUTAZONE
BASIS OF STRENGTH->SUBSTANCE
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Structure of DIETHANOLAMINE PHENYLBUTAZONE
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BASIS OF STRENGTH->SUBSTANCE
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Oxyphenbutazone, having the same antirheumatic and sodium retaining activities as phenylbutazone, is in clinical use.
Structure of OXYPHENBUTAZONE
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Percent of dose excreted in urine as metabolite.
AMOUNT ADMINISTERED
URINE
Structure of OXYPHENBUTAZONE ANHYDROUS
METABOLITE ACTIVE -> PARENT
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UNSPECIFIED
EP
Structure of BUMADIZONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 1,2-DIPHENYLHYDRAZINE
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 0.55
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 4-HYDROXYPHENYLBUTAZONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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Related Record Type Details
Structure of PHENYLBUTAZONE
ACTIVE MOIETY
NIH
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