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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 C19H20N2O2
Molecular Weight 308.3743
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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
[The renal incidents of phenylbutazone].
1966 Dec 3
[Renal complications following phenylbutazone treatment].
1966 May 19
Phenylbutazone anuria.
1967 Dec
Nephrotic syndrome caused by probenecid.
1967 Jan 2
Bone marrow depression induced by chloramphenicol or phenylbutazone. Leukemia and other sequelae.
1967 Sep 11
Probenecid, nephrotic syndrome, and renal failure.
1968 May
[A fatal pathological condition with hyperglobulinemic purpura and polymyositis after phenylbutazone].
1968 Nov 15
Rheumatoid arthritis: comparison of treatment with monophenylbutazone and phenylbutazone.
1969 Dec 27
Treatment of aplastic anemia with nandrolone decanoate.
1970 Dec
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
Papillary necrosis following phenylbutazone ingestion.
1971 Sep
Femoral neuropathy due to retroperitoneal bleeding. An unusual complication of heparin therapy.
1973 Jul
Acetanilide oxidation in phenylbutazone-associated hypoplastic anaemia.
1974 Aug 3
[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
Letter: Idiosyncrasy to phenothiazines in phenylbutazone-associated aplastic anaemia.
1974 Oct 5
Proceedings: A pharmacokinetic study of phenylbutazone-associated hypoplastic anaemia.
1974 Sep
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
Aplastic anemia from veterinary phenylbutazone.
1976 Aug 30
Granulomas and cholestatic--hepatocellular injury associated with phenylbutazone. Report of two cases.
1977 Jul
Development of a lymphocytic lymphoma during immunosuppressive therapy with azathioprine for systemic lupus erythematosus with renal involvement induced by phenylbutazone.
1977 Jul
Association of renal papillary necrosis and ankylosing spondylitis.
1977 May
Drug-related gustatory disorders.
1978 Jan-Feb
Interstitial nephritis in a case of phenylbutazone hypersensitivity.
1978 May 20
Exacerbation of phenylbutazone-related renal failure by indomethacin.
1978 Nov
Use of phenylbutazone in sports medicine: understanding the risks.
1980 Jul-Aug
Phenylbutazone-induced blood dyscrasias suspected in three dogs.
1980 Sep 13
Intrahepatic cholestasis induced by phenylbutazone.
1981
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
Animal experiments on the safety pharmacology of lofexidine.
1982
Phenylbutazone associated glomerulonephritis. Glomerulonephritis and fever.
1982 Dec
Sialadenitis and systemic reaction associated with phenylbutazone.
1982 Jun
Phenylbutazone nephrotoxicity--a light and electron microscopic study.
1983 Dec
Effects of large doses of phenylbutazone administration to horses.
1983 May
[Kidney damage after treatment with butapyrazole].
1983 Nov 15
Antrafenine: anti-inflammatory activity with respect to oedema and leucocyte infiltration in the rat.
1984 Feb
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
Aplastic anemia induced by an adulterated herbal medication.
1995
Misuse of veterinary phenylbutazone.
1995 Jun 12
Long-term exposure to the anti-inflammatory agent phenylbutazone induces kidney tumors in rats and liver tumors in mice.
1995 Mar
Antiinflammatory 4,5-diarylpyrroles. 2. Activity as a function of cyclooxygenase-2 inhibition.
1995 Sep 29
Inhibition of tolbutamide 4-methylhydroxylation by a series of non-steroidal anti-inflammatory drugs in V79-NH cells expressing human cytochrome P4502C10.
1996 Dec
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
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 Thu Jul 06 02:12:02 UTC 2023
Edited
by admin
on Thu Jul 06 02:12:02 UTC 2023
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 Thu Jul 06 02:12:02 UTC 2023 , Edited by admin on Thu Jul 06 02:12:02 UTC 2023
PRIMARY
EVMPD
SUB37106
Created by admin on Thu Jul 06 02:12:02 UTC 2023 , Edited by admin on Thu Jul 06 02:12:02 UTC 2023
PRIMARY
ECHA (EC/EINECS)
225-639-4
Created by admin on Thu Jul 06 02:12:02 UTC 2023 , Edited by admin on Thu Jul 06 02:12:02 UTC 2023
PRIMARY
EVMPD
SUB03774MIG
Created by admin on Thu Jul 06 02:12:02 UTC 2023 , Edited by admin on Thu Jul 06 02:12:02 UTC 2023
PRIMARY
CAS
4985-25-5
Created by admin on Thu Jul 06 02:12:02 UTC 2023 , Edited by admin on Thu Jul 06 02:12:02 UTC 2023
PRIMARY
RXCUI
236354
Created by admin on Thu Jul 06 02:12:02 UTC 2023 , Edited by admin on Thu Jul 06 02:12:02 UTC 2023
PRIMARY RxNorm
MERCK INDEX
M8660
Created by admin on Thu Jul 06 02:12:02 UTC 2023 , Edited by admin on Thu Jul 06 02:12:02 UTC 2023
PRIMARY Merck Index
MESH
C100279
Created by admin on Thu Jul 06 02:12:02 UTC 2023 , Edited by admin on Thu Jul 06 02:12:02 UTC 2023
PRIMARY
EPA CompTox
DTXSID60198119
Created by admin on Thu Jul 06 02:12:02 UTC 2023 , Edited by admin on Thu Jul 06 02:12:02 UTC 2023
PRIMARY
SMS_ID
100000085278
Created by admin on Thu Jul 06 02:12:02 UTC 2023 , Edited by admin on Thu Jul 06 02:12:02 UTC 2023
PRIMARY
PUBCHEM
78682
Created by admin on Thu Jul 06 02:12:02 UTC 2023 , Edited by admin on Thu Jul 06 02:12:02 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY