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Details

Stereochemistry ACHIRAL
Molecular Formula C19H20N2O2.C4H11NO2
Molecular Weight 413.5099
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIETHANOLAMINE PHENYLBUTAZONE

SMILES

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

InChI

InChIKey=RZQGMINQPCEZCE-UHFFFAOYSA-N
InChI=1S/C19H20N2O2.C4H11NO2/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;6-3-1-5-2-4-7/h4-13,17H,2-3,14H2,1H3;5-7H,1-4H2

HIDE SMILES / InChI
Molecular Formula C4H11NO2
Molecular Weight 105.1356
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
115
Targets

Targets

Primary TargetPharmacologyConditionPotency
Prostacyclin synthase
4
Target ID: Q16647
Gene ID: 5740.0
Gene Symbol: PTGIS
Target Organism: Homo sapiens (Human)
Inhibitor
8297
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Unknown

Approved Use

Unknown
Palliative
Approved
8429
BUTAZOLIDIN

Approved Use

Unknown
Palliative
Approved
8429
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
n = 1
Health Status: healthy
Age Group: 17 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/7427601
Other AEs: Renal disorder NOS, Jaundice...
Other AEs:
Renal disorder NOS
Jaundice
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
Condition: acute gouty arthritis
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
n = 1
Health Status: healthy
Age Group: 17 years
Sex: F
Population Size: 1
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
n = 1
Health Status: healthy
Age Group: 17 years
Sex: F
Population Size: 1
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
Condition: acute gouty arthritis
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
Condition: acute gouty arthritis
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
Condition: acute gouty arthritis
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
Condition: acute gouty arthritis
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
Condition: acute gouty arthritis
Age Group: 52.8 years (range: 24-89 years)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907678
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inducer
781
inhibitor
1767

OverviewOther

Other InhibitorOther SubstrateOther Inducer
OAT1
599

OAT3
642

OAT4
146

MRP4
204

BCRP
699

MRP2
383

UGT1A6
108
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
MRP2
475
 no
BCRP
773
 partial
CYP2C9
1819
 yes [Ki 11 uM]
MRP4
238
 yes [Ki 354 uM]
OAT3
644
 yes [Ki 6.82 uM]
OAT1
603
 yes [Ki 71.6 uM]
CYP3A4
1925
 yes
OAT4
146
 yes
UGT1A6
141
 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
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
eMolecules
27523332
https://www.emolecules.com/cgi-bin/more?vid=27523332
eMolecules
593834
https://www.emolecules.com/cgi-bin/more?vid=593834
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
[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
Double-bind cross-over tiral of flurbiprofen and phenylbutazone in ankylosing spondylitis.
1974 Nov 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
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
Renal medullary crest necrosis associated with phenylbutazone therapy in horses.
1983 Nov
[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
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
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
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 Fri Dec 15 15:33:00 GMT 2023
Edited
by admin
on Fri Dec 15 15:33:00 GMT 2023
Record UNII
A09K6UG6UJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIETHANOLAMINE PHENYLBUTAZONE
Common Name English
ETHANOL, 2,2'-IMINOBIS-, COMPD. WITH 4-BUTYL-1,2-DIPHENYL-3,5-PYRAZOLIDINEDIONE (1:1)
Systematic Name English
3,5-PYRAZOLIDINEDIONE, 4-BUTYL-1,2-DIPHENYL-, COMPD. WITH 2,2'-IMINOBIS(ETHANOL) (1:1)
Systematic Name English
Code System Code Type Description
PUBCHEM
109374152
Created by admin on Fri Dec 15 15:33:00 GMT 2023 , Edited by admin on Fri Dec 15 15:33:00 GMT 2023
PRIMARY
CAS
36551-68-5
Created by admin on Fri Dec 15 15:33:00 GMT 2023 , Edited by admin on Fri Dec 15 15:33:00 GMT 2023
PRIMARY
FDA UNII
A09K6UG6UJ
Created by admin on Fri Dec 15 15:33:00 GMT 2023 , Edited by admin on Fri Dec 15 15:33:00 GMT 2023
PRIMARY
Related Record Type Details
Structure of DIETHANOLAMINE
PARENT -> SALT/SOLVATE
Structure of PHENYLBUTAZONE
PARENT -> SALT/SOLVATE
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