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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
[Vasculitis allergica cutis caused by phenylbutazone].
1966
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
[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
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
Polycythaemia in androgen-dependent aplastic anaemia.
1976 Jan 24
Granulomas and cholestatic--hepatocellular injury associated with phenylbutazone. Report of two cases.
1977 Jul
Association of renal papillary necrosis and ankylosing spondylitis.
1977 May
Use of phenylbutazone in sports medicine: understanding the risks.
1980 Jul-Aug
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
Diagnosis of antibody-mediated drug allergy. Pyrazolinone and pyrazolidinedione cross-reactivity relationships.
1987 Nov
Aplastic anemia induced by an adulterated herbal medication.
1995
Misuse of veterinary phenylbutazone.
1995 Jun 12
Development of an in vitro reporter gene assay to assess xenobiotic induction of the human CYP3A4 gene.
1997 Oct-Dec
Structure-function relationship and role of tumor necrosis factor-alpha-converting enzyme in the down-regulation of L-selectin by non-steroidal anti-inflammatory drugs.
2002 Oct 11
Identification of genomic biomarkers for concurrent diagnosis of drug-induced renal tubular injury using a large-scale toxicogenomics database.
2009 Nov 9
Toxicogenomic biomarkers for renal papillary injury in rats.
2013 Jan 7
Use of micropatterned cocultures to detect compounds that cause drug-induced liver injury in humans.
2013 Mar
Genomic biomarkers for cardiotoxicity in rats as a sensitive tool in preclinical studies.
2013 Oct
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 Fri Dec 15 15:33:00 UTC 2023
Edited
by admin
on Fri Dec 15 15:33:00 UTC 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 UTC 2023 , Edited by admin on Fri Dec 15 15:33:00 UTC 2023
PRIMARY
CAS
36551-68-5
Created by admin on Fri Dec 15 15:33:00 UTC 2023 , Edited by admin on Fri Dec 15 15:33:00 UTC 2023
PRIMARY
FDA UNII
A09K6UG6UJ
Created by admin on Fri Dec 15 15:33:00 UTC 2023 , Edited by admin on Fri Dec 15 15:33:00 UTC 2023
PRIMARY
Related Record Type Details
Structure of DIETHANOLAMINE
PARENT -> SALT/SOLVATE
Structure of PHENYLBUTAZONE
PARENT -> SALT/SOLVATE
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