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P8386

Sigma-Aldrich

Phenylbutazone

Synonym(s):

4-Butyl-1,2-diphenyl-3,5-pyrazolidinedione

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About This Item

Empirical Formula (Hill Notation):
C19H20N2O2
CAS Number:
50-33-9
Molecular Weight:
308.37
EC Number:
200-029-0
MDL number:
MFCD00005500
UNSPSC Code:
12352200
PubChem Substance ID:
24277729
NACRES:
NA.77

biological source

synthetic (organic)

assay

≥98% (HPLC)

form

powder

mp

106-108 °C (lit.)

solubility

ethanol: 50 mg/mL, clear, colorless to light yellow

SMILES string

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

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

InChI key

VYMDGNCVAMGZFE-UHFFFAOYSA-N

Gene Information

human ... CYP2C9(1559) , PTGIS(5740) , PTGS1(5742) , PTGS2(5743)

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Application

Phenylbutazone has been used:
  • as a hepatotoxin in transgenic zebrafish line (LiPan) hepatotoxin assay
  • as a standard in high-performance liquid chromatography-ultraviolet (HPLC-UV) method
  • as an anti-inflammatory compound in hen′s egg chorioallantoic membrane test (HET-CAM assay)

Biochem/physiol Actions

Phenylbutazone is a hepatotoxin and binds to plasma proteins. It is used to treat inflammation in horse. Phenylbutazone has potential to treat ankylosing spondylitis. It has therapeutic potential to treat myotonic dystrophy type 1 (DM1) by inducing muscle blind-like protein 1 (MBNL1) expression. It also favors the expression of muscle chloride channel in skeletal muscles.

Substrates

Non-steroidal anti-inflammatory compound; inhibitor of cyclooxygenase that is also a substrate for peroxidation by cyclooxygenase.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Phenylbutazone purity challenge
McRae G, et al.
Analytical and Bioanalytical Chemistry, 408(12), 3051-3053 (2016)
Phenylbutazone induces expression of MBNL1 and suppresses formation of MBNL1-CUG RNA foci in a mouse model of myotonic dystrophy
Chen G, et al.
Scientific Reports, 6, 25317-25317 (2016)
Amit Verma et al.
European journal of medicinal chemistry, 43(5), 897-905 (2007-09-18)
The broad and potent activity of 4-thiazolidinones has established it as one of the biologically important scaffolds. This article is an effort to highlight the importance of the 4-thiazolidinones in the present context and promise they hold for the future.
HET-CAM bioassay in comparison to the croton oil test for investigating steroidal and non-steroidal compounds
Brandtner AH, et al.
ALTEX, 19(2), 51-56 (2016)
Development of a convenient in vivo hepatotoxin assay using a transgenic zebrafish line with liver-specific DsRed expression
Zhang X, et al.
Testing, 9(3), e91874-e91874 (2014)
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