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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

Signal Word

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 Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, 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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