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P8386

Sigma-Aldrich

Phenylbutazone

Synonym(s):
4-Butyl-1,2-diphenyl-3,5-pyrazolidinedione
Empirical Formula (Hill Notation):
C19H20N2O2
CAS Number:
Molecular Weight:
308.37
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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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)

Packaging

25, 100, 500 g in poly bottle

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

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

Certificate of Analysis

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Certificate of Origin

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