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P8386 Sigma-Aldrich

Phenylbutazone

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

  • CAS Number 50-33-9

  • Empirical Formula (Hill Notation) C19H20N2O2

  • Molecular Weight 308.37

  •  EC Number 200-029-0

  •  MDL number MFCD00005500

  •  PubChem Substance ID 24277729

  •  NACRES NA.77

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Properties

Related Categories A to C, Anti-inflammatory, Application Index, Arachidonic Acid Cascade, Bioactive Small Molecule Alphabetical Index,
Quality Level   200
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)

Description

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.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Substrates

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

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
WGK 3
RTECS 
UQ8225000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

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Peer-Reviewed Papers
15

References

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