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Merck

P8386

Phenylbutazone

synthetic (organic), ≥98% (HPLC), NSAID and COX inhibitor, powder

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
NACRES:
NA.77
PubChem Substance ID:
24277729
UNSPSC Code:
12352200
EC Number:
200-029-0
MDL number:
MFCD00005500
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
200

Key Documents

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Product Name

Phenylbutazone,

InChI key

VYMDGNCVAMGZFE-UHFFFAOYSA-N

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

SMILES string

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

biological source

synthetic (organic)

assay

≥98% (HPLC)

form

powder

mp

106-108 °C (lit.)

solubility

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

Quality Level

200

Gene Information

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

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General description

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

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.

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

P8386-VAR: + P8386-100G: + P8386-BULK: + P8386-500G: + P8386-25G:

jan

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Certificates of Analysis (COA)

Lot/Batch Number
MKCH0342
MKCC3053
MKBX7857V
MKBW4801V
SLBH0779V

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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.
Phenylbutazone purity challenge
McRae G, et al.
Analytical and Bioanalytical Chemistry, 408(12), 3051-3053 (2016)
J H Foreman et al.
Equine veterinary journal. Supplement, (38)(38), 601-605 (2011-05-27)
Objective blinded efficacy data during exercise are lacking on the use of single-dose i.v. nonsteroidal anti-inflammatory drugs (NSAIDs) before, during and after exercise. Single i.v. doses of either phenylbutazone (PBZ) or flunixin meglumine (FM) would prove more efficacious than negative
J H Foreman et al.
Equine veterinary journal. Supplement, (40)(40), 12-17 (2011-12-07)
Using an adjustable heart bar shoe model of foot pain, the objective of this study was to test the hypothesis that the combined use of phenylbutazone (PBZ) and flunixin meglumine (FM) would prove more efficacious in alleviating lameness than either
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