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P8386

Sigma-Aldrich

Phenylbutazone

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C19H20N2O2
Número CAS:
50-33-9
Peso molecular:
308.37
Número CE:
200-029-0
Número MDL:
MFCD00005500
Código UNSPSC:
12352200
ID de substância PubChem:
24277729
NACRES:
NA.77

fonte biológica

synthetic (organic)

Ensaio

≥98% (HPLC)

forma

powder

pf

106-108 °C (lit.)

solubilidade

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

cadeia de caracteres SMILES

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

chave InChI

VYMDGNCVAMGZFE-UHFFFAOYSA-N

Informações sobre genes

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

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Aplicação

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)

Ações bioquímicas/fisiológicas

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.

Substratos

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

Pictogramas

Skull and crossbones
GHS06

Palavra indicadora

Danger

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

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

Certificados de análise (COA)

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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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