An NSAID and an active metabolite of phenylbutazone
Related Products
Isomer(s)
11479Bindarit
Parent Compound(s)
70400Phenylbutazone
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Oxyphenbutazone

Item No. 18723

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione
CAS Number
129-20-4
Synonyms
  • G 27202
  • p-Hydroxyphenylbutazone
  • NSC 526053
  • Ro 04-4410
Molecular Formula
C19H20N2O3
Formula Weight
324.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 25 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 0.5 mg/mlWater: 1 mg/ml
λmax
240 nm
SMILES
O=C(C1CCCC)N(C2=CC=CC=C2)N(C3=CC=C(O)C=C3)C1=O
InChi Code
InChI=1S/C19H20N2O3/c1-2-3-9-17-18(23)20(14-7-5-4-6-8-14)21(19(17)24)15-10-12-16(22)13-11-15/h4-8,10-13,17,22H,2-3,9H2,1H3
InChi Key
HFHZKZSRXITVMK-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

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    Product Description

    Oxyphenbutazone is a non-steroidal anti-inflammatory drug (NSAID) and an active metabolite of the NSAID and COX inhibitor phenylbutazone (Item No. 70400).1 It is formed from phenylbutazone by the cytochrome P450 (CYP) isoform CYP2C9.2 Oxyphenbutazone is an inhibitor of organic anion transporter 1 (OAT1; Ki = 32 µM).3 It reduces IL-6-induced proliferation of MH60 B cells (IC50 = 7.5 µM).4 Oxyphenbutazone (1.5 µM) potentiates neurite growth induced by nerve growth factor (NGF) in NS-1 cells.5 It is active against non-replicating M. tuberculosis when used at a concentration of 12.5 µM.6 Oxyphenbutazone (300 and 100 mg/kg, respectively) reduces knee joint swelling in a rat model of silver nitrate-induced arthritis and decreases distal joint swelling and paw edema in a rat model of mycoplasma-induced polyarthritis.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wilhelmi, G. Newer pharmacological data on oxyphenbutazone. Jpn. J. Pharmacol. 15(2), 187-198 (1965).

    2. Miners, J.P., and Birkett, D.J. Cytochrome P4502C9: An enzyme of major importance in human drug metabolism. Br. J. Clin. Pharmacol. 45(6), 525-538 (1998).

    3. Apiwattanakul, N., Sekine, T., Chairoungda, A., et al. Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol. Pharmacol. 55(5), 847-854 (2015).

    4. Kang, B.S., Chung, E.Y., Yun, Y.P., et al. Inhibitory effects of anti-inflammatory drugs on interleukin-6 bioactivity. Biol. Pharm. Bull. 24(6), 701-703 (2001).

    5. Yeyeodu, S.T., Witherspoon, S.M., Gilyazova, N., et al. A rapid, inexpensive high throughput screen method for neurite outgrowth. Curr. Chem. Genomics 4, 74-83 (2010).

    6. Gold, B., Pingle, M., Brickner, S.J., et al. Nonsteroidal anti-inflammatory drug sensitizes Mycobacterium tuberculosis to endogenous and exogenous antimicrobials. Proc. Natl. Acad. Sci. USA 109(40), 16004-16011 (2012).