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SML0540

Sigma-Aldrich

Oxyphenbutazone

≥98% (HPLC)

Synonym(s):

4-Butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione, G 27202, NSC 526053, Ro 04-4410, p-Hydroxyphenylbutazone, p-Oxyphenylbutazone

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About This Item

Empirical Formula (Hill Notation):
C19H20N2O3
CAS Number:
129-20-4
Molecular Weight:
324.37
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to brown

solubility

DMSO: 10 mg/mL, clear

storage temp.

−20°C

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

General description

Oxyphenbutazone is a derivative compound of phenylbutazone.

Biochem/physiol Actions

Oxyphenbutazone is a non-steroid anti inflammatory; anti Mycobacterium tuberculosis agent. Oxyphenbutazone is known to cause inflammatory effects on tissues. Oxyphenbutazone, as a drug, decreases cellular exudates, without involving the pituitary-adrenal axis or the immunity response. Though the drug delivers a number of side effects, it is considered to be less toxic than phenylbutazone, due to decreased rate of intestinal absorption.
Oxyphenbutazone is an NSAID that has been shown to preferentially kill non-replicating Mycobaterium tuberculosis maintained in media that simulates the mildly acidic, in vivo conditions where drug-resistant, non replicating subpopulations of the bacteria reside in hosts. The compound has little or no affect on replication M. tuberculosis grown in normal liquid cultures.

Other Notes

Air sensitive

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H400

Precautionary Statements

P273 - P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Anja Ten Brinke et al.
European cytokine network, 16(2), 144-151 (2005-06-09)
4-Hydroxy-oxyphenbutazone (4OH-OPB), is currently in phase II trials for its immunosuppressive effect in patients with rheumatoid arthritis. 4OH-OPB and other compounds related to phenylbutazone were tested for their effect on in vitro cytokine production by monocytes and lymphocytes present in
B C Sallustio et al.
Drug metabolism and disposition: the biological fate of chemicals, 25(1), 55-60 (1997-01-01)
Acyl glucuronides are electrophilic metabolites that are readily hydrolyzed, undergo intramolecular rearrangement, and bind covalently to endogenous proteins. Gemfibrozil is a fibrate lipid-lowering agent that is extensively metabolized to an acyl glucuronide conjugate in humans. The aims of this study
Z Cheng et al.
Journal of veterinary pharmacology and therapeutics, 21(4), 315-321 (1998-09-10)
Flunixin meglumine (FM, 1.1 mg/kg) and phenylbutazone (PBZ, 4.4 mg/kg) were administered intravenously (i.v.) as a single dose to eight sheep prepared with subcutaneous (s.c.) tissue-cages in which an acute inflammatory reaction was stimulated with carrageenan. Pharmacokinetics of FM, PBZ
Takamitsu Kosa et al.
Journal of pharmaceutical sciences, 96(11), 3117-3124 (2007-11-06)
In the process of drug development, preclinical testing using experimental animals is an important aspect, for verification of the efficacy and safety of a drug. Serum albumin is a major binding protein for endogenous and exogenous ligands and regulates their
E Grippa et al.
Journal of chromatography. B, Biomedical sciences and applications, 738(1), 17-25 (2000-04-25)
Ethyl acetate extracts of equine serum, containing 0-5 microg/ml of hydrocortisone (HYD), dexamethasone (DEX), oxyphenbutazone (OPB), indomethacin (IND), phenylbutazone (PB) and probenecid as internal standard, were evaporated with nitrogen, resuspended in methanol and analyzed by HPLC, using a C-18 column
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