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Oxyphenbutazone

CAT: 0804-HY-B1355A-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-B1355A-01Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Oxyphenbutazone is a Phenylbutazone metabolite, with anti-inflammatory effect. Oxyphenbutazone is an orally active non-selective COX inhibitor. Oxyphenbutazone selectively kills non-replicating Mycobaterium tuberculosis[1][2].
CAS Number
129-20-4
UNSPSC
12352005
Hazard Statement
H302, H400
Target
Bacterial; COX
Type
Reference compound
Related Pathways
Anti-infection; Immunology/Inflammation
Applications
COVID-19-immunoregulation
Field of Research
Infection; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/oxyphenbutazone.html
Purity
99.0
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=C(C1CCCC)N(C2=CC=CC=C2)N(C3=CC=C(O)C=C3)C1=O
Molecular Formula
C19H20N2O3
Molecular Weight
324.37
Precautions
H302, H400
References & Citations
[1]Saleem S, et al. Oxyphenbutazone promotes cytotoxicity in rats and Hep3B cellsvia suppression of PGE2 and deactivation of Wnt/β-catenin signaling pathway. Mol Cell Biochem. 2018 Jul;444 (1-2) :187-196.|[2]Gold B, et al. Nonsteroidal anti-inflammatory drug sensitizes Mycobacterium tuberculosis to endogenous and exogenous antimicrobials. Proc Natl Acad Sci U S A. 2012 Oct 2;109 (40) :16004-11.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C, 3 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

Oxazolidin

Oxyphenbutazone is a metabolite of phenylbutazone obtained by hydroxylation at position 4 of one of the phenyl rings. Commonly used (as its hydrate) to treat pain, swelling and stiffness associated with arthritis and gout, it was withdrawn from the market 1984 following association with blood dyscrasis and Stevens-Johnson syndrome. It has a role as an antimicrobial agent, a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antipyretic, an antineoplastic agent, a gout suppressant, a drug metabolite and a xenobiotic metabolite. It is a member of phenols and a member of pyrazolidines. It is functionally related to a phenylbutazone.

CAS Number129-20-4
PubChem CID4641
IUPAC Name4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione
Molecular FormulaC19H20N2O3
Molecular Weight324.4
XLogP2.7
Topological Polar Surface Area60.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count5
Heavy Atom Count24
Formal Charge0
Complexity454
SMILES
CCCCC1C(=O)N(N(C1=O)C2=CC=C(C=C2)O)C3=CC=CC=C3
InChI
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
InChIKey
HFHZKZSRXITVMK-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Oxazolidin
CAS: 129-20-4
CID: 4641
Formula: C19H20N2O3
MW: 324.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight324.4
XLogP32.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count5
Exact Mass324.14739250
Monoisotopic Mass324.14739250
Topological Polar Surface Area60.9 Ų
Heavy Atom Count24
Formal Charge0
Complexity454
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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