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O6881

Sigma-Aldrich

Oxypurinol

≥98% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C5H4N4O2
CAS Number:
2465-59-0
Molecular Weight:
152.11
EC Number:
219-570-9
MDL number:
MFCD00056934
UNSPSC Code:
41106305
PubChem Substance ID:
24898041
NACRES:
NA.51

Quality Level

200

assay

≥98% (HPLC)

form

powder

solubility

1 M NaOH: 49.00-51.00 mg/mL, clear to slightly hazy, colorless to yellow (heated NaOH)

SMILES string

O=C1NC(=O)c2cn[nH]c2N1

InChI

1S/C5H4N4O2/c10-4-2-1-6-9-3(2)7-5(11)8-4/h1H,(H3,6,7,8,9,10,11)

InChI key

HXNFUBHNUDHIGC-UHFFFAOYSA-N

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Application

Oxypurinol has been used as a xanthine oxidase inhibitor, to evaluate its effects on hepatocellular carcinoma cell proliferation. It has also been used as a xanthine inhibitor to elucidate its contribution in the induction of hpv16 late gene expression.
Oxypurinol, an allopurinol metabolite, is used as an inhibitor to study the specificity and kinetics of of xanthine oxidase(s). Oxypurinol is also used as an anti-inflammatory agent via inhibition of xanthine oxidase.

Biochem/physiol Actions

Oxypurinol has the ability to stimulate osteoblast differentiation and enhance the formation of bone. It is used to treat gout and hyperuricemia. Oxypurinol is considered as a strong antioxidant. It can prevent the actions of xanthine oxidase (XO) in osteoblasts.
An allopurinol metabolite.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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Paolo Puddu et al.
Journal of cardiology, 59(3), 235-242 (2012-03-09)
Uric acid is the end product of purine metabolism. Its immediate precursor, xanthine, is converted to uric acid by an enzymatic reaction involving xanthine oxidoreductase. Uric acid has been formerly considered a major antioxidant in human plasma with possible beneficial
Jan B Derks et al.
Pediatric research, 68(5), 374-380 (2010-07-09)
In complicated labor, neonatal outcome may depend not only on the extent of fetal asphyxia and acidosis but also on the effects on the fetal cardiovascular system of reactive oxygen species (ROS) generated during the ischemia-reperfusion (I/R) associated with repeated
L K Stamp et al.
Clinical pharmacology and therapeutics, 90(3), 392-398 (2011-07-29)
The treatment of gout requires a lowering of serum urate (SU) levels, and allopurinol is the drug that is most commonly used for this purpose. The objectives of this study were to define the relationships between allopurinol dose on the
Xanthine dehydrogenase downregulation promotes TGF beta signaling and cancer stem cell-related gene expression in hepatocellular carcinoma
Chen GL, et al.
Oncogenesis, 6(9), e382-e382 (2017)
Umair Z Malik et al.
Free radical biology & medicine, 51(1), 179-184 (2011-05-11)
Xanthine oxidase (XO) is a critical source of reactive oxygen species (ROS) that contribute to vascular inflammation. Binding of XO to vascular endothelial cell glycosaminoglycans (GAGs) results in significant resistance to inhibition by traditional pyrazolopyrimidine-based inhibitors such as allopurinol. Therefore
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