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Merck
CN

O6881

Oxypurinol

≥98% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C5H4N4O2
CAS Number:
2465-59-0
Molecular Weight:
152.11
NACRES:
NA.51
PubChem Substance ID:
24898041
UNSPSC Code:
41106305
EC Number:
219-570-9
MDL number:
MFCD00056934
Assay:
≥98% (HPLC)
Form:
powder
Solubility:
1 M NaOH: 49.00-51.00 mg/mL, clear to slightly hazy, colorless to yellow (heated NaOH)

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InChI key

HXNFUBHNUDHIGC-UHFFFAOYSA-N

InChI

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

SMILES string

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

assay

≥98% (HPLC)

form

powder

solubility

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

Quality Level

200

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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

An allopurinol metabolite.
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.

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000525038
0000525038
0000469855
0000469855
0000458111

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Allopurinol and oxypurinol promote osteoblast differentiation and increase bone formation
Orriss I R, et al.
Experimental Cell Research, 342(2), 166-174 (2016)
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
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)
Sophie L Stocker et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 878(25), 2363-2368 (2010-08-13)
Oxypurinol is the active metabolite of allopurinol which is used to treat hyperuricaemia associated with gout. Both oxypurinol and allopurinol inhibit xanthine oxidase which forms uric acid from xanthine and hypoxanthine. Plasma oxypurinol concentrations vary substantially between individuals and the
Adenosine causes read-through into the late region of the HPV16 genome in a guanosine-dependent manner
Yu H, et al.
Virology, 521(9), 1-19 (2018)
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Product Information Sheet - O6881

Product Information Sheet

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