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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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Allopurinol and oxypurinol promote osteoblast differentiation and increase bone formation
Orriss I R, et al.
Experimental Cell Research, 342(2), 166-174 (2016)
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
Sophie L Stocker et al.
British journal of clinical pharmacology, 74(3), 477-489 (2012-02-04)
Our aim was to identify and quantify the sources of variability in oxypurinol pharmacokinetics and explore relationships with plasma urate concentrations. Non-linear mixed effects modelling was applied to concentration-time data from 155 gouty patients with demographic, medical history and renal
Lisa K Stamp et al.
Rheumatology (Oxford, England), 51(9), 1670-1676 (2012-04-28)
To determine the effects of furosemide on serum urate (SU), plasma oxypurinol and urinary urate. Twenty-three cases with gout receiving furosemide and allopurinol were recruited. Twenty-three controls with gout receiving allopurinol but no diuretics were matched on age, gender, estimated
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