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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
Pricing and availability is not currently available.

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.[1] It has also been used as a xanthine inhibitor to elucidate its contribution in the induction of hpv16 late gene expression.[2]
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.[3]

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000380103
0000380103
0000309357
0000320099
0000320100

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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
Daniel Y Ng et al.
European journal of clinical pharmacology, 67(7), 709-713 (2010-12-25)
To determine whether low-dose aspirin and hydrochlorothiazide (HCTZ) affect the renal clearance of oxypurinol and/or urate. Healthy volunteers (n = 8) were treated with allopurinol (600 mg, control), and allopurinol (600 mg) co-administered with single doses of aspirin (100 mg) or HCTZ (25 mg) or a
Allopurinol and oxypurinol promote osteoblast differentiation and increase bone formation
Orriss I R, et al.
Experimental Cell Research, 342(2), 166-174 (2016)
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