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O6881

Sigma-Aldrich

Oxypurinol

≥98% (HPLC)

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About This Item

Formule empirique (notation de Hill):
C5H4N4O2
Numéro CAS:
2465-59-0
Poids moléculaire :
152.11
Numéro CE :
219-570-9
Numéro MDL:
MFCD00056934
Code UNSPSC :
41106305
ID de substance PubChem :
24898041
Nomenclature NACRES :
NA.51

Niveau de qualité

200

Pureté

≥98% (HPLC)

Forme

powder

Solubilité

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

Chaîne SMILES 

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)

Clé InChI

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.

Actions biochimiques/physiologiques

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "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
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
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
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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