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A8003

Sigma-Aldrich

Allopurinol

xanthine oxidase inhibitor

Synonyme(s) :

1H-Pyrazolo(3,4-d)pyrimidin-4-ol, 4-Hydroxypyrazolo(3,4-d)pyrimidine, 4-Hydroxypyrazolo[3,4-d]pyrimidine, HPP

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About This Item

Formule empirique (notation de Hill):
C5H4N4O
Numéro CAS:
315-30-0
Poids moléculaire :
136.11
Numéro CE :
206-250-9
Numéro MDL:
MFCD00599413
Code UNSPSC :
12352202
ID de substance PubChem :
24278141
Nomenclature NACRES :
NA.77

Source biologique

synthetic (organic)

Pureté

≥99% (TLC)

Forme

powder

Pf

>300 °C (lit.)

Solubilité

1 M NaOH: soluble 50 mg/mL, clear to very slightly hazy, colorless to faintly yellow

Température de stockage

room temp

Chaîne SMILES 

O=C1NC=Nc2[nH]ncc12

InChI

1S/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)

Clé InChI

OFCNXPDARWKPPY-UHFFFAOYSA-N

Informations sur le gène

human ... XDH(7498)

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Application

Allopurinol has been used:
  • to decrease the uric acid levels and study its effect on renal injury and inflammation in mice
  • as a xanthine oxidase inhibitor to test panton-valentine leukocidin (PVL) neutrophil extracellular traps (NETosis) dependence on different enzymes, channels, or organelles using human polymorphonuclear cells (hPMNs)
  • as a reference standard to study the inhibitory effect of olive leaf components on xanthine oxidase in vitro

Allopurinol is suitable for:
  • intravenous injection in mice for inhibition of xanthine oxidase
  • use as an inhibitor of xanthine oxidase
  • use as a positive control in xanthine oxidase inhibition assay
  • use in the preparation of University of Wisconsin solution for osmotic stabilization to enhance the density differences between islets and acinar fragments during porcine islet purification

Actions biochimiques/physiologiques

Allopurinol is a purine analog that inhibits certain enzymes involved in purine metabolism. It is known to reduce the synthesis of uric acid in the body. Allopurinol mediated inhibition of xanthine oxidase exhibits anti-inflammatory effects on atherosclerosis, acute lung injury, and congestive heart failure.
Inhibitor of xanthine oxidase and de novo pyrimidine biosynthesis. A classical agent in treatment of hyperuricemia and gout.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301,H317

Classification des risques

Acute Tox. 3 Oral - Skin Sens. 1

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

H Kubo et al.
The Journal of clinical investigation, 97(11), 2680-2684 (1996-06-01)
Mice with chronic granulomatous disease (X-CGD mice) generated by mutating the X-linked gene for a subunit of NADPH oxidase have been analyzed for their ability to respond to intravenous injection of purified cobra venom factor (CVF). This agent in wild-type
Nitrate partially inhibits lipopolysaccharide-induced inflammation by maintaining mitochondrial function.
Yang Yang et al.
The Journal of international medical research, 48(2), 300060520902605-300060520902605 (2020-02-12)
Andreas Haryono et al.
The Kobe journal of medical sciences, 64(3), E107-E114 (2019-01-23)
Hyperuricemia contributed to endothelial dysfunction, activation of the RAS system, increased oxidative stress and maladaptive immune system response. M1 and M2 macrophages were known to contribute to the onset of renal fibrosis. This study aimed to look at the effect
Michael P M van der Burg et al.
TheScientificWorldJournal, 3, 1154-1159 (2003-12-04)
Generally, prior to the purification of isolated pancreatic islets, the collagenase-digested tissue is incubated in the University of Wisconsin solution (UWS; approximately 320 mOsm) for osmotic stabilization to preserve or improve the density differences between islets and acinar fragments. The
J Flemmig et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 18(7), 561-566 (2010-12-15)
In Mediterranean folk medicine Olea europaea L. leaf (Ph.Eur.) preparations are used as a common remedy for gout. In this in vitro study kinetic measurements were performed on both an 80% ethanolic (v/v) Olea europaea leaf dry extract (OLE) as
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