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A8003

Sigma-Aldrich

Allopurinol

xanthine oxidase inhibitor

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Synonym(s):
1H-Pyrazolo(3,4-d)pyrimidin-4-ol, 4-Hydroxypyrazolo(3,4-d)pyrimidine, 4-Hydroxypyrazolo[3,4-d]pyrimidine, HPP
Empirical Formula (Hill Notation):
C5H4N4O
CAS Number:
Molecular Weight:
136.11
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

Assay

≥99% (TLC)

form

powder

mp

>300 °C (lit.)

solubility

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

storage temp.

room temp

SMILES string

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)

InChI key

OFCNXPDARWKPPY-UHFFFAOYSA-N

Gene Information

human ... XDH(7498)

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This Item
PHR13771013002BP870
Allopurinol xanthine oxidase inhibitor

Sigma-Aldrich

A8003

Allopurinol

Allopurinol Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1377

Allopurinol

Allopurinol United States Pharmacopeia (USP) Reference Standard

USP

1013002

Allopurinol

Allopurinol British Pharmacopoeia (BP) Reference Standard

BP870

Allopurinol

assay

≥99% (TLC)

assay

-

assay

-

assay

-

form

powder

form

-

form

-

form

-

mp

>300 °C (lit.)

mp

>300 °C (lit.)

mp

>300 °C (lit.)

mp

>300 °C (lit.)

solubility

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

solubility

-

solubility

-

solubility

-

storage temp.

room temp

storage temp.

2-30°C

storage temp.

15-25°C

storage temp.

2-8°C

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

Biochem/physiol Actions

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.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral - Skin Sens. 1

Storage Class Code

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

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
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