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A8003

Sigma-Aldrich

Allopurinol

xanthine oxidase inhibitor

Synonym(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

Empirical Formula (Hill Notation):
C5H4N4O
CAS Number:
315-30-0
Molecular Weight:
136.11
EC Number:
206-250-9
MDL number:
MFCD00599413
UNSPSC Code:
12352202
PubChem Substance ID:
24278141
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

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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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
GHS06

Signal Word

Danger

Hazard Statements

H301 - H317

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

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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