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A2026

Sigma-Aldrich

Allopurinol riboside

Synonym(s):

1-β-D-Ribofuranosyl-1H-pyrazolo[3,4-d]pyrimidine-4-one

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About This Item

Empirical Formula (Hill Notation):
C10H12N4O5
CAS Number:
16220-07-8
Molecular Weight:
268.23
MDL number:
MFCD00057096
UNSPSC Code:
41106305
PubChem Substance ID:
24890617

form

solid

storage temp.

2-8°C

SMILES string

OCC1OC(C(O)C1O)n2ncc3C(=O)N=CNc23

InChI

1S/C10H12N4O5/c15-2-5-6(16)7(17)10(19-5)14-8-4(1-13-14)9(18)12-3-11-8/h1,3,5-7,10,15-17H,2H2,(H,11,12,18)

InChI key

KFQUAMTWOJHPEJ-UHFFFAOYSA-N

Application

Allopurinol riboside is an experimental agent for the treatment of leishmaniasis and American trypanosomiasis. Allopurinol riboside is an inhibitor of orotidine 5′-monophosphate (OMP) decarboxylase from Plasmodium falciparum ((PfODCase, EC 4.1.1.23).

Biochem/physiol Actions

An anti-leishmanial agent

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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T Spector et al.
Biochemical pharmacology, 33(10), 1611-1617 (1984-05-15)
Formycin B 5'-monophosphate (Form B-MP) and allopurinol riboside 5'-monophosphate ( HPPR -MP) are isomers of IMP that are metabolically produced when Leishmania spp. are incubated with the antileishmanial agents formycin B and allopurinol or allopurinol riboside. The interactions of Form
J B Were et al.
Antimicrobial agents and chemotherapy, 37(5), 1193-1196 (1993-05-01)
Allopurinol riboside is an experimental agent for the treatment of leishmaniasis and American trypanosomiasis. Previous studies showed that after oral administration, unexpectedly low levels of allopurinol riboside in plasma are attributable to incomplete absorption and rapid renal clearance. In this
Urinary oxipurinol-1-riboside excretion and allopurinol-induced oroticaciduria.
S Reiter et al.
Advances in experimental medicine and biology, 195 Pt A, 453-460 (1986-01-01)
David B Langley et al.
Biochemistry, 47(12), 3842-3854 (2008-02-29)
Orotidine 5'-monophosphate (OMP) decarboxylase from Plasmodium falciparum (PfODCase, EC 4.1.1.23) has been overexpressed, purified, subjected to kinetic and biochemical analysis, and crystallized. The native enzyme is a homodimer with a subunit molecular mass of 38 kDa. The saturation curve for
Allopurinol-1-riboside formation and HGPRT-deficiency.
S Reiter et al.
Advances in experimental medicine and biology, 195 Pt A, 447-451 (1986-01-01)
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