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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H12N4O5
Molecular Weight 268.2265
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALLOPURINOL RIBOSIDE

SMILES

c1c2c(ncnc2O)n([C@@]3([H])[C@@]([H])([C@@]([H])([C@@]([H])(CO)O3)O)O)n1

InChI

InChIKey=KFQUAMTWOJHPEJ-DAGMQNCNSA-N
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)/t5-,6-,7-,10-/m1/s1

HIDE SMILES / InChI
Allopurinol riboside is a metabolite of allopurinol, a xanthine oxidase inhibitor indicated for the management of patients with leukemia, lymphoma, and solid tumor malignancies who are receiving cancer therapy which causes elevations of serum and urinary uric acid levels and who cannot tolerate oral therapy. Allopurinol riboside is not an inhibitor of xanthine oxidase. Allopurinol riboside is commonly thought to be directly synthesized by purine nucleoside phosphorylase (PNP) in vivo. Allopurinol riboside competitively inhibits the action of PNP on inosine in vitro. Allopurinol riboside potently inhibits growth in vitro of promastigotes of Leishmania species. Patients with American cutaneous leishmaniasis who received allopurinol riboside had clinical improvement. In addition, allopurinol riboside demonstrated some effectivity against Trypanosoma cruzi infections in animals.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
277.0 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Allopurinol ribonucleoside as an antileishmanial agent. Biological effects, metabolism, and enzymatic phosphorylation.
1979 Nov 25
Synthesis and antiviral activity of certain carbamoylpyrrolopyrimidine and pyrazolopyrimidine nucleosides.
1982 Nov
On the metabolism of allopurinol. Formation of allopurinol-1-riboside in purine nucleoside phosphorylase deficiency.
1983 Jul 15
Treatment of American cutaneous leishmaniasis with orally administered allopurinol riboside.
1989 Jul
New drug developments for opportunistic infections in immunosuppressed patients: Pneumocystis carinii.
1995 Nov 24
Patents

Patents

Sample Use Guides

Patients with American cutaneous leishmaniasis received 1,250 mg of allopurinol riboside four times daily for 28 d.
Route of Administration: Oral
In Vitro Use Guide
Allopurinol riboside (micromolar range) is a remarkably effective growth inhibitor in vitro of promastigotes of three Leishmania species. L. braziliensis was the most sensitive, L. donovani was intermediate, and L. mexicana was the most resistant of the three species.
Name Type Language
ALLOPURINOL RIBOSIDE
Common Name English
4H-PYRAZOLO(3,4-D)PYRIMIDIN-4-ONE, 1,5-DIHYDRO-1-.BETA.-D-RIBOFURANOSYL-
Common Name English
ALLOPURINOL-1-RIBONUCLEOSIDE
Common Name English
NSC-252629
Code English
NSC-138437
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 10685
Created by admin on Sat Jun 26 09:47:21 UTC 2021 , Edited by admin on Sat Jun 26 09:47:21 UTC 2021
Code System Code Type Description
CAS
16220-07-8
Created by admin on Sat Jun 26 09:47:21 UTC 2021 , Edited by admin on Sat Jun 26 09:47:21 UTC 2021
PRIMARY
MESH
C021958
Created by admin on Sat Jun 26 09:47:21 UTC 2021 , Edited by admin on Sat Jun 26 09:47:21 UTC 2021
PRIMARY
FDA UNII
WZS8452SEC
Created by admin on Sat Jun 26 09:47:21 UTC 2021 , Edited by admin on Sat Jun 26 09:47:21 UTC 2021
PRIMARY
PUBCHEM
135407110
Created by admin on Sat Jun 26 09:47:21 UTC 2021 , Edited by admin on Sat Jun 26 09:47:21 UTC 2021
PRIMARY