Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C10H12N4O5 |
Molecular Weight | 268.2261 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2N=CC3=C2N=CNC3=O
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
Molecular Formula | C10H12N4O5 |
Molecular Weight | 268.2261 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4338 Sources: https://www.ncbi.nlm.nih.gov/pubmed/121041 |
277.0 µM [Ki] | ||
Target ID: CHEMBL367 Sources: https://www.ncbi.nlm.nih.gov/pubmed/500658 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Unknown Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Comparative metabolism of a new antileishmanial agent, allopurinol riboside, in the parasite and the host cell. | 1979 |
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Inhibition of purine nucleoside phosphorylase activity and of T-cell function with allopurinol-riboside. | 1979 Dec |
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On the metabolism of allopurinol. Formation of allopurinol-1-riboside in purine nucleoside phosphorylase deficiency. | 1983 Jul 15 |
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Activity of inosine analogs against Pneumocystis carinii in culture. | 1986 Jul |
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Treatment of American cutaneous leishmaniasis with orally administered allopurinol riboside. | 1989 Jul |
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Pharmacokinetics and metabolism of allopurinol riboside. | 1991 May |
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Effects of probenecid on the pharmacokinetics of allopurinol riboside. | 1993 May |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2659681
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/500658
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:31:10 UTC 2023
by
admin
on
Fri Dec 15 15:31:10 UTC 2023
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Record UNII |
WZS8452SEC
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Record Status |
Validated (UNII)
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Record Version |
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FDA ORPHAN DRUG |
10685
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