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 |
|||
Curative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Allopurinol ribonucleoside as an antileishmanial agent. Biological effects, metabolism, and enzymatic phosphorylation. | 1979 Nov 25 |
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Inosine analogs. Their metabolism in mouse L cells and in Leishmania donovani. | 1985 Aug 15 |
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New drug developments for opportunistic infections in immunosuppressed patients: Pneumocystis carinii. | 1995 Nov 24 |
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Blood group B glycosphingolipids in alpha-galactosidase deficiency (Fabry disease): influence of secretor status. | 1997 Apr 1 |
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 GMT 2023
by
admin
on
Fri Dec 15 15:31:10 GMT 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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