ALLOPURINOL RIBOSIDE

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

Structure Search

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/500658 | https://www.rxlist.com/aloprim-drug.htm | https://www.ncbi.nlm.nih.gov/pubmed/6409116 | https://www.ncbi.nlm.nih.gov/pubmed/121041 | https://www.ncbi.nlm.nih.gov/pubmed/2659681 | https://www.ncbi.nlm.nih.gov/pubmed/6436394 | https://www.ncbi.nlm.nih.gov/pubmed/3936241

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
Purine nucleoside phosphorylase 5 Target ID: CHEMBL4338 Sources: https://www.ncbi.nlm.nih.gov/pubmed/121041	Inhibitor 8297		277.0 µM [Ki]
Leishmania donovani 13 Target ID: CHEMBL367 Sources: https://www.ncbi.nlm.nih.gov/pubmed/500658	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Leishmaniasis 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2659681	Curative		Not Provided 504	Unknown Approved Use Unknown
Trypanosomiasis 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3936241 https://www.ncbi.nlm.nih.gov/pubmed/6436394	Curative		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Comparative metabolism of a new antileishmanial agent, allopurinol riboside, in the parasite and the host cell.	1979	546162
Inhibition of purine nucleoside phosphorylase activity and of T-cell function with allopurinol-riboside.	1979 Dec	121041
Allopurinol ribonucleoside as an antileishmanial agent. Biological effects, metabolism, and enzymatic phosphorylation.	1979 Nov 25	500658
Synthesis and antiviral activity of certain carbamoylpyrrolopyrimidine and pyrazolopyrimidine nucleosides.	1982 Nov	7143371
On the metabolism of allopurinol. Formation of allopurinol-1-riboside in purine nucleoside phosphorylase deficiency.	1983 Jul 15	6409116
Metabolic studies of high doses of allopurinol in humans.	1984	6720373
Inosine analogs. Their metabolism in mouse L cells and in Leishmania donovani.	1985 Aug 15	4019491
Activity of inosine analogs against Pneumocystis carinii in culture.	1986 Jul	3489438
Treatment of American cutaneous leishmaniasis with orally administered allopurinol riboside.	1989 Jul	2659681
Pharmacokinetics and metabolism of allopurinol riboside.	1991 May	2029827
Effects of probenecid on the pharmacokinetics of allopurinol riboside.	1993 May	8517715
New drug developments for opportunistic infections in immunosuppressed patients: Pneumocystis carinii.	1995 Nov 24	7490723
Blood group B glycosphingolipids in alpha-galactosidase deficiency (Fabry disease): influence of secretor status.	1997 Apr 1	9106497

Patents

Sample Use Guides

In Vivo Use Guide

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