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16220-07-8

16220-07-8 structure
16220-07-8 structure

Name allopurinol riboside
Synonyms 8-Aza-6-hydroxy-7-deazapurine riboside
Allopurinol ribonucleoside
8-AZA-7-DEAZAINOSINE
<4-Hydroxy-1H-pyrazolo<3,4-d>pyrimidin>-ribosid
Allopurinol-1-ribonucleoside
Description Allopurinol riboside, a metabolite of allopurinol, shows potent activities against parasites.
Related Catalog
Target

Human Endogenous Metabolite

In Vitro Allopurinol-riboside competitively inhibits the action of purine nucleoside phosphorylase on inosine with a Ki of 277 μM. Lymphocyte blastogensis induced by PHA and Con A is significantly suppressed by allopurinol-riboside in a concentration-dependent manner. When LPS is used as a mitogen, the inhibition of allopurinol-ribosideon lymphocyte proliferation is less marked. Humoral immunity is not suppressed by allopurinol-riboside[1]. Allopurinol riboside is an experimental agent for the treatment of leishmaniasis and American trypanosomiasis. Allopurinol riboside is effective against parasites, because a series of enzymes (analogous to those that mediate purine salvage in humans) convert it into 4-aminopyrazolopyrimidine ribonucleoside triphosphate, a cytotoxic product. Allopurinol riboside is selectively toxic, because it is not metabolized by the corresponding enzymes in humans[2].
In Vivo Allopurinol riboside peaks in plasma 1.6 hours after administration, has an elimination half-life of 3 hours, and steady-state concentrations in the therapeutic range[3]. After oral administration, unexpectedly low levels of allopurinol riboside in plasma are attributable to incomplete absorption and rapid renal clearance. Probenecid reduces the renal clearance of allopurinol riboside, extends the half-life of allopurinol riboside in plasma, and triples the levels of allopurinol riboside in plasma[4].
References

[1]. Nishida Y, et al. Inhibition of purine nucleoside phosphorylase activity and of T-cell function with allopurinol-riboside. Agents Actions. 1979 Dec;9(5-6):549-52.

[2]. Pacher P, et al. Therapeutic effects of xanthine oxidase inhibitors: renaissance half a century after the discovery of allopurinol. Pharmacol Rev. 2006 Mar;58(1):87-114.

[3]. Shapiro TA, et al. Pharmacokinetics and metabolism of allopurinol riboside. Clin Pharmacol Ther. 1991 May;49(5):506-14.

[4]. Were JB, et al. Effects of probenecid on the pharmacokinetics of allopurinol riboside. Antimicrob Agents Chemother. 1993 May;37(5):1193-6.

Density 2.08g/cm3
Boiling Point 570.9ºC at 760mmHg
Molecular Formula C10H12N4O5
Molecular Weight 268.22600
Flash Point 299ºC
Exact Mass 268.08100
PSA 133.49000
Vapour Pressure 3.62E-15mmHg at 25°C
Index of Refraction 1.925
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
RIDADR NONH for all modes of transport
WGK Germany 3