CAS Number16220-07-8
Synonyms8-Aza-6-hydroxy-7-deazapurine riboside; Allopurinol ribonucleoside; 8-AZA-7-DEAZAINOSINE; <4-Hydroxy-1H-pyrazolo<3,4-d>pyrimidin>-ribosid; Allopurinol-1-ribonucleoside
Molecular FormulaC10H12O5N4
Molecular Weight268.23
Purity98%
Density2.08g/cm3
Boiling Point570.9ºC at 760mmHg
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 16220-07-8 |
| Catalog No. | 2A-9009114 |
| Chinese Name | 别嘌呤醇核糖苷 |
| 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 |
| Molecular Formula | C10H12O5N4 |
| Molecular Weight | 268.23 |
| Purity | 98 |
| Density | 2.08g/cm3 |
| Boiling Point | 570.9ºC at 760mmHg |
| Storage Condition | -20°C, sealed, dry |
| Application | Allopurinol riboside is a metabolite of allopurinol and can effectively inhibit parasites. |
| MDL Number | MFCD00057096 |
| SMILES | OCC1OC(C(O)C1O)N2NC=C3C(=O)N=CN=C23 |
| InChI | 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/h1,3,5-7,10,13,15-17H,2H2 |
| InChI Key | InChIKey=UKNHQPDCWMADJW-UHFFFAOYSA-N |
| Hazard Symbols | Transport |
| MSDS | msds/9114_1_16220_07_8.pdf |
| Bioactivity | Allopurinol riboside, a metabolite of allopurinol, shows potent activities against parasites. Related Catalog Signaling Pathways >> Anti-infection >> Parasite Research Areas >> Infection Natural Products >> Saccharides and Glycosides 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. Chemical & Physical Properties 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 |
| Use of | Allopurinol riboside, a metabolite of allopurinol, shows potent activities against parasites. Properties Articles27 Name allopurinol riboside Synonym More Synonyms Allopurinol riboside Biological Activity Description Allopurinol riboside, a metabolite of allopurinol, shows potent activities against parasites. Related Catalog Signaling Pathways >> Anti-infection >> Parasite Research Areas >> Infection Natural Products >> Saccharides and Glycosides 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. Chemical & Physical Properties Molecular Formula C10H12N4O5 Exact Mass 268.08100 PSA 133.49000 Index of Refraction 1.925 |
| Transport Info | Product name: Purity: 95.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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