Allopurinol riboside
(Synonyms: 别嘌呤醇核糖苷) 目录号 : GC35295
A ribonucleoside
Cas No.:16220-07-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Allopurinol riboside is a ribonucleoside and a ribose-containing derivative of the xanthine oxidase inhibitor allopurinol .1 It inhibits the growth of Leishmania promastigotes and prevents amastigote maturation into the promastigote phase of the parasite life cycle in cell-free assays.2 Allopurinol riboside (239, 511, and 929 mg/kg per day) prevents mortality in mouse models of T. cruzi infection but does not eradicate the infection.1
1.Croft, S.L., and Neal, R.A.The effect of allopurinol ribonucleoside and formycin B on Trypanosoma cruzi infections in miceTrans. R. Soc. Trop. Med. Hyg.79(4)517-518(1985) 2.Nelson, D.J., LaFon, S.W., Tuttle, J.V., et al.Allopurinol ribonucleoside as an antileishmanial agent. Biological effects, metabolism, and enzymatic phosphorylation254(22)11544-11549(1979)
| Cas No. | 16220-07-8 | SDF | |
| 别名 | 别嘌呤醇核糖苷 | ||
| Canonical SMILES | O=C1C2=C(N([C@H]3[C@H](O)[C@H](O)[C@@H](CO)O3)N=C2)NC=N1 | ||
| 分子式 | C10H12N4O5 | 分子量 | 268.23 |
| 溶解度 | DMSO : 100 mg/mL (372.81 mM; Need ultrasonic) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.7281 mL | 18.6407 mL | 37.2814 mL |
| 5 mM | 0.7456 mL | 3.7281 mL | 7.4563 mL |
| 10 mM | 0.3728 mL | 1.8641 mL | 3.7281 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Pharmacokinetics and metabolism of Allopurinol riboside
Clin Pharmacol Ther 1991 May;49(5):506-14.PMID:2029827DOI:10.1038/clpt.1991.61.
There are no safe and effective oral drugs to treat leishmaniasis and Chagas' disease. The safety, pharmacokinetics, and metabolism of single and multiple oral doses of Allopurinol riboside, an investigational antiparasitic agent, were evaluated in a randomized, double-blinded, placebo-controlled study in 32 healthy male volunteers, at levels up to 25 mg/kg q.i.d. for 13 doses. No significant toxicity was detected. 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. However, in contrast to preclinical studies in dogs (plasma levels proportional to oral doses up to 200 mg/kg), we found that plasma levels were unexpectedly low and did not rise with increasing dose. Furthermore, allopurinol and oxypurinol (unanticipated metabolites) were detected at levels proportional to the dose of Allopurinol riboside. We present a model that includes incomplete absorption, metabolism of residual drug by enteric flora, and absorption of bacterial metabolites to explain these findings in humans.
Effects of probenecid on the pharmacokinetics of Allopurinol riboside
Antimicrob Agents Chemother 1993 May;37(5):1193-6.PMID:8517715DOI:10.1128/AAC.37.5.1193.
Allopurinol riboside is an experimental agent for the treatment of leishmaniasis and American trypanosomiasis. Previous studies showed that after oral administration, unexpectedly low levels of Allopurinol riboside in plasma are attributable to incomplete absorption and rapid renal clearance. In this randomized, crossover evaluation in healthy volunteers, 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.
An association study of ABCG2 rs2231142 on the concentrations of allopurinol and its metabolites
Clin Transl Sci 2022 Aug;15(8):2024-2034.PMID:35689378DOI:10.1111/cts.13318.
ABCG2 is a gene that codes for the human breast cancer resistance protein (BCRP). It is established that rs2231142 G>T, a single nucleotide polymorphism of the ABCG2 gene, is associated with gout and poor response to allopurinol, a uric acid-lowering agent used to treat this condition. It has also been suggested that oxypurinol, the primary active metabolite of allopurinol, is a substrate of the BCRP. We thus hypothesized that carrying the rs2231142 variant would be associated with decreased oxypurinol concentrations, which would explain the lower reduction in uric acid. We performed a cross-sectional study to investigate the association between the ABCG2 rs2231142 variant and oxypurinol, allopurinol, and Allopurinol riboside concentrations in 459 participants from the Montreal Heart Institute Hospital Cohort. Age, sex, weight, use of diuretics, and estimated glomerular filtration rate were all significantly associated with oxypurinol plasma concentration. No association was found between rs2231142 and oxypurinol, allopurinol and Allopurinol riboside plasma concentrations. Rs2231142 was not significantly associated with daily allopurinol dose in the overall population, but an association was observed in men, with T carriers receiving higher doses. Our results do not support a major role of ABCG2 in the pharmacokinetics of allopurinol or its metabolites. The underlying mechanism of the association between rs2231142 and allopurinol efficacy requires further investigation.
Monophosphates of formycin B and Allopurinol riboside. Interactions with leishmanial and mammalian succino-AMP synthetase and GMP reductase
Biochem Pharmacol 1984 May 15;33(10):1611-7.PMID:6732835DOI:10.1016/0006-2952(84)90282-x.
Formycin B 5'-monophosphate (Form B-MP) and Allopurinol riboside 5'-monophosphate ( HPPR -MP) are isomers of IMP that are metabolically produced when Leishmania spp. are incubated with the antileishmanial agents formycin B and allopurinol or Allopurinol riboside. The interactions of Form B-MP with succino -AMP synthetase and GMP reductase from both leishmanial and mammalian sources were compared with the data of earlier studies with HPPR -MP. Both analogs could substitute for IMP as a substrate for succino -AMP synthetase isolated from Leishmania donovani. The V'max values of Form B-MP and HPPR -MP were about 1% of the V'max of IMP. Only Form B-MP (and not HPPR -MP) could serve as an alternative substrate for mammalian succino -AMP synthetase. The V'max of Form B-MP was 40% that of IMP. The corresponding analogs of AMP, ADP and ATP were produced when Formycin B was incubated with mouse L cells. The Formycin A residue was incorporated into the cellular RNA. The amount of Formycin A-TP produced (relative to ATP) in mouse L cells was considerably less than that produced in Leishmania spp. Both Form B-MP and HPPR -MP were inhibitors of partially purified GMP reductase from L. donovani. The binding of Form B-MP and HPPR -MP to human GMP reductase was 40- and 100-fold weaker, respectively, than the binding to leishmanial GMP reductase. Pretreatment of promastigotes of L. donovani with either allopurinol or Formycin B resulted in greater than 95% reduction of the incorporation of the radiolabel from [14C]xanthine into ATP and greater than 80% reduction of the incorporation of the label into GTP. The HPPR -MP and Form B-MP present in these cells may have inhibited the leishmanial succino -AMP synthetase and GMP reductase. The analogs had little or no effect on the pool sizes of ATP and GTP of either mouse L cells or L. donovani.
Metabolic studies of high doses of allopurinol in humans
Adv Exp Med Biol 1984;165 Pt A:167-70.PMID:6720373DOI:10.1007/978-1-4684-4553-4_31.
In animals and in humans given high doses of allopurinol, the oxidation of allopurinol to oxipurinol is inhibited, resulting in a higher proportion of unchanged allopurinol and of Allopurinol riboside in plasma and urine than is seen at low doses. The dose which produces this inhibition of allopurinol oxidation is higher in rodents than in man or in the dog. Urinary orotate and orotidine increased in proportion to the dose of allopurinol. These increased levels of orotate would be expected to compete more effectively with 5-fluorouracil for conversion to a nucleotide by orotate phosphoribosyltransferase. Since allopurinol and Allopurinol riboside are active against leishmaniae in vitro, it may be possible to attain therapeutic levels of allopurinol and Allopurinol riboside in vivo by using high doses of allopurinol.