Synonym
Allopurinol; Zyloprim; Lopurin; Zyloric; Allohexal; Allohexan; Alloprin; Allopurin
IUPAC/Chemical Name
1,2-dihydropyrazolo[3,4-d]pyrimidin-4-one
InChi Key
OFCNXPDARWKPPY-UHFFFAOYSA-N
InChi Code
InChI=1S/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)
SMILES Code
C1=C2C(=NC=NC2=O)NN1
Appearance
White of off-white solid powder.
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Allopurinol (Zyloprim) is a xanthine oxidase inhibitor with an IC50 of 7.82±0.12 μM.
In vitro activity:
As shown in Fig. 1A excess glucose (10 mM) significantly increased trophoblast secretion of IL-1β to 135.2 ± 10.6 pg/mL) when compared to glucose at 5 mM (34.0 ± 4.4 pg/mL). This was significantly inhibited by allopurinol at 200 µM (allo 200) to 109.7 ± 9.7 pg/mL and by allopurinol at 400 µM (allo 400) to 87.3 ± 10.2 pg/mL. To determine whether the inhibition of excess glucose-induced trophoblast IL-1β was a result of allopurinol inhibiting inflammasome function, caspase-1 activity was measured. As shown in Fig. 1B, excess glucose significantly increased trophoblast caspase-1 activity to 78.0 ± 3.7 RLU when compared to glucose at 5 mM (54.9 ± 3.7 RLU), and this was significantly inhibited by allopurinol at 400 µM to 53.9 ± 3.1 RLU. Allopurinol at 200 µM had no effect on trophoblast caspase-1 activity under excess glucose conditions. However, both doses of allopurinol significantly reduced trophoblast caspase-1 activity under 5 mM glucose conditions (Fig. 1B).
Reference: Reproduction. 2020 Jan;159(1):73-80. https://pubmed.ncbi.nlm.nih.gov/31705795/
In vivo activity:
ALP (Allopurinol) treatment significantly decreased water intake in diabetic rats (D + ALP group), but did not significantly affect their blood glucose levels, food consumption and body weight. The changes of the serum specific markers related to hepatic damage were displayed in Figure 3a and b. Both serum AST and ALT were significantly increased in diabetic group compared with the control group (P < 0.05 vs C), and were significantly reduced by ALP treatment (P < 0.05 vs D). The above changes indicate that ALP effectively alleviated the histological changes in the liver of diabetic rats. In addition, tissue section TUNEL assay showed that the apoptosis of liver tissue in D group was significantly increased (P < 0.05 vs C), while the apoptosis of liver tissue was significantly decreased in diabetic rats with ALP treatment (Figure 4a and b). Moreover, the protein expression of cleave-caspase 3 was significantly increased in D group compared with C group, and its overexpression was significantly decreased in diabetic rats with ALP treatment (Figure 4c).
Reference: Int J Immunopathol Pharmacol. 2021 Jan-Dec;35:20587384211031417. https://pubmed.ncbi.nlm.nih.gov/34240649/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
14.7 |
107.78 |
|
| DMSO:PBS (pH 7.2) (1:10) |
0.1 |
0.73 |
|
| Ethanol |
3.0 |
22.04 |
|
| Water |
1.0 |
7.35 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
136.11
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Negi M, Mulla MJ, Han CS, Abrahams VM. Allopurinol inhibits excess glucose-induced trophoblast IL-1β and ROS production. Reproduction. 2020 Jan;159(1):73-80. doi: 10.1530/REP-19-0422. PMID: 31705795.
2. Eleftheriadis T, Pissas G, Antoniadi G, Liakopoulos V, Stefanidis I. Allopurinol protects human glomerular endothelial cells from high glucose-induced reactive oxygen species generation, p53 overexpression and endothelial dysfunction. Int Urol Nephrol. 2018 Jan;50(1):179-186. doi: 10.1007/s11255-017-1733-5. Epub 2017 Nov 1. PMID: 29094329.
3. Zeng F, Luo J, Han H, Xie W, Wang L, Han R, Chen H, Cai Y, Huang H, Xia Z. Allopurinol ameliorates liver injury in type 1 diabetic rats through activating Nrf2. Int J Immunopathol Pharmacol. 2021 Jan-Dec;35:20587384211031417. doi: 10.1177/20587384211031417. PMID: 34240649.
4. Cho IJ, Oh DH, Yoo J, Hwang YC, Ahn KJ, Chung HY, Jeong SW, Moon JY, Lee SH, Lim SJ, Jeong IK. Allopurinol ameliorates high fructose diet induced hepatic steatosis in diabetic rats through modulation of lipid metabolism, inflammation, and ER stress pathway. Sci Rep. 2021 May 10;11(1):9894. doi: 10.1038/s41598-021-88872-7. PMID: 33972568; PMCID: PMC8110790.
In vitro protocol:
1. Negi M, Mulla MJ, Han CS, Abrahams VM. Allopurinol inhibits excess glucose-induced trophoblast IL-1β and ROS production. Reproduction. 2020 Jan;159(1):73-80. doi: 10.1530/REP-19-0422. PMID: 31705795.
2. Eleftheriadis T, Pissas G, Antoniadi G, Liakopoulos V, Stefanidis I. Allopurinol protects human glomerular endothelial cells from high glucose-induced reactive oxygen species generation, p53 overexpression and endothelial dysfunction. Int Urol Nephrol. 2018 Jan;50(1):179-186. doi: 10.1007/s11255-017-1733-5. Epub 2017 Nov 1. PMID: 29094329.
In vivo protocol:
1. Zeng F, Luo J, Han H, Xie W, Wang L, Han R, Chen H, Cai Y, Huang H, Xia Z. Allopurinol ameliorates liver injury in type 1 diabetic rats through activating Nrf2. Int J Immunopathol Pharmacol. 2021 Jan-Dec;35:20587384211031417. doi: 10.1177/20587384211031417. PMID: 34240649.
2. Cho IJ, Oh DH, Yoo J, Hwang YC, Ahn KJ, Chung HY, Jeong SW, Moon JY, Lee SH, Lim SJ, Jeong IK. Allopurinol ameliorates high fructose diet induced hepatic steatosis in diabetic rats through modulation of lipid metabolism, inflammation, and ER stress pathway. Sci Rep. 2021 May 10;11(1):9894. doi: 10.1038/s41598-021-88872-7. PMID: 33972568; PMCID: PMC8110790.
1: Nakajima A, Oda S, Yokoi T. Allopurinol induces innate immune responses through mitogen-activated protein kinase signaling pathways in HL-60 cells. J Appl Toxicol. 2015 Dec 7. doi: 10.1002/jat.3272. [Epub ahead of print] PubMed PMID: 26641773.
2: Al-Zahrani YA, Al-Harthi SE, Khan LM, El-Bassossy HM, Edris SM, A Sattar MA. The possible antianginal effect of allopurinol in vasopressin-induced ischemic model in rats. Saudi Pharm J. 2015 Oct;23(5):487-498. Epub 2015 Jan 7. PubMed PMID: 26594114; PubMed Central PMCID: PMC4605908.
3: Larsen KS, Pottegård A, Lindegaard HM, Hallas J. Effect of Allopurinol on Cardiovascular Outcomes in Hyperuricemic patients A Cohort Study. Am J Med. 2015 Nov 14. pii: S0002-9343(15)01047-5. doi: 10.1016/j.amjmed.2015.11.003. [Epub ahead of print] PubMed PMID: 26589484.
4: Altan A, Shiozawa A, Bancroft T, Singh JA. A Real-World Study of Switching From Allopurinol to Febuxostat in a Health Plan Database. J Clin Rheumatol. 2015 Dec;21(8):411-8. doi: 10.1097/RHU.0000000000000322. PubMed PMID: 26580304; PubMed Central PMCID: PMC4654265.
5: Verma AT, Gin K. Allopurinol in Vascular Disease: Is There a New Role for an Old Drug? Can J Cardiol. 2015 Sep 5. pii: S0828-282X(15)01397-5. doi: 10.1016/j.cjca.2015.08.027. [Epub ahead of print] PubMed PMID: 26577891.
6: Takir M, Kostek O, Ozkok A, Elcioglu OC, Bakan A, Erek A, Mutlu HH, Telci O, Semerci A, Odabas AR, Afsar B, Smits G, ALanaspa M, Sharma S, Johnson RJ, Kanbay M. Lowering Uric Acid With Allopurinol Improves Insulin Resistance and Systemic Inflammation in Asymptomatic Hyperuricemia. J Investig Med. 2015 Dec;63(8):924-9. doi: 10.1097/JIM.0000000000000242. PubMed PMID: 26571421.
7: Dong D, Tan-Koi WC, Teng GG, Finkelstein E, Sung C. Cost-effectiveness analysis of genotyping for HLA-B*5801 and an enhanced safety program in gout patients starting allopurinol in Singapore. Pharmacogenomics. 2015 Nov;16(16):1781-93. doi: 10.2217/pgs.15.125. Epub 2015 Nov 10. PubMed PMID: 26554739.
8: Perreault S, Nuevo J, Baumgartner S, Morlock R. Adherence and Persistence to Allopurinol among Hypertensive Patients with Gout. Value Health. 2015 Nov;18(7):A655. doi: 10.1016/j.jval.2015.09.2366. Epub 2015 Oct 20. PubMed PMID: 26533673.
9: Singh J, Yang S. Effectiveness of Allopurinol In Achieving And Sustaining Target Serum Urate: An Analysis of A National Integrated U.S. Healthcare System. Value Health. 2015 Nov;18(7):A635-6. doi: 10.1016/j.jval.2015.09.2257. Epub 2015 Oct 20. PubMed PMID: 26533566.
10: Perreault S, Nuevo J, Baumgartner S, Morlock R. Compliance With Allopurinol Among Hypertensive Patients With Gout Diagnosis and The Relationship to Onset of End-Stage Renal Disease. Value Health. 2015 Nov;18(7):A634-5. doi: 10.1016/j.jval.2015.09.2251. Epub 2015 Oct 20. PubMed PMID: 26533559.
