Allopurinol | Zyloprim | CAS#315-30-0

Allopurinol
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 317168

CAS#: 315-30-0 (free)

Description: Allopurinol is a structural isomer of hypoxanthine. Allopurinol inhibits the enzyme xanthine oxidase, which converts oxypurines to uric acid. By blocking the production of uric acid, this agent decreases serum and urine concentrations of uric acid, which provvides protection against uric acid-mediated end organ damage in conditions associated with excessive production of uric acid, i.e. the massive cell lysis associated with the treatment of some malignancies.

Chemical Structure

Allopurinol

CAS# 315-30-0 (free)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317168
Name: Allopurinol
CAS#: 315-30-0 (free)
Chemical Formula: C5H4N4O
Exact Mass: 136.04
Molecular Weight: 136.110
Elemental Analysis: C, 44.12; H, 2.96; N, 41.16; O, 11.75

Price and Availability

Size	Price	Availability
25g	USD 250	2 Weeks
100g	USD 450	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 315-30-0 (free) 16220-07-8 (ribonucleoside)

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

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Product Data:

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
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

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.

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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.

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