6-Mercaptopurine hydrate
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 540285

CAS#: 6112-76-1 (hydrate)

Description: Mercaptopurine is a thiopurine inhibitor of PRPP amidotransferase used to treat autoimmune diseases, leukemias, and lymphomas. It inhibits IMP metabolism, preventing the synthesis of purines, DNA and RNA.

Chemical Structure

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6-Mercaptopurine hydrate
CAS# 6112-76-1 (hydrate)
Instruction

Theoretical Analysis

MedKoo Cat#: 540285
Name: 6-Mercaptopurine hydrate
CAS#: 6112-76-1 (hydrate)
Chemical Formula: C5H6N4OS
Exact Mass: 170.03
Molecular Weight: 170.190
Elemental Analysis: C, 35.29; H, 3.55; N, 32.92; O, 9.40; S, 18.84

Price and Availability

Size Price Availability Quantity
10g USD 250 2 weeks
25g USD 450 2 weeks
100g USD 750 2 weeks
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Related CAS #: 6112-76-1 (hydrate)   50-44-2    

Synonym: 1,7-Dihydro-6H-purin-6-thion, monohydrat; Mercaptopurine; NSC 755; NSC755; NSC-755; 6-Mercaptopurine hydrate

IUPAC/Chemical Name: 1,7-dihydro-6H-purine-6-thione hydrate

InChi Key: WFFQYWAAEWLHJC-UHFFFAOYSA-N

InChi Code: InChI=1S/C5H4N4S.H2O/c10-5-3-4(7-1-6-3)8-2-9-5;/h1-2H,(H2,6,7,8,9,10);1H2

SMILES Code: S=C1NC=NC2=C1NC=N2.[H]O[H]

Appearance: 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

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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 170.19 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.

Recalculate based on batch purity %
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:
In vitro protocol:
In vivo protocol:

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1: Lv X, Zhao M, Wang Y, Hu X, Wu J, Jiang X, Li S, Cui C, Peng S. Loading cisplatin onto 6-mercaptopurine covalently modified MSNS: a nanomedicine strategy to improve the outcome of cisplatin therapy. Drug Des Devel Ther. 2016 Dec 1;10:3933-3946. eCollection 2016. PubMed PMID: 27942204; PubMed Central PMCID: PMC5138022.

2: Chande N, Townsend CM, Parker CE, MacDonald JK. Azathioprine or 6-mercaptopurine for induction of remission in Crohn's disease. Cochrane Database Syst Rev. 2016 Oct 26;10:CD000545. Review. PubMed PMID: 27783843.

3: Li AP, Peng JD, Zhou M, Zhang J. Resonance light scattering determination of 6-mercaptopurine coupled with HPLC technique. Spectrochim Acta A Mol Biomol Spectrosc. 2016 Feb 5;154:1-7. doi: 10.1016/j.saa.2015.09.010. Epub 2015 Sep 25. PubMed PMID: 26479445.

4: Timmer A, Patton PH, Chande N, McDonald JW, MacDonald JK. Azathioprine and 6-mercaptopurine for maintenance of remission in ulcerative colitis. Cochrane Database Syst Rev. 2016 May 18;(5):CD000478. doi: 10.1002/14651858.CD000478.pub4. Review. PubMed PMID: 27192092.

5: Israeli E, Goldin E, Fishman S, Konikoff F, Lavy A, Chowers Y, Melzer E, Lahat A, Mahamid M, Shirin H, Nussinson E, Segol O, Ya'acov AB, Shabbat Y, Ilan Y. Oral administration of non-absorbable delayed release 6-mercaptopurine is locally active in the gut, exerts a systemic immune effect and alleviates Crohn's disease with low rate of side effects: results of double blind Phase II clinical trial. Clin Exp Immunol. 2015 Aug;181(2):362-72. doi: 10.1111/cei.12640. PubMed PMID: 25846055; PubMed Central PMCID: PMC4516452.

6: Tiphaine Ade B, Hjalgrim LL, Nersting J, Breitkreutz J, Nelken B, Schrappe M, Stanulla M, Thomas C, Bertrand Y, Leverger G, Baruchel A, Schmiegelow K, Jacqz-Aigrain E. Evaluation of a pediatric liquid formulation to improve 6-mercaptopurine therapy in children. Eur J Pharm Sci. 2016 Feb 15;83:1-7. doi: 10.1016/j.ejps.2015.12.002. Epub 2015 Dec 2. PubMed PMID: 26657824.

7: Jin M, Mou ZL, Zhang RL, Liang SS, Zhang ZQ. An efficient ratiometric fluorescence sensor based on metal-organic frameworks and quantum dots for highly selective detection of 6-mercaptopurine. Biosens Bioelectron. 2017 May 15;91:162-168. doi: 10.1016/j.bios.2016.12.022. Epub 2016 Dec 9. PubMed PMID: 28006684.

8: Yusung S, McGovern D, Lin L, Hommes D, Lagishetty V, Braun J. NK cells are biologic and biochemical targets of 6-mercaptopurine in Crohn's disease patients. Clin Immunol. 2017 Feb;175:82-90. doi: 10.1016/j.clim.2016.12.004. Epub 2016 Dec 21. PubMed PMID: 28011186.

9: Yang Y, Zhou S, Ouyang R, Yang Y, Tao H, Feng K, Zhang X, Xiong F, Guo N, Zong T, Cao P, Li Y, Miao Y. Improvement in the Anticancer Activity of 6-Mercaptopurine via Combination with Bismuth(III). Chem Pharm Bull (Tokyo). 2016;64(11):1539-1545. PubMed PMID: 27803465.

10: Al-Ghobashy MA, Hassan SA, Abdelaziz DH, Elhosseiny NM, Sabry NA, Attia AS, El-Sayed MH. Development and validation of LC-MS/MS assay for the simultaneous determination of methotrexate, 6-mercaptopurine and its active metabolite 6-thioguanine in plasma of children with acute lymphoblastic leukemia: Correlation with genetic polymorphism. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Dec 1;1038:88-94. doi: 10.1016/j.jchromb.2016.10.035. Epub 2016 Oct 28. PubMed PMID: 27802917.

11: Hübener S, Oo YH, Than NN, Hübener P, Weiler-Normann C, Lohse AW, Schramm C. Efficacy of 6-Mercaptopurine as Second-Line Treatment for Patients With Autoimmune Hepatitis and Azathioprine Intolerance. Clin Gastroenterol Hepatol. 2016 Mar;14(3):445-53. doi: 10.1016/j.cgh.2015.09.037. Epub 2015 Oct 19. PubMed PMID: 26492846.

12: Zgheib NK, Akika R, Mahfouz R, Aridi CA, Ghanem KM, Saab R, Abboud MR, Tarek N, El Solh H, Muwakkit SA. NUDT15 and TPMT genetic polymorphisms are related to 6-mercaptopurine intolerance in children treated for acute lymphoblastic leukemia at the Children's Cancer Center of Lebanon. Pediatr Blood Cancer. 2017 Jan;64(1):146-150. doi: 10.1002/pbc.26189. Epub 2016 Aug 31. PubMed PMID: 27577869.

13: Li Z, Ni Y, Kokot S. A new fluorescent nitrogen-doped carbon dot system modified by the fluorophore-labeled ssDNA for the analysis of 6-mercaptopurine and Hg (II). Biosens Bioelectron. 2015 Dec 15;74:91-7. doi: 10.1016/j.bios.2015.06.014. Epub 2015 Jun 12. PubMed PMID: 26120815.

14: Han G, Liu R, Han MY, Jiang C, Wang J, Du S, Liu B, Zhang Z. Label-free surface-enhanced Raman scattering imaging to monitor the metabolism of antitumor drug 6-mercaptopurine in living cells. Anal Chem. 2014 Dec 2;86(23):11503-7. doi: 10.1021/ac503539w. Epub 2014 Nov 10. PubMed PMID: 25372629.

15: Li Z, Wang Y, Ni Y, Kokot S. Fluorescence analysis of 6-mercaptopurine with the use of a nano-composite consisting of BSA-capped Au nano-clusters and core-shell Fe3O4-SiO2 nanoparticles. Biosens Bioelectron. 2015 Aug 15;70:246-53. doi: 10.1016/j.bios.2015.03.035. Epub 2015 Mar 17. PubMed PMID: 25829222.

16: Huang HY, Chang HF, Tsai MJ, Chen JS, Wang MJ. 6-Mercaptopurine attenuates tumor necrosis factor-α production in microglia through Nur77-mediated transrepression and PI3K/Akt/mTOR signaling-mediated translational regulation. J Neuroinflammation. 2016 Apr 13;13(1):78. doi: 10.1186/s12974-016-0543-5. PubMed PMID: 27075886; PubMed Central PMCID: PMC4831152.

17: Hareedy MS, El Desoky ES, Woillard JB, Thabet RH, Ali AM, Marquet P, Picard N. Genetic variants in 6-mercaptopurine pathway as potential factors of hematological toxicity in acute lymphoblastic leukemia patients. Pharmacogenomics. 2015;16(10):1119-34. doi: 10.2217/PGS.15.62. Epub 2015 Aug 3. PubMed PMID: 26237184.

18: Biparva P, Abedirad SM, Kazemi SY. Silver nanoparticles enhanced a novel TCPO-H₂O₂-safranin O chemiluminescence system for determination of 6-mercaptopurine. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Jun 15;145:454-60. doi: 10.1016/j.saa.2015.03.019. Epub 2015 Mar 10. PubMed PMID: 25796015.

19: Heerasing NM, Ng JF, Dowling D. Does lymphopenia or macrocytosis reflect 6-thioguanine levels in patients with inflammatory bowel disease treated with azathioprine or 6-mercaptopurine? Intern Med J. 2016 Apr;46(4):465-9. doi: 10.1111/imj.12915. PubMed PMID: 26425841.

20: Gordon M, Taylor K, Akobeng AK, Thomas AG. Azathioprine and 6-mercaptopurine for maintenance of surgically-induced remission in Crohn's disease. Cochrane Database Syst Rev. 2014 Aug 1;(8):CD010233. doi: 10.1002/14651858.CD010233.pub2. Review. PubMed PMID: 25081347.