yingweiwo

6-Mercaptopurine (6-MP) Monohydrate

Alias: 6-MP; Mercaptopurine; NSC 755; 6 MP; NSC755; 6MP; NSC-755; 6-Mercaptopurine hydrate
Cat No.:V1428 Purity: ≥98%
6-Mercaptopurine monohydrate (6-MP; NSC 755; 6 MP; NSC755; 6MP; NSC-755; Purinethol), the hydrated form of 6-Mercaptopurine, is an approved anticancer and immunosuppressive drug used for the treatment of ALL-acute lymphocytic leukemia, CML-chronic myeloid leukemia, Crohns disease, and ulcerative colitis.
6-Mercaptopurine (6-MP) Monohydrate
6-Mercaptopurine (6-MP) Monohydrate Chemical Structure CAS No.: 6112-76-1
Product category: DNA(RNA) Synthesis
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
1g
2g
5g
10g
50g
Other Sizes

Other Forms of 6-Mercaptopurine (6-MP) Monohydrate:

  • Mercaptopurine (6-MP)
Official Supplier of:
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Top Publications Citing lnvivochem Products
Purity & Quality Control Documentation

Purity: ≥98%

Product Description

6-Mercaptopurine monohydrate (6-MP; NSC 755; 6 MP; NSC755; 6MP; NSC-755; Purinethol), the hydrated form of 6-Mercaptopurine, is an approved anticancer and immunosuppressive drug used for the treatment of ALL-acute lymphocytic leukemia, CML-chronic myeloid leukemia, Crohn's disease, and ulcerative colitis. Thiopurine methyltransferase metabolites are incorporated into DNA and RNA, inhibiting de novo purine synthesis.

Biological Activity I Assay Protocols (From Reference)
Targets
endogenous purines
ln Vitro

6-Mercaptopurine hydrate (6-MP) dose-responsively increases NR4A3 transcriptional activity by 1.6–11 fold (P<0.01). A dose-dependent increase in NR4A3 protein levels is observed with 6-Mercaptopurine hydrate. Insulin-stimulated cells’ cell surface GLUT4 increases 2.9–4.4 fold (P<0.01) and basal cells’ cell surface GLUT4 increases 1.8–3.6 fold (P<0.01) over controls after 6-MP treatment. Furthermore, under both basal and insulin-stimulated conditions, 6-Mercaptopurine hydrate is found to significantly and dose-responsively increase phospho-AS160[2].

ln Vivo
After receiving 6-Mercaptopurine hydrate (6-MP) treatment, the S phase cell population in the fetal telencephalons of that group increases at 36 and 48 hours and reaches the control level at 72 hours. The G2/M phase cell population increases over the course of 24 hours, peaks at 36 hours, declines at 48 hours, and then returns to the control level at 72 hours. In contrast, the sub-G1 phase cell population, also known as apoptotic cells, starts to grow at 36 h, peaks at 48 h, and then starts to decline at 72 h[3].
Enzyme Assay
L6 myotubes are incubated for 24 hours in either DMSO control or 6-Mercaptopurine hydrate (6-MP), with treatments in serum-free DMEM during the last 3 hours. They are then incubated for an additional 60 minutes at 37°C in the presence or absence of 100 nM insulin. Subsequently, 50 μg of protein lysates are gathered, put through SDS-PAGE, and then immunoblotted using primary antibodies for an entire night at 4°C. Using Image J software, densitometric analysis of scanned films is used to finally quantify the proteins[2].
Cell Assay
The Cell Viability Assay is used to quantify cell viability. 10,000 L6 skeletal muscle cells are seeded per well in 96-well plates, and after 7 days, the cells differentiate into myotubes. Before the assay, cells are treated for 24 hours with varying doses of 6-Mercaptopurine hydrate (6-MP). After 30 minutes of room temperature equilibration, 50 μL of Cell Titer-Glo reagent is added to each well, and the plates are mixed for 12 minutes on an orbital shaker to analyze the viability of the cells. A luminometer is used to measure luminosity[2].
Animal Protocol
In this study, pregnant rats that are about thirteen weeks old are employed. The animals are kept in separate wire-mesh cages in an air-conditioned room with constant temperature and humidity levels (23±3°C and 50±20%, respectively), 10 cycles of ventilation (lights on for 12 hours and dark for 12 hours), and free access to pelleted food and water. In the experiment, three dams are each sacrificed by exsanguination from the abdominal aorta under ether anesthesia at 12, 24, 36, 48, and 72 hours after fifteen pregnant rats receive an intraperitoneal injection of 50 mg/kg 6-Mercaptopurine hydrate (6-MP) on E13. Each dam's fetuses are removed via Caesarean section. Three dams are sacrificed at each of the same time points, and fifteen pregnant rats are injected intraperitoneally (i.p.) with a 2.0% methylcellulose solution in distilled water as controls at E13[3].
Toxicity/Toxicokinetics
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation
In the treatment of conditions such as ulcerative colitis and Crohn's disease, most professional guidelines and other experts consider breastfeeding to be acceptable during mercaptopurine therapy.[1-9] Azathioprine is rapidly converted to mercaptopurine, so data from mothers taking azathioprine apply to mercaptopurine. No active metabolites of mercaptopurine were found in the blood of breastfed infants whose mothers were taking azathioprine and only poorly documented cases of mild, asymptomatic neutropenia and increased rates of infection have been reported occasionally. It might be desirable to monitor exclusively breastfed infants with a complete blood count with differential, and liver function tests if azathioprine is used during lactation, although some authors feel that such monitoring is unnecessary.[10]. See the Azathioprine record for details. Mothers with decreased activity of the enzyme that detoxifies mercaptopurine metabolites may transmit higher levels of drug to their infants in breastmilk. It might be desirable to monitor exclusively breastfed infants with a complete blood count with differential, and liver function tests if mercaptopurine is used during lactation, although some authors feel that monitoring is unnecessary.[11] Avoiding breastfeeding for 4 hours after a dose should markedly decrease the dose received by the infant in breastmilk.[12]
Most sources consider breastfeeding to be contraindicated during maternal antineoplastic drug therapy, although antimetabolites such as mercaptopurine appear to pose the least risk to breastfed infants.[13] After high-dose chemotherapy, it might be possible to breastfeed safely during intermittent therapy with an appropriate period of breastfeeding abstinence. Although no data are available to determine an appropriate period to withhold breastfeeding, the drug's terminal half-life suggests that withholding breastfeeding for 1 to 2 days may be sufficient. Chemotherapy may adversely affect the normal microbiome and chemical makeup of breastmilk.[14]
◉ Effects in Breastfed Infants
In The Netherlands, 30 infants of mothers taking either azathioprine (n = 28) or mercaptopurine (n = 2) for inflammatory bowel disease during pregnancy and postpartum were followed at 1 to 6 years of age using a 43-item quality of life questionnaire. Of this cohort, 9 infants were breastfed for a mean of 7 months (range 3 to 13 months) No statistically significant differences were found between breastfed and formula-fed infants in any of the 12 domains of the survey.[19]
In a multi-center study of women with inflammatory bowel disease in pregnancy (the PIANO registry), 102 women received a thiopurine (azathioprine or mercaptopurine) and another 67 received a thiopurine plus a biological agent (adalimumab, certolizumab, golimumab, infliximab, natalizumab, or ustekinumab) while breastfeeding their infants. Among those who received a thiopurine or combination therapy while breastfeeding, infant growth, development or infection rate was no different from 208 breastfed infants whose mothers received no treatment.[20]
A national survey of gastroenterologists in Australia identified 21 infants who were breastfed by mothers taking a combination of allopurinol and a thiopurine (e.g. azathioprine, mercaptopurine) to treat inflammatory bowel disease. All had taken the combination during pregnancy also. Two postpartum infant deaths occurred, both at 3 months of age. One was a twin (premature birth-related) and the other from SIDS. The authors did not believe the deaths were medication related.[21] No information was provided on the extent of breastfeeding, drug dosages or the outcomes of the other infants.
◉ Effects on Lactation and Breastmilk
Relevant published information was not found as of the revision date.
References

[1]. Clinical pharmacology and pharmacogenetics of thiopurines. Eur J Clin Pharmacol. 2008 Aug;64(8):753-67.

[2]. 6-Mercaptopurine augments glucose transport activity in skeletal muscle cells in part via a mechanism dependent upon orphan nuclear receptor NR4A3. Am J Physiol Endocrinol Metab. 2013 Nov 1;305(9):E1081-92.

[3]. 6-Mercaptopurine (6-MP) induces cell cycle arrest and apoptosis of neural progenitor cells in the developing fetal rat brain. Neurotoxicol Teratol. 2009 Mar-Apr;31(2):104-9.

Additional Infomation
6-mercaptopurine monohydrate is an odorless light yellow to yellow crystalline powder. Becomes anhydrous at 284 °F. (NTP, 1992)
Mercaptopurine hydrate is a hydrate. It contains a mercaptopurine.
Mercaptopurine is a thiopurine-derivative antimetabolite with antineoplastic and immunosuppressive activities. Produced through the metabolism of mercaptopurine by hypoxanthine-guanine phosphoribosyltransferase (HGPRT), mercaptopurine metabolites 6-thioguanosine-5'-phosphate (6-thioGMP) and 6-thioinosine monophosphate (T-IMP) inhibit nucleotide interconversions and de novo purine synthesis, thereby blocking the formation of purine nucleotides and inhibiting DNA synthesis. This agent is also incorporated into DNA in the form of deoxythioguanosine, which results in the disruption of DNA replication. In addition, mercaptopurine is converted to 6-methylmercaptopurine ribonucleoside (MMPR) by 6-thiopurine methyltransferase; MMPRs are also potent inhibitors of de novo purine synthesis. (NCI04)
An antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia.
See also: Mercaptopurine (annotation moved to).
Drug Indication
Xaluprine is indicated for the treatment of acute lymphoblastic leukaemia (ALL) in adults, adolescents and children.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C5H6N4OS
Molecular Weight
170.19
Exact Mass
170.026
Elemental Analysis
C, 35.29; H, 3.55; N, 32.92; O, 9.40; S, 18.84
CAS #
6112-76-1
Related CAS #
50-44-2
PubChem CID
2724350
Appearance
Light yellow to yellow solid powder
Boiling Point
490.6ºC at 760 mmHg
Melting Point
>300 °C(lit.)
Flash Point
250.5ºC
LogP
0.951
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
0
Heavy Atom Count
11
Complexity
190
Defined Atom Stereocenter Count
0
SMILES
S=C1C2=C(N=C([H])N2[H])N([H])C([H])=N1.O([H])[H]
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
Chemical Name
3,7-dihydropurine-6-thione;hydrate
Synonyms
6-MP; Mercaptopurine; NSC 755; 6 MP; NSC755; 6MP; NSC-755; 6-Mercaptopurine hydrate
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 35.7~100 mg/mL (234.7~587.6 mM)
Water: <1 mg/mL
Ethanol: <1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (14.69 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 + to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.8758 mL 29.3789 mL 58.7579 mL
5 mM 1.1752 mL 5.8758 mL 11.7516 mL
10 mM 0.5876 mL 2.9379 mL 5.8758 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
/

Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
+
+
+

Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT05506332 Recruiting Drug: 6-mercaptopurine
Drug: Venetoclax
Acute Myeloid Leukemia,
in Relapse
Acute Myeloid Leukemia
Refractory
University Hospital, Antwerp July 15, 2022 Phase 1
NCT05276284 Recruiting Combination Product: Atezolizumab,
6-mercaptopurine, 6-thioguanine
Solid Tumor, Adult
Metastatic Cancer
Kristoffer Rohrberg September 1, 2022 Phase 1
Phase 2
NCT01432145 Completed Drug: 6-Mercaptopurine
Drug: Methotrexate
Breast Cancer
Ovarian Cancer
University of Oxford May 2011 Phase 2
NCT01324336 Completed Drug: 6-Mercaptopurine Acute Lymphoblastic Leukemia Children's Mercy Hospital Kansas
City
July 2011 N/A
NCT00548431 Completed Drug: 6-mercaptopurine Leukemia, Lymphocytic, Acute Rigshospitalet, Denmark December 2007 Phase 2
Biological Data
  • Effects of 6-mercaptopurine (6-MP) on glucose transport activity and cell viability in L6 myotubes. Am J Physiol Endocrinol Metab . 2013 Nov 1;305(9):E1081-92.
  • Effects of 6-MP on NR4A3 transcriptional activity and protein expression. Am J Physiol Endocrinol Metab . 2013 Nov 1;305(9):E1081-92.
  • Effects of NR4A3 knockdown and 6-MP on glucose transport in L6 skeletal muscle cells. Am J Physiol Endocrinol Metab . 2013 Nov 1;305(9):E1081-92.
  • Effects of 6-MP treatment on the protein expression of glucose transporters GLUT1 and GLUT4 and GLUT4 translocation to the cell surface. Am J Physiol Endocrinol Metab . 2013 Nov 1;305(9):E1081-92.
Contact Us