6-Mercaptopurine monohydrate

Modify Date: 2024-01-02 16:51:52

6-Mercaptopurine monohydrate Structure
6-Mercaptopurine monohydrate structure
 Common Name 6-Mercaptopurine monohydrate
CAS Number 6112-76-1 Molecular Weight 170.192
Density N/A Boiling Point 490.6ºC at 760 mmHg
Molecular Formula C5H6N4OS Melting Point >300 °C(lit.)
MSDS Chinese USA Flash Point 250.5ºC
Symbol GHS07
GHS07		 Signal Word Warning

 Use of 6-Mercaptopurine monohydrate


6-Mercaptopurine hydrate is a purine analogue which acts as an antagonist of the endogenous purines and has been widely used as antileukemic agent and immunosuppressive drug.

 Names

Name mercaptopurine hydrate
Synonym More Synonyms

 6-Mercaptopurine monohydrate Biological Activity

Description 6-Mercaptopurine hydrate is a purine analogue which acts as an antagonist of the endogenous purines and has been widely used as antileukemic agent and immunosuppressive drug.
Related Catalog
Target

endogenous purines[1]

In Vitro 6-Mercaptopurine hydrate (6-MP) induces NR4A3 transcriptional activity 1.6- to 11-fold (P<0.01) in a dose-responsive manner. It is found that 6-Mercaptopurine hydrate leads to a dose-dependent increase in NR4A3 protein levels. 6-Mercaptopurine hydrate treatment increases cell surface GLUT4 in both basal cells 1.8- to 3.6-fold (P<0.01) and insulin-stimulated cells 2.9- to 4.4-fold (P<0.01) over that in controls. It is also found that 6-Mercaptopurine hydrate increases phospho-AS160 significantly in a dose-responsive manner under both basal and insulin-stimulated conditions[2].
In Vivo In the fetal telencephalons of the 6-Mercaptopurine hydrate (6-MP)-treated group, the S phase cell population increases at 36 and 48 h and returns to the control level at 72 h after treatment. The G2/M phase cell population begins to increase at 24 h, peaks at 36 h, decreases at 48 h, and finally returnes to the control level at 72 h. On the other hand, the sub-G1 phase cell population (apoptotic cells) begins to increase at 36 h, peaks at 48 h, and then decreases at 72 h[3].
Kinase Assay L6 myotubes are treated with DMSO control or 6-Mercaptopurine hydrate (6-MP) for 24 h, with the final 3 h of incubation including treatments in serum-free DMEM, and further incubated in the absence or presence of 100 nM insulin for 60 min at 37°C. Then, protein lysates (50 μg) are collected and subjected to SDS-PAGE. The proteins are finally quantified by densitometric analysis of scanned films using Image J software[2].
Cell Assay Cell viability is measured using Cell Viability Assay. L6 skeletal muscle cells are seeded in 96-well plates at a density of 10,000 cells/well and differentiated into myotubes within 7 days. Cells are treated with different doses of 6-Mercaptopurine hydrate (6-MP) for 24 h before the assay. For analysis of cell viability, plates are equilibrated at room temperature for 30 min; 50 μL of Cell Titer-Glo reagent is added to each well, and plates are mixed for 12 min on an orbital shaker. Luminescence is quantified using a luminometer[2].
Animal Admin Around thirteen-week-old pregnant rats are used in this study. The animals are housed individually in wire-mesh cages in an air-conditioned room (temperature, 23±3°C; humidity, 50±20%; ventilation, 10 times/hour; lighting, 12 h light to12 h dark cycle) and are given pelleted diet and water ad libitum. In the experiment, fifteen pregnant rats are injected i.p. with 50 mg/kg 6-Mercaptopurine hydrate (6-MP) on E13, and three dams each are sacrificed by exsanguination from the abdominal aorta under ether anesthesia at 12, 24, 36, 48, and 72 h. Fetuses are collected from each dam by Caesarean section. As controls, fifteen pregnant rats are injected i.p. with 2.0% methylcellulose solution in distilled water at E13, and three dams are sacrificed at each of the same time-points[3].
References

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

[2]. Liu Q, et al. 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]. Kanemitsu H, et al. 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.

 Chemical & Physical Properties

Boiling Point 490.6ºC at 760 mmHg
Melting Point >300 °C(lit.)
Molecular Formula C5H6N4OS
Molecular Weight 170.192
Flash Point 250.5ºC
Exact Mass 170.026230
PSA 98.68000
LogP 0.95120
Storage condition Store at 0-5
Stability Stable. Incompatible with strong oxidizing agents, acids, strong bases. Light sensitive.
Water Solubility INSOLUBLE

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UP0400000
CHEMICAL NAME :
Purine-6-thiol, monohydrate
CAS REGISTRY NUMBER :
6112-76-1
LAST UPDATED :
199410
DATA ITEMS CITED :
10
MOLECULAR FORMULA :
C5-H4-N4-S.H2-O
MOLECULAR WEIGHT :
170.21
WISWESSER LINE NOTATION :
T56 BM DN FN HNJ ISH &QH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1250 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
224 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
27500 ug/kg
SEX/DURATION :
female 11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
500 mg/kg
SEX/DURATION :
male 40 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
250 mg/kg
SEX/DURATION :
male 5 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
4 mg/kg
SEX/DURATION :
female 6-9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Micronucleus test

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
500 mg/kg/40D (Intermittent)
REFERENCE :
DCTODJ Drug and Chemical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.1- 1977/78- Volume(issue)/page/year: 6,83,1983

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302-H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn:Harmful
Risk Phrases R22;R36/37/38
Safety Phrases S22-S36/37/39-S45
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS UP0400000
HS Code 29335995

 Customs

HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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 Synonyms

9H-purine-6-thiol, hydrate (1:1)
7H-purine-6-thiol, hydrate (1:1)
LEUKERIN MONOHYDRATE
6-Mercaptopurine monohydrate
6H-Purine-6-thione, 3,7-dihydro-, hydrate (1:1)
9H-Purine-6-thiol hydrate (1:1)
6MP H2O
MERCALEUKIN MONOHYDRATE
purin-6-thiol,monohydrate
1,7-Dihydro-6H-purine-6-thione hydrate (1:1)
6MP MONOHYDRATE
EINECS 212-968-3
MFCD03854445
7H-purine-6-thiol hydrate
6-Mercaptopurine hydrate
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