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Merck
CN

1392002

USP

Mercaptopurine

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

6-Mercaptopurine monohydrate, 6-Purinethiol, 6-Thiohypoxanthine

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About This Item

Empirical Formula (Hill Notation):
C5H4N4S · H2O
CAS Number:
6112-76-1
Molecular Weight:
170.19
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329750368
MDL number:
MFCD03854445
Beilstein/REAXYS Number:
4012091

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Product Name

Mercaptopurine, United States Pharmacopeia (USP) Reference Standard

InChI key

WFFQYWAAEWLHJC-UHFFFAOYSA-N

SMILES string

O.Sc1ncnc2[nH]cnc12

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

grade

pharmaceutical primary standard

API family

mercaptopurine

manufacturer/tradename

USP

mp

>300 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

Gene Information

human ... PPAT(5471)

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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Other Notes

Sales restrictions may apply.

Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Application

Mercaptopurine USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:
  • Azathioprine
  • Azathioprine Sodium for Injection
  • Azathioprine Tablets
  • Mercaptopurine
  • Mercaptopurine Tablets

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Muta. 2 - Repr. 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

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Kanika V Choughule et al.
Drug metabolism and disposition: the biological fate of chemicals, 42(8), 1334-1340 (2014-05-16)
Anticancer agent 6-mercaptopurine (6MP) has been in use since 1953 for the treatment of childhood acute lymphoblastic leukemia (ALL) and inflammatory bowel disease. Despite being available for 60 years, several aspects of 6MP drug metabolism and pharmacokinetics in humans are
Balraj Singh et al.
PloS one, 9(10), e109487-e109487 (2014-10-04)
A major obstacle in developing effective therapies against solid tumors stems from an inability to adequately model the rare subpopulation of panresistant cancer cells that may often drive the disease. We describe a strategy for optimally modeling highly abnormal and
Qing Qin et al.
Journal of molecular and cellular cardiology, 77, 20-28 (2014-10-07)
Endothelin-1 (ET-1) produced by vascular endothelial cells plays essential roles in the regulation of vascular tone and development of cardiovascular diseases. The objective of this study is to identify novel regulators implicated in the regulation of ET-1 expression in vascular
S Bunda et al.
Oncogene, 34(6), 789-797 (2014-01-29)
Juvenile myelomonocytic leukaemia (JMML) is an aggressive myeloproliferative neoplasm in children characterized by granulocyte macrophage colony-stimulating factor (GM-CSF) hypersensitivity and resistance to chemotherapy. We recently identified c-Cbl (henceforth referred to as Cbl) as a GM-CSF receptor (GMR) responsive protein that
Leanna Cheung et al.
Biochemical pharmacology, 91(1), 97-108 (2014-06-29)
Multidrug resistance protein 4 (MRP4/ABCC4), a member of the ATP-binding cassette (ABC) transporter superfamily, is an organic anion transporter capable of effluxing a wide range of physiologically important signalling molecules and drugs. MRP4 has been proposed to contribute to numerous
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