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Merck
CN

1660000

USP

Thioguanine

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

6-Thioguanine, 2-Amino-6-mercaptopurine, 2-Amino-6-purinethiol

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About This Item

Empirical Formula (Hill Notation):
C5H5N5S
CAS Number:
Molecular Weight:
167.19
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
157765
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grade

pharmaceutical primary standard

API family

thioguanine, tioguanine

manufacturer/tradename

USP

mp

≥300 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

SMILES string

NC1=Nc2nc[nH]c2C(=S)N1

InChI

1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)

InChI key

WYWHKKSPHMUBEB-UHFFFAOYSA-N

Gene Information

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.

Application

Thioguanine USP Reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monograph such as Thioguanine Tablets

Biochem/physiol Actions

Ribosylated and phosphorylated by the same pathway as natural purine bases; as the nucleotide, inhibits a variety of cellular processes involved in nucleic acid synthesis. Has a long history as an effective treatment of leukemia.

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.  ​

Other Notes

Sales restrictions may apply.


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pictograms

Skull and crossbones

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable



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Paola Di Matteo et al.
Clinical & experimental metastasis, 32(3), 289-300 (2015-02-05)
Tumor vessels are an attractive target for cancer therapy, including metastasis treatment. Angiogenesis inhibitors targeting the VEGF signalling pathway have proven to be efficacious in preclinical cancer models and in clinical trials. However, angiogenesis inhibition concomitantly elicits tumor adaptation and
Lynne Lennard et al.
British journal of haematology, 169(2), 228-240 (2014-12-03)
The impact of thiopurine methyltransferase (TPMT) genotype on thiopurine dose intensity, myelosuppression and treatment outcome was investigated in the United Kingdom childhood acute lymphoblastic leukaemia (ALL) trial ALL97. TPMT heterozygotes had significantly more frequent cytopenias and therefore required dose adjustments
Chenglong Sun et al.
Journal of immunology (Baltimore, Md. : 1950), 194(4), 1819-1831 (2015-01-18)
Herpesviruses are DNA viruses harboring the capacity to establish lifelong latent-recurrent infections. There is limited knowledge about viruses targeting the innate DNA-sensing pathway, as well as how the innate system impacts on the latent reservoir of herpesvirus infections. In this



Global Trade Item Number

SKUGTIN
1660000-200MG04061833833445