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852678

Sigma-Aldrich

6-Mercaptopurine monohydrate

98%

Sinónimos:

6-Purinethiol, 6-Thiohypoxanthine

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About This Item

Fórmula empírica (notación de Hill):
C5H4N4S · H2O
Número de CAS:
6112-76-1
Peso molecular:
170.19
Beilstein/REAXYS Number:
4012091
EC Number:
200-037-4
MDL number:
MFCD03854445
UNSPSC Code:
12352005
PubChem Substance ID:
24888330
NACRES:
NA.22

Quality Level

100

assay

98%

form

powder

mp

>300 °C (lit.)

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

InChI key

WFFQYWAAEWLHJC-UHFFFAOYSA-N

Gene Information

human ... PPAT(5471)

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General description

6-Mercaptopurine monohydrate is an antimetabolite and antineoplastic drug. Its cocrystallization with 4-hydroxybenzoic acid and 2,4-dihydroxybenzoic acid or salt formation with piperazine may improve its aqueous solubility.

Application

6-Mercaptopurine is a widely used antileukemic agent that inhibits de novo purine synthesis through incorporation of thiopurine methyltransferase metabolites into DNA and RNA.

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_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
MKCW4101
MKCQ4491
MKCN6574
MKCH0145
MKCD3597

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The crystal and molecular structure of 6-mercaptopurine monohydrate.
Sletten E, et al.
Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials, 25(7), 1330-1338 (1969)
Comparative structural and spectrum analyses of 6-mercaptopurine monohydrate and 6-mercaptopurine hydrochloride
Perez-Ruiz E, et al.
Canadian Journal of Analytical Sciences and Spectroscopy, 43(3), 59-67 (1998)
M J Casanova et al.
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The safety of thiopurines and anti-tumor necrosis factor-α (TNF-α) drugs during pregnancy remains controversial, as the experience with these drugs in this situation is limited. Our aim is to assess the safety of thiopurines and anti-TNF-α drugs for the treatment
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In aortic aneurysms the arterial vessel wall is dilated because of destruction of its integrity, which may lead to lethal vessel rupture. Chronic infiltration of inflammatory cells into the vessel wall is fundamental to aneurysm pathology. We aim to limit
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Blood, 121(25), 5006-5014 (2013-04-17)
Langerhans cell histiocytosis (LCH)-III tested risk-adjusted, intensified, longer treatment of multisystem LCH (MS-LCH), for which optimal therapy has been elusive. Stratified by risk organ involvement (high [RO+] or low [RO-] risk groups), > 400 patients were randomized. RO+ patients received
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