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852686

Sigma-Aldrich

6-Mercaptopurine-9-β-D-ribofuranoside

≥95.0% (HPLC)

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Synonym(s):
6-Mercaptopurine riboside, 6-Purinethiol riboside, 6-Thioinosine
Empirical Formula (Hill Notation):
C10H12N4O4S
CAS Number:
Molecular Weight:
284.29
Beilstein:
40536
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:

Assay

≥95.0% (HPLC)

form

powder

optical activity

[α]/D −74±4°, c = 1% in 0.1 M NaOH

mp

220-223 °C (lit.)

storage temp.

−20°C

SMILES string

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(S)ncnc23

InChI

1S/C10H12N4O4S/c15-1-4-6(16)7(17)10(18-4)14-3-13-5-8(14)11-2-12-9(5)19/h2-4,6-7,10,15-17H,1H2,(H,11,12,19)/t4-,6-,7-,10-/m1/s1

InChI key

NKGPJODWTZCHGF-KQYNXXCUSA-N

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Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Lennard P L Gilissen et al.
Journal of Crohn's & colitis, 6(6), 698-707 (2012-03-09)
Therapeutic drug monitoring of active metabolites of thiopurines, azathioprine and 6-mercaptopurine, is relatively new. The proposed therapeutic threshold level of the active 6-thioguanine nucleotides (6-TGN) is ≥235 pmol/8×10(8) erythrocytes. The aim of this prospective cross-sectional study was to compare 6-TGN
M Ben Sghaier et al.
Environmental toxicology and pharmacology, 31(1), 220-232 (2011-07-27)
The evaluation of the mutagenic and antimutagenic actions of extracts obtained from aerial part of Teucrium ramosissimum was assayed using the Salmonella typhimurium assay system. The effect of the same extracts on genotoxicity and SOS response induced by aflatoxin B(1)
Tomohiro Nishimura et al.
Drug metabolism and pharmacokinetics, 27(4), 439-446 (2012-02-23)
The purpose of this study was to clarify the transport characteristics of nucleosides in rat placenta and the changes of functional expression of nucleoside transporters in rat placenta with experimental diabetes mellitus. Placental uptake clearances of [(3)H]adenosine and [(3)H]zidovudine from
Amitabha Chakrabarti et al.
The Journal of biological chemistry, 287(28), 23635-23643 (2012-05-25)
Despite advances in oncology drug development, most commonly used cancer therapeutics exhibit serious adverse effects. Often the toxicities of chemotherapeutics are due to the induction of significant DNA damage that is necessary for their ability to kill cancer cells. In
Microwave-promoted "one-pot" synthesis of 4-nitrobenzylthioinosine analogues using thiourea as a sulfur precursor.
Hong-Ying Niu et al.
Chemistry, an Asian journal, 7(1), 45-49 (2011-10-18)

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