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852686

Sigma-Aldrich

6-Mercaptopurine-9-β-D-ribofuranoside

≥95.0% (HPLC)

Synonym(s):

6-Mercaptopurine riboside, 6-Purinethiol riboside, 6-Thioinosine

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About This Item

Empirical Formula (Hill Notation):
C10H12N4O4S
CAS Number:
574-25-4
Molecular Weight:
284.29
Beilstein:
40536
EC Number:
209-371-5
MDL number:
MFCD00005743
UNSPSC Code:
12352200
PubChem Substance ID:
24888331

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
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBS6413V
BCBM9212V
BCBM0676V
BCBH9757V
BCBF4281V

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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
Jaap A Bakker et al.
Nucleosides, nucleotides & nucleic acids, 30(11), 839-849 (2011-11-09)
The role of inosine triphosphatase (ITPase) in adverse drug reactions associated with thiopurine therapy is still under heavy debate. Surprisingly, little is known about the way thiopurines are handled by ITPase. We studied the effect of ITPA polymorphisms on the
Daniel Pecher et al.
Molecules (Basel, Switzerland), 23(7) (2018-07-19)
Thiopurines (TP) represent an important therapeutic tool for the treatment of inflammatory bowel diseases (IBD) in the current situation of rising incidence and health care costs. The results of multiple clinical studies aimed at finding correlations between levels of TP
Minami Iikura et al.
Antimicrobial agents and chemotherapy, 56(3), 1407-1413 (2012-01-11)
We previously showed that equilibrative nucleoside transporter 1 (ENT1) is a primary ribavirin transporter in human hepatocytes. However, because the role of this transporter in the antiviral mechanism of the drug remains unclear, the present study aimed to elucidate the
Christelle Moreau et al.
Journal of medicinal chemistry, 55(4), 1478-1489 (2012-01-18)
Two nicotinamide adenine dinucleotide (NAD(+)) analogues modified at the 6 position of the purine ring were synthesized, and their substrate properties toward Aplysia californica ADP-ribosyl cyclase were investigated. 6-N-Methyl NAD(+) (6-N-methyl nicotinamide adenosine 5'-dinucleotide 10) hydrolyzes to give the linear
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