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Merck
CN

88800

Sigma-Aldrich

6-Thioguanine

purum, ≥96% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C5H5N5S
CAS Number:
154-42-7
Molecular Weight:
167.19
Beilstein:
157765
EC Number:
205-827-2
MDL number:
MFCD00233553
UNSPSC Code:
12352202

Key Documents

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grade

purum

Assay

≥96% (HPLC)

impurities

≤3% guanine

mp

≥300 °C (lit.)

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

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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.

Other Notes

Antineoplastic agent; substrate for HGPRTase, converted to 6-thio-GMP, which then inhibits vital metabolic sequences in myelocytic and acute lymphocytic leukemia.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

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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T Kataoka et al.
Cancer research, 44(2), 519-524 (1984-02-01)
While the combination of L1210 murine leukemia cell vaccine (L1210 vaccine) with 6-mercaptopurine (6-MP) or 6-thioguanine produces a therapeutic response greater than that induced by either of these agents alone, its combination with cyclophosphamide, N4-behenoyl-1-beta-D-arabinofuranosylcytosine, or 5-fluorouracil does not produce
Galal H Elgemeie
Current pharmaceutical design, 9(31), 2627-2642 (2003-10-08)
6-Mercaptopurine (6MP) and 6-thioguanine (6TG) are analogs of the natural purines: hypoxanthine and guanine. Both mercaptopurine and thioguanine are substrates for hypoxanthine-guanine phosphoribosyltransferase and are converted into the ribonucleotides 6-thioguanosine monophosphate (6-thioGMP) and 6-thioinosine monophosphate (T-IMP) respectively. The accumulation of
Elif Gürsoy et al.
European journal of medicinal chemistry, 42(3), 320-326 (2006-12-06)
A series of arylidenehydrazides (3a-3i) were synthesized from [6-(4-bromophenyl)imidazo[2,1-b]thiazol-3-yl]acetic acid hydrazide. The structures of new compounds were determined by analytical and spectral (IR, (1)H NMR, (13)C NMR, EIMS) methods. The synthesized compounds (3a-3i) were evaluated in the National Cancer Institute's
Jignesh M Doshi et al.
Journal of medicinal chemistry, 49(26), 7731-7739 (2006-12-22)
The structure-activity relationship studies of ethyl 2-amino-6-cyclopentyl-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (1, HA 14-1), an antagonist of the antiapoptotic Bcl-2 proteins, are reported. A series of analogues of 1 with varied functional groups at the 6-position of the chromene ring were synthesized. These candidates
Mark Drost et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(23), 9403-9408 (2013-05-22)
In many individuals suspected of the common cancer predisposition Lynch syndrome, variants of unclear significance (VUS), rather than an obviously pathogenic mutations, are identified in one of the DNA mismatch repair (MMR) genes. The uncertainty of whether such VUS inactivate
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