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MedKoo product information:
MedKoo Code#: 100850
Tabloid; Tabloid brand thioguanine;
Tioguanine. Foreign brand names: Lanvis;
Tioguanin. Abbreviations: 6-TG; TG. Code names: BW
5071; Wellcome U3B; WR-1141; X 27. Chemical structure
names: * 2-Amino 6MP; *
2-Amino-6-mercaptopurine; * 2-Amino-6-purinethiol; *
2-Aminopurin-6-thiol; * 2-Aminopurine-6(1H)-thione;
* 2-Aminopurine-6-thiol; * 6 Mercaptoguanine;
* 6 Thioguanine; * 6H-Purine-6-thione, 2-amino-1,7-dihydro-
(9CI); * 6-Mercapto-2-aminopurine; *
6-mercaptoguanine; * 6-thioguanine.
Chemical Formula: C5H5N5S
Exact Mass: 167.02657
Molecular Weight: 167.19
m/z: 167.02657 (100.0%), 168.02992 (5.4%),
169.02236 (4.5%), 168.02360 (1.8%)
Elemental Analysis: C, 35.92; H, 3.01; N,
41.89; S, 19.18
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Information about this agent
Thioguanine is a synthetic
guanosine analogue antimetabolite. Phosphorylated by
hypoxanthine-guanine phosphoribosyltransferase, thioguanine
incorporates into DNA and RNA, resulting in inhibition of DNA and
RNA syntheses and cell death. This agent also inhibits
glutamine-5-phosphoribosylpyrophosphate amidotransferase, thereby
inhibiting purine synthesis. Check for
active clinical trials or
closed clinical trials using this agent. (NCI
Thesaurus).Its principal use is in acute leukaemias and chronic
myeloid leukaemia. It has been investigated for use in treatment of
Mechanism of Action
After incorporation into DNA, the thiocarbonyl of thioguanine has a
tendency to be methylated. This produces a base similar to
6-O-methylguanine. During a second round of replication, the
mismatch repair system will recognize the mismatch between the
methylated base and cytosine. The attempt to repair such a mismatch
is abortive since no nucleotides can be properly matched with the
methylated base. This leads to persistent 100-200 base single strand
breaks. Such a genotoxic stress will trigger cell cycle arrest and
cell death. In this regard, thioguanine and mercaptopurine, although
categorized as antimetabolites, exert their functions more like a
genotoxic methylating agents, such as temozolomide, which methylates
DNA and generate 6-O-methylguanine and cytosine mismatch. The
ability of thioguanine and mercaptopurine to trigger genotoxic
stress is also exemplified by their treatment-related acute myeloid
leukemia (AML), which is uncommon for antimetabolites, but common
for alkylating agents and topoisomerase inhibitors. (source:
TABLOID brand Thioguanine was synthesized and developed by
Hitchings, Elion, and associates at the Wellcome Research
Laboratories. It is one of a large series of purine analogues which
interfere with nucleic acid biosynthesis, and has been found active
against selected human neoplastic diseases. Thioguanine, known
chemically as 2-amino-1,7-dihydro-6H-purine-6-thione, is an analogue
of the nucleic acid constituent guanine, and is closely related
structurally and functionally to PURINETHOL® (mercaptopurine).
TABLOID brand Thioguanine is available in tablets for oral
administration. Each scored tablet contains 40 mg thioguanine and
the inactive ingredients gum acacia, lactose, magnesium stearate,
potato starch, and stearic acid.
Clinical studies have shown that the absorption of an
oral dose of thioguanine in humans is incomplete and variable, averaging
approximately 30% of the administered dose (range: 14% to 46%).
Following oral administration of 35S-6-thioguanine, total plasma
radioactivity reached a maximum at 8 hours and declined slowly
thereafter. Parent drug represented only a very small fraction of the
total plasma radioactivity at any time, being virtually undetectable
throughout the period of measurements. The oral administration of
radiolabeled thioguanine revealed only trace quantities of parent drug
in the urine. However, a methylated metabolite,
2-amino-6-methylthiopurine (MTG), appeared very early, rose to a maximum
6 to 8 hours after drug administration, and was still being excreted
after 12 to 22 hours. Radiolabeled sulfate appeared somewhat later than
MTG but was the principal metabolite after 8 hours. Thiouric acid and
some unidentified products were found in the urine in small amounts.
Intravenous administration of 35S-6-thioguanine disclosed a median
plasma half-disappearance time of 80 minutes (range: 25 to 240 minutes)
when the compound was given in single doses of 65 to 300 mg/m2. Although
initial plasma levels of thioguanine did correlate with the dose level,
there was no correlation between the plasma half-disappearance time and
Thioguanine is incorporated into the DNA and the RNA of human bone
marrow cells. Studies with intravenous 35S-6-thioguanine have shown that
the amount of thioguanine incorporated into nucleic acids is more than
100 times higher after 5 daily doses than after a single dose. With the
5-dose schedule, from one-half to virtually all of the guanine in the
residual DNA was replaced by thioguanine. Tissue distribution studies of
35S-6-thioguanine in mice showed only traces of radioactivity in brain
after oral administration. No measurements have been made of thioguanine
concentrations in human cerebrospinal fluid (CSF), but observations on
tissue distribution in animals, together with the lack of CNS
penetration by the closely related compound, mercaptopurine, suggest
that thioguanine does not reach therapeutic concentrations in the CSF.
Monitoring of plasma levels of thioguanine during therapy is of
questionable value. There is technical difficulty in determining plasma
concentrations, which are seldom greater than 1 to 2 mcg/mL after a
therapeutic oral dose. More significantly, thioguanine enters rapidly
into the anabolic and catabolic pathways for purines, and the active
intracellular metabolites have appreciably longer half-lives than the
parent drug. The biochemical effects of a single dose of thioguanine are
evident long after the parent drug has disappeared from plasma. Because
of this rapid metabolism of thioguanine to active intracellular
derivatives, hemodialysis would not be expected to appreciably reduce
toxicity of the drug.
Thioguanine competes with hypoxanthine and guanine for the enzyme
hypoxanthine-guanine phosphoribosyltransferase (HGPRTase) and is itself
converted to 6-thioguanylic acid (TGMP). This nucleotide reaches high
intracellular concentrations at therapeutic doses. TGMP interferes at
several points with the synthesis of guanine nucleotides. It inhibits de
novo purine biosynthesis by pseudo-feedback inhibition of
glutamine-5-phosphoribosylpyrophosphate amidotransferase-the first
enzyme unique to the de novo pathway for purine ribonucleotide
synthesis. TGMP also inhibits the conversion of inosinic acid (IMP) to
xanthylic acid (XMP) by competition for the enzyme IMP dehydrogenase. At
one time TGMP was felt to be a significant inhibitor of ATP:GMP
phosphotransferase (guanylate kinase), but recent results have shown
this not to be so. Thioguanylic acid is further converted to the di- and
tri-phosphates, thioguanosine diphosphate (TGDP) and thioguanosine
triphosphate (TGTP) (as well as their 2' -deoxyribosyl analogues) by the
same enzymes which metabolize guanine nucleotides. Thioguanine
nucleotides are incorporated into both the RNA and the DNA by
phosphodiester linkages and it has been argued that incorporation of
such fraudulent bases contributes to the cytotoxicity of thioguanine.
Thus, thioguanine has multiple metabolic effects and at present it is
not possible to designate one major site of action. Its tumor inhibitory
properties may be due to one or more of its effects on (a) feedback
inhibition of de novo purine synthesis; (b) inhibition of purine
nucleotide interconversions; or (c) incorporation into the DNA and the
RNA. The net consequence of its actions is a sequential blockade of the
synthesis and utilization of the purine nucleotides. The catabolism of
thioguanine and its metabolites is complex and shows significant
differences between humans and the mouse. In both humans and mice, after
oral administration of 35S-6-thioguanine, urine contains virtually no
detectable intact thioguanine. While deamination and subsequent
oxidation to thiouric acid occurs only to a small extent in humans, it
is the main pathway in mice. The product of deamination by guanase,
6-thioxanthine is inactive, having negligible antitumor activity. This
pathway of thioguanine inactivation is not dependent on the action of
xanthine oxidase, and an inhibitor of that enzyme (such as allopurinol)
will not block the detoxification of thioguanine even though the
inactive 6-thioxanthine is normally further oxidized by xanthine oxidase
to thiouric acid before it is eliminated. In humans, methylation of
thioguanine is much more extensive than in the mouse. The product of
methylation, 2-amino-6-methylthiopurine, is also substantially less
active and less toxic than thioguanine and its formation is likewise
unaffected by the presence of allopurinol. Appreciable amounts of
inorganic sulfate are also found in both murine and human urine,
presumably arising from further metabolism of the methylated
In some animal tumors, resistance to the effect of thioguanine
correlates with the loss of HGPRTase activity and the resulting
inability to convert thioguanine to thioguanylic acid. However, other
resistance mechanisms, such as increased catabolism of TGMP by a
nonspecific phosphatase, may be operative. Although not invariable, it
is usual to find cross-resistance between thioguanine and its close
analogue, PURINETHOL (mercaptopurine).
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