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Details

Stereochemistry ACHIRAL
Molecular Formula 2C5H5N5S.H2O
Molecular Weight 352.399
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THIOGUANINE

SMILES

O.NC1=NC2=C(N=CN2)C(=S)N1.NC3=NC4=C(N=CN4)C(=S)N3

InChI

InChIKey=VOXBZHOHGGBLCQ-UHFFFAOYSA-N
InChI=1S/2C5H5N5S.H2O/c2*6-5-9-3-2(4(11)10-5)7-1-8-3;/h2*1H,(H4,6,7,8,9,10,11);1H2

HIDE SMILES / InChI

Molecular Formula C5H5N5S
Molecular Weight 167.192
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/12429slr021_tabloid_lbl.pdf

Thioguanine is an antineoplastic anti-metabolite used in the treatment of several forms of leukemia including acute nonlymphocytic leukemia. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances becoming incorporated in to DNA during the "S" phase (of the cell cycle), stopping normal development and division. Thioguanine was first synthesized and entered into clinical trial more than 30 years ago. It is a 6-thiopurine analogue of the naturally occurring purine bases hypoxanthine and guanine. Intracellular activation results in incorporation into DNA as a false purine base. An additional cytotoxic effect is related to its incorporation into RNA. Thioguanine is cross-resistant with mercaptopurine. Cytotoxicity is cell cycle phase-specific (S-phase). Thioguanine competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRTase) and is itself converted to 6-thioguanilyic acid (TGMP), which reaches high intracellular concentrations at therapeutic doses. TGMP interferes with the synthesis of guanine nucleotides by its inhibition of purine biosynthesis by pseudofeedback inhibition of glutamine-5-phosphoribosylpyrophosphate amidotransferase, the first enzyme unique to the de novo pathway of purine ribonucleotide synthesis. TGMP also inhibits the conversion of inosinic acid (IMP) to xanthylic acid (XMP) by competition for the enzyme IMP dehydrogenase. Thioguanine nucleotides are incorporated into both the DNA and the RNA by phosphodiester linkages, and some studies have shown that incorporation of such false bases contributes to the cytotoxicity of thioguanine. Its tumor inhibitory properties may be due to one or more of its effects on feedback inhibition of de novo purine synthesis; inhibition of purine nucleotide interconversions; or incorporation into the DNA and RNA. The overall result of its action is a sequential blockade of the utilization and synthesis of the purine nucleotides. Thioguanine is used for remission induction and remission consolidation treatment of acute nonlymphocytic leukemias. It is marketed under the trade name Lanvis and Tabloid among others.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TABLOID

Approved Use

Indications and Usage for Thioguanine a) Acute Nonlymphocytic Leukemias TABLOID brand Thioguanine is indicated for remission induction and remission consolidation treatment of acute nonlymphocytic leukemias. However, it is not recommended for use during maintenance therapy or similar long-term continuous treatments due to the high risk of liver toxicity. The response to this agent depends upon the age of the patient (younger patients faring better than older) and whether Thioguanine is used in previously treated or previously untreated patients. Reliance upon Thioguanine alone is seldom justified for initial remission induction of acute nonlymphocytic leukemias because combination chemotherapy including Thioguanine results in more frequent remission induction and longer duration of remission than Thioguanine alone. b) Other Neoplasms TABLOID brand Thioguanine is not effective in chronic lymphocytic leukemia, Hodgkin’s lymphoma, multiple myeloma, or solid tumors. Although Thioguanine is one of several agents with activity in the treatment of the chronic phase of chronic myelogenous leukemia, more objective responses are observed with MYLERAN® (busulfan), and therefore busulfan is usually regarded as the preferred drug.

Launch Date

1966
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
313 nM
40 mg/m² 1 times / day multiple, oral
dose: 40 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
THIOGUANINE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
586 pmol × h/mL
40 mg/m² 1 times / day multiple, oral
dose: 40 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
THIOGUANINE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.4 h
40 mg 1 times / day multiple, oral
dose: 40 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
THIOGUANINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
Doses

Doses

DosePopulationAdverse events​
20 mg 1 times / day multiple, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Other AEs: Pain, Nausea and vomiting...
Other AEs:
Pain (grade 1-2, 9.6%)
Nausea and vomiting (grade 1-2, 20%)
Leukopenia (grade 1-2, 11.8%)
Thrombocytopenia (grade 1-3, 3.7%)
Hepatotoxicity (grade 1-2, 24.4%)
Headache (grade 1-2, 8.9%)
Anemia (grade 1-3, 8.9%)
Gamma-glutamyltransferase increased (grade 1-4, 16.3%)
Diarrhea (grade 2, 1.4%)
Skin toxicity (grade 1-2, 11.8%)
Hair loss (grade 1, 5.2%)
Infection (grade 1-3, 26.7%)
Blood urea nitrogen increased (grade 1, 1.4%)
Neurotoxicity (grade 1-2, 1.4%)
Hemorrhage (grade 3, 0.7%)
Stomatitis (grade 1, 0.7%)
Creatinine increased (grade 2, 0.7%)
Cardiac arrhythmias (grade 1, 0.7%)
Constipation (grade 1, 0.7%)
Sources:
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Disc. AE: Pain, Nausea and vomiting...
AEs leading to
discontinuation/dose reduction:
Pain (grade 1-3, 6.1%)
Nausea and vomiting (grade 1-2, 4.4%)
Leukopenia (grade 1-3, 2.7%)
Thrombocytopenia (grade 1-3, 2.7%)
Hepatotoxicity (grade 1-2, 2.4%)
Headache (grade 1-2, 1.7%)
Anemia (grade 1-4, 0.7%)
Gamma-glutamyltransferase increased (grade 2-3, 1%)
Diarrhea (grade 2-4, 1%)
Skin toxicity (grade 1, 0.7%)
Hair loss (grade 1, 0.7%)
Cardiac dysfunction (grade 3, 0.3%)
Pericarditis (grade 2, 0.3%)
Sources:
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Disc. AE: Pancreatitis, Headache...
Other AEs: Headache, Nausea...
AEs leading to
discontinuation/dose reduction:
Pancreatitis (2.7%)
Headache (5.4%)
Pneumonia (2.7%)
Leucopenia (5.4%)
Other AEs:
Headache (45.9%)
Nausea (27%)
Vomiting (5.4%)
Pruritus (8.1%)
Arthralgia (8.1%)
Alopecia (8.1%)
Dysaesthesia (2.7%)
Eczema (10.8%)
Exanthema (5.4%)
Photosensitivity allergic reac (5.4%)
Erythema nodosum (2.7%)
Rotavirus infection (2.7%)
Respiratory tract infections (29.7%)
Urinary tract infections (10.8%)
Genital candidiasis (5.4%)
Herpes labialis (2.7%)
Transaminases increased (5.4%)
Leucopenia (8.1%)
Anaemia (2.7%)
Thrombopenia (2.7%)
Sources:
1200 mg/m2 1 times / 3 weeks multiple, intravenous
Highest studied dose
Dose: 1200 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1200 mg/m2, 1 times / 3 weeks
Sources:
unhealthy, 37-70 years
Health Status: unhealthy
Age Group: 37-70 years
Sex: M+F
Sources:
Disc. AE: Creatinine increased...
Other AEs: Leukopenia...
AEs leading to
discontinuation/dose reduction:
Creatinine increased (25%)
Other AEs:
Leukopenia (25%)
Sources:
300 mg/m2 1 times / week multiple, intravenous
MTD
Dose: 300 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 300 mg/m2, 1 times / week
Sources:
unhealthy, Patients < 21 years
Health Status: unhealthy
Age Group: Patients < 21 years
Sources:
Other AEs: Neutropenia, Anemia...
Other AEs:
Neutropenia (grade 3, 16.1%)
Anemia (grade 3, 16.1%)
Thrombocytopenia (grade 3, 16.1%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Cardiac arrhythmias grade 1, 0.7%
20 mg 1 times / day multiple, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Constipation grade 1, 0.7%
20 mg 1 times / day multiple, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Stomatitis grade 1, 0.7%
20 mg 1 times / day multiple, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Blood urea nitrogen increased grade 1, 1.4%
20 mg 1 times / day multiple, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Hair loss grade 1, 5.2%
20 mg 1 times / day multiple, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Neurotoxicity grade 1-2, 1.4%
20 mg 1 times / day multiple, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Leukopenia grade 1-2, 11.8%
20 mg 1 times / day multiple, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Skin toxicity grade 1-2, 11.8%
20 mg 1 times / day multiple, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Nausea and vomiting grade 1-2, 20%
20 mg 1 times / day multiple, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Hepatotoxicity grade 1-2, 24.4%
20 mg 1 times / day multiple, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Headache grade 1-2, 8.9%
20 mg 1 times / day multiple, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Pain grade 1-2, 9.6%
20 mg 1 times / day multiple, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Infection grade 1-3, 26.7%
20 mg 1 times / day multiple, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Thrombocytopenia grade 1-3, 3.7%
20 mg 1 times / day multiple, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Anemia grade 1-3, 8.9%
20 mg 1 times / day multiple, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Gamma-glutamyltransferase increased grade 1-4, 16.3%
20 mg 1 times / day multiple, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Creatinine increased grade 2, 0.7%
20 mg 1 times / day multiple, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Diarrhea grade 2, 1.4%
20 mg 1 times / day multiple, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Hemorrhage grade 3, 0.7%
20 mg 1 times / day multiple, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Hair loss grade 1, 0.7%
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Skin toxicity grade 1, 0.7%
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Headache grade 1-2, 1.7%
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Hepatotoxicity grade 1-2, 2.4%
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Nausea and vomiting grade 1-2, 4.4%
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Leukopenia grade 1-3, 2.7%
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Thrombocytopenia grade 1-3, 2.7%
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Pain grade 1-3, 6.1%
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Anemia grade 1-4, 0.7%
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Pericarditis grade 2, 0.3%
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Gamma-glutamyltransferase increased grade 2-3, 1%
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Diarrhea grade 2-4, 1%
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Cardiac dysfunction grade 3, 0.3%
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
Health Status: unhealthy
Age Group: 16–82 years
Sex: M+F
Sources:
Eczema 10.8%
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Urinary tract infections 10.8%
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Anaemia 2.7%
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Dysaesthesia 2.7%
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Erythema nodosum 2.7%
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Herpes labialis 2.7%
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Rotavirus infection 2.7%
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Thrombopenia 2.7%
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Pancreatitis 2.7%
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Pneumonia 2.7%
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Nausea 27%
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Respiratory tract infections 29.7%
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Headache 45.9%
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Exanthema 5.4%
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Genital candidiasis 5.4%
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Photosensitivity allergic reac 5.4%
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Transaminases increased 5.4%
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Vomiting 5.4%
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Headache 5.4%
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Leucopenia 5.4%
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Alopecia 8.1%
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Arthralgia 8.1%
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Leucopenia 8.1%
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Pruritus 8.1%
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 22–61 years
Health Status: unhealthy
Age Group: 22–61 years
Sex: M+F
Sources:
Leukopenia 25%
1200 mg/m2 1 times / 3 weeks multiple, intravenous
Highest studied dose
Dose: 1200 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1200 mg/m2, 1 times / 3 weeks
Sources:
unhealthy, 37-70 years
Health Status: unhealthy
Age Group: 37-70 years
Sex: M+F
Sources:
Creatinine increased 25%
Disc. AE
1200 mg/m2 1 times / 3 weeks multiple, intravenous
Highest studied dose
Dose: 1200 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1200 mg/m2, 1 times / 3 weeks
Sources:
unhealthy, 37-70 years
Health Status: unhealthy
Age Group: 37-70 years
Sex: M+F
Sources:
Anemia grade 3, 16.1%
300 mg/m2 1 times / week multiple, intravenous
MTD
Dose: 300 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 300 mg/m2, 1 times / week
Sources:
unhealthy, Patients < 21 years
Health Status: unhealthy
Age Group: Patients < 21 years
Sources:
Neutropenia grade 3, 16.1%
300 mg/m2 1 times / week multiple, intravenous
MTD
Dose: 300 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 300 mg/m2, 1 times / week
Sources:
unhealthy, Patients < 21 years
Health Status: unhealthy
Age Group: Patients < 21 years
Sources:
Thrombocytopenia grade 3, 16.1%
300 mg/m2 1 times / week multiple, intravenous
MTD
Dose: 300 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 300 mg/m2, 1 times / week
Sources:
unhealthy, Patients < 21 years
Health Status: unhealthy
Age Group: Patients < 21 years
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
weak
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
minor
yes
yes (pharmacogenomic study)
Comment: patients with reduced TPMT receiving usual doses of mercaptopurine, accumulate excessive cellular concentrations of active 6-TGNs
Page: 3.0
PubMed

PubMed

TitleDatePubMed
Generation of single-copy transgenic mouse embryos directly from ES cells by tetraploid embryo complementation.
2001
Pharmacogenetics: the therapeutic drug monitoring of the future?
2001
Gene- and tissue-specificity of mutation in Big Blue rats treated with the hepatocarcinogen N-hydroxy-2-acetylaminofluorene.
2001
Remission induction therapy: the more intensive the better?
2001 Aug
Reversal of cytosine arabinoside (ara-C) resistance by the synergistic combination of 6-thioguanine plus ara-C plus PEG-asparaginase (TGAP) in human leukemia lines lacking or expressing p53 protein.
2001 Aug
An open-label pilot study using thioguanine as a therapeutic alternative in Crohn's disease patients resistant to 6-mercaptopurine therapy.
2001 Aug
hMSH3 overexpression and cellular response to cytotoxic anticancer agents.
2001 Aug
Renal cell carcinoma as a secondary malignancy after treatment of acute promyelocytic leukemia.
2001 Dec
Comparative pharmacokinetics of oral 6-mercaptopurine and intravenous 6-mercaptopurine riboside in children.
2001 Dec
New developments in the immunosuppressive drug monitoring of cyclosporine, tacrolimus, and azathioprine.
2001 Feb
Bilateral breast relapse in acute myelogenous leukemia.
2001 Feb
A novel protein complex distinct from mismatch repair binds thioguanylated DNA.
2001 Feb
P53 modulates the effect of loss of DNA mismatch repair on the sensitivity of human colon cancer cells to the cytotoxic and mutagenic effects of cisplatin.
2001 Feb 15
6-mercaptopurine dosage and pharmacokinetics influence the degree of bone marrow toxicity following high-dose methotrexate in children with acute lymphoblastic leukemia.
2001 Jan
Therapeutic drug monitoring of azathioprine and 6-mercaptopurine metabolites in Crohn disease.
2001 Jan
Topoisomerase I-mediated cytotoxicity of N-methyl-N'-nitro-N-nitrosoguanidine: trapping of topoisomerase I by the O6-methylguanine.
2001 Jan 1
The use of denaturing high-pressure liquid chromatography for the detection of mutations in thiopurine methyltransferase.
2001 Jan 30
[Thioguanine, pancreatotoxicity?].
2001 Jan-Feb
Hamster and rat fetal cells have low spontaneous mutation frequencies and rates.
2001 Jul 1
Heterozygosity for the thiopurine methyltransferase *3A allele in an acute non-lymphoblastic leukaemia patient with delayed marrow regeneration following H-DAT chemotherapy.
2001 Mar
Plasma pharmacokinetics and cerebrospinal fluid penetration of thioguanine in children with acute lymphoblastic leukemia: a collaborative Pediatric Oncology Branch, NCI, and Children's Cancer Group study.
2001 Mar
Immunosuppressive and cytotoxic drugs in the treatment of rheumatic skin disorders.
2001 Mar
Analysis of mutational effects at the HPRT locus in human G(0) phase lymphocytes irradiated in vitro with gamma rays.
2001 Mar 1
Utilisation of erythrocyte 6-thioguanine metabolite levels to optimise azathioprine therapy in patients with inflammatory bowel disease.
2001 May
Cell killing and mutation induction by heavy ion beams.
2001 May
Substitution F569S converts UapA, a specific uric acid-xanthine transporter, into a broad specificity transporter for purine-related solutes.
2001 Nov 2
Targeting DNA mismatch repair for radiosensitization.
2001 Oct
Suppression of spontaneous and hydrogen peroxide-induced mutagenesis by the antioxidant ascorbate in mismatch repair-deficient human colon cancer cells.
2001 Oct
Intensive timed sequential remission induction chemotherapy with high-dose cytarabine for childhood acute myeloid leukemia.
2001 Oct
Hypoxia-induced enrichment and mutagenesis of cells that have lost DNA mismatch repair.
2001 Oct 15
Deoxythioguanosine triphosphate impairs HIV replication: a new mechanism for an old drug.
2001 Sep
Transport of cyclic nucleotides and estradiol 17-beta-D-glucuronide by multidrug resistance protein 4. Resistance to 6-mercaptopurine and 6-thioguanine.
2001 Sep 7
Effect of methotrexate polyglutamates on thioguanine nucleotide concentrations during continuation therapy of acute lymphoblastic leukemia with mercaptopurine.
2002 Feb
Role of glutathione in the multidrug resistance protein 4 (MRP4/ABCC4)-mediated efflux of cAMP and resistance to purine analogues.
2002 Feb 1
Aphidicolin induces 6-thioguanine resistant mutants in human diploid fibroblasts.
2002 Feb 20
Inflammatory bowel disease.
2002 Jan
Genetic toxicology studies with glutaraldehyde.
2002 Jan-Feb
Patents

Sample Use Guides

Single Agent Chemotherapy: Usual Initial dose: 2 mg/kg/day orally. If, after 4 weeks on this dosage, there is no clinical improvement and no leukocyte or platelet depression, the dosage may be cautiously increased to 3 mg/kg per day. The total daily dose may be given at one time. As a part of combination therapy for induction of remission in patients with acute nonlymphocytic leukemia: 75 to 200 mg/m2/day in 1 to 2 divided doses for 5 to 7 days or until remission is attained.
Route of Administration: Oral
In Vitro Use Guide
Maximum cytotoxicity against leukemic cells from patients with ALL occured at 0.5 uM
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:23:42 GMT 2025
Edited
by admin
on Mon Mar 31 21:23:42 GMT 2025
Record UNII
FTK8U1GZNX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THIOGUANINE
ORANGE BOOK   USAN   USP   VANDF  
USAN  
Official Name English
TIOGUANINE HEMIHYDRATE
WHO-DD  
Preferred Name English
LANVIS
Brand Name English
Tioguanine hemihydrate [WHO-DD]
Common Name English
THIOGUANINE [VANDF]
Common Name English
TIOGUANINE [MART.]
Common Name English
THIOGUANINE [USP MONOGRAPH]
Common Name English
TABLOID
Brand Name English
THIOGUANINE HEMIHYDRATE
Common Name English
THIOGUANINE [USP-RS]
Common Name English
THIOGUANINE [USAN]
Common Name English
THIOGUANINE [ORANGE BOOK]
Common Name English
6H-PURINE-6-THIONE, 2-AMINO-1,9-DIHYDRO-, HYDRATE (2:1)
Systematic Name English
THIOGUANINE [USP IMPURITY]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2254
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 8.2
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
EU-Orphan Drug EU/3/09/694
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
NCI_THESAURUS C1556
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
LIVERTOX NBK548502
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
NDF-RT N0000180853
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
Code System Code Type Description
RS_ITEM_NUM
1660000
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
PRIMARY
MESH
D013866
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
PRIMARY
EVMPD
SUB11084MIG
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
PRIMARY
CAS
41354-41-0
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
NON-SPECIFIC STOICHIOMETRY
FDA UNII
FTK8U1GZNX
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
PRIMARY
PUBCHEM
91669166
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
PRIMARY
CHEBI
9555
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
PRIMARY
DAILYMED
FTK8U1GZNX
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
PRIMARY
EPA CompTox
DTXSID30971198
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
PRIMARY
ChEMBL
CHEMBL727
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
PRIMARY
IUPHAR
6845
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
PRIMARY
LACTMED
Thioguanine
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
PRIMARY
RXCUI
10485
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
PRIMARY RxNorm
DRUG CENTRAL
2632
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
PRIMARY
NCI_THESAURUS
C876
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
PRIMARY
CAS
5580-03-0
Created by admin on Mon Mar 31 21:23:42 GMT 2025 , Edited by admin on Mon Mar 31 21:23:42 GMT 2025
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY