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

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

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 pM × h
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 (median)
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 135
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 135
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 (median)
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 296
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 296
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 4
Health Status: unhealthy
Condition: colorectal carcinoma
Age Group: 37-70 years
Sex: M+F
Population Size: 4
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
n = 31
Health Status: unhealthy
Condition: advanced malignancies
Age Group: Patients < 21 years
Population Size: 31
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 (median)
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 135
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 135
Sources:
Constipation grade 1, 0.7%
20 mg 1 times / day multiple, oral (median)
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 135
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 135
Sources:
Stomatitis grade 1, 0.7%
20 mg 1 times / day multiple, oral (median)
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 135
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 135
Sources:
Blood urea nitrogen increased grade 1, 1.4%
20 mg 1 times / day multiple, oral (median)
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 135
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 135
Sources:
Hair loss grade 1, 5.2%
20 mg 1 times / day multiple, oral (median)
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 135
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 135
Sources:
Neurotoxicity grade 1-2, 1.4%
20 mg 1 times / day multiple, oral (median)
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 135
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 135
Sources:
Leukopenia grade 1-2, 11.8%
20 mg 1 times / day multiple, oral (median)
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 135
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 135
Sources:
Skin toxicity grade 1-2, 11.8%
20 mg 1 times / day multiple, oral (median)
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 135
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 135
Sources:
Nausea and vomiting grade 1-2, 20%
20 mg 1 times / day multiple, oral (median)
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 135
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 135
Sources:
Hepatotoxicity grade 1-2, 24.4%
20 mg 1 times / day multiple, oral (median)
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 135
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 135
Sources:
Headache grade 1-2, 8.9%
20 mg 1 times / day multiple, oral (median)
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 135
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 135
Sources:
Pain grade 1-2, 9.6%
20 mg 1 times / day multiple, oral (median)
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 135
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 135
Sources:
Infection grade 1-3, 26.7%
20 mg 1 times / day multiple, oral (median)
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 135
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 135
Sources:
Thrombocytopenia grade 1-3, 3.7%
20 mg 1 times / day multiple, oral (median)
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 135
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 135
Sources:
Anemia grade 1-3, 8.9%
20 mg 1 times / day multiple, oral (median)
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 135
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 135
Sources:
Gamma-glutamyltransferase increased grade 1-4, 16.3%
20 mg 1 times / day multiple, oral (median)
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 135
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 135
Sources:
Creatinine increased grade 2, 0.7%
20 mg 1 times / day multiple, oral (median)
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 135
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 135
Sources:
Diarrhea grade 2, 1.4%
20 mg 1 times / day multiple, oral (median)
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 135
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 135
Sources:
Hemorrhage grade 3, 0.7%
20 mg 1 times / day multiple, oral (median)
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 135
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 135
Sources:
Hair loss grade 1, 0.7%
Disc. AE
40 mg 1 times / day multiple, oral (median)
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 296
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 296
Sources:
Skin toxicity grade 1, 0.7%
Disc. AE
40 mg 1 times / day multiple, oral (median)
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 296
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 296
Sources:
Headache grade 1-2, 1.7%
Disc. AE
40 mg 1 times / day multiple, oral (median)
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 296
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 296
Sources:
Hepatotoxicity grade 1-2, 2.4%
Disc. AE
40 mg 1 times / day multiple, oral (median)
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 296
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 296
Sources:
Nausea and vomiting grade 1-2, 4.4%
Disc. AE
40 mg 1 times / day multiple, oral (median)
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 296
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 296
Sources:
Leukopenia grade 1-3, 2.7%
Disc. AE
40 mg 1 times / day multiple, oral (median)
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 296
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 296
Sources:
Thrombocytopenia grade 1-3, 2.7%
Disc. AE
40 mg 1 times / day multiple, oral (median)
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 296
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 296
Sources:
Pain grade 1-3, 6.1%
Disc. AE
40 mg 1 times / day multiple, oral (median)
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 296
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 296
Sources:
Anemia grade 1-4, 0.7%
Disc. AE
40 mg 1 times / day multiple, oral (median)
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 296
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 296
Sources:
Pericarditis grade 2, 0.3%
Disc. AE
40 mg 1 times / day multiple, oral (median)
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 296
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 296
Sources:
Gamma-glutamyltransferase increased grade 2-3, 1%
Disc. AE
40 mg 1 times / day multiple, oral (median)
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 296
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 296
Sources:
Diarrhea grade 2-4, 1%
Disc. AE
40 mg 1 times / day multiple, oral (median)
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 296
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 296
Sources:
Cardiac dysfunction grade 3, 0.3%
Disc. AE
40 mg 1 times / day multiple, oral (median)
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 16–82 years
n = 296
Health Status: unhealthy
Condition: inflammatory bowel disease
Age Group: 16–82 years
Sex: M+F
Population Size: 296
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 37
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 22–61 years
Sex: M+F
Population Size: 37
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
n = 4
Health Status: unhealthy
Condition: colorectal carcinoma
Age Group: 37-70 years
Sex: M+F
Population Size: 4
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
n = 4
Health Status: unhealthy
Condition: colorectal carcinoma
Age Group: 37-70 years
Sex: M+F
Population Size: 4
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
n = 31
Health Status: unhealthy
Condition: advanced malignancies
Age Group: Patients < 21 years
Population Size: 31
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
n = 31
Health Status: unhealthy
Condition: advanced malignancies
Age Group: Patients < 21 years
Population Size: 31
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
n = 31
Health Status: unhealthy
Condition: advanced malignancies
Age Group: Patients < 21 years
Population Size: 31
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
Gene- and tissue-specificity of mutation in Big Blue rats treated with the hepatocarcinogen N-hydroxy-2-acetylaminofluorene.
2001
Determinants of outcome after intensified therapy of childhood lymphoblastic leukaemia: results from Medical Research Council United Kingdom acute lymphoblastic leukaemia XI protocol.
2001 Apr
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
hMSH3 overexpression and cellular response to cytotoxic anticancer agents.
2001 Aug
Differing contribution of thiopurine methyltransferase to mercaptopurine versus thioguanine effects in human leukemic cells.
2001 Aug 1
The histone deacetylase inhibitor trichostatin A reduces nickel-induced gene silencing in yeast and mammalian cells.
2001 Aug 8
Therapeutic drug monitoring of azathioprine and 6-mercaptopurine metabolites in Crohn disease.
2001 Jan
Patients with de novo acute myeloid leukaemia and complex karyotype aberrations show a poor prognosis despite intensive treatment: a study of 90 patients.
2001 Jan
Molecular dynamics of DNA quadruplex molecules containing inosine, 6-thioguanine and 6-thiopurine.
2001 Jan
Antimetabolites and cytotoxic drugs.
2001 Jan
Thioguanine for refractory psoriasis: a 4-year experience.
2001 Jan
Antimutagenic activity of fluphenazine in short-term tests.
2001 Jan
The use of denaturing high-pressure liquid chromatography for the detection of mutations in thiopurine methyltransferase.
2001 Jan 30
Photoactivation of DNA thiobases as a potential novel therapeutic option.
2001 Jul 24
[Primary pulmonary manifestation of extramedullary acute myelocytic leukemia].
2001 Jun
Acute myeloid leukaemia (AML): treatment of the older patient.
2001 Mar
Pretreatment leukaemia cell drug resistance is correlated to clinical outcome in acute myeloid leukaemia.
2001 Mar
Immunosuppressive and cytotoxic drugs in the treatment of rheumatic skin disorders.
2001 Mar
Molecular characterisation of camptothecin-induced mutations at the hprt locus in Chinese hamster cells.
2001 May 9
Loss of DNA mismatch repair imparts defective cdc2 signaling and G(2) arrest responses without altering survival after ionizing radiation.
2001 Nov 15
Substitution F569S converts UapA, a specific uric acid-xanthine transporter, into a broad specificity transporter for purine-related solutes.
2001 Nov 2
Acute arterial occlusion as the presenting feature in acute promyelocytic leukaemia.
2001 Oct
Targeting DNA mismatch repair for radiosensitization.
2001 Oct
Novel glutathione-dependent thiopurine prodrugs: evidence for enhanced cytotoxicity in tumor cells and for decreased bone marrow toxicity in mice.
2002 Apr
Aphidicolin induces 6-thioguanine resistant mutants in human diploid fibroblasts.
2002 Feb 20
HPLC determination of thiopurine nucleosides and nucleotides in vivo in lymphoblasts following mercaptopurine therapy.
2002 Jan
Flow cytometric determination of HPRT-variants in human peripheral blood lymphocytes.
2002 Jan 29
Genetic toxicology studies with glutaraldehyde.
2002 Jan-Feb
X-ray induced mutation in Syrian hamster fetal cells.
2002 Mar 20
Implication of protein kinase C in the regulation of DNA mismatch repair protein expression and function.
2002 May 17
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 Sat Dec 16 04:48:13 GMT 2023
Edited
by admin
on Sat Dec 16 04:48:13 GMT 2023
Record UNII
FTK8U1GZNX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THIOGUANINE
ORANGE BOOK   USAN   USP   VANDF  
USAN  
Official Name English
LANVIS
Brand Name English
Tioguanine hemihydrate [WHO-DD]
Common Name English
THIOGUANINE [VANDF]
Common Name English
TIOGUANINE HEMIHYDRATE
WHO-DD  
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 Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 8.2
Created by admin on Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
EU-Orphan Drug EU/3/09/694
Created by admin on Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
NCI_THESAURUS C1556
Created by admin on Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
LIVERTOX NBK548502
Created by admin on Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
NDF-RT N0000180853
Created by admin on Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
Code System Code Type Description
RS_ITEM_NUM
1660000
Created by admin on Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
PRIMARY
MESH
D013866
Created by admin on Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
PRIMARY
EVMPD
SUB11084MIG
Created by admin on Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
PRIMARY
CAS
41354-41-0
Created by admin on Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
NON-SPECIFIC STOICHIOMETRY
FDA UNII
FTK8U1GZNX
Created by admin on Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
PRIMARY
PUBCHEM
91669166
Created by admin on Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
PRIMARY
CHEBI
9555
Created by admin on Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
PRIMARY
DAILYMED
FTK8U1GZNX
Created by admin on Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
PRIMARY
EPA CompTox
DTXSID30971198
Created by admin on Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
PRIMARY
ChEMBL
CHEMBL727
Created by admin on Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
PRIMARY
IUPHAR
6845
Created by admin on Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
PRIMARY
LACTMED
Thioguanine
Created by admin on Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
PRIMARY
RXCUI
10485
Created by admin on Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
PRIMARY RxNorm
DRUG CENTRAL
2632
Created by admin on Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
PRIMARY
NCI_THESAURUS
C876
Created by admin on Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
PRIMARY
CAS
5580-03-0
Created by admin on Sat Dec 16 04:48:13 GMT 2023 , Edited by admin on Sat Dec 16 04:48:13 GMT 2023
PRIMARY
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PARENT -> SALT/SOLVATE
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