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
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
DescriptionSources: http://www.drugbank.ca/drugs/DB00352Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/12429slr021_tabloid_lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00352
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.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: DNA Sources: http://www.drugbank.ca/drugs/DB00352 |
|||
Target ID: CHEMBL614844 |
20.0 µM [IC50] | ||
Target ID: CHEMBL2111369 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | TABLOID Approved UseIndications 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 Date1966 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
313 nM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11422012 |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
586 pM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11422012 |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.4 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27463047 |
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
| Dose | Population | Adverse 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%) Sources: 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%) |
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%) Sources: 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%) |
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%) Other AEs:Headache (5.4%) Pneumonia (2.7%) Leucopenia (5.4%) Headache (45.9%) Sources: 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%) |
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%) Sources: Anemia (grade 3, 16.1%) Thrombocytopenia (grade 3, 16.1%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 4.0 |
no | |||
Page: 4.0 |
no | |||
Page: 4.0 |
weak |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 1.0 |
major | |||
Page: 1.0 |
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
| Title | Date | PubMed |
|---|---|---|
| Veno-occlusive disease of the liver associated with thiopurines in a child with acute lymphoblastic leukemia. | 2000 Jul-Aug |
|
| Expression and prognostic significance of IAP-family genes in human cancers and myeloid leukemias. | 2000 May |
|
| Recent advances in the pharmacogenomics of thiopurine methyltransferase. | 2001 |
|
| Generation of single-copy transgenic mouse embryos directly from ES cells by tetraploid embryo complementation. | 2001 |
|
| Favorable outcome for children and adolescents with T-cell lymphoblastic lymphoma with an intensive ALL-type therapy without local radiotherapy. | 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 |
|
| 6-Thioguanine: a naked bullet? (Or how pharmacogenomics can make old drugs brand new). | 2001 Aug |
|
| Continuing therapy for childhood acute lymphoblastic leukaemia: clinical and cellular pharmacology of methotrexate, 6-mercaptopurine and 6-thioguanine. | 2001 Dec |
|
| Why measure thiopurine methyltransferase activity? Direct administration of 6-thioguanine might be the alternative for 6-mercaptopurine or azathioprine. | 2001 Dec |
|
| Mechanisms of tolerance to DNA damaging therapeutic drugs. | 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| [Primary pulmonary manifestation of extramedullary acute myelocytic leukemia]. | 2001 Jun |
|
| Amplification of ERBB2, RARA, and TOP2A genes in a myelodysplastic syndrome transforming to acute myeloid 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 |
|
| Heterozygosity for the thiopurine methyltransferase *3A allele in an acute non-lymphoblastic leukaemia patient with delayed marrow regeneration following H-DAT chemotherapy. | 2001 Mar |
|
| Isodicentric 7p, idic(7)(q11.2), in acute myeloid leukemia associated with older age and favorable response to induction chemotherapy: a new clinical entity? | 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 |
|
| In vivo mutant frequency of thioguanine-resistant T-cells in the peripheral blood and lymph nodes of melanoma patients. | 2001 May 9 |
|
| Molecular characterisation of camptothecin-induced mutations at the hprt locus in Chinese hamster cells. | 2001 May 9 |
|
| High 6-thioguanine nucleotide levels and low thiopurine methyltransferase activity in patients with lupus erythematosus treated with azathioprine. | 2001 May-Jun |
|
| The mouse guanylate kinase double mutant E72Q/D103N is a functional adenylate kinase. | 2001 Nov |
|
| Acute arterial occlusion as the presenting feature in acute promyelocytic leukaemia. | 2001 Oct |
|
| 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 |
|
| The predictive value of hierarchical cytogenetic classification in older adults with acute myeloid leukemia (AML): analysis of 1065 patients entered into the United Kingdom Medical Research Council AML11 trial. | 2001 Sep 1 |
|
| Attempts to improve treatment outcomes in acute myeloid leukemia (AML) in older patients: the results of the United Kingdom Medical Research Council AML11 trial. | 2001 Sep 1 |
|
| Novel glutathione-dependent thiopurine prodrugs: evidence for enhanced cytotoxicity in tumor cells and for decreased bone marrow toxicity in mice. | 2002 Apr |
|
| Photodynamic therapy of DNA mismatch repair-deficient and -proficient tumour cells. | 2002 Apr 8 |
|
| Role of glutathione in the multidrug resistance protein 4 (MRP4/ABCC4)-mediated efflux of cAMP and resistance to purine analogues. | 2002 Feb 1 |
|
| The thiopurine S-methyltransferase gene locus -- implications for clinical pharmacogenomics. | 2002 Jan |
|
| Inflammatory bowel disease. | 2002 Jan |
|
| HPLC determination of thiopurine nucleosides and nucleotides in vivo in lymphoblasts following mercaptopurine therapy. | 2002 Jan |
|
| Different drug sensitivity profiles of acute myeloid and lymphoblastic leukemia and normal peripheral blood mononuclear cells in children with and without Down syndrome. | 2002 Jan 1 |
|
| Frequent detection of T cells with mutations of the hypoxanthine-guanine phosphoribosyl transferase gene in patients with paroxysmal nocturnal hemoglobinuria. | 2002 Jan 1 |
|
| Flow cytometric determination of HPRT-variants in human peripheral blood lymphocytes. | 2002 Jan 29 |
|
| Hypomethylation and multiple sclerosis, the susceptibility factor? | 2002 Mar |
|
| Pharmacological characterization of the ATP-dependent low K(m) guanosine 3',5'-cyclic monophosphate (cGMP) transporter in human erythrocytes. | 2002 Mar 1 |
|
| Implication of protein kinase C in the regulation of DNA mismatch repair protein expression and function. | 2002 May 17 |
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
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NCI_THESAURUS |
C2254
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WHO-ESSENTIAL MEDICINES LIST |
8.2
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EU-Orphan Drug |
EU/3/09/694
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NCI_THESAURUS |
C1556
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LIVERTOX |
NBK548502
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NDF-RT |
N0000180853
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1660000
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D013866
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SUB11084MIG
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41354-41-0
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FTK8U1GZNX
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91669166
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9555
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FTK8U1GZNX
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DTXSID30971198
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CHEMBL727
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6845
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Thioguanine
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10485
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2632
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C876
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5580-03-0
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ACTIVE MOIETY
SUBSTANCE RECORD
