Details
Stereochemistry | ACHIRAL |
Molecular Formula | C5H4N4S.H2O |
Molecular Weight | 170.192 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.S=C1NC=NC2=C1N=CN2
InChI
InChIKey=WFFQYWAAEWLHJC-UHFFFAOYSA-N
InChI=1S/C5H4N4S.H2O/c10-5-3-4(7-1-6-3)8-2-9-5;/h1-2H,(H2,6,7,8,9,10);1H2
Mercaptopurine, marketed under the brand name Purinethol among others, is a medication used for cancer and autoimmune diseases. Mercaptopurine competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRTase) and is itself converted to thioinosinic acid (TIMP). This intracellular nucleotide inhibits several reactions involving inosinic acid (IMP), including the conversion of IMP to xanthylic acid (XMP) and the conversion of IMP to adenylic acid (AMP) via adenylosuccinate (SAMP). In addition, 6-methylthioinosinate (MTIMP) is formed by the methylation of TIMP. Both TIMP and MTIMP have been reported to inhibit glutamine-5-phosphoribosylpyrophosphate amidotransferase, the first enzyme unique to the de novo pathway for purine ribonucleotide synthesis. Experiments indicate that radiolabeled mercaptopurine may be recovered from the DNA in the form of deoxythioguanosine. Some mercaptopurine is converted to nucleotide derivatives of 6-thioguanine (6-TG) by the sequential actions of inosinate (IMP) dehydrogenase and xanthylate (XMP) aminase, converting TIMP to thioguanylic acid (TGMP). PURINETHOL (mercaptopurine) is indicated for maintenance therapy of acute lymphatic
(lymphocytic, lymphoblastic) leukemia as part of a combination regimen. The response to this
agent depends upon the particular subclassification of acute lymphatic leukemia and the age of
the patient (pediatric or adult).
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2362992 |
|||
Target ID: GO:0001516 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3247467 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | PURINETHOL Approved UseMercaptopurine tablets are indicated for maintenance therapy of acute lymphatic (lymphocytic, lymphoblastic) leukemia as part of a combination regimen. The response to this agent depends upon the particular subclassification of acute lymphatic leukemia and the age of the patient (pediatric or adult). Mercaptopurine tablets are not effective for prophylaxis or treatment of central nervous system leukemia. Mercaptopurine tablets are not effective in acute myelogenous leukemia, chronic lymphatic leukemia, the lymphomas (including Hodgkins Disease), or solid tumors. Launch Date1953 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
69.5 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/9048271 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
MERCAPTOPURINE ANHYDROUS plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
74 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3470165 |
75 mg/m² single, intravenous dose: 75 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
MERCAPTOPURINE ANHYDROUS plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
135.8 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/9048271 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
MERCAPTOPURINE ANHYDROUS plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
200 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3470165 |
75 mg/m² single, intravenous dose: 75 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
MERCAPTOPURINE ANHYDROUS plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3470165 |
75 mg/m² single, intravenous dose: 75 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
MERCAPTOPURINE ANHYDROUS plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
81% |
MERCAPTOPURINE ANHYDROUS plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
100 mg 3 times / day multiple, oral Studied dose Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: |
unhealthy, 37 years n = 1 Health Status: unhealthy Condition: hyperthyroidism Age Group: 37 years Sex: F Population Size: 1 Sources: |
Other AEs: Anorexia, Nausea... Other AEs: Anorexia Sources: Nausea Vomiting Myelosuppression Hepatic disease |
50 mg/m2/hour 1 times / 2 days multiple, intravenous Studied dose Dose: 50 mg/m2/hour, 1 times / 2 days Route: intravenous Route: multiple Dose: 50 mg/m2/hour, 1 times / 2 days Sources: |
unhealthy, Median age 9.5 years n = 51 Health Status: unhealthy Condition: leukemia Age Group: Median age 9.5 years Population Size: 51 Sources: |
Other AEs: ALT increased, AST increased... Other AEs: ALT increased (grade 3) Sources: AST increased (grade 3) Bilirubin increased (grade 3) |
1125 mg/m2 1 times / day multiple, intravenous (mean) Studied dose Dose: 1125 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1125 mg/m2, 1 times / day Co-administed with:: cytarabine(500 mg/m2 IV; 4 days) Sources: |
unhealthy, age range 2 to 17 years n = 23 Health Status: unhealthy Condition: acute leukemia Age Group: age range 2 to 17 years Sex: M+F Population Size: 23 Sources: |
Other AEs: Pancytopenia, Neutropenic fever... Other AEs: Pancytopenia (100%) Sources: Neutropenic fever (91%) Bacteremia (65%) Candidemia (13%) Cytomegalovirus infection (4%) Bleeding (4%) Nausea (100%) Mucosal ulceration (52%) Diarrhea (26%) Typhlitis (4%) Alopecia (100%) Peeling of hands & feet on soles (52%) Papular skin eruption (30%) Conjunctivitis (13%) Death (8%) |
1250 mg/m2 1 times / day multiple, intravenous Highest studied dose Dose: 1250 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1250 mg/m2, 1 times / day Co-administed with:: cytarabine(500 mg/m2 IV; 4 days) Sources: |
unhealthy, age range 4 to 14 years n = 12 Health Status: unhealthy Condition: acute leukemia Age Group: age range 4 to 14 years Sex: M+F Population Size: 12 Sources: |
|
50 mg/m2/hour 1 times / 3 weeks multiple, intravenous Studied dose Dose: 50 mg/m2/hour, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 50 mg/m2/hour, 1 times / 3 weeks Sources: |
unhealthy, median age 10 years n = 10 Health Status: unhealthy Condition: cancer Age Group: median age 10 years Population Size: 10 Sources: |
DLT: Mucositis... |
35 mg/m2 1 times / day multiple, parenteral MTD Dose: 35 mg/m2, 1 times / day Route: parenteral Route: multiple Dose: 35 mg/m2, 1 times / day Sources: |
unhealthy, median age 60 years n = 7 Health Status: unhealthy Condition: colon cancer Age Group: median age 60 years Population Size: 7 Sources: |
DLT: Neutropenia, Thrombocytopenia... Other AEs: Neutropenia, Hyperbilirubinaemia... Dose limiting toxicities: Neutropenia (grade 3, 12.5%) Other AEs:Thrombocytopenia (grade 3, 12.5%) Neutropenia (grade 2, 75%) Sources: Hyperbilirubinaemia (50%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Anorexia | 100 mg 3 times / day multiple, oral Studied dose Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: |
unhealthy, 37 years n = 1 Health Status: unhealthy Condition: hyperthyroidism Age Group: 37 years Sex: F Population Size: 1 Sources: |
|
Hepatic disease | 100 mg 3 times / day multiple, oral Studied dose Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: |
unhealthy, 37 years n = 1 Health Status: unhealthy Condition: hyperthyroidism Age Group: 37 years Sex: F Population Size: 1 Sources: |
|
Myelosuppression | 100 mg 3 times / day multiple, oral Studied dose Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: |
unhealthy, 37 years n = 1 Health Status: unhealthy Condition: hyperthyroidism Age Group: 37 years Sex: F Population Size: 1 Sources: |
|
Nausea | 100 mg 3 times / day multiple, oral Studied dose Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: |
unhealthy, 37 years n = 1 Health Status: unhealthy Condition: hyperthyroidism Age Group: 37 years Sex: F Population Size: 1 Sources: |
|
Vomiting | 100 mg 3 times / day multiple, oral Studied dose Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: |
unhealthy, 37 years n = 1 Health Status: unhealthy Condition: hyperthyroidism Age Group: 37 years Sex: F Population Size: 1 Sources: |
|
ALT increased | grade 3 | 50 mg/m2/hour 1 times / 2 days multiple, intravenous Studied dose Dose: 50 mg/m2/hour, 1 times / 2 days Route: intravenous Route: multiple Dose: 50 mg/m2/hour, 1 times / 2 days Sources: |
unhealthy, Median age 9.5 years n = 51 Health Status: unhealthy Condition: leukemia Age Group: Median age 9.5 years Population Size: 51 Sources: |
AST increased | grade 3 | 50 mg/m2/hour 1 times / 2 days multiple, intravenous Studied dose Dose: 50 mg/m2/hour, 1 times / 2 days Route: intravenous Route: multiple Dose: 50 mg/m2/hour, 1 times / 2 days Sources: |
unhealthy, Median age 9.5 years n = 51 Health Status: unhealthy Condition: leukemia Age Group: Median age 9.5 years Population Size: 51 Sources: |
Bilirubin increased | grade 3 | 50 mg/m2/hour 1 times / 2 days multiple, intravenous Studied dose Dose: 50 mg/m2/hour, 1 times / 2 days Route: intravenous Route: multiple Dose: 50 mg/m2/hour, 1 times / 2 days Sources: |
unhealthy, Median age 9.5 years n = 51 Health Status: unhealthy Condition: leukemia Age Group: Median age 9.5 years Population Size: 51 Sources: |
Alopecia | 100% | 1125 mg/m2 1 times / day multiple, intravenous (mean) Studied dose Dose: 1125 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1125 mg/m2, 1 times / day Co-administed with:: cytarabine(500 mg/m2 IV; 4 days) Sources: |
unhealthy, age range 2 to 17 years n = 23 Health Status: unhealthy Condition: acute leukemia Age Group: age range 2 to 17 years Sex: M+F Population Size: 23 Sources: |
Nausea | 100% | 1125 mg/m2 1 times / day multiple, intravenous (mean) Studied dose Dose: 1125 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1125 mg/m2, 1 times / day Co-administed with:: cytarabine(500 mg/m2 IV; 4 days) Sources: |
unhealthy, age range 2 to 17 years n = 23 Health Status: unhealthy Condition: acute leukemia Age Group: age range 2 to 17 years Sex: M+F Population Size: 23 Sources: |
Pancytopenia | 100% | 1125 mg/m2 1 times / day multiple, intravenous (mean) Studied dose Dose: 1125 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1125 mg/m2, 1 times / day Co-administed with:: cytarabine(500 mg/m2 IV; 4 days) Sources: |
unhealthy, age range 2 to 17 years n = 23 Health Status: unhealthy Condition: acute leukemia Age Group: age range 2 to 17 years Sex: M+F Population Size: 23 Sources: |
Candidemia | 13% | 1125 mg/m2 1 times / day multiple, intravenous (mean) Studied dose Dose: 1125 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1125 mg/m2, 1 times / day Co-administed with:: cytarabine(500 mg/m2 IV; 4 days) Sources: |
unhealthy, age range 2 to 17 years n = 23 Health Status: unhealthy Condition: acute leukemia Age Group: age range 2 to 17 years Sex: M+F Population Size: 23 Sources: |
Conjunctivitis | 13% | 1125 mg/m2 1 times / day multiple, intravenous (mean) Studied dose Dose: 1125 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1125 mg/m2, 1 times / day Co-administed with:: cytarabine(500 mg/m2 IV; 4 days) Sources: |
unhealthy, age range 2 to 17 years n = 23 Health Status: unhealthy Condition: acute leukemia Age Group: age range 2 to 17 years Sex: M+F Population Size: 23 Sources: |
Diarrhea | 26% | 1125 mg/m2 1 times / day multiple, intravenous (mean) Studied dose Dose: 1125 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1125 mg/m2, 1 times / day Co-administed with:: cytarabine(500 mg/m2 IV; 4 days) Sources: |
unhealthy, age range 2 to 17 years n = 23 Health Status: unhealthy Condition: acute leukemia Age Group: age range 2 to 17 years Sex: M+F Population Size: 23 Sources: |
Papular skin eruption | 30% | 1125 mg/m2 1 times / day multiple, intravenous (mean) Studied dose Dose: 1125 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1125 mg/m2, 1 times / day Co-administed with:: cytarabine(500 mg/m2 IV; 4 days) Sources: |
unhealthy, age range 2 to 17 years n = 23 Health Status: unhealthy Condition: acute leukemia Age Group: age range 2 to 17 years Sex: M+F Population Size: 23 Sources: |
Bleeding | 4% | 1125 mg/m2 1 times / day multiple, intravenous (mean) Studied dose Dose: 1125 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1125 mg/m2, 1 times / day Co-administed with:: cytarabine(500 mg/m2 IV; 4 days) Sources: |
unhealthy, age range 2 to 17 years n = 23 Health Status: unhealthy Condition: acute leukemia Age Group: age range 2 to 17 years Sex: M+F Population Size: 23 Sources: |
Cytomegalovirus infection | 4% | 1125 mg/m2 1 times / day multiple, intravenous (mean) Studied dose Dose: 1125 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1125 mg/m2, 1 times / day Co-administed with:: cytarabine(500 mg/m2 IV; 4 days) Sources: |
unhealthy, age range 2 to 17 years n = 23 Health Status: unhealthy Condition: acute leukemia Age Group: age range 2 to 17 years Sex: M+F Population Size: 23 Sources: |
Typhlitis | 4% | 1125 mg/m2 1 times / day multiple, intravenous (mean) Studied dose Dose: 1125 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1125 mg/m2, 1 times / day Co-administed with:: cytarabine(500 mg/m2 IV; 4 days) Sources: |
unhealthy, age range 2 to 17 years n = 23 Health Status: unhealthy Condition: acute leukemia Age Group: age range 2 to 17 years Sex: M+F Population Size: 23 Sources: |
Mucosal ulceration | 52% | 1125 mg/m2 1 times / day multiple, intravenous (mean) Studied dose Dose: 1125 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1125 mg/m2, 1 times / day Co-administed with:: cytarabine(500 mg/m2 IV; 4 days) Sources: |
unhealthy, age range 2 to 17 years n = 23 Health Status: unhealthy Condition: acute leukemia Age Group: age range 2 to 17 years Sex: M+F Population Size: 23 Sources: |
Peeling of hands & feet on soles | 52% | 1125 mg/m2 1 times / day multiple, intravenous (mean) Studied dose Dose: 1125 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1125 mg/m2, 1 times / day Co-administed with:: cytarabine(500 mg/m2 IV; 4 days) Sources: |
unhealthy, age range 2 to 17 years n = 23 Health Status: unhealthy Condition: acute leukemia Age Group: age range 2 to 17 years Sex: M+F Population Size: 23 Sources: |
Bacteremia | 65% | 1125 mg/m2 1 times / day multiple, intravenous (mean) Studied dose Dose: 1125 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1125 mg/m2, 1 times / day Co-administed with:: cytarabine(500 mg/m2 IV; 4 days) Sources: |
unhealthy, age range 2 to 17 years n = 23 Health Status: unhealthy Condition: acute leukemia Age Group: age range 2 to 17 years Sex: M+F Population Size: 23 Sources: |
Death | 8% | 1125 mg/m2 1 times / day multiple, intravenous (mean) Studied dose Dose: 1125 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1125 mg/m2, 1 times / day Co-administed with:: cytarabine(500 mg/m2 IV; 4 days) Sources: |
unhealthy, age range 2 to 17 years n = 23 Health Status: unhealthy Condition: acute leukemia Age Group: age range 2 to 17 years Sex: M+F Population Size: 23 Sources: |
Neutropenic fever | 91% | 1125 mg/m2 1 times / day multiple, intravenous (mean) Studied dose Dose: 1125 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1125 mg/m2, 1 times / day Co-administed with:: cytarabine(500 mg/m2 IV; 4 days) Sources: |
unhealthy, age range 2 to 17 years n = 23 Health Status: unhealthy Condition: acute leukemia Age Group: age range 2 to 17 years Sex: M+F Population Size: 23 Sources: |
Mucositis | grade 3, 30% DLT |
50 mg/m2/hour 1 times / 3 weeks multiple, intravenous Studied dose Dose: 50 mg/m2/hour, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 50 mg/m2/hour, 1 times / 3 weeks Sources: |
unhealthy, median age 10 years n = 10 Health Status: unhealthy Condition: cancer Age Group: median age 10 years Population Size: 10 Sources: |
Hyperbilirubinaemia | 50% | 35 mg/m2 1 times / day multiple, parenteral MTD Dose: 35 mg/m2, 1 times / day Route: parenteral Route: multiple Dose: 35 mg/m2, 1 times / day Sources: |
unhealthy, median age 60 years n = 7 Health Status: unhealthy Condition: colon cancer Age Group: median age 60 years Population Size: 7 Sources: |
Neutropenia | grade 2, 75% | 35 mg/m2 1 times / day multiple, parenteral MTD Dose: 35 mg/m2, 1 times / day Route: parenteral Route: multiple Dose: 35 mg/m2, 1 times / day Sources: |
unhealthy, median age 60 years n = 7 Health Status: unhealthy Condition: colon cancer Age Group: median age 60 years Population Size: 7 Sources: |
Neutropenia | grade 3, 12.5% DLT |
35 mg/m2 1 times / day multiple, parenteral MTD Dose: 35 mg/m2, 1 times / day Route: parenteral Route: multiple Dose: 35 mg/m2, 1 times / day Sources: |
unhealthy, median age 60 years n = 7 Health Status: unhealthy Condition: colon cancer Age Group: median age 60 years Population Size: 7 Sources: |
Thrombocytopenia | grade 3, 12.5% DLT |
35 mg/m2 1 times / day multiple, parenteral MTD Dose: 35 mg/m2, 1 times / day Route: parenteral Route: multiple Dose: 35 mg/m2, 1 times / day Sources: |
unhealthy, median age 60 years n = 7 Health Status: unhealthy Condition: colon cancer Age Group: median age 60 years Population Size: 7 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
no [IC50 133 uM] | |||
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no | |||
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no | |||
Sources: https://pubs.acs.org/doi/10.1021/tx300075j Page: - |
no | |||
Sources: https://pubs.acs.org/doi/10.1021/tx300075j Page: - |
no | |||
Sources: https://pubs.acs.org/doi/10.1021/tx300075j Page: - |
no | |||
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no | |||
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no | |||
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no | |||
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Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 8.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Pharmacogenetics: the therapeutic drug monitoring of the future? | 2001 |
|
Pharmacokinetic considerations in the treatment of inflammatory bowel disease. | 2001 |
|
Therapeutic drug monitoring of cytotoxic drugs. | 2001 |
|
[Experimental study of radiosensitizing effect of analogs of purines and pyrimidine bases in cultured HeLa cells]. | 2001 |
|
[Treatment of acute lymphoblastic leukemia in adults as an unsolved problem]. | 2001 |
|
Cyclosporine in ulcerative colitis: state of the art. | 2001 Apr-Jun |
|
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 |
|
[Metastatic Crohn's disease in childhood]. | 2001 Aug |
|
Glucocorticoids and IL-10, but not 6-MP, 5-ASA or sulfasalazine block endothelial expression of MAdCAM-1: implications for inflammatory bowel disease therapy. | 2001 Aug |
|
Review article: the risk of lymphoma associated with inflammatory bowel disease and immunosuppressive treatment. | 2001 Aug |
|
Differing contribution of thiopurine methyltransferase to mercaptopurine versus thioguanine effects in human leukemic cells. | 2001 Aug 1 |
|
Mechanism of azathioprine-induced injury to hepatocytes: roles of glutathione depletion and mitochondrial injury. | 2001 Dec |
|
Comparative pharmacokinetics of oral 6-mercaptopurine and intravenous 6-mercaptopurine riboside in children. | 2001 Dec |
|
Evolving medical therapies for ulcerative colitis. | 2001 Dec |
|
New bioactive sulfated metabolites from the Mediterranean tunicate Sidnyum turbinatum. | 2001 Feb |
|
Results of a randomized phase III trial in children and adolescents with advanced stage diffuse large cell non Hodgkin's lymphoma: a Pediatric Oncology Group study. | 2001 Jul |
|
Prognostic impact of CD45 antigen expression in high-risk, childhood B-cell precursor acute lymphoblastic leukemia. | 2001 Jul |
|
Pneumococcal arthritis affects performance status in patients with chronic GVHD of the skin following allogeneic bone marrow transplantation. | 2001 Jul |
|
Repetitious appearance and disappearance of different kinds of clonal cytogenetic abnormalities after allogeneic bone marrow transplantation. | 2001 Jul |
|
Involvement of the NUP98 gene in a chromosomal translocation t(11;20)(p15;q11.2) in a patient with acute monocytic leukemia (FAB-M5b). | 2001 Jul |
|
Treatment of acute promyelocytic leukaemia using a combination of all-trans retinoic acid and chemotherapy. | 2001 Jul |
|
Azathioprine for atopic dermatitis. | 2001 Jul |
|
If at first you don't succeed...Try again? | 2001 Jul |
|
Outcome of acute lymphoblastic leukemia in children with AL90 regimen: impact of response to treatment and sex difference on prognostic factors. | 2001 Jul |
|
A comparison of early intensive methotrexate/mercaptopurine with early intensive alternating combination chemotherapy for high-risk B-precursor acute lymphoblastic leukemia: a Pediatric Oncology Group phase III randomized trial. | 2001 Jul |
|
Photoactivation of DNA thiobases as a potential novel therapeutic option. | 2001 Jul 24 |
|
Mechanism of activation of an immunosuppressive drug: azathioprine. Quantum chemical study on the reaction of azathioprine with cysteine. | 2001 Jul 4 |
|
Management of fistulas in patients with Crohn's disease: antibiotic to antibody. | 2001 Nov |
|
Azathioprine for prevention of postoperative recurrence in Crohn's disease. | 2001 Nov |
|
Review article: the treatment of inflammatory bowel disease with 6-mercaptopurine or azathioprine. | 2001 Nov |
|
Pitfalls in the determination of mutant alleles of the thiopurine methyltransferase gene. | 2001 Nov |
|
Possible implication of thiopurine S-methyltransferase in occurrence of infectious episodes during maintenance therapy for childhood lymphoblastic leukemia with mercaptopurine. | 2001 Nov |
|
Azathioprine treatment and male fertility in inflammatory bowel disease. | 2001 Nov |
|
Measurement of thiopurine methyltransferase activity and azathioprine metabolites in patients with inflammatory bowel disease. | 2001 Nov |
|
Leucopenia resulting from a drug interaction between azathioprine or 6-mercaptopurine and mesalamine, sulphasalazine, or balsalazide. | 2001 Nov |
|
Diagnosis and treatment of perianal fistulas in Crohn disease. | 2001 Nov 20 |
|
In vitro bioassays for anticancer drug screening: effects of cell concentration and other assay parameters on growth inhibitory activity. | 2001 Nov 8 |
|
Medical management of ulcerative proctitis, proctosigmoiditis, and left-sided colitis. | 2001 Oct |
|
Managing the glucocorticoid dependent inflammatory bowel disease patient. | 2001 Oct |
|
6-mercaptopurine metabolite levels in children with inflammatory bowel disease. | 2001 Oct |
|
Determination of thiopurine methyltransferase activity in human erythrocytes by high-performance liquid chromatography: comparison with the radiochemical method. | 2001 Oct |
|
Review article: the limitations of corticosteroid therapy in Crohn's disease. | 2001 Oct |
|
Single-agent therapy with oral mercaptopurine for nonlymphoid blast crisis of chronic myeloid leukemia. | 2001 Sep |
|
Therapy-related CD7+ acute myeloid leukemia with trisomy 8 following acute monocytic leukemia. | 2001 Sep |
|
Use of azathioprine or 6-mercaptopurine for treatment of steroid-dependent lymphocytic and collagenous colitis. | 2001 Sep |
|
Neutropenia is not required for clinical remission during azathioprine therapy in inflammatory bowel disease. | 2001 Sep |
|
Deoxythioguanosine triphosphate impairs HIV replication: a new mechanism for an old drug. | 2001 Sep |
|
Development of obesity and neurochemical backing in aurothioglucose-treated mice. | 2001 Sep 17 |
|
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 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/mercaptopurine.html
Usual Adult Dose for Intestinal Arterial Insufficiency
Initial Dosage:
Oral: 2.5 mg/kg of body weight per day (100 to 200 mg in the average adult). This dose may be continued daily for several weeks or more in some patients. If, after 4 weeks at this dosage, there is no clinical improvement and no definite evidence of leukocyte or platelet depression, the dosage may be increased up to 5 mg/kg daily. A dosage of 2.5 mg/kg per day may result in a rapid fall in leukocyte count within 1 to 2 weeks in some adults with acute lymphatic leukemia and high total leukocyte counts.
The total daily dosage may be given at one time. It is calculated to the nearest multiple of 25 mg.
Maintenance Therapy: Once a complete hematologic remission is obtained, maintenance therapy is considered essential. A usual daily maintenance dose of mercaptopurine is 1.5 to 2.5 mg/kg per day as a single dose. Mercaptopurine should rarely be relied upon as a single agent for the maintenance of remissions induced in acute leukemia.
Usual Adult Dose for Acute Lymphoblastic Leukemia
Initial Dosage:
Oral: 2.5 mg/kg of body weight per day (100 to 200 mg in the average adult). This dose may be continued daily for several weeks or more in some patients. If, after 4 weeks at this dosage, there is no clinical improvement and no definite evidence of leukocyte or platelet depression, the dosage may be increased up to 5 mg/kg daily. A dosage of 2.5 mg/kg per day may result in a rapid fall in leukocyte count within 1 to 2 weeks in some adults with acute lymphatic leukemia and high total leukocyte counts.
The total daily dosage may be given at one time. It is calculated to the nearest multiple of 25 mg.
Maintenance Therapy: Once a complete hematologic remission is obtained, maintenance therapy is considered essential. A usual daily maintenance dose of mercaptopurine is 1.5 to 2.5 mg/kg per day as a single dose. Mercaptopurine should rarely be relied upon as a single agent for the maintenance of remissions induced in acute leukemia.
Usual Adult Dose for Crohn's Disease - Acute
Oral: 1.0 to 1.5 mg/kg of body weight per day
Usual Adult Dose for Crohn's Disease - Maintenance
Oral: 1.0 to 1.5 mg/kg of body weight per day
Usual Adult Dose for Ulcerative Colitis - Maintenance
Oral: 1.0 to 1.5 mg/kg of body weight per day
Usual Adult Dose for Inflammatory Bowel Disease
Oral: 1.0 to 1.5 mg/kg of body weight per day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3247467
Mercaptopurine (10-500 ug/ml) inhibits in a dose-dependent manner the production of PGE2, PGF2 alpha, 6-keto-PGF1 alpha and TXB2 by unseparated spleen cells as well as that of 6-keto-PGF1 alpha by adherent peritoneal macrophages.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C1556
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WHO-ATC |
L01BB02
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FDA ORPHAN DRUG |
373512
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NDF-RT |
N0000175595
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WHO-ESSENTIAL MEDICINES LIST |
8.2
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EU-Orphan Drug |
EU/3/09/628
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NCI_THESAURUS |
C574
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WHO-VATC |
QL01BB02
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EMA ASSESSMENT REPORTS |
XALUPRINE (AUTHORIZED: LEUKEMIA, LYMPHOID)
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LIVERTOX |
NBK548546
Created by
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Code System | Code | Type | Description | ||
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MERCAPTOPURINE
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DTXSID9025538
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PRIMARY | |||
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50667
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PRIMARY | |||
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1708
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PRIMARY | |||
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SUB20430
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PRIMARY | |||
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1392002
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PRIMARY | |||
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m7208
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PRIMARY | Merck Index | ||
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MERCAPTOPURINE
Created by
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PRIMARY | Description: A yellow, crystalline powder.Solubility: Practically insoluble in water and ether R; slightly soluble in ethanol (~750 g/l) TS; dissolves in solutions of alkali hydroxides. Category: Cytotoxic drug. Storage: Mercaptopurine should be kept in a well-closed container, protected from light.Additional information: CAUTION: Mercaptopurine must be handled with care, avoiding contact with the skin and inhalation of airborne particles.It melts at a temperature exceeding 308 ?C with decomposition. Requirements:Mercaptopurine contains not less than 97.0% and not more than the equivalent of 102.0% of C5H4N4S, calculated with reference to the anhydrous substance. | ||
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759614
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PRIMARY | |||
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DB01033
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PRIMARY | |||
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103
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PRIMARY | RxNorm | ||
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31822
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PRIMARY | |||
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E7WED276I5
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PRIMARY | |||
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7226
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PRIMARY | |||
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2724350
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PRIMARY | |||
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6112-76-1
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CHEMBL1425
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PRIMARY | |||
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C195
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100000085529
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PRIMARY | |||
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Mercaptopurine
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PRIMARY | |||
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755
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PRIMARY | |||
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E7WED276I5
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PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD