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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
Structure of MERCAPTOPURINE

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

HIDE SMILES / InChI
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).

CNS Activity

Curator's Comment: Drug crosses the blood-brain barrier, but the CSF level is too low for treatment of meningeal leukemias.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PURINETHOL

Approved Use

Mercaptopurine 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 Date

1953
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
69.5 ng/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
135.8 ng × h/mL
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
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

Funbound

ValueDoseCo-administeredAnalytePopulation
81%
MERCAPTOPURINE ANHYDROUS plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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...
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)
AST increased (grade 3)
Bilirubin increased (grade 3)
Sources:
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%)
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%)
Sources:
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...
Dose limiting toxicities:
Mucositis (grade 3, 30%)
Sources:
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%)
Thrombocytopenia (grade 3, 12.5%)
Other AEs:
Neutropenia (grade 2, 75%)
Hyperbilirubinaemia (50%)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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

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
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.
Name Type Language
MERCAPTOPURINE
EP   MART.   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
Systematic Name English
MERCAPTOPURINE [WHO-IP]
Common Name English
MERCAPTOPURINE [USP MONOGRAPH]
Common Name English
MERCAPTOPURINUM [WHO-IP LATIN]
Common Name English
MERCAPTOPURINE HYDRATE
JAN  
Systematic Name English
MERCAPTOPURINE MONOHYDRATE
Systematic Name English
6H-PURINE-6-THIONE, 1,7-DIHYDRO-, MONOHYDRATE
Systematic Name English
PURINETHOL
Brand Name English
6H-PURINE-6-THIONE, 1,2,3,9-TETRAHYDRO-, HYDRATE (1:1)
Systematic Name English
1,7-DIHYDRO-6H-PURINE-6-THIONE HYDRATE
Systematic Name English
MERCAPTOPURINE MONOHYDRATE [EP MONOGRAPH]
Common Name English
NSC-759614
Code English
7H-PURINE-6-THIOL MONOHYDRATE
Systematic Name English
MERCAPTOPURINE [VANDF]
Common Name English
6-MERCAPTOPURINE MONOHYDRATE
MI  
Systematic Name English
MERCAPTOPURINE [USP-RS]
Common Name English
MERCAPTOPURINE [MART.]
Common Name English
MERCAPTOPURINE HYDRATE [JAN]
Common Name English
MERCAPTOPURINE [ORANGE BOOK]
Common Name English
NSC-755
Code English
Purine-6-thiol monohydrate
Systematic Name English
PURIXAN
Brand Name English
6-MERCAPTOPURINE MONOHYDRATE [MI]
Common Name English
Mercaptopurine [WHO-DD]
Common Name English
XALUPRINE
Brand Name English
MERCAPTOPURINE [EP IMPURITY]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1556
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
WHO-ATC L01BB02
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
FDA ORPHAN DRUG 373512
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
NDF-RT N0000175595
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 8.2
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
EU-Orphan Drug EU/3/09/628
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
NCI_THESAURUS C574
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
WHO-VATC QL01BB02
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
EMA ASSESSMENT REPORTS XALUPRINE (AUTHORIZED: LEUKEMIA, LYMPHOID)
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
LIVERTOX NBK548546
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
Code System Code Type Description
WIKIPEDIA
MERCAPTOPURINE
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
PRIMARY
EPA CompTox
DTXSID9025538
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
PRIMARY
CHEBI
50667
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
PRIMARY
DRUG CENTRAL
1708
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
PRIMARY
EVMPD
SUB20430
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
PRIMARY
RS_ITEM_NUM
1392002
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
PRIMARY
MERCK INDEX
m7208
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
PRIMARY Merck Index
WHO INTERNATIONAL PHARMACOPEIA
MERCAPTOPURINE
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
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.
NSC
759614
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
PRIMARY
DRUG BANK
DB01033
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
PRIMARY
RXCUI
103
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
PRIMARY RxNorm
CHEBI
31822
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
PRIMARY
DAILYMED
E7WED276I5
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
PRIMARY
IUPHAR
7226
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
PRIMARY
PUBCHEM
2724350
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
PRIMARY
CAS
6112-76-1
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
PRIMARY
ChEMBL
CHEMBL1425
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
PRIMARY
NCI_THESAURUS
C195
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
PRIMARY
SMS_ID
100000085529
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
PRIMARY
LACTMED
Mercaptopurine
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
PRIMARY
NSC
755
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
PRIMARY
FDA UNII
E7WED276I5
Created by admin on Fri Dec 15 15:13:26 GMT 2023 , Edited by admin on Fri Dec 15 15:13:26 GMT 2023
PRIMARY