U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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

Description

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

CNS Penetrant
2588
Curator's Comment: Drug crosses the blood-brain barrier, but the CSF level is too low for treatment of meningeal leukemias.

Originator

Approval Year

1953
193
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Inhibitor
8504
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
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
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
81%
DRUG LABEL
https://nctr-crs.fda.gov/fdalabel/services/spl/set-ids/15904472-4c32-4224-95d3-eb131a7ff9c8/spl-doc?hl=mercaptopurine
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205919s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/19555631/
unhealthy, 37 years
Health Status: unhealthy
Age Group: 37 years
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205919s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/19555631/
Other AEs: Anorexia, Nausea...
Other AEs:
Anorexia
Nausea
Vomiting
Myelosuppression
Hepatic disease
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205919s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/19555631/
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:
https://pubmed.ncbi.nlm.nih.gov/1600597/
unhealthy, Median age 9.5 years
Health Status: unhealthy
Age Group: Median age 9.5 years
Sources:
https://pubmed.ncbi.nlm.nih.gov/1600597/
Other AEs: ALT increased, AST increased...
Other AEs:
ALT increased (grade 3)
AST increased (grade 3)
Bilirubin increased (grade 3)
Sources:
https://pubmed.ncbi.nlm.nih.gov/1600597/
1125 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 1125 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 1125 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
unhealthy, age range 2 to 17 years
Health Status: unhealthy
Age Group: age range 2 to 17 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
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:
https://pubmed.ncbi.nlm.nih.gov/8120558/
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
unhealthy, age range 4 to 14 years
Health Status: unhealthy
Age Group: age range 4 to 14 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
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:
https://pubmed.ncbi.nlm.nih.gov/4038917/
unhealthy, median age 10 years
Health Status: unhealthy
Age Group: median age 10 years
Sources:
https://pubmed.ncbi.nlm.nih.gov/4038917/
DLT: Mucositis...
Dose limiting toxicities:
Mucositis (grade 3, 30%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/4038917/
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:
https://pubmed.ncbi.nlm.nih.gov/9713314/
unhealthy, median age 60 years
Health Status: unhealthy
Age Group: median age 60 years
Sources:
https://pubmed.ncbi.nlm.nih.gov/9713314/
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:
https://pubmed.ncbi.nlm.nih.gov/9713314/
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205919s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/19555631/
unhealthy, 37 years
Health Status: unhealthy
Age Group: 37 years
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205919s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/19555631/
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205919s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/19555631/
unhealthy, 37 years
Health Status: unhealthy
Age Group: 37 years
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205919s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/19555631/
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205919s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/19555631/
unhealthy, 37 years
Health Status: unhealthy
Age Group: 37 years
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205919s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/19555631/
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205919s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/19555631/
unhealthy, 37 years
Health Status: unhealthy
Age Group: 37 years
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205919s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/19555631/
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205919s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/19555631/
unhealthy, 37 years
Health Status: unhealthy
Age Group: 37 years
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205919s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/19555631/
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:
https://pubmed.ncbi.nlm.nih.gov/1600597/
unhealthy, Median age 9.5 years
Health Status: unhealthy
Age Group: Median age 9.5 years
Sources:
https://pubmed.ncbi.nlm.nih.gov/1600597/
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:
https://pubmed.ncbi.nlm.nih.gov/1600597/
unhealthy, Median age 9.5 years
Health Status: unhealthy
Age Group: Median age 9.5 years
Sources:
https://pubmed.ncbi.nlm.nih.gov/1600597/
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:
https://pubmed.ncbi.nlm.nih.gov/1600597/
unhealthy, Median age 9.5 years
Health Status: unhealthy
Age Group: Median age 9.5 years
Sources:
https://pubmed.ncbi.nlm.nih.gov/1600597/
Alopecia 100%
1125 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 1125 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 1125 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
unhealthy, age range 2 to 17 years
Health Status: unhealthy
Age Group: age range 2 to 17 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
Nausea 100%
1125 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 1125 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 1125 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
unhealthy, age range 2 to 17 years
Health Status: unhealthy
Age Group: age range 2 to 17 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
Pancytopenia 100%
1125 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 1125 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 1125 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
unhealthy, age range 2 to 17 years
Health Status: unhealthy
Age Group: age range 2 to 17 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
Candidemia 13%
1125 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 1125 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 1125 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
unhealthy, age range 2 to 17 years
Health Status: unhealthy
Age Group: age range 2 to 17 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
Conjunctivitis 13%
1125 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 1125 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 1125 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
unhealthy, age range 2 to 17 years
Health Status: unhealthy
Age Group: age range 2 to 17 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
Diarrhea 26%
1125 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 1125 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 1125 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
unhealthy, age range 2 to 17 years
Health Status: unhealthy
Age Group: age range 2 to 17 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
Papular skin eruption 30%
1125 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 1125 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 1125 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
unhealthy, age range 2 to 17 years
Health Status: unhealthy
Age Group: age range 2 to 17 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
Bleeding 4%
1125 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 1125 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 1125 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
unhealthy, age range 2 to 17 years
Health Status: unhealthy
Age Group: age range 2 to 17 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
Cytomegalovirus infection 4%
1125 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 1125 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 1125 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
unhealthy, age range 2 to 17 years
Health Status: unhealthy
Age Group: age range 2 to 17 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
Typhlitis 4%
1125 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 1125 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 1125 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
unhealthy, age range 2 to 17 years
Health Status: unhealthy
Age Group: age range 2 to 17 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
Mucosal ulceration 52%
1125 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 1125 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 1125 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
unhealthy, age range 2 to 17 years
Health Status: unhealthy
Age Group: age range 2 to 17 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
Peeling of hands & feet on soles 52%
1125 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 1125 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 1125 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
unhealthy, age range 2 to 17 years
Health Status: unhealthy
Age Group: age range 2 to 17 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
Bacteremia 65%
1125 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 1125 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 1125 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
unhealthy, age range 2 to 17 years
Health Status: unhealthy
Age Group: age range 2 to 17 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
Death 8%
1125 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 1125 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 1125 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
unhealthy, age range 2 to 17 years
Health Status: unhealthy
Age Group: age range 2 to 17 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
Neutropenic fever 91%
1125 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 1125 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 1125 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
unhealthy, age range 2 to 17 years
Health Status: unhealthy
Age Group: age range 2 to 17 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8120558/
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:
https://pubmed.ncbi.nlm.nih.gov/4038917/
unhealthy, median age 10 years
Health Status: unhealthy
Age Group: median age 10 years
Sources:
https://pubmed.ncbi.nlm.nih.gov/4038917/
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:
https://pubmed.ncbi.nlm.nih.gov/9713314/
unhealthy, median age 60 years
Health Status: unhealthy
Age Group: median age 60 years
Sources:
https://pubmed.ncbi.nlm.nih.gov/9713314/
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:
https://pubmed.ncbi.nlm.nih.gov/9713314/
unhealthy, median age 60 years
Health Status: unhealthy
Age Group: median age 60 years
Sources:
https://pubmed.ncbi.nlm.nih.gov/9713314/
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:
https://pubmed.ncbi.nlm.nih.gov/9713314/
unhealthy, median age 60 years
Health Status: unhealthy
Age Group: median age 60 years
Sources:
https://pubmed.ncbi.nlm.nih.gov/9713314/
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:
https://pubmed.ncbi.nlm.nih.gov/9713314/
unhealthy, median age 60 years
Health Status: unhealthy
Age Group: median age 60 years
Sources:
https://pubmed.ncbi.nlm.nih.gov/9713314/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252
inhibitor
2438
inhibitor
2507

OverviewOther

Other InhibitorOther SubstrateOther Inducer
OATP1B3
961

OATP1B1
1079

BSEP
550

MRP4
290

MRP3
246

CYP2C19
2057

CYP1A2
2153
TPMT
5
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
BSEP
554
 no [IC50 133 uM]
CYP1A2
2333
 no
CYP2C19
2141
 no
CYP2C9
2497
 no
CYP2D6
2546
 no
CYP3A4
2633
 no
MRP3
326
 no
MRP4
345
 no
OATP1B1
1095
 no
OATP1B3
970
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
TPMT
5
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY556883
https://www.001chemical.com/chem/50-44-2
3B Scientific (Wuhan) Corp
3B3-010771
http://www.3bsc.com/index/pro_info.php?id=33264
AA Blocks
AA0038MP
http://www.aablocks.com/goods/Goods/detail?id=AA0038MP
Aaron Chemicals
AR0039EH
http://www.aaronchem.com/50-44-2
abcr GmbH
AB310793
http://www.abcr.com/shop/en/AB310793
AbMole Bioscience
M5771
http://www.abmole.com/products/mercaptopurine-(6-mp).html
Acadechem
ACDS-063904
http://www.acadechemical.com/product/138603
Achemica
ACMC-1AUNA
http://www.achemica.com/prodinfo/?id=23363
Achemo Scientific Limited
AC-13751
http://www.achemo.com/product_view.asp?ID=3641
Achemtek
0104-015751
http://www.achemtek.com/50-44-2
Adooq BioScience
A10568
https://www.adooq.com/mercaptopurine.html
AHH Chemical co.,ltd
MT-16617
http://www.ahhchemical.com/product/MT-16617.html
AK Scientific, Inc. (AKSCI)
6450AJ
http://www.aksci.com/item_detail.php?cat=6450AJ
AK Scientific, Inc. (AKSCI)
H348
http://www.aksci.com/item_detail.php?cat=H348
Allbio Pharm Co., Ltd
AD04542
http://www.allbiopharm.com/product/n/AD04542
Ambeed
A262086
https://www.ambeed.com/products/50-44-2.html
Ambinter
Amb19871503
http://www.ambinter.com/reference/19871503
Ambinter
Amb22094177
http://www.ambinter.com/reference/22094177
Angene
AGN-PC-0OBCLT
http://www.angenechemical.com/productshow/AGN-PC-0OBCLT.html
Anward
ANW-30999
http://www.anward.com/pro_result/20361
Anward
ANW-57555
http://www.anward.com/pro_result/44006
ApexBio Technology
A2355
http://www.apexbt.com/mercaptopurine-6-mp.html
Aromalake
LS20858
http://www.aromalake.com/6-Mercaptopurine-p4173.html
Aronis
ARONIS27054
http://www.aronis.ru/store/index.php?main_page=product_info&cPath=1&products_id=19951
Aurora Fine Chemicals LLC
A00.451.223
http://online.aurorafinechemicals.com/info?ID=A00.451.223
Aurora Fine Chemicals LLC
K00.363.564
http://online.aurorafinechemicals.com/info?ID=K00.363.564
Aurum Pharmatech LLC
W-5114
http://www.Aurumpharmatech.com/Product/ProductDetails/W_5114
BioCrick
BCC1186
http://www.biocrick.com/Mercaptopurine-6-MP-BCC1186.html
BioSynth
W-105961
https://www.biosynth.com/en/products/chemical-intermediates/basic-intermediates/products/W-105961.html
BLD Pharm
BD01223348
http://www.bldpharm.com/products/157930-11-5.html
BLD Pharm
BD33839
http://www.bldpharm.com/products/50-44-2.html
Boerchem
BC202313
http://www.boerchem.com/?product_33963.html
Capot Chemical
9680
http://www.capotchem.com/en/9680.htm
Capot Chemical
PubChem9680
http://www.capotchem.com/en/9680.htm
Chem Scene
CS-1499
http://www.chemscene.com/50-44-2.html
ChemMol
1201510
http://www.chemmol.com/chemmol/1201510.html
ChemMol
30101353
http://www.chemmol.com/chemmol/30101353.html
ChemMol
42303035
http://www.chemmol.com/chemmol/42303035.html
ChemMol
44025678
http://www.chemmol.com/chemmol/44025678.html
ChemMol
49401460
http://www.chemmol.com/chemmol/49401460.html
Chemspace
CSSB00000748415
https://chem-space.com/CSSB00000748415
Clearsynth
CS-O-30642
http://www.clearsynth.com/en/CSO30642.html
CSNpharm
CSN16373
https://www.csnpharm.com/products/6-mercaptopurine.html
Debye Scientific
DB-026398
http://www.debyesci.com/DB-026398.html
eNovation Chemicals
D584258
https://www.enovationchem.com/ProductDetails.asp?ProductID=D584258
Finetech
FT-0621175
http://www.finetechnology-ind.com/prod/detail/pub/50-44-2.html
Glentham Life Sciences
GP0789
http://www.glentham.com/products/product/GP0789/
Hairui
HR135280
http://www.hairuichem.com/en/product/50-44-2.html
iChemical
EBD540779
http://www.ichemical.com/products/50-44-2.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network
LN00222396
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00222396
Matrix Scientific
147903
https://www.matrixscientific.com/147903.html
mcule
MCULE-4811219863
https://mcule.com/MCULE-4811219863/
MedChem Express
HY-13677
https://www.medchemexpress.com/6-Mercaptopurine.html
Molcore
MC556883
https://www.molcore.com/product/50-44-2
Oakwood
219749
http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=100748&ExtHyperLink=1
Oakwood
50540
http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=196267&ExtHyperLink=1
OChem
10489
http://www.ocheminc.com/index.php?act=psearch&pid=462M721
OChem
11066
http://www.ocheminc.com/index.php?act=psearch&pid=233D552
OChem
3904
http://www.ocheminc.com/index.php?act=psearch&pid=599M524
OChem
3905
http://www.ocheminc.com/index.php?act=psearch&pid=50M442
Renno Tech
RP21622
http://www.rennotech.com/product_show.asp?id=27335
Selleck Chemicals
S1305
http://www.selleckchem.com/products/Mercaptopurine.html
Sigma-Aldrich
38171_SIAL
https://www.sigmaaldrich.com/catalog/product/sial/38171?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech
S048247
http://www.sinfoobiotech.com/product/1051645
Smolecule
S548851
http://www.smolecule.com/products/s548851
Synthink Research Chemicals
SA17903
https://synthinkchemicals.com/product/azathioprine-ep-impurity-b/
TCI (Tokyo Chemical Industry)
M0063
http://www.tcichemicals.com/eshop/en/us/commodity/M0063/index.html
THE BioTek
bt-288262
https://www.thebiotek.com/product/inhibitors/bt-288262
Vitas-M Laboratory
BBL033743
http://www.request.vitasmlab.biz/index.php?option=com_search_stk&Itemid=22&stk=BBL033743&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
Yuhao Chemical
RT18294
http://www.chemyuhao.com/50-44-2.html
PubMed

PubMed

TitleDatePubMed
Pharmacogenetics: the therapeutic drug monitoring of the future?
2001
Allelotype frequency of the thiopurine methyltransferase (TPMT) gene in Japanese.
2001 Apr
Genetic polymorphisms of thiopurine S-methyltransferase and 6-mercaptopurine toxicity in Japanese children with acute lymphoblastic leukaemia.
2001 Apr
Preponderance of thiopurine S-methyltransferase deficiency and heterozygosity among patients intolerant to mercaptopurine or azathioprine.
2001 Apr 15
[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
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
New bioactive sulfated metabolites from the Mediterranean tunicate Sidnyum turbinatum.
2001 Feb
Induction therapy of adult acute lymphocytic leukemia without the use of vincristine or prednisone.
2001 Feb
New developments in the immunosuppressive drug monitoring of cyclosporine, tacrolimus, and azathioprine.
2001 Feb
Smooth muscle tumor developing in an immunocompromised child after therapy for leukemia.
2001 Feb
Hepatic dysfunction as the presenting feature of acute lymphoblastic leukemia.
2001 Feb
[Guidelines of the DGVS. Chronic active course. German Society of Digestive and Metabolic Diseases].
2001 Jan
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
Plasma pharmacokinetics and cerebrospinal fluid penetration of thioguanine in children with acute lymphoblastic leukemia: a collaborative Pediatric Oncology Branch, NCI, and Children's Cancer Group study.
2001 Mar
Crohn's disease of the esophagus: clinical features and outcomes.
2001 May
Approach to corticosteroid-dependent and corticosteroid-refractory Crohn's disease.
2001 May
Conventional treatment of Crohn's disease: objectives and outcomes.
2001 May
Treatment of refractory microscopic colitis with azathioprine and 6-mercaptopurine.
2001 May
Utilisation of erythrocyte 6-thioguanine metabolite levels to optimise azathioprine therapy in patients with inflammatory bowel disease.
2001 May
Rational dosing of azathioprine and 6-mercaptopurine.
2001 May
Management of fistulas in patients with Crohn's disease: antibiotic to antibody.
2001 Nov
Medical management of ulcerative proctitis, proctosigmoiditis, and left-sided colitis.
2001 Oct
6-mercaptopurine metabolite levels in children with inflammatory bowel disease.
2001 Oct
Review article: the limitations of corticosteroid therapy in Crohn's disease.
2001 Oct
Therapy-related CD7+ acute myeloid leukemia with trisomy 8 following acute monocytic leukemia.
2001 Sep
Transport of cyclic nucleotides and estradiol 17-beta-D-glucuronide by multidrug resistance protein 4. Resistance to 6-mercaptopurine and 6-thioguanine.
2001 Sep 7
Patents

Patents

03935184
5
04183786
3
05705499
6
20010004454
41

Sample Use Guides

In Vivo Use Guide
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
6-MERCAPTOPURINE MONOHYDRATE
MI  
Preferred 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
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 Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
WHO-ATC L01BB02
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
FDA ORPHAN DRUG 373512
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
NDF-RT N0000175595
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 8.2
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
EU-Orphan Drug EU/3/09/628
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
NCI_THESAURUS C574
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
WHO-VATC QL01BB02
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
EMA ASSESSMENT REPORTS XALUPRINE (AUTHORIZED: LEUKEMIA, LYMPHOID)
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
LIVERTOX NBK548546
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
Code System Code Type Description
WIKIPEDIA
MERCAPTOPURINE
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
PRIMARY
EPA CompTox
DTXSID9025538
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
PRIMARY
CHEBI
50667
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
PRIMARY
DRUG CENTRAL
1708
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
PRIMARY
EVMPD
SUB20430
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
PRIMARY
RS_ITEM_NUM
1392002
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
PRIMARY
MERCK INDEX
m7208
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
PRIMARY Merck Index
WHO INTERNATIONAL PHARMACOPEIA
MERCAPTOPURINE
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
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 Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
PRIMARY
DRUG BANK
DB01033
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
PRIMARY
RXCUI
103
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
PRIMARY RxNorm
CHEBI
31822
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
PRIMARY
DAILYMED
E7WED276I5
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
PRIMARY
IUPHAR
7226
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
PRIMARY
PUBCHEM
2724350
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
PRIMARY
CAS
6112-76-1
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
PRIMARY
ChEMBL
CHEMBL1425
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
PRIMARY
NCI_THESAURUS
C195
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
PRIMARY
SMS_ID
100000085529
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
PRIMARY
LACTMED
Mercaptopurine
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
PRIMARY
NSC
755
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
PRIMARY
FDA UNII
E7WED276I5
Created by admin on Mon Mar 31 17:50:45 GMT 2025 , Edited by admin on Mon Mar 31 17:50:45 GMT 2025
PRIMARY
SUBSTANCE RECORD
Structure of MERCAPTOPURINE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966