General
Preferred name
MERCAPTOPURINE
Synonyms
6-Mercaptopurine ()
6-Mercaptopurine hydrate ()
6-Mercaptopurine (6-MP) Monohydrate ()
6-MP ()
6-Mercaptopurine monohydrate ()
MERCAPTOPURINE ANHYDROUS ()
6-Purinethiol ()
6-Thiopurine ()
Purinethol ()
3H-Purine-6-thiol ()
Purine, 6-mercapto- ()
7-Mercapto-1,3,4,6-tetrazaindene ()
Ismipur ()
MERCAPTOPURINE HYDRATE ()
6-MP hydrate ()
Mercaptopurine (6-MP) ()
Mercaptopurine ()
NSC-759614 ()
Mercaptopurine hydrate ()
6-mercaptopurine ()
Puri-Nethol ()
NSC-755 ()
Purixan ()
6-mercaptopurine monohydrate ()
Mercaptopurinum ()
Xaluprine ()
6-Mercaptopurine (hydrate) ()
P&D ID
PD001869
CAS
6112-76-1
50-44-2
1194-62-3
Tags
prodrug
nuisance
natural product
drug
available
Approved by
FDA
First approval
1953
Drug Status
approved
Drug indication
Severe acute respiratory syndrome (SARS)
Antineoplastic
Crohn disease
Acute lymphoblastic leukaemia
Middle East Respiratory Syndrome (MERS)
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
MOA Mercaptopurine competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRTase) and is itself converted to thioinosinic acid (TIMP). TIMP inhibits several reactions that involve inosinic acid (IMP), such as the conversion of IMP to xanthylic acid (XMP) and the conversion of IMP to adenylic acid (AMP) via adenylosuccinate (SAMP). Upon methylation, TIMP forms 6-methylthioinosinate (MTIMP) which inhibits glutamine-5-phosphoribosylpyrophosphate amidotransferase in addition to TIMP. Glutamine-5-phosphoribosylpyrophosphate amidotransferase is the first enzyme unique to the _de novo_ pathway for purine ribonucleotide synthesis. According to experimental findings using radiolabeled mercaptopurine, mercaptopurine may be recovered from the DNA in the form of deoxythioguanosine. In comparison, some mercaptopurine may be converted to nucleotide derivatives of 6-thioguanine (6-TG) via actions of inosinate (IMP) dehydrogenase and xanthylate (XMP) aminase that convert TIMP to thioguanylic acid (TGMP).
DESCRIPTION Mercaptopurine has immunosuppressive action as well as antineoplastic activity. (GtoPdb)
DESCRIPTION Mercaptopurine is a widely used antileukemic agent and immunosuppressive drug that inhibits de novo purine synthesis through incorporation of thiopurine methyltransferase metabolites into DNA and RNA. (BOC Sciences Bioactive Compounds)
Cell lines
24
Organisms
1
Compound Sets
30
AdooQ Bioactive Compound Library
A10568
A15898
Axon Medchem Screening Library
3245
BOC Sciences Bioactive Compounds
mercaptopurine-cas-50-44-2-item-84-93223
Cayman Chemical Bioactives
23675
CeMM library of unique drugs (CLOUD)
ChEMBL Approved Drugs
CHEMBL1425
CHEMBL1200751
ChEMBL Drugs
CHEMBL1425
CHEMBL1200751
Drug Repurposing Hub
DrugBank
DB01033
DrugBank Approved Drugs
DB01033
DrugCentral
1708
DrugCentral Approved Drugs
1708
DrugMAP
DMTM2IK
DMTQXS7
DrugMAP Approved Drugs
DMTM2IK
DrugMatrix
Enamine BioReference Compounds
Guide to Pharmacology
7226
MedChem Express Bioactive Compound Library
HY-13677
HY-13677A
NCATS Inxight Approved Drugs
PKK6MUZ20G
NIH Approved Oncology Drugs
538245
NIH Clinical Collections (NCC)
NIH Mechanistic Set
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Nuisance compounds in cellular assays
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
Mercaptopurine
6-mercaptopurine-6-mp-monohydrate
TargetMol Bioactive Compound Library
T0010
T2201
The Spectrum Collection
External IDs
87
Properties
(calculated by RDKit )
Molecular Weight
152.02
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
2
Rotatable Bonds
0
Ring Count
2
Aromatic Ring Count
2
cLogP
1.02
TPSA
57.36
Fraction CSP3
0.0
Chiral centers
0.0
Largest ring
6.0
QED
0.55
Structural alerts
1
Nonspecific reactivity
Nuisance compounds in cellular assays
Related compounds
Custom attributes
(extracted from source data)
MOA
ribonucleoside-diphosphate reductase inhibitor
Immunosuppressive
Purine Antagonists
immunosuppressant, protein synthesis inhibitor, purine antagonist
Target
DNA
Amidophosphoribosyltransferase
DNA synthesis
PRPP Amidotransferase
IMPDH
HPRT
HPRT1, IMPDH1, IMPDH2, PPAT
Purine analog
Endogenous Metabolite
Nucleoside antimetabolite/analog
DNA/RNA Synthesis
Pathway
DNA Damage/DNA Repair
Metabolism
Autophagy
Cell Cycle/DNA Damage
Metabolic Enzyme/Protease
Member status
member
Indication
acute lymphoblastic leukemia (ALL)
Therapeutic Class
Anticancer Agents
Antiviral Agents
Source data