mercaptopurine   

GtoPdb Ligand ID: 7226

Synonyms: 6-mercaptopurine | Purinethol® | Xaluprine®
mercaptopurine is an approved drug (FDA (1953), EMA (2012))
Compound class: Synthetic organic
Comment: Mercaptopurine has immunosuppressive action as well as antineoplastic activity.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 93.26
Molecular weight 152.02
XLogP 0.22
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES Sc1ncnc2c1nc[nH]2
Isomeric SMILES Sc1ncnc2c1nc[nH]2
InChI InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
InChI Key GLVAUDGFNGKCSF-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1953), EMA (2012))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
Prodrug azathioprine
IUPAC Name
9H-purine-6-thiol
International Nonproprietary Names
INN number INN
587 mercaptopurine
Synonyms
6-mercaptopurine | Purinethol® | Xaluprine®
Database Links
CAS Registry No. 50-44-2
ChEMBL Ligand CHEMBL1425
DrugBank Ligand DB01033
DrugCentral Ligand 1708
GtoPdb PubChem SID 178103800
PubChem CID 667490
RCSB PDB Ligand PM6
Search Google for chemical match using the InChIKey GLVAUDGFNGKCSF-UHFFFAOYSA-N
Search Google for chemicals with the same backbone GLVAUDGFNGKCSF
Search PubMed clinical trials mercaptopurine
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Search UniChem for chemical match using the InChIKey GLVAUDGFNGKCSF-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone GLVAUDGFNGKCSF
Wikipedia Mercaptopurine