azathioprine   Click here for help

GtoPdb Ligand ID: 7120

Synonyms: Azasan® | BW-57-322 | Imuran® | Jayempi®
Approved drug Immunopharmacology Ligand
azathioprine is an approved drug (FDA (1968), EMA (2021))
Compound class: Synthetic organic
Comment: Azathioprine is an immunosuppressive antimetabolite. The active drug is believed to be mercaptopurine.
Marketed formulations may contain azathioprine sodium (PubChem CID 23678403).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 143.4
Molecular weight 277.04
XLogP 0.67
No. Lipinski's rules broken 0
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Canonical SMILES Cn1cnc(c1Sc1ncnc2c1nc[nH]2)N(=O)=O
Isomeric SMILES Cn1cnc(c1Sc1ncnc2c1nc[nH]2)N(=O)=O
InChI InChI=1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1968), EMA (2021))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
Is prodrug? Yes
Active form mercaptopurine
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
1291 azathioprine
Synonyms Click here for help
Azasan® | BW-57-322 | Imuran® | Jayempi®
Database Links Click here for help
BitterDB Ligand 56
CAS Registry No. 446-86-6
ChEMBL Ligand CHEMBL1542
DrugBank Ligand DB00993
DrugCentral Ligand 269
GtoPdb PubChem SID 178103697
Immunopaedia Search azathioprine
PubChem CID 2265
Search Google for chemical match using the InChIKey LMEKQMALGUDUQG-UHFFFAOYSA-N
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UniChem Compound Search for chemical match using the InChIKey LMEKQMALGUDUQG-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey LMEKQMALGUDUQG-UHFFFAOYSA-N
Wikipedia Azathioprine

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Azathioprine (links to external site)
Cat. No. 4099