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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: azathioprine

azathioprine is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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)
InChI Key LMEKQMALGUDUQG-UHFFFAOYSA-N
Bioactivity Comments
Azathioprine is reported to inhibit peptidylarginine deiminase 4 (PADI4), albeit with very low in vitro affinity [5]. PADI enzymes catalyze the hydrolytic deimination of protein arginine to produce protein citrulline and ammonia [4] and cause chromatin decondensation. Dysregulated PADI4 activity may be involved in cancer progression as it is overexpressed in many malignant tumours, where enhanced chromatin decondensation is involved in promoting pluripotency and stem cell maintenance.
Targets where the ligand is described in the comment field
Target Comment
C5a1 receptor C5a1 receptor is currently referred to as C5aR1 in the literature. C5a1 has been an attractive target for pharmacological inhibition to treat a myriad of inflammatory and neurodegenerative diseases. Several C5a1 antagonists have been reported that have progressed to various stages of clinical development [3,6-7], although none are yet approved for use in humans. The non-peptide C5aR1 inhibitor CCX168 (Avacopan®), developed by ChemoCentryx, is currently the most clinically advanced C5aR1 inhibitor [1]. The drug has recently completed a Phase III clinical trial for ANCA-associated vasculitis under a concomitant treatment scheme with rituximab or cyclophosphamide/azathioprine (NCT02994927). Considering the potential benefits of blocking the C5a-C5aR1 axis to limit myeloid infiltration and prevent excessive lung inflammation in Coronavirus disease 2019 (COVID-19) [2], the two anti-C5a/C5aR1 blocking antibodies, avdoralimab (IPH5401) and vilobelimab (IFX-1), are currently being studied in patients with COVID-19 severe pneumonia (NCT04371367 and NCT04333420 for IPH5401 and IFX-1, respectively) [8].