azathioprine   Click here for help

GtoPdb Ligand ID: 7120

Synonyms: Azasan® | BW-57-322 | Imuran®
Approved drug Immunopharmacology Ligand
azathioprine is an approved drug (FDA (1968))
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).
Click here for help

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.

✖

View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: azathioprine

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
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
Click here for help

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.

✖
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
References
1. Bekker P, Dairaghi D, Seitz L, Leleti M, Wang Y, Ertl L, Baumgart T, Shugarts S, Lohr L, Dang T et al.. (2016)
Characterization of Pharmacologic and Pharmacokinetic Properties of CCX168, a Potent and Selective Orally Administered Complement 5a Receptor Inhibitor, Based on Preclinical Evaluation and Randomized Phase 1 Clinical Study.
PLoS ONE, 11 (10): e0164646. [PMID:27768695]
2. Carvelli J, Demaria O, Vély F, Batista L, Chouaki Benmansour N, Fares J, Carpentier S, Thibult ML, Morel A, Remark R et al.. (2020)
Association of COVID-19 inflammation with activation of the C5a-C5aR1 axis.
Nature, 588 (7836): 146-150. [PMID:32726800]
3. Hawksworth OA, Li XX, Coulthard LG, Wolvetang EJ, Woodruff TM. (2017)
New concepts on the therapeutic control of complement anaphylatoxin receptors.
Mol Immunol, 89: 36-43. [PMID:28576324]
4. Jones JE, Causey CP, Knuckley B, Slack-Noyes JL, Thompson PR. (2009)
Protein arginine deiminase 4 (PAD4): Current understanding and future therapeutic potential.
Curr Opin Drug Discov Devel, 12 (5): 616-27. [PMID:19736621]
5. Knuckley B, Luo Y, Thompson PR. (2008)
Profiling Protein Arginine Deiminase 4 (PAD4): a novel screen to identify PAD4 inhibitors.
Bioorg Med Chem, 16 (2): 739-45. [PMID:17964793]
6. Li XX, Lee JD, Massey NL, Guan C, Robertson AAB, Clark RJ, Woodruff TM. (2020)
Pharmacological characterisation of small molecule C5aR1 inhibitors in human cells reveals biased activities for signalling and function.
Biochem Pharmacol, 180: 114156. [PMID:32682759]
7. Monk PN, Scola AM, Madala P, Fairlie DP. (2007)
Function, structure and therapeutic potential of complement C5a receptors.
Br J Pharmacol, 152 (4): 429-48. [PMID:17603557]
8. Vlaar APJ, de Bruin S, Busch M, Timmermans SAMEG, van Zeggeren IE, Koning R, Ter Horst L, Bulle EB, van Baarle FEHP, van de Poll MCG et al.. (2020)
Anti-C5a antibody IFX-1 (vilobelimab) treatment versus best supportive care for patients with severe COVID-19 (PANAMO): an exploratory, open-label, phase 2 randomised controlled trial.
Lancet Rheumatol, 2 (12): e764-e773. DOI: 10.1016/S2665-9913(20)30341-6 [PMID:33015643]