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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1542
CHEMBL1542
Compound Name AZATHIOPRINE
ChEMBL Synonyms OPRISINE 50 | IMURAN | AZASAN | BW-57-322 | IMMUNOPRIN 50 | AZATHIOPRINE SODIUM | AZAPRESS | KENTAPRINE | AZAMUNE | AZATHIOPRINE | BERKAPRINE
Max Phase 4 (Approved)
Trade Names AZAMUNE | KENTAPRINE | OPRISINE 50 | AZAPRESS | AZASAN | IMURAN | IMMUNOPRIN 50 | AZATHIOPRINE | BERKAPRINE | AZATHIOPRINE SODIUM
Molecular Formula C9H7N7O2S

Additional synonyms for CHEMBL1542 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Cn1cnc(c1Sc2ncnc3nc[nH]c23)[N+](=O)[O-]
Standard InChI InChI=1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2- ...
Download InChI
Standard InChI Key LMEKQMALGUDUQG-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Curated Drug Metabolism Pathways
  • Curated Drug Pharmacokinetic Data
  • DrugMatrix
  • HeCaToS Compounds
  • Open TG-GATEs
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL1542

Molecule Features

CHEMBL1542 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:Y Oral:Y Parenteral:Y Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Amidophosphoribosyltransferase inhibitor Amidophosphoribosyltransferase PubMed
DNA inhibitor DNA PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Colitis, UlcerativeD003093EFO:0000729ulcerative colitis3ClinicalTrials
LeukemiaD007938EFO:0000565leukemia1ClinicalTrials
Lung DiseasesD008171EFO:0003818lung disease2ClinicalTrials
Myasthenia GravisD009157EFO:0004991Myasthenia gravis3ClinicalTrials
Pemphigoid, BullousD010391EFO:0007187bullous pemphigoid2ClinicalTrials
Anti-Neutrophil Cytoplasmic Antibody-Associated VasculitisD056648EFO:0004826anti-neutrophil antibody associated vasculitis3ClinicalTrials
Hepatitis, AutoimmuneD019693EFO:0005676Autoimmune Hepatitis2ClinicalTrials
Immune System DiseasesD007154EFO:0000540immune system disease4ATC
Lupus Erythematosus, SystemicD008180EFO:0002690systemic lupus erythematosus3ClinicalTrials
PemphigusD010392EFO:0004719pemphigus vulgaris2ClinicalTrials
Takayasu ArteritisD013625EFO:1001857Takayasu arteritis3ClinicalTrials
Arthritis, RheumatoidD001172EFO:0000685rheumatoid arthritis4ClinicalTrials
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Lung Diseases, InterstitialD017563EFO:0004244interstitial lung disease2ClinicalTrials
Lupus NephritisD008181EFO:0005761lupus nephritis3ClinicalTrials
Churg-Strauss SyndromeD015267EFO:0007208Churg-Strauss syndrome3ClinicalTrials
EczemaD004485HP:0000964Eczema3ClinicalTrials
Granulomatosis with PolyangiitisD014890EFO:0005297Wegener's granulomatosis3ClinicalTrials
Idiopathic Pulmonary FibrosisD054990EFO:0000768idiopathic pulmonary fibrosis3ClinicalTrials
Glomerulonephritis, IGAD005922EFO:0004194IGA glomerulonephritis3ClinicalTrials
GoutD006073EFO:0004274gout2ClinicalTrials
MucopolysaccharidosesD009083Orphanet:79213Mucopolysaccharidosis1ClinicalTrials
ThrombocytopeniaD013921HP:0001873thrombocytopenia3ClinicalTrials
UrticariaD014581EFO:0005531urticaria1ClinicalTrials
CardiomyopathiesD009202EFO:0000318cardiomyopathy3ClinicalTrials
Microscopic PolyangiitisD055953EFO:1000784microscopic polyangiitis3ClinicalTrials
Neuromyelitis OpticaD009471EFO:0004256neuromyelitis optica2ClinicalTrials
Renal Insufficiency, ChronicD051436EFO:0003884chronic kidney disease3ClinicalTrials
Inflammatory Bowel DiseasesD015212EFO:0003767inflammatory bowel disease1ClinicalTrials
Carcinoma, HepatocellularD006528EFO:0000182hepatocellular carcinoma3ClinicalTrials
Crohn DiseaseD003424EFO:0000384Crohn's disease3ClinicalTrials
VasculitisD014657EFO:0006803vasculitis3ClinicalTrials

Clinical Data

ClinicalTrials.gov AZATHIOPRINE
The Cochrane Collaboration AZATHIOPRINE

Metabolites for CHEMBL1542

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Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL1542. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL1293237 Bloom syndrome protein Homo sapiens 1.000
CHEMBL1997 Equilibrative nucleoside transporter 1 Homo sapiens 0.998
CHEMBL1929 Xanthine dehydrogenase Homo sapiens 0.998
CHEMBL2864 6-O-methylguanine-DNA methyltransferase Homo sapiens 0.997
CHEMBL3638349 Glutaminyl-peptide cyclotransferase-like protein Homo sapiens 0.993
CHEMBL2372 Catechol O-methyltransferase Rattus norvegicus 0.971
CHEMBL2023 Catechol O-methyltransferase Homo sapiens 0.935
CHEMBL4508 Glutaminyl-peptide cyclotransferase Homo sapiens 0.389
CHEMBL3004 Multidrug resistance-associated protein 1 Homo sapiens 0.294



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2605 Adenosine A2a receptor Cavia porcellus 1.000
CHEMBL2864 6-O-methylguanine-DNA methyltransferase Homo sapiens 1.000
CHEMBL3638349 Glutaminyl-peptide cyclotransferase-like protein Homo sapiens 0.998
CHEMBL1770034 Phosphatidylinositol-5-phosphate 4-kinase type-2 gamma Homo sapiens 0.998
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.997
CHEMBL1929 Xanthine dehydrogenase Homo sapiens 0.994
CHEMBL1997 Equilibrative nucleoside transporter 1 Homo sapiens 0.990
CHEMBL2284 Glyceraldehyde-3-phosphate dehydrogenase liver Homo sapiens 0.984
CHEMBL2372 Catechol O-methyltransferase Rattus norvegicus 0.766
CHEMBL4218 Alpha trans-inducing protein (VP16) Herpes simplex virus (type 1 / strain 17) 0.738
CHEMBL6144 G protein-coupled receptor kinase 6 Homo sapiens 0.738
CHEMBL2023 Catechol O-methyltransferase Homo sapiens 0.641
CHEMBL1828 DNA polymerase alpha subunit Homo sapiens 0.493
CHEMBL5648 Purine nucleoside phosphorylase Plasmodium falciparum 0.394
CHEMBL3784 Histone acetyltransferase p300 Homo sapiens 0.372
CHEMBL2573 P-glycoprotein 3 Mus musculus 0.267
CHEMBL2982 Adenosine kinase Toxoplasma gondii 0.263

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
277.3 277.0382 1.15 3 115.42 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
8 1 0 9 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
8.29 1.39 .02 -.03 3 19 0.43

Structural Alerts

There are 4 structural alerts for CHEMBL1542. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L04 - IMMUNOSUPPRESSANTS
L04A - IMMUNOSUPPRESSANTS
L04AX - Other immunosuppressants
L04AX01 - azathioprine

ChemSpider ChemSpider:LMEKQMALGUDUQG-UHFFFAOYSA-N
DailyMed azathioprine azathioprine sodium
PubChem SID: 104171105 SID: 11110740 SID: 11110741 SID: 124879189 SID: 144203625 SID: 144213985 SID: 170464989 SID: 17390031 SID: 174006316 SID: 26670994 SID: 26747870 SID: 26747871 SID: 26747872 SID: 26752814 SID: 50105466 SID: 50105467 SID: 50105468 SID: 85230906 SID: 90340846
Wikipedia Azathioprine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1542



ACToR 446-86-6
Atlas azathioprine
BindingDB 50373919
Brenda 4790
ChEBI 2948
ChemicalBook CB2170327
DrugBank DB00993
DrugCentral 269
eMolecules 731311 533997
EPA CompTox Dashboard DTXSID4020119
FDA SRS MRK240IY2L
Guide to Pharmacology 7120
Human Metabolome Database HMDB0015128
IBM Patent System CFDA7DE4A1948C330E183F55B6EC8243 A71C67CFF3DD414823C5B5C7BADEED29 E73CBB17C9EB2DC54DEAF9976382BAE9
KEGG Ligand C06837
LINCS LSM-42936
Mcule MCULE-8637589610
MolPort MolPort-000-764-262 MolPort-000-745-914
NIH Clinical Collection SAM002589938
PharmGKB PA448515
PubChem 2265
PubChem: Thomson Pharma 14824335 14775167 15222101
Selleck Azathioprine(Azasan)
SureChEMBL SCHEMBL4278
ZINC ZINC000004258316

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/LMEKQMALGUDUQG-UHFFFAOYSA-N spacer
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