AZATHIOPRINE

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC L04AX01
UNII MRK240IY2L
EPA CompTox DTXSID4020119

Structure

InChI Key LMEKQMALGUDUQG-UHFFFAOYSA-N
Smiles Cn1cnc([N+](=O)[O-])c1Sc1ncnc2[nH]cnc12
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C9H7N7O2S
Molecular Weight 277.27
AlogP 1.15
Hydrogen Bond Acceptor 8.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 3.0
Polar Surface Area 115.42
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 19.0

Metabolites Network

visNetwork

Bioactivity

Mechanism of Action Action Reference
Amidophosphoribosyltransferase inhibitor INHIBITOR PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 107
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 4
Assay Description Organism Bioactivity Reference
Percent inhibition against incorporation of [3H]-thymidine in Human mixed lymphocyte reaction at a concentration of 25 uM Homo sapiens 79.0 %
Immunosuppressant activity in mouse T cells assessed as inhibition of concanavalin A-induced cell proliferation Mus musculus 2.7 ug.mL-1
Immunosuppressant activity in mouse B cells assessed as inhibition of LPS-induced cell proliferation Mus musculus 2.7 ug.mL-1
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 4.2 %
Immunosuppressive activity in rat T cell assessed as inhibition of mitogenesis Rattus norvegicus 2.0 ug.mL-1
Immunosuppressive activity in baboon T cell assessed as inhibition of mitogenesis Papio hamadryas 0.4 ug.mL-1
Immunosuppressive activity in human T cell assessed as inhibition of mitogenesis Homo sapiens 9.0 ug.mL-1
Immunosuppressive activity in human B cell assessed as inhibition of mitogenesis Homo sapiens 1.0 ug.mL-1
Immunosuppressive activity in human lymphocytes by mixed lymphocyte reaction assay Homo sapiens 3.0 ug.mL-1
Immunosuppressive activity in baboon lymphocytes by mixed lymphocyte reaction assay Papio hamadryas 2.9 ug.mL-1
Immunosuppressive activity in human lymphocytes assessed as inhibition of protein synthesis Homo sapiens 85.0 ug.mL-1
Immunosuppressive activity in BALB/c mouse splenic T lymphocytes assessed as inhibition of Con A-induced cell proliferation after 72 hrs by MTT assay Mus musculus 2.7 ug.mL-1
Immunosuppressive activity in BALB/c mouse splenic B lymphocytes assessed as inhibition of LPS-induced cell proliferation after 72 hrs by MTT assay Mus musculus 2.7 ug.mL-1
Inhibition of T cell mitogen-induced blastogenesis in human PBMC after 4 days Homo sapiens 230.4 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 128.35 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 107.26 %
PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 207.39 nM
PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 363.53 nM
PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 623.22 nM
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 18.19 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 3.51 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 13.95 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 22.34 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 25.3 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 4.62 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -6.38 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 53.96 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -7.293 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.19 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.19 %

Cross References

Resources Reference
ChEBI 2948
ChEMBL CHEMBL1542
DrugBank DB00993
DrugCentral 269
FDA SRS MRK240IY2L
Human Metabolome Database HMDB0015128
Guide to Pharmacology 7120
KEGG C06837
PharmGKB PA448515
PubChem 2265
SureChEMBL SCHEMBL4278
ZINC ZINC000004258316
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