Details of the Drug
General Information of Drug (ID: DMMZSXQ)
| Drug Name |
Azathioprine
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| Synonyms |
Azamun; Azanin; Azasan; Azathioprin; Azathioprinum; Azathiopurine; Azatioprin; Azatioprina; Azothioprine; Ccucol; Cytostatics; Immuran; Imuran; Imurek; Imurel; Methylnitroimidazolylmercaptopurine; Muran; Azamun [Czech]; Azathioprine sodium; Azatiopr in; A 4638; BW 57322; Azamun (TN); Azasan (TN); Azathioprinum [INN-Latin]; Azatioprina [INN-Spanish]; BW 57-322; Imuran (TN); Imurel (TN); [Methyl(nitroimidazolyl)mercaptopurine]; AI-981/34845012; BW-57-322; Azathioprine (JP15/USP/INN); Azathioprine [USAN:INN:BAN:JAN]; B. W. 57-322; Thiopurine 6-(1-methyl-4-nitroimidazol-5-yl); Azasan, Imuran, Azamun, BW-57-322, NSC-39084, Azathioprine; 6-((1-Methyl-4-nitro-1H-imidazol-5-yl)thio)-1H-purine; 6-((1-Methyl-4-nitroimidazol-5-yl)thio)purine; 6-(1'-Methyl-4'-nitro-5'-imidazolyl)-mercaptopurine; 6-(1'-Methyl-4'-nitro-5'-imidazolyl)mercaptopurine; 6-(1-Methyl-4-nitroimidazol-5-yl)thiopurine; 6-(1-Methyl-4-nitroimidazol-5-ylthio)purin; 6-(1-Methyl-4-nitroimidazol-5-ylthio)purin [Czech]; 6-(1-Methyl-p-nitro-5-imidazolyl)-thiopurine; 6-(1-Methyl-p-nitro-5-imidazolyl)thiopurine; 6-(3-Methyl-5-nitro-3H-imidazol-4-ylsulfanyl)-7H-purine; 6-(3-methyl-5-nitroimidazol-4-yl)sulfanyl-7H-purine; 6-(Methyl-p-nitro-5-imidazolyl)-thiopurine; 6-(Methyl-p-nitro-5-imidazolyl)thiopurine; 6-({4-nitro-1-methyl-1H-imidazol-5-yl}sulfanyl)-7H-purine; 6-1'-Methyl,4'-nitro,5'-imidazolyl mercaptopurine; 6-[(1-Methyl-4-nitroimidazol-5-yl)-thio] purine; 6-[(1-Methyl-4-nitroimidazol-5-yl)thio]purine; 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-7H-purine; 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)thio]-1H-Purine; 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)thio]-7H-purine; 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)thio]-9H-purine
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| Indication |
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| Therapeutic Class |
Immunosuppressive Agents
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| Affected Organisms |
Humans and other mammals
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| ATC Code | |||||||||||||||||||||||
| Drug Type |
Small molecular drug
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| Structure |
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| 3D MOL | 2D MOL | ||||||||||||||||||||||
| #Ro5 Violations (Lipinski): 0 | Molecular Weight (mw) | 277.27 | |||||||||||||||||||||
| Logarithm of the Partition Coefficient (xlogp) | 0.1 | ||||||||||||||||||||||
| Rotatable Bond Count (rotbonds) | 2 | ||||||||||||||||||||||
| Hydrogen Bond Donor Count (hbonddonor) | 1 | ||||||||||||||||||||||
| Hydrogen Bond Acceptor Count (hbondacc) | 7 | ||||||||||||||||||||||
| ADMET Property |
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| Adverse Drug Reaction (ADR) |
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| Chemical Identifiers |
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| Drug-Molecule Activity Atlas (DMA)NEW | Click to Jump to the Detailed DMA Information of This Drug | ||||||||||||||||||||||
| Drug Pharmacogenomic Perturbation (DPP)NEW | Click to Jump to the Detailed DPP Information of This Drug | ||||||||||||||||||||||
| Drug ADMET Endpoint Profile (DAE)NEW | Click to Jump to the Detailed DAE Information of This Drug | ||||||||||||||||||||||
| Combinatorial Drugs (CBD) | Click to Jump to the Detailed CBD Information of This Drug | ||||||||||||||||||||||
| Repurposed Drugs (RPD) | Click to Jump to the Detailed RPD Information of This Drug | ||||||||||||||||||||||
Molecular Interaction Atlas of This Drug
![]() Drug Therapeutic Target (DTT) |
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| Molecular Interaction Atlas (MIA) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Drug-Drug Interaction (DDI) Information of This Drug
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Coadministration of a Drug Treating the Same Disease as Azathioprine
Coadministration of a Drug Treating the Disease Different from Azathioprine (Comorbidity)
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug
References
| 1 | Azathioprine FDA Label | ||||
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| 2 | URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7120). | ||||
| 3 | FDA Approved Drug Products: Imuran Azathioprine Oral Tablets | ||||
| 4 | BDDCS applied to over 900 drugs | ||||
| 5 | Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches | ||||
| 6 | Prasanta Raghab Mohapatra, Deepak Aggarwal: Carbocisteine for acute exacerbations of COPD . 2008 Nov 8;372(9650):1630-1631. | ||||
| 7 | Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose | ||||
| 8 | ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899. | ||||
| 9 | IMPDH activity in thiopurine-treated patients with inflammatory bowel disease - relation to TPMT activity and metabolite concentrations. Br J Clin Pharmacol. 2008 Jan;65(1):69-77. | ||||
| 10 | Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22. | ||||
| 11 | Brassica vegetables increase and apiaceous vegetables decrease cytochrome P450 1A2 activity in humans: changes in caffeine metabolite ratios in response to controlled vegetable diets. Carcinogenesis. 2000 Jun;21(6):1157-62. | ||||
| 12 | PharmGKB: A worldwide resource for pharmacogenomic information. Wiley Interdiscip Rev Syst Biol Med. 2018 Jul;10(4):e1417. (ID: PA2040) | ||||
| 13 | Nodular regenerative liver hyperplasia as a complication of azathioprine-containing immunosuppressive treatment for Crohn's disease. Immunopharmacol Immunotoxicol. 2011 Jun;33(2):398-402. | ||||
| 14 | A transcriptomics-based in vitro assay for predicting chemical genotoxicity in vivo. Carcinogenesis. 2012 Jul;33(7):1421-9. | ||||
| 15 | Antirheumatic drug response signatures in human chondrocytes: potential molecular targets to stimulate cartilage regeneration. Arthritis Res Ther. 2009;11(1):R15. | ||||
| 16 | Cerner Multum, Inc. "Australian Product Information.". | ||||
| 17 | Cerner Multum, Inc. "UK Summary of Product Characteristics.". | ||||
| 18 | Havrda DE, Rathbun S, Scheid D "A case report of warfarin resistance due to azathioprine and review of the literature." Pharmacotherpy 21 (2001): 355-7. [PMID: 11253860] | ||||
| 19 | Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ. | ||||
| 20 | Product Information. Arava (leflunomide). Hoechst Marion-Roussel Inc, Kansas City, MO. | ||||
| 21 | Product Information. Uloric (febuxostat). Takeda Pharmaceuticals America, Lincolnshire, IL. | ||||
| 22 | Lewis LD, Benin A, Szumlanski CL, et al. "Olsalazine and 6-mercaptopurine-related bone marrow suppression: a possible drug-drug interaction." Clin Pharmacol Ther 62 (1997): 464-75. [PMID: 9357398] | ||||
| 23 | Product Information. Prolia (denosumab). Amgen USA, Thousand Oaks, CA. | ||||
| 24 | Petit E, Langouet S, Akhdar H, Nicolas-Nicolaz C, Guillouzo A, Morel F. Differential toxic effects of azathioprine, 6-mercaptopurine and 6-thioguanine on human hepatocytes. Toxicol In Vitro. 2008;22(3):632-642. [PMID: 18222062] | ||||
| 25 | Product Information. Gilenya (fingolimod). Novartis Pharmaceuticals, East Hanover, NJ. | ||||
| 26 | Product Information. Arcalyst (rilonacept). Regeneron Pharmaceuticals Inc, Tarrytown, NY. | ||||
| 27 | Product Information. Cimzia (certolizumab). UCB Pharma Inc, Smyrna, GA. | ||||
| 28 | CDC. Centers for Disease Control and Prevention/ "Recommendations of the advisory committtee on immunization practices (ACIP): use of vaccines and immune globulins in persons with altered immunocompetence." MMWR Morb Mortal Wkly Rep 42(RR-04) (1993): 1-18. [PMID: 20300058] | ||||





