Identification
- Summary
Azathioprine is an immunosuppressant used to prevent renal transplant rejection, treat rheumatoid arthritis, Crohn's disease, and ulcerative colitis.
- Brand Names
- Azasan, Imuran
- Generic Name
- Azathioprine
- DrugBank Accession Number
- DB00993
- Background
Azathioprine is a prodrug of 6-mercaptopurine, first synthesized in 1956 by Gertrude Elion, William Lange, and George Hitchings in an attempt to produce a derivative of 6-mercaptopurine with a better therapeutic index.9,10,11 Azathioprine is used to treat inflammatory conditions like rheumatoid arthritis and as an immunosuppressant in the prevention of renal transplant rejection.12
Azathiprine was granted FDA approval on 20 March 1968.12
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Azathioprine (DB00993)
- Weight
- Average: 277.263
Monoisotopic: 277.038193193 - Chemical Formula
- C9H7N7O2S
- Synonyms
- 6-((1-Methyl-4-nitro-1H-imidazol-5-yl)thio)-1H-purine
- 6-(1'-Methyl-4'-nitro-5'-imidazolyl)-mercaptopurine
- Azamun
- Azathioprine
- Azathioprinum
- Azatioprina
- External IDs
- BW 57-322
- BW-57-322
- NSC-39084
Pharmacology
- Indication
Azathioprine is indicated to treat rheumatoid arthritis and prevent renal transplant rejection.12
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Atopic dermatitis (ad) ••• ••••• Management of Crohn disease ••• ••••• Management of Immune thrombocytopenia ••• ••••• Prophylaxis of Kidney transplant rejection •••••••••••• Management of Lupus nephritis ••• ••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Azathioprine is an immunosuppressive agent which functions through modulation of rac1 to induce T cell apoptosis, as well as other unknown immunosuppressive functions.5 It has a long duration of action as it is given daily, and has a narrow therapeutic index.12 Patients should be counselled regarding the risk of malignancies of the skin and lymphomas.12
- Mechanism of action
Azathioprine's mechanism of action is not entirely understood but it may be related to inhibition of purine synthesis, along with inhibition of B and T cells.5
6-thioguanine triphosphate, a metabolite of azathioprine, modulates activation of rac1 when costimulated with CD28, inducing T cell apoptosis.5 This may be mediated through rac1's action on mitogen-activated protein kinase, NF-kappaB.5
Target Actions Organism URas-related C3 botulinum toxin substrate 1 modulatorHumans - Absorption
Oral azathioprine is well absorbed, with a Tmax of 1-2h.12 Further data regarding the absorption of azathioprine is not readily available.6,7
- Volume of distribution
Data regarding the volume of distribution of azathioprine is not readily available.6,7
- Protein binding
Azathioprine is 30%12 bound to proteins such as human serum albumin in circulation.1
- Metabolism
Azathioprine is converted to 6-mercaptopurine nonenzymatically.4 6-mercaptopurine is then metabolized to 6-methylmercaptopurine by thiopurine methyltransferase, 6-thiouric acid by xanthine oxidase, or 6-thiosine-5'-monophosphate by hypoxanthine phosphoribosyltransferase.4 6-thiosine-5'-monophosphate is metabolized to 6-methylthiosine-5'-monophosphate by thiopurine methyltransferase or 6-thioxanthylic acid by inosine monophosphate dehydrogenase.4 6-thioxanthylic acid is metabolized by guanosine monophosphate synthetase to 6-thioguanine monophosphate, the first of the 6-thioguanine nucleotides.4 6-thioguanine monophosphate is phosphorylated to produce the remaining 6-thioguanine nucleotides, 6-thioguanine diphosphate and 6-thioguanine triphosphate.4
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- Route of elimination
Azathioprine and mercaptopurine are not detectable in urine after 8 hours.12 Further data regarding the route of elimination of azathioprine are not available.8
- Half-life
The half life of azathioprine is approximately 5 hours.12
- Clearance
Data regarding the clearance of azathioprine is not readily available.6,7
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
The oral LD50 in mice is 2500mg/kg and in rats is 400mg/kg.12
Patients experiencing an overdose may present with bone marrow hypoplasia, bleeding, and infection, which may progress to death.12 Patients should be treated with supportive and symptomatic treatments. 8 hour hemodialysis may remove 45% of a dose from serum.12
- Pathways
Pathway Category Azathioprine Action Pathway Drug action Azathioprine Metabolism Pathway Drug metabolism - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Thiopurine S-methyltransferase TPMT*2 (G;G) / (C;G) G Allele ADR Directly Studied Patients with this genotype have reduced metabolism of azathioprine resulting in increased toxicity. Details Thiopurine S-methyltransferase TPMT*3A (A;A) / (A;G) A Allele ADR Directly Studied Patients with this genotype have reduced metabolism of azathioprine resulting in increased toxicity. Details Thiopurine S-methyltransferase TPMT*3C (G;G) / (A;G) G Allele ADR Directly Studied Patients with this genotype have reduced metabolism of azathioprine resulting in increased toxicity. Details Thiopurine S-methyltransferase TPMT*3B Not Available c.460G>A ADR Inferred Myelosuppression Details Thiopurine S-methyltransferase TPMT*4A Not Available G > A ADR Inferred Myelosuppression Details
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Azathioprine may decrease the excretion rate of Abacavir which could result in a higher serum level. Abametapir The serum concentration of Azathioprine can be increased when it is combined with Abametapir. Abatacept The metabolism of Azathioprine can be increased when combined with Abatacept. Abiraterone The serum concentration of Azathioprine can be increased when it is combined with Abiraterone. Aceclofenac Aceclofenac may decrease the excretion rate of Azathioprine which could result in a higher serum level. - Food Interactions
- Take with food. Food reduces irritation.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Azathioprine sodium AM94R510MS 55774-33-9 WISNYKIQFMKSDQ-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Azamun (Ascent) / Azanin (Tanabe Mitsubishi Pharma) / Imurek (Aspen) / Imurel (GlaxoSmithKline)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Azathioprine Tablet 50 mg / tab Oral Bdh Inc. 1998-10-08 2000-08-03 Canada 
Azathioprine Tablet 50 mg Oral Sanis Health Inc 2010-02-16 2017-07-31 Canada Azathioprine Sodium for Injection Powder, for solution 100 mg / vial Intravenous Novopharm Limited Not applicable Not applicable Canada Azathioprine-50 Tablet 50 mg Oral Pro Doc Limitee 2009-06-10 2023-07-10 Canada Imuran Tablet 50 mg Oral Aspen Pharmacare Canada Inc. 1966-12-31 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-azathioprine Tablet 50 mg Oral Apotex Corporation 2000-10-17 Not applicable Canada Azasan Tablet 100 mg/1 Oral Salix Pharmaceuticals 2003-04-01 Not applicable US 
Azasan Tablet 75 mg/1 Oral Salix Pharmaceuticals 2003-04-01 Not applicable US Azathioprine Tablet 50 mg/1 Oral Cardinal Health 1996-02-16 2015-11-30 US Azathioprine Tablet 100 mg/1 Oral Zydus Lifesciences Limited 2017-12-02 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image IMURAN 25 MG TABLET, 100 ADET Azathioprine (25 mg) Tablet Oral VLD DANIŞMANLIK TIBBİ ÜRÜNLER VE TANITIM HİZMETLERİ LTD. ŞTİ. 2018-05-29 Not applicable Turkey 
IMURAN 50 MG TABLET, 100 ADET Azathioprine (50 mg) Tablet Oral VLD DANIŞMANLIK TIBBİ ÜRÜNLER VE TANITIM HİZMETLERİ LTD. ŞTİ. 2018-05-29 Not applicable Turkey
Categories
- ATC Codes
- L04AX01 — Azathioprine
- Drug Categories
- Antimetabolites
- Antineoplastic and Immunomodulating Agents
- Antirheumatic Agents
- Carbohydrates
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 Substrates
- Drugs that are Mainly Renally Excreted
- Glycosides
- Heterocyclic Compounds, Fused-Ring
- Immunologic Factors
- Immunosuppressive Agents
- Immunotherapy
- Noxae
- Nucleic Acid Synthesis Inhibitors
- Nucleic Acids, Nucleotides, and Nucleosides
- Nucleosides
- P-glycoprotein substrates
- Purine Antimetabolite
- Purines
- Sulfhydryl Compounds
- Sulfur Compounds
- Thionucleosides
- Thiopurine Analogs
- Toxic Actions
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as diarylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two aryl groups.
- Kingdom
- Organic compounds
- Super Class
- Organosulfur compounds
- Class
- Thioethers
- Sub Class
- Aryl thioethers
- Direct Parent
- Diarylthioethers
- Alternative Parents
- 6-thiopurines / Nitroimidazoles / Nitroaromatic compounds / Pyrimidines and pyrimidine derivatives / Imidolactams / N-substituted imidazoles / Heteroaromatic compounds / Sulfenyl compounds / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds show 6 more
- Substituents
- 6-thiopurine / Allyl-type 1,3-dipolar organic compound / Aromatic heteropolycyclic compound / Azacycle / Azole / C-nitro compound / Diarylthioether / Heteroaromatic compound / Hydrocarbon derivative / Imidazole show 19 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- C-nitro compound, aryl sulfide, imidazoles, thiopurine (CHEBI:2948)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- MRK240IY2L
- CAS number
- 446-86-6
- InChI Key
- LMEKQMALGUDUQG-UHFFFAOYSA-N
- 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)
- IUPAC Name
- 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-7H-purine
- SMILES
- CN1C=NC(=C1SC1=NC=NC2=C1NC=N2)[N+]([O-])=O
References
- General References
- Sochacka J: Docking of thiopurine derivatives to human serum albumin and binding site analysis with Molegro Virtual Docker. Acta Pol Pharm. 2014 Mar-Apr;71(2):343-9. [Article]
- Van Os EC, Zins BJ, Sandborn WJ, Mays DC, Tremaine WJ, Mahoney DW, Zinsmeister AR, Lipsky JJ: Azathioprine pharmacokinetics after intravenous, oral, delayed release oral and rectal foam administration. Gut. 1996 Jul;39(1):63-8. doi: 10.1136/gut.39.1.63. [Article]
- Anstey A, Lear JT: Azathioprine: clinical pharmacology and current indications in autoimmune disorders. BioDrugs. 1998 Jan;9(1):33-47. [Article]
- Dubinsky MC: Azathioprine, 6-mercaptopurine in inflammatory bowel disease: pharmacology, efficacy, and safety. Clin Gastroenterol Hepatol. 2004 Sep;2(9):731-43. [Article]
- Tiede I, Fritz G, Strand S, Poppe D, Dvorsky R, Strand D, Lehr HA, Wirtz S, Becker C, Atreya R, Mudter J, Hildner K, Bartsch B, Holtmann M, Blumberg R, Walczak H, Iven H, Galle PR, Ahmadian MR, Neurath MF: CD28-dependent Rac1 activation is the molecular target of azathioprine in primary human CD4+ T lymphocytes. J Clin Invest. 2003 Apr;111(8):1133-45. [Article]
- Stocco G, Martelossi S, Arrigo S, Barabino A, Aloi M, Martinelli M, Miele E, Knafelz D, Romano C, Naviglio S, Favretto D, Cuzzoni E, Franca R, Decorti G, Ventura A: Multicentric Case-Control Study on Azathioprine Dose and Pharmacokinetics in Early-onset Pediatric Inflammatory Bowel Disease. Inflamm Bowel Dis. 2017 Apr;23(4):628-634. doi: 10.1097/MIB.0000000000001051. [Article]
- Pelin M, Genova E, Fusco L, Marisat M, Hofmann U, Favretto D, Lucafo M, Taddio A, Martelossi S, Ventura A, Stocco G, Schwab M, Decorti G: Pharmacokinetics and pharmacodynamics of thiopurines in an in vitro model of human hepatocytes: Insights from an innovative mass spectrometry assay. Chem Biol Interact. 2017 Sep 25;275:189-195. doi: 10.1016/j.cbi.2017.08.009. Epub 2017 Aug 12. [Article]
- Schusziarra V, Ziekursch V, Schlamp R, Siemensen HC: Pharmacokinetics of azathioprine under haemodialysis. Int J Clin Pharmacol Biopharm. 1976 Dec;14(4):298-302. [Article]
- Wright S, Sanders DS, Lobo AJ, Lennard L: Clinical significance of azathioprine active metabolite concentrations in inflammatory bowel disease. Gut. 2004 Aug;53(8):1123-8. doi: 10.1136/gut.2003.032896. [Article]
- Elion GB: The purine path to chemotherapy. Science. 1989 Apr 7;244(4900):41-7. doi: 10.1126/science.2649979. [Article]
- Elion G, Lange W, Hitchings G: Studies on Condensed Pyrimidine Systems. XIII. Some Amino-substituted Derivatives of Guanine and 6-Thioguanine Journal of the American Chemical Society. 1956 Jan 1;78(1):217-220. [Article]
- FDA Approved Drug Products: Imuran Azathioprine Oral Tablets [Link]
- External Links
- Human Metabolome Database
- HMDB0015128
- KEGG Drug
- D00238
- KEGG Compound
- C06837
- PubChem Compound
- 2265
- PubChem Substance
- 46508252
- ChemSpider
- 2178
- BindingDB
- 50373919
- 1256
- ChEBI
- 2948
- ChEMBL
- CHEMBL1542
- ZINC
- ZINC000004258316
- Therapeutic Targets Database
- DAP000782
- PharmGKB
- PA448515
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Azathioprine
- FDA label
- Download (212 KB)
- MSDS
- Download (75.4 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Active Not Recruiting Health Services Research Liver Transplantation 1 4 Active Not Recruiting Treatment Autoimmune Hepatitis 1 4 Active Not Recruiting Treatment Crohn's Disease (CD) 1 4 Active Not Recruiting Treatment Hepatocellular Carcinoma 1 4 Completed Prevention Acute Graft Rejection / Delayed Graft Function 1
Pharmacoeconomics
- Manufacturers
- Aaipharma llc
- Mylan pharmaceuticals inc
- Roxane laboratories inc
- Zydus pharmaceuticals usa inc
- Prometheus laboratories inc
- Bedford laboratories div ben venue laboratories inc
- Packagers
- AAIPharma Inc.
- Amerisource Health Services Corp.
- Bedford Labs
- Ben Venue Laboratories Inc.
- Cadila Healthcare Ltd.
- Cardinal Health
- Glenmark Generics Ltd.
- Heartland Repack Services LLC
- Mallinckrodt Inc.
- Medisca Inc.
- Mylan
- Nucare Pharmaceuticals Inc.
- Oso Biopharmaceuticals Manufacturing LLC
- Pharmedix
- Physicians Total Care Inc.
- Prometheus Laboratories Inc.
- Rebel Distributors Corp.
- Resolution Chemicals Ltd.
- Roxane Labs
- Salix Pharmaceuticals
- Sandoz
- UDL Laboratories
- Vangard Labs Inc.
- Xanodyne Pharmaceuticals Inc.
- Zydus Pharmaceuticals
- Dosage Forms
Form Route Strength Tablet Oral Tablet, film coated Oral 100 MG Tablet, film coated Oral 75 MG Tablet Oral 100 mg/1 Tablet Oral 75 mg/1 Tablet, film coated Oral 25 MG Powder Not applicable 1 g/1g Tablet Oral 25 mg/1 Tablet Oral 50 mg/1 Tablet Oral 50 mg / tab Tablet Oral 50 1/1 Tablet, film coated Oral 50 mg/1 Tablet Oral 50 mg Tablet Oral 50.0 mg Injection, powder, lyophilized, for solution Intravenous 100 mg/10mL Tablet Oral 50.000 mg Tablet, film coated Oral Injection, powder, lyophilized, for solution Intravenous 100 mg/1mL Powder, for solution Intravenous 50 mg / vial Tablet, film coated Oral 50 MG Tablet, coated Oral 50 mg Tablet Oral 25 mg Injection Intravenous 50 mg Powder, for solution Intravenous 100 mg / vial Suspension Oral 10 MG/ML Tablet Oral 50 mg/50mg - Prices
Unit description Cost Unit Azathioprine sod 100 mg vial 132.0USD vial Azathioprine powder 28.15USD g Azasan 100 mg tablet 5.8USD tablet Azasan 75 mg tablet 4.34USD tablet Imuran 50 mg Tablet 2.76USD tablet Azathioprine 50 mg tablet 0.94USD tablet Apo-Azathioprine 50 mg Tablet 0.57USD tablet Mylan-Azathioprine 50 mg Tablet 0.57USD tablet Novo-Azathioprine 50 mg Tablet 0.57USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 243.5 °C PhysProp water solubility Insoluble FDA label logP 0.10 HANSCH,C ET AL. (1995) pKa 7.87 (at 25 °C) MITRA,AK & NARURKAR,MM (1986) - Predicted Properties
Property Value Source Water Solubility 1.07 mg/mL ALOGPS logP 0.84 ALOGPS logP 1.17 Chemaxon logS -2.4 ALOGPS pKa (Strongest Acidic) 8.62 Chemaxon pKa (Strongest Basic) 2.16 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 115.42 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 69.94 m3·mol-1 Chemaxon Polarizability 24.37 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9607 Blood Brain Barrier + 0.9226 Caco-2 permeable + 0.5057 P-glycoprotein substrate Non-substrate 0.7766 P-glycoprotein inhibitor I Non-inhibitor 0.8049 P-glycoprotein inhibitor II Non-inhibitor 0.6683 Renal organic cation transporter Non-inhibitor 0.8493 CYP450 2C9 substrate Non-substrate 0.7861 CYP450 2D6 substrate Non-substrate 0.8273 CYP450 3A4 substrate Non-substrate 0.5944 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9733 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7 Ames test AMES toxic 0.9152 Carcinogenicity Non-carcinogens 0.9182 Biodegradation Not ready biodegradable 0.9576 Rat acute toxicity 2.7519 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7434 hERG inhibition (predictor II) Non-inhibitor 0.8449
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 166.5737147 predictedDarkChem Lite v0.1.0 [M-H]- 162.9815906 predictedDarkChem Lite v0.1.0 [M-H]- 162.1448147 predictedDarkChem Lite v0.1.0 [M-H]- 140.74017 predictedDeepCCS 1.0 (2019) [M+H]+ 167.2635147 predictedDarkChem Lite v0.1.0 [M+H]+ 165.7404921 predictedDarkChem Lite v0.1.0 [M+H]+ 163.8964147 predictedDarkChem Lite v0.1.0 [M+H]+ 143.63179 predictedDeepCCS 1.0 (2019) [M+Na]+ 166.7284147 predictedDarkChem Lite v0.1.0 [M+Na]+ 179.4226263 predictedDarkChem Lite v0.1.0 [M+Na]+ 163.1049147 predictedDarkChem Lite v0.1.0 [M+Na]+ 151.61162 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Modulator
- General Function
- Thioesterase binding
- Specific Function
- Plasma membrane-associated small GTPase which cycles between active GTP-bound and inactive GDP-bound states. In its active state, binds to a variety of effector proteins to regulate cellular respon...
- Gene Name
- RAC1
- Uniprot ID
- P63000
- Uniprot Name
- Ras-related C3 botulinum toxin substrate 1
- Molecular Weight
- 21449.895 Da
References
- Tiede I, Fritz G, Strand S, Poppe D, Dvorsky R, Strand D, Lehr HA, Wirtz S, Becker C, Atreya R, Mudter J, Hildner K, Bartsch B, Holtmann M, Blumberg R, Walczak H, Iven H, Galle PR, Ahmadian MR, Neurath MF: CD28-dependent Rac1 activation is the molecular target of azathioprine in primary human CD4+ T lymphocytes. J Clin Invest. 2003 Apr;111(8):1133-45. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Protein homodimerization activity
- Specific Function
- Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role...
- Gene Name
- HPRT1
- Uniprot ID
- P00492
- Uniprot Name
- Hypoxanthine-guanine phosphoribosyltransferase
- Molecular Weight
- 24579.155 Da
References
- Dubinsky MC: Azathioprine, 6-mercaptopurine in inflammatory bowel disease: pharmacology, efficacy, and safety. Clin Gastroenterol Hepatol. 2004 Sep;2(9):731-43. [Article]
- Reuther LO, Sonne J, Larsen NE, Larsen B, Christensen S, Rasmussen SN, Tofteng F, Haaber A, Johansen N, Kjeldsen J, Schmiegelow K: Pharmacological monitoring of azathioprine therapy. Scand J Gastroenterol. 2003 Sep;38(9):972-7. doi: 10.1080/00365520310005082. [Article]
- FDA Approved Drug Products: Imuran Azathioprine Oral Tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- May catalyze the hydrolysis of nucleoside triphosphates including dGTP, dTTP, dCTP, their oxidized forms like 8-oxo-dGTP and the prodrug thiopurine derivatives 6-thio-dGTP and 6-thio-GTP (PubMed:26238318). Could also catalyze the hydrolysis of some nucleoside diphosphate derivatives (PubMed:22556419, PubMed:26238318). Hydrolyzes oxidized nucleosides triphosphates like 8-oxo-dGTP in vitro, but the specificity and efficiency towards these substrates are low. Therefore, the potential in vivo sanitizing role of this enzyme, that would consist in removing oxidatively damaged forms of nucleosides to prevent their incorporation into DNA, is unclear (PubMed:26238318, PubMed:22556419). Through the hydrolysis of thioguanosine triphosphates may participate in the catabolism of thiopurine drugs (PubMed:26238318, PubMed:25108385). May also have a role in DNA synthesis and cell cycle progression by stabilizing PCNA (PubMed:19419956).
- Specific Function
- 8-oxo-7,8-dihydrodeoxyguanosine triphosphate pyrophosphatase activity
- Gene Name
- NUDT15
- Uniprot ID
- Q9NV35
- Uniprot Name
- Nucleotide triphosphate diphosphatase NUDT15
- Molecular Weight
- 18608.965 Da
References
- Reuther LO, Sonne J, Larsen NE, Larsen B, Christensen S, Rasmussen SN, Tofteng F, Haaber A, Johansen N, Kjeldsen J, Schmiegelow K: Pharmacological monitoring of azathioprine therapy. Scand J Gastroenterol. 2003 Sep;38(9):972-7. doi: 10.1080/00365520310005082. [Article]
- Stocco G, Pelin M, Franca R, De Iudicibus S, Cuzzoni E, Favretto D, Martelossi S, Ventura A, Decorti G: Pharmacogenetics of azathioprine in inflammatory bowel disease: a role for glutathione-S-transferase? World J Gastroenterol. 2014 Apr 7;20(13):3534-41. doi: 10.3748/wjg.v20.i13.3534. [Article]
- FDA Approved Drug Products: Imuran Azathioprine Oral Tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xanthine oxidase activity
- Specific Function
- Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Ha...
- Gene Name
- XDH
- Uniprot ID
- P47989
- Uniprot Name
- Xanthine dehydrogenase/oxidase
- Molecular Weight
- 146422.99 Da
References
- Dubinsky MC: Azathioprine, 6-mercaptopurine in inflammatory bowel disease: pharmacology, efficacy, and safety. Clin Gastroenterol Hepatol. 2004 Sep;2(9):731-43. [Article]
- Reuther LO, Sonne J, Larsen NE, Larsen B, Christensen S, Rasmussen SN, Tofteng F, Haaber A, Johansen N, Kjeldsen J, Schmiegelow K: Pharmacological monitoring of azathioprine therapy. Scand J Gastroenterol. 2003 Sep;38(9):972-7. doi: 10.1080/00365520310005082. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Thiopurine s-methyltransferase activity
- Specific Function
- Catalyzes the S-methylation of thiopurine drugs such as 6-mercaptopurine.
- Gene Name
- TPMT
- Uniprot ID
- P51580
- Uniprot Name
- Thiopurine S-methyltransferase
- Molecular Weight
- 28180.09 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Glutathione transferase activity
- Specific Function
- Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
- Gene Name
- GSTA1
- Uniprot ID
- P08263
- Uniprot Name
- Glutathione S-transferase A1
- Molecular Weight
- 25630.785 Da
References
- Stocco G, Pelin M, Franca R, De Iudicibus S, Cuzzoni E, Favretto D, Martelossi S, Ventura A, Decorti G: Pharmacogenetics of azathioprine in inflammatory bowel disease: a role for glutathione-S-transferase? World J Gastroenterol. 2014 Apr 7;20(13):3534-41. doi: 10.3748/wjg.v20.i13.3534. [Article]
- Lucafo M, Stocco G, Martelossi S, Favretto D, Franca R, Malusa N, Lora A, Bramuzzo M, Naviglio S, Cecchin E, Toffoli G, Ventura A, Decorti G: Azathioprine Biotransformation in Young Patients with Inflammatory Bowel Disease: Contribution of Glutathione-S Transferase M1 and A1 Variants. Genes (Basel). 2019 Apr 4;10(4). pii: genes10040277. doi: 10.3390/genes10040277. [Article]
- Link [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Glutathione transferase activity
- Specific Function
- Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
- Gene Name
- GSTA2
- Uniprot ID
- P09210
- Uniprot Name
- Glutathione S-transferase A2
- Molecular Weight
- 25663.675 Da
References
- Stocco G, Pelin M, Franca R, De Iudicibus S, Cuzzoni E, Favretto D, Martelossi S, Ventura A, Decorti G: Pharmacogenetics of azathioprine in inflammatory bowel disease: a role for glutathione-S-transferase? World J Gastroenterol. 2014 Apr 7;20(13):3534-41. doi: 10.3748/wjg.v20.i13.3534. [Article]
- Link [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Protein homodimerization activity
- Specific Function
- Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
- Gene Name
- GSTM1
- Uniprot ID
- P09488
- Uniprot Name
- Glutathione S-transferase Mu 1
- Molecular Weight
- 25711.555 Da
References
- Stocco G, Pelin M, Franca R, De Iudicibus S, Cuzzoni E, Favretto D, Martelossi S, Ventura A, Decorti G: Pharmacogenetics of azathioprine in inflammatory bowel disease: a role for glutathione-S-transferase? World J Gastroenterol. 2014 Apr 7;20(13):3534-41. doi: 10.3748/wjg.v20.i13.3534. [Article]
- Lucafo M, Stocco G, Martelossi S, Favretto D, Franca R, Malusa N, Lora A, Bramuzzo M, Naviglio S, Cecchin E, Toffoli G, Ventura A, Decorti G: Azathioprine Biotransformation in Young Patients with Inflammatory Bowel Disease: Contribution of Glutathione-S Transferase M1 and A1 Variants. Genes (Basel). 2019 Apr 4;10(4). pii: genes10040277. doi: 10.3390/genes10040277. [Article]
- Link [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Rna binding
- Specific Function
- Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore pl...
- Gene Name
- IMPDH1
- Uniprot ID
- P20839
- Uniprot Name
- Inosine-5'-monophosphate dehydrogenase 1
- Molecular Weight
- 55405.365 Da
References
- Stocco G, Pelin M, Franca R, De Iudicibus S, Cuzzoni E, Favretto D, Martelossi S, Ventura A, Decorti G: Pharmacogenetics of azathioprine in inflammatory bowel disease: a role for glutathione-S-transferase? World J Gastroenterol. 2014 Apr 7;20(13):3534-41. doi: 10.3748/wjg.v20.i13.3534. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Rna binding
- Specific Function
- Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore pl...
- Gene Name
- IMPDH2
- Uniprot ID
- P12268
- Uniprot Name
- Inosine-5'-monophosphate dehydrogenase 2
- Molecular Weight
- 55804.495 Da
References
- Stocco G, Pelin M, Franca R, De Iudicibus S, Cuzzoni E, Favretto D, Martelossi S, Ventura A, Decorti G: Pharmacogenetics of azathioprine in inflammatory bowel disease: a role for glutathione-S-transferase? World J Gastroenterol. 2014 Apr 7;20(13):3534-41. doi: 10.3748/wjg.v20.i13.3534. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Pyrophosphatase activity
- Specific Function
- Involved in the de novo synthesis of guanine nucleotides which are not only essential for DNA and RNA synthesis, but also provide GTP, which is involved in a number of cellular processes important ...
- Gene Name
- GMPS
- Uniprot ID
- P49915
- Uniprot Name
- GMP synthase [glutamine-hydrolyzing]
- Molecular Weight
- 76714.79 Da
References
- Stocco G, Pelin M, Franca R, De Iudicibus S, Cuzzoni E, Favretto D, Martelossi S, Ventura A, Decorti G: Pharmacogenetics of azathioprine in inflammatory bowel disease: a role for glutathione-S-transferase? World J Gastroenterol. 2014 Apr 7;20(13):3534-41. doi: 10.3748/wjg.v20.i13.3534. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xtp diphosphatase activity
- Specific Function
- Pyrophosphatase that hydrolyzes the non-canonical purine nucleotides inosine triphosphate (ITP), deoxyinosine triphosphate (dITP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) an...
- Gene Name
- ITPA
- Uniprot ID
- Q9BY32
- Uniprot Name
- Inosine triphosphate pyrophosphatase
- Molecular Weight
- 21445.495 Da
References
- Stocco G, Pelin M, Franca R, De Iudicibus S, Cuzzoni E, Favretto D, Martelossi S, Ventura A, Decorti G: Pharmacogenetics of azathioprine in inflammatory bowel disease: a role for glutathione-S-transferase? World J Gastroenterol. 2014 Apr 7;20(13):3534-41. doi: 10.3748/wjg.v20.i13.3534. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Lampe JW, King IB, Li S, Grate MT, Barale KV, Chen C, Feng Z, Potter JD: 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. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Sochacka J: Docking of thiopurine derivatives to human serum albumin and binding site analysis with Molegro Virtual Docker. Acta Pol Pharm. 2014 Mar-Apr;71(2):343-9. [Article]
- Tanaka M, Asahi Y, Masuda S, Ota T: Binding position of azathioprine with bovine serum albumin determined by measuring nuclear magnetic resonance relaxation time. Chem Pharm Bull (Tokyo). 1991 Nov;39(11):2771-4. doi: 10.1248/cpb.39.2771. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Nucleoside transmembrane transporter activity
- Specific Function
- Mediates equilibrative transport of purine, pyrimidine nucleosides and the purine base hypoxanthine. Very less sensitive than SLC29A1 to inhibition by nitrobenzylthioinosine (NBMPR), dipyridamole, ...
- Gene Name
- SLC29A2
- Uniprot ID
- Q14542
- Uniprot Name
- Equilibrative nucleoside transporter 2
- Molecular Weight
- 50112.335 Da
References
- Conklin LS, Cuffari C, Okazaki T, Miao Y, Saatian B, Chen TE, Tse M, Brant SR, Li X: 6-Mercaptopurine transport in human lymphocytes: correlation with drug-induced cytotoxicity. J Dig Dis. 2012 Feb;13(2):82-93. doi: 10.1111/j.1751-2980.2011.00556.x. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Pyrimidine- and adenine-specific:sodium symporter activity
- Specific Function
- Sodium-dependent, pyrimidine- and purine-selective. Involved in the homeostasis of endogenous nucleosides. Exhibits the transport characteristics of the nucleoside transport system cib or N3 subtyp...
- Gene Name
- SLC28A3
- Uniprot ID
- Q9HAS3
- Uniprot Name
- Solute carrier family 28 member 3
- Molecular Weight
- 76929.61 Da
References
- Conklin LS, Cuffari C, Okazaki T, Miao Y, Saatian B, Chen TE, Tse M, Brant SR, Li X: 6-Mercaptopurine transport in human lymphocytes: correlation with drug-induced cytotoxicity. J Dig Dis. 2012 Feb;13(2):82-93. doi: 10.1111/j.1751-2980.2011.00556.x. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Conklin LS, Cuffari C, Okazaki T, Miao Y, Saatian B, Chen TE, Tse M, Brant SR, Li X: 6-Mercaptopurine transport in human lymphocytes: correlation with drug-induced cytotoxicity. J Dig Dis. 2012 Feb;13(2):82-93. doi: 10.1111/j.1751-2980.2011.00556.x. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Putative transporter.
- Specific Function
- Not Available
- Gene Name
- SLC43A3
- Uniprot ID
- Q8NBI5
- Uniprot Name
- Solute carrier family 43 member 3
- Molecular Weight
- 54528.23 Da
References
- Ruel NM, Nguyen KH, Vilas G, Hammond JR: Characterization of 6-Mercaptopurine Transport by the SLC43A3-Encoded Nucleobase Transporter. Mol Pharmacol. 2019 Jun;95(6):584-596. doi: 10.1124/mol.118.114389. Epub 2019 Mar 25. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55