Drug ID:Drug10
Drug Name:Azathioprine
CID:2265
DrugBank ID:DB00993
Modality:Small Molecule
Groups:approved
US Approved:YES
Other Approved:YES
Identifier: NCT03370601, , NCT02413047, , NCT06213857, , NCT02281799, , NCT03101800, , NCT04882683, , NCT03151525, , NCT00984568, , NCT02579733, , NCT01817972
Molecular Formula:C9H7N7O2S
Molecular Weight:277.27 g/mol
Isomeric SMILES:CN1C=NC(=C1SC2=NC=NC3=C2NC=N3)[N+](=O)[O-]
Synonyms:azathioprine; 446-86-6; Azothioprine; Azathioprin; Azamun; Azanin; Azatioprin; Azasan; Ccucol; Imurek
Phase 0: 3
Phase 1: 7
Phase 2: 38
Phase 3: 59
Phase 4: 44
Description:An immunosuppressive antimetabolite pro-drug. It is an imidazolyl derivative of 6-mercaptopurine and many of its biological effects are similar to those of the parent compound. Azathioprine is converted into 6-mercaptopurine in the body where it blocks purine metabolism and DNA synthesis.

Molecular Structure

2D Molecular Structure

Knowledge Graph

dtIDCIDCompound NameGene IDGene NameSpeciesPubMed IDsAction
dt80 2265 Azathioprine 5243 ABCB1 Homo sapiens (human) 17262810 ABCB1 gene polymorphism affects the susceptibility to azathioprine
dt81 2265 Azathioprine 8647 ABCB11 Rattus norvegicus (Norway rat) 27765674 Azathioprine results in decreased expression of ABCB11 mRNA
dt82 2265 Azathioprine 5244 ABCB4 Rattus norvegicus (Norway rat) 27765674 Azathioprine results in increased expression of ABCB4 mRNA
dt83 2265 Azathioprine 1244 ABCC2 Homo sapiens (human) 22623647 Azathioprine results in increased expression of ABCC2 mRNA
dt84 2265 Azathioprine 1244 ABCC2 Rattus norvegicus (Norway rat) 27765674 Azathioprine results in increased expression of ABCC2 mRNA
dt85 2265 Azathioprine 8714 ABCC3 Rattus norvegicus (Norway rat) 27765674 Azathioprine results in increased expression of ABCC3 mRNA
dt86 2265 Azathioprine 10257 ABCC4 Rattus norvegicus (Norway rat) 27765674 Azathioprine results in increased expression of ABCC4 mRNA
dt87 2265 Azathioprine 9429 ABCG2 Rattus norvegicus (Norway rat) 27765674 Azathioprine results in decreased expression of ABCG2 mRNA
dt88 2265 Azathioprine 64240 ABCG5 Rattus norvegicus (Norway rat) 27765674 Azathioprine results in decreased expression of ABCG5 mRNA
dt89 2265 Azathioprine 63874 ABHD4 Homo sapiens (human) 22623647 Azathioprine results in increased expression of ABHD4 mRNA

  • No data available

Phase Distribution
Phase Description
  • Phase 0: Exploratory trials to assess drug behavior in humans
  • Phase 1: Safety trials to determine safe dosage range
  • Phase 2: Efficacy trials to evaluate therapeutic effects
  • Phase 3: Large-scale trials to confirm efficacy and safety
  • Phase 4: Post-marketing surveillance for long-term safety and efficacy

Trial IDTitlePhaseStatusSponsorIndicationsInterventions
NCT04882683 Clinical Study of Cord Blood Mononuclear Cells on Treatment of Hormone-resistant or Hormone-dependent Ulcerative Colitis None UNKNOWN Shandong Qilu Stem Cells Engineering Co., Ltd. Ulcerative Colitis DRUG: Prednisone|DRUG: Azathioprine|DRUG: Adalimu… Details
NCT03151525 Two Therapeutic Strategies for the Maintenance of Remission in Patients With Ulcerative Colitis PHASE4 UNKNOWN Istituto Clinico Humanitas Colitis, Ulcerative DRUG: Azathioprine|DRUG: Infliximab Details
NCT00984568 Conventional Step-Up Versus Infliximab Monotherapy in Patients With Ulcerative Colitis (P05553) PHASE3 TERMINATED Merck Sharp & Dohme LLC Colitis, Ulcerative BIOLOGICAL: Infliximab|DRUG: Prednisolone|DRUG: 5… Details
NCT00537316 Efficacy & Safety of Infliximab Monotherapy Vs Combination Therapy Vs AZA Monotherapy in Ulcerative Colitis (Part 1) Maintenance Vs Intermittent Therapy for Maintaining Remission (Part 2)(Study P04807) PHASE3 TERMINATED Merck Sharp & Dohme LLC Ulcerative Colitis BIOLOGICAL: Infliximab (IFX)|DRUG: Azathioprine (… Details
NCT02579733 Azathioprine Based on Endoscopy After Clinical Remission in Moderate to Severe Ulcerative Colitis PHASE4 TERMINATED Kyungpook National University Hospital Ulcerative Colitis DRUG: Azathioprine|DRUG: Placebo Details
NCT01817972 Cimzia Versus Cimzia Plus Azathioprine in the Treatment of Active Crohn's Disease PHASE3 UNKNOWN Gastroenterology Research of America Crohn's Disease BIOLOGICAL: Certolizumab pegol|DRUG: Azathioprine Details
CTRI/2023/10/058514 Evaluation of effectiveness and safety of oral tofacitinib in patients with Parthenium dermatitis: A prospective interventional open label study - NIL Not Available Not Recruiting AIIMS, New Delhi Health Condition 1: L237- Allergic contact dermat… Intervention1: Oral Tofacitinib: Tofacitinib is a… Details
ISRCTN95420128 Subcutaneous CT-P13 monotherapy versus combination with immunomodulation when switching from intravenous infliximab in inflammatory bowel disease A multicentre, randomised withdrawal trial PHASE4 Recruiting Kings Health Partners Crohn's disease and ulcerative colitis Digestive… The intervention is the withdrawal of immunomodul… Details
NCT05456776 Azathioprine Linked With Impaired Intestinal Epithelial Postoperative Regeneration in Crohn's Disease Not Available Not recruiting Centre of Postgraduate Medical Education None None Details
NCT04761952 N-3 Polyunsaturated Fatty Acids Prevent Postoperative Recurrence of Crohn's Disease:a Prospective Randomized Controlled Trial Not Available Not recruiting Sixth Affiliated Hospital, Sun Yat-sen University Inflammatory Bowel Diseases;Crohn Disease;Polyuns… Drug: azathioprine;Drug: infliximab;Drug: N-3 Pol… Details
EUCTR2019-002942-19-DK NORDTREAT_The Nordic IBD treatment strategy trial a randomized controlled trial of access to a protein profile_ PHASE4 Not Recruiting Region ebro l Crohn's disease and Ulcerative colitis MedDRA ve… Trade Name: Remicade Infliximab Pharmaceutical Fo… Details
DRKS00013246 6-TGN levels (azathioprine drug monitoring) and markers of mucosal healing in patients with inflammatory bowel disease Not Available Not Recruiting MHH OE6810 K50 K51;Crohn disease [regional enteritis];Ulcer… Group 1: Patients with IBD and azathioprine monot… Details
EUCTR2016-004112-35-SE Low-dose azathioprine and allopurinol- versus azathioprine monotherapy in patients with Inflammatory Bowel Disease: An investigator-initiated, open, multicentre, parallel-arm, randomized controlled trial __A SOIBD (The Swedish Organisation for the study of Inflammatory Bowel Diseases) study __ PHASE4 Authorised SOIBD (The Swedish Organisation for the study of Inflammatory Bowel Diseases) Patients with inflammatory bowel diseae (Ulcerati… Trade Name: Imurel Product Name: Azathioprine Pro… Details
ChiCTR-OOC-17010617 Study on the relationship between TPMT and NUDT15 gene polymorphism and azathioprine-induced adverse reactions in patients with inflammatory bowel disease Not Available Recruiting Xiangya Hospital, Central South University Inflammatory Bowel Disease Two cohorts:azathioprine treatment; Details
NCT02929706 Effectiveness of Thiopurine Dose Optimization by NUDT 15 R139C on Reducing Thiopurine-induced Leucopenia in Inflammatory Bowel Disease Not Available Not recruiting Sixth Affiliated Hospital, Sun Yat-sen University Thiopurine-induced Leukopenia Genetic: Pre-genotype NUDT15 and optimize azathio… Details
EUCTR2016-000522-18-FR Risk stratified randomized controlled trial in paediatric Crohn Disease: Methotrexate versus azathioprine or adalimumab for maintaining remission in patients at low or at high risk for aggressive disease course, respectively a treatment strategy - REDUCE-RISKincd-PIBD-TRIAL PHASE4 Not Available PIBDNet Crohn disease;Therapeutic area: Diseases [C] - Di… Product Name: humira Pharmaceutical Form: Solutio… Details
ACTRN12613001347752 A randomized controlled trial of patients with IBD attending specialist clinics comparing de novo combination allopurinol and thiopurine versus thiopurine and placebo (ie standard practice) in terms of objective and clinical outcomes at six months PHASE3|PHASE4 Recruiting Eastern Health Inflammatory Bowel Disease; Inflammatory Bowel D… De novo combination therapy with allopurinol 100m… Details
EUCTR2013-001503-37-DK Effect of low-dose Azathioprine and Allopurinol compared to Azathioprine on clinical outcomes in Inflammatory Bowel Disease PHASE3 Not Recruiting Marianne Kiszka-Kanowitz Inflammatory Bowel Disease, (Ulcerativ colitis, C… Trade Name: Imurel Pharmaceutical Form: Tablet IN… Details
ACTRN12611000363987 The Triple A (Adjunctive Allopurinol and Azathioprine) Study: Use of Ajunctive Allopurinol in Azathioprine/6-Mercaptopurine Non-responders to Optimize 6-Thioguanine Nucleotide Production and Improve Clinical Outcomes in Patients with Inflammatory Bowel Disease (IBD). PHASE3|PHASE4 Not Recruiting The Alfred Hospital Inflammatory Bowel Disease (IBD); Inflammatory B… Eligible IBD patients will be randomly allocated … Details
NL-OMON22783 Long term hepatotoxicity of azathioprine, 6-mercaptopurine and 6-thioguanine in inflammatory bowel disease. Not Available Not Recruiting Department of Gastroenterology and Hepatology, VU University Medical Center, Amsterdam, The Netherlands Inflammatory bowel disease, azathioprine, 6-merca… 1. Liver biopsy; 2. Venapuncture; 3. Abdominal … Details

Disease IDDisease NameDefinitionCategoryRelated DrugsMechanism
No data available

Strategy IDTherapeutic StrategySynonymsRelated DrugsMechanism
S02 Immunosuppression Classic immunosuppressive drugs azathioprine; 6-mercaptopurine; methotrexate; ciclosporin-A; tacrolimus Ciclosporin-A and tacrolimus bind to specific intracellular… Details

Treatment with infliximab or azathioprine negatively impact the efficacy of hep…

PMID: 25967740
Year: 2015
Relationship Type: Treatment Score: 6.3

OBJECTIVE: To assess the effectiveness of solution-focused therapy (SFT) on fatigue and quality of life (QoL) in patients with fatigued inflammatory…

Relationship between azathioprine dosage, 6-thioguanine nucleotide levels, and …

PMID: 25851563
Year: 2015
Relationship Type: Treatment Score: 6.3

Comment in Gastrointest Endosc. 2014 Nov;80(5):849-51. BACKGROUND: Colonoscopic surveillance for neoplasia is recommended for patients with inf…

Concomitant use of azathioprine/6-mercaptopurine decreases the risk of anti-TNF…

PMID: 25789922
Year: 2015
Relationship Type: Treatment Score: 6.3

BACKGROUND: Chronic periodontitis (CP) is an inflammatory condition affecting tooth-supporting tissues and alveolar bone that surround the tooth, le…

Dexamethasone and azathioprine promote cytoskeletal changes and affect mesenchy…

PMID: 25756665
Year: 2015
Relationship Type: Association Score: 6.3

Infectious bursal disease (IBD) is an acute, infectious, immunosuppressive disease affecting young chicken worldwide. The etiological agent IBD viru…

Differences in the adverse effects of azathioprine between inflammatory bowel d…

PMID: 25530586
Year: 2014
Relationship Type: Adverse Effect Score: 6.3

OBJECTIVES: Questionnaires exist to assess inflammatory bowel disease (IBD)-related knowledge of adults. Owing to wording and content concerns, thes…

Update 2014: advances to optimize 6-mercaptopurine and azathioprine to reduce t…

PMID: 25248004
Year: 2015
Relationship Type: Adverse Effect Score: 6.3

Not found

Azathioprine induced Epstein Barr virus-positive mucocutaneous ulcer arising in…

PMID: 25213810
Year: 2014
Relationship Type: Association Score: 6.3

Long-term prevention of postoperative Crohn's disease recurrence with azathiopr…

PMID: 25139367
Year: 2015
Relationship Type: Treatment Score: 6.3

INTRODUCTION: Due to their immunomodulatory properties, mesenchymal stromal cells (MSCs) have been used for auto-immune disease treatment. Crohn dis…

Long-term combination therapy with infliximab plus azathioprine predicts sustai…

PMID: 24983979
Year: 2014
Relationship Type: Treatment Score: 6.3

BACKGROUND: The results of previous studies on the effectiveness of antibiotics in ulcerative colitis (UC) seem more effective when used orally. In …

Use of azathioprine in IBD: modern aspects of an old drug

PMID: 24943205
Year: 2014
Relationship Type: Association Score: 6.3

BACKGROUND AND AIMS: The etiopathogenesis of inflammatory bowel diseases (IBD) remains largely unexplained. Flotillins (flotillin-1 and flotillin-2)…

Risk of lymphoma in patients with inflammatory bowel disease treated with azath…

PMID: 24879926
Year: 2015
Relationship Type: Association Score: 6.3

OBJECTIVES: Antibodies to infliximab (ATIs) have been associated with loss of clinical response and lower serum infliximab (IFX) levels in some stud…

New genetic biomarkers predicting azathioprine blood concentrations in combinat…

PMID: 24762746
Year: 2014
Relationship Type: Treatment Score: 6.3

BACKGROUND: Obesity has been associated with a more severe disease course in inflammatory bowel disease (IBD) and epidemiological data identified di…

Awareness of adverse effects of azathioprine in patients with inflammatory bowe…

PMID: 24757277
Year: 2014
Relationship Type: Adverse Effect Score: 6.3

Pharmacogenetics of azathioprine in inflammatory bowel disease: a role for glut…

PMID: 24707136
Year: 2014
Relationship Type: Association Score: 6.3

Not found

Early use of azathioprine in Crohn's disease

PMID: 24468182
Year: 2014
Relationship Type: Association Score: 6.3

Shrinking indications for azathioprine in Crohn's disease: a conclusion too pre…

PMID: 24468178
Year: 2014
Relationship Type: Association Score: 6.3

Azathioprine in early Crohn's disease: time to revisit patient selection and en…

PMID: 24468167
Year: 2014
Relationship Type: Clinical Trial Score: 6.3

Comment on Aliment Pharmacol Ther. 2013 Jan;37(2):225-33.

6-Mercaptopurine/Azathioprine remains an important contributor in managing Croh…

PMID: 24462321
Year: 2014
Relationship Type: Treatment Score: 6.3

Two large studies concluded that AZA started early after diagnosis of Crohn's disease have no late maintenance value. This is contrary to previous st…

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