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
NCT05584228 Medical Treatment Versus Surgery in Stricturing Small Bowel Crohn's Disease NA NOT_YET_RECRUITING Nantes University Hospital Crohn Disease DRUG: Azathioprine + infliximab|PROCEDURE: Intest… Details
NCT05456776 Azathioprine Linked With Impaired Intestinal Epithelial Postoperative Regeneration in Crohn's Disease NULL COMPLETED Centre of Postgraduate Medical Education Inflammatory Bowel Diseases None Details
NCT05321485 The Effect of MedicijnWijs on Adherence to Azathioprine Therapy in Adolescents With IBD NA UNKNOWN Maxima Medical Center Inflammatory Bowel Diseases|Crohn Disease|Ulcerat… OTHER: MedicijnWijs Details
NCT07138898 Immunosuppressant Management in Rheumatology Patients Undergoing Elective Total Shoulder Arthroplasty PHASE2 NOT_YET_RECRUITING NYU Langone Health Rheumatic Disease DRUG: Methotrexate|DRUG: Sulfasalazine|DRUG: Hydr… Details
NCT05040464 Comparison of Azathioprine to Methotrexate in Combination Therapy With Adalimumab in Crohn's Disease: an Open-label Randomized Controlled Trial PHASE3 RECRUITING Centre Hospitalier Universitaire, Amiens Crohn Disease|Azathioprine|Methotrexate DRUG: AZA capsules|DRUG: MTX|BIOLOGICAL: blood sa… Details
NCT04882683 Clinical Study of Cord Blood Mononuclear Cells on Treatment of Hormone-resistant or Hormone-dependent Ulcerative Colitis NA UNKNOWN Shandong Qilu Stem Cells Engineering Co., Ltd. Ulcerative Colitis DRUG: Prednisone|DRUG: Azathioprine|DRUG: Adalimu… Details
NCT04761952 N-3 Polyunsaturated Fatty Acids Prevent Postoperative Recurrence of Crohn's Disease NA UNKNOWN Sixth Affiliated Hospital, Sun Yat-sen University Inflammatory Bowel Diseases|Crohn Disease|Polyuns… DRUG: azathioprine|DRUG: infliximab|DRUG: N-3 Pol… Details
NCT04160325 Effect of the Exclusive Enteral Nutrition Combined With Azathioprine for Remission of Crohn's Diseases After Surgery NA UNKNOWN Zhu Weiming Crohn Disease DIETARY_SUPPLEMENT: postoperative 3-month exclusi… Details
NCT03681652 Post-Operative Crohn's Disease Outcome in Children NULL RECRUITING Schneider Children's Medical Center, Israel Crohn Disease DRUG: Azathioprine|DRUG: Anti-TNF Drug Details
NCT03580876 Addition of Azathioprine in IBD Patients With Immunogenic Failure PHASE4 UNKNOWN Védrines, Philippe, M.D. Clinical Failure After Switch DRUG: addition of azathioprine|DRUG: Switch to a … Details
NCT03393247 The Therapy Effect of Azathioprine Initial or 14 Weeks After Combined With Infliximab on CD NA UNKNOWN Sixth Affiliated Hospital, Sun Yat-sen University Crohn Disease DRUG: infliximab and azathioprine combination at … Details
NCT03370601 Evaluation of the Clinical and Immunological Impact of Two Therapeutic Strategies in Chronic Inflammatory Diseases NA TERMINATED University Hospital, Lille Inflammatory Bowel Diseases DRUG: Infliximab|DRUG: Mercaptopurine|DRUG: Azath… Details
NCT03185611 Effectiveness of Rifaximin Combined With Thiopurine on Preventing Postoperative Recurrence in Crohn's Disease PHASE3 UNKNOWN Sixth Affiliated Hospital, Sun Yat-sen University Crohn Disease DRUG: Rifaximin|DRUG: Azathioprine 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
NCT03101800 Beneficial and Harmful Effects of Azathioprine and Allopurinol Versus Standard Azathioprine Therapy for Patients With Ulcerative Colitis PHASE3 UNKNOWN Hvidovre University Hospital Colitis, Ulcerative|Colitis Ulcerative Exacerbati… DRUG: Azathioprine and Allopurinol|DRUG: Azathiop… Details
NCT02998827 Thalidomide Results in Diminished Ovarian Reserve in Reproductive Age Female IBD Patients NA UNKNOWN Sixth Affiliated Hospital, Sun Yat-sen University Crohn Disease DRUG: Thalidomide|DRUG: infliximab, azathioprine|… Details
NCT02929706 Pre-genotype NUDT 15 R139C on Reducing Thiopurine-induced Leucopenia in Inflammatory Bowel Disease NA UNKNOWN Sixth Affiliated Hospital, Sun Yat-sen University Thiopurine-induced Leukopenia GENETIC: Pre-genotype NUDT15 and optimize azathio… Details
NCT02852694 Reduce Risk for Crohn's Disease Patients PHASE4 COMPLETED PIBD-Net Crohn's Disease DRUG: Methotrexate|DRUG: Adalimumab|DRUG: Azathio… 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
NCT02517684 Top-down Infliximab Study in Kids With Crohn's Disease PHASE4 COMPLETED Erasmus Medical Center Crohn's Disease DRUG: Infliximab|DRUG: Prednisolone|OTHER: Exclus… 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

Economic impact of combination therapy with infliximab plus azathioprine for dr…

PMID: 22626508
Year: 2013
Relationship Type: Treatment Score: 9.1

BACKGROUND: Combination therapy with infliximab (IFX) and azathioprine (AZA) is significantly more effective for treatment of active Crohn's disease …

A case of therapy-related myeloid neoplasm in a patient with Crohn's disease tr…

PMID: 22572218
Year: 2012
Relationship Type: Treatment Score: 9.1

Acute leukaemia (AL) has been observed in association with Crohn's disease (CD) notably in patients treated with azathioprine (AZA), which is an immu…

Gene polymorphisms involved in manifestation of leucopenia, digestive intoleran…

PMID: 22535280
Year: 2012
Relationship Type: Treatment Score: 9.1

BACKGROUND: Approximately 10-28 % of patients experience adverse drug reactions related to treatment with thiopurines. The most serious reaction is m…

Oral squamous cell carcinoma in a Crohn's disease patient taking azathioprine: …

PMID: 22464812
Year: 2012
Relationship Type: Association Score: 9.1

Thiopurines are widely used for remission maintenance and post-operative recurrence prevention in Crohn's disease. The increased risk of cancer in tr…

Initiating azathioprine for Crohn's disease

PMID: 22330233
Year: 2012
Relationship Type: Treatment Score: 9.1

Azathioprine (AZA) and 6-mercaptopurine are therapeutic options for patients with moderate to severe inflammatory Crohn's disease. AZA has both a com…

Azathioprine hypersensitivity presenting as sweet syndrome in a child with ulce…

PMID: 22253154
Year: 2011
Relationship Type: Treatment Score: 9.1

Sweet syndrome is a cutaneous lesion characterized by tender, red inflammatory nodules or papules. We describe a pediatric case of Sweet syndrome pre…

Safety of azathioprine use during pregnancy

PMID: 22170192
Year: 2011
Relationship Type: Association Score: 9.1

QUESTION: Quite a few of my female patients with rheumatic diseases and inflammatory bowel disease are using azathioprine. They are afraid to take a …

A pharmacogenetics study of TPMT and ITPA genes detects a relationship with sid…

PMID: 21961091
Year: 2011
Relationship Type: Treatment Score: 9.1

BACKGROUND AND AIMS: Pharmacogenetic studies in inflammatory bowel diseases (IBD) are mainly focused on genes involved in the metabolism of Azathiopr…

Tolerance and efficacy of azathioprine in pediatric Crohn's disease

PMID: 21910176
Year: 2011
Relationship Type: Adverse Effect Score: 9.1

BACKGROUND: Thiopurines are considered first-line immunomodulators for the prevention of relapse in moderate to severe pediatric Crohn's disease (CD)…

Thiopurine methyl-transferase activity and azathioprine metabolite concentratio…

PMID: 21722149
Year: 2011
Relationship Type: Treatment Score: 9.1

BACKGROUND: Low thiopurine-methyl-transferase (TPMT) activity and high 6-thioguanine-nucleotide (6TGN) concentrations have been linked to therapeutic…

Azathioprine and mercaptopurine: lymphoma

PMID: 21648178
Year: 2011
Relationship Type: Treatment Score: 9.1

Prospective follow-up for a median of 35 months of a French cohort of 19 486 patients with inflammatory bowel disease showed a nearly 4-fold increase…

Association between adverse effects under azathioprine therapy and inosine trip…

PMID: 21544018
Year: 2011
Relationship Type: Treatment Score: 9.1

BACKGROUND: Inosine triphosphate pyrophosphatase (ITPA) catalyzes the pyrophosphohydrolysis of inosine triphosphate to inosine monophosphate. Recentl…

Recurrent atrial fibrillation in a patient with ulcerative colitis treated with…

PMID: 21496410
Year: 2011
Relationship Type: Treatment Score: 9.1

We present a clinical case report regarding recurrent atrial fibrillation in a patient with ulcerative colitis treated with azathioprine. Atrial fibr…

Relapse rate following azathioprine withdrawal in maintaining remission for Cro…

PMID: 21476031
Year: 2011
Relationship Type: Treatment Score: 9.1

BACKGROUND: The duration of use of azathioprine (Aza) and 6-mercaptopurine (6-MP) for maintaining remission for Crohn's disease is debatable. AIM: To…

Evidence for a functional genetic polymorphism of the Rho-GTPase Rac1. Implicat…

PMID: 21372752
Year: 2011
Relationship Type: Treatment Score: 9.1

BACKGROUND: Adverse effects of thiopurine drugs occur in 15-28% of patients and the majority is not explained by thiopurine-S-methyltransferase defic…

Pregnancy after azathioprine therapy for ulcerative colitis in a woman with aut…

PMID: 21367409
Year: 2011
Relationship Type: Treatment Score: 9.1

OBJECTIVE: To present a case of fertility restored by azathioprine treatment in a woman with autoimmune premature ovarian failure, Addison's disease,…

Mucosal healing with methotrexate in Crohn's disease: a prospective comparative…

PMID: 21235604
Year: 2011
Relationship Type: Treatment Score: 9.1

BACKGROUND: Mucosal healing has become a new therapeutic goal in Crohn's disease and can be achieved with azathioprine (AZA) or biologics. Methotrexa…

Impact of azathioprine and tumour necrosis factor antagonists on the need for s…

PMID: 21228429
Year: 2011
Relationship Type: Treatment Score: 9.1

OBJECTIVE: The aim of the study was to assess whether azathioprine and antitumour necrosis factor (TNF) treatment decrease the long-term need for sur…

Allopurinol might improve response to azathioprine and 6-mercaptopurine by corr…

PMID: 21175793
Year: 2011
Relationship Type: Treatment Score: 9.1

BACKGROUND AND AIM: Allopurinol potentiates azathioprine and 6-mercaptopurine (6-MP) by increasing 6-thioguanine nucleotide (6-TGN) metabolite concen…

Change in hematologic indices over time in pediatric inflammatory bowel disease…

PMID: 21171667
Year: 2010
Relationship Type: Adverse Effect Score: 9.1

Azathioprine leads to changes in mean corpuscular volume (MCV) and white blood cell (WBC) indices reflecting efficacy or toxicity. Understanding the …

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