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

Thiopurine S-methyltransferase and inosine triphosphate pyrophosphohydrolase ge…

PMID: 19214663
Year: 2009
Relationship Type: Treatment Score: 6.1

BACKGROUND: Patient information has been viewed as a key component of self-management. However, little attention has been given to methods of disse…

Understanding the delayed onset of action of azathioprine in IBD: are we there …

PMID: 19211850
Year: 2009
Relationship Type: Association Score: 6.1

Not found

A 6-thioguanine nucleotide threshold level of 400 pmol/8 x 10(8) erythrocytes p…

PMID: 19086961
Year: 2008
Relationship Type: Association Score: 6.1

BACKGROUND: Inflammatory bowel disease (IBD) results from an aberrant immune response to the indigenous intestinal flora in genetically susceptible …

Use of pharmacogenetics, enzymatic phenotyping, and metabolite monitoring to gu…

PMID: 19040311
Year: 2009
Relationship Type: Treatment Score: 6.1

MRP1 (multidrug resistance-associated protein 1) is well known for its role in providing multidrug resistance to cancer cells. In addition, MRP1 has…

Are we giving azathioprine too late? The case for early immunomodulation in inf…

PMID: 18810768
Year: 2008
Relationship Type: Treatment Score: 6.1

Inflammatory bowel diseases (IBD) are driven by imbalances in innate and acquired immune response. In IBD two dysregulated T cell subsets are in the…

Prospective evaluation of the pharmacogenetics of azathioprine in the treatment…

PMID: 18616518
Year: 2008
Relationship Type: Treatment Score: 6.1

BACKGROUND AND AIMS: This retrospective study analyzed the clinical characteristics of hospitalized patients with ulcerative colitis (UC) in China. …

Acute pancreatitis in inflammatory bowel disease, with special reference to aza…

PMID: 18513380
Year: 2008
Relationship Type: Treatment Score: 6.1

BACKGROUND: For a patient to make informed, preference based decisions, they must be able to balance the risks and benefits of treatment. The aim of…

Increased dosing requirements for 6-mercaptopurine and azathioprine in inflamma…

PMID: 18266236
Year: 2008
Relationship Type: Association Score: 6.1

To investigate the basis for the LEDGF/p75 dependence of HIV-1 integrase (IN) nuclear localization and chromatin association, we used cell lines mad…

[Optimization of immunomodulatory treatment with azathioprine or 6-mercaptopuri…

PMID: 17980127
Year: 2007
Relationship Type: Treatment Score: 6.1

BACKGROUND: Inflammatory bowel disease (IBD) is proposed to result from a dysregulated mucosal immune response to the colonic flora in genetically …

Hepatotoxicity of 6-mercaptopurine (6-MP) and Azathioprine (AZA) in adult IBD p…

PMID: 17764490
Year: 2007
Relationship Type: Adverse Effect Score: 6.1

BACKGROUND: NOD2 mutations are associated with Crohn's disease (CD) in Caucasian clinic-based cohorts. Data from population-based cohorts are limite…

Alcohol binging causes peliosis hepatis during azathioprine therapy in Crohn's …

PMID: 17729423
Year: 2007
Relationship Type: Treatment Score: 6.1

Sleep is vital to health and quality of life while sleep abnormalities are associated with adverse health consequences. Nevertheless, sleep problems…

Severe pulmonary toxicity after azathioprine/6-mercaptopurine initiation for th…

PMID: 17667053
Year: 2007
Relationship Type: Treatment Score: 6.1

Inflammatory bowel disease (IBD) is a chronic inflammatory disorder of the gastrointestinal tract involving aberrant activation of innate and adapti…

Therapeutic drug monitoring in patients with inflammatory bowel disease and est…

PMID: 17523708
Year: 2004
Relationship Type: Treatment Score: 6.1

BACKGROUND/AIMS: Keratin-8 (KRT8)-null mice develop spontaneous colitis and predisposition to liver injury. Human studies show that some KRT8 varian…

Assessment of thiopurine methyltransferase enzyme activity is superior to genot…

PMID: 17439508
Year: 2007
Relationship Type: Treatment Score: 6.1

Not found

Effect of allopurinol on clinical outcomes in inflammatory bowel disease nonres…

PMID: 17296529
Year: 2007
Relationship Type: Association Score: 6.1

AIM: To understand the local pathophysiological alterations and gene ontology-based functional classification of colonic biopsies into inflammatory …

Glutathione-S-transferase genotypes and the adverse effects of azathioprine in …

PMID: 17206640
Year: 2007
Relationship Type: Adverse Effect Score: 6.1

BACKGROUND AND OBJECTIVES: Evidence for the hygiene hypothesis in the etiology of Crohn's disease (CD) is unclear. We investigated the relationship …

Azathioprine and mesalazine-induced effects on the mucosal flora in patients wi…

PMID: 17206639
Year: 2007
Relationship Type: Association Score: 6.1

BACKGROUND: The goal of this study was to determine the rate of work disability, unemployment, and sick leave in an unselected inflammatory bowel di…

IMPDH1 promoter mutations in a patient exhibiting azathioprine resistance

PMID: 17001353
Year: 2007
Relationship Type: Treatment Score: 6.1

The mechanisms controlling retroviral integration have been the topic of intense interest, in part because of adverse clinical events that occurred …

Long-term effectiveness of azathioprine in IBD beyond 4 years: a European multi…

PMID: 16927148
Year: 2006
Relationship Type: Treatment Score: 6.1

Crohn's disease (CD) and ulcerative colitis (UC) make up the so-called chronic inflammatory bowel disease (IBD). Advances in the understanding of IB…

5-aminosalicylate therapy is associated with higher 6-thioguanine levels in adu…

PMID: 16633046
Year: 2006
Relationship Type: Treatment Score: 6.1

Not found

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