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

Letter to the Editor: Activated Toxoplasma May Attenuate the Effect of Azathiop…

PMID: 31300821
Year: 2019
Relationship Type: Association Score: 6.5

Recent studies have identified various bacterial groups that are altered in dogs with chronic inflammatory enteropathies (CE) compared to healthy do…

Azathioprine dosing and metabolite measurement in pediatric inflammatory bowel …

PMID: 31263361
Year: 2019
Relationship Type: Association Score: 6.5

Not found

Importance of 6-Thioguanine Nucleotide Metabolite Monitoring in Inflammatory Bo…

PMID: 31152640
Year: 2019
Relationship Type: Treatment Score: 6.5

Background: Inflammatory bowel disease (IBD) is characterized by both acute and chronic phase inflammation of the gastro-intestinal (GI) tract that …

Positive pharmacokinetic effect of azathioprine co-medication on infliximab tro…

PMID: 31147215
Year: 2019
Relationship Type: Mechanism Score: 6.5

Complement C4 genes are linked to paediatric inflammatory bowel disease (PIBD), but the mechanisms have remained unclear. We examined the influence …

Azathioprine Is Useful for Maintaining Long-term Remission Induced by Tacrolimu…

PMID: 31118391
Year: 2019
Relationship Type: Treatment Score: 6.5

Objective The need for and efficacy of immunomodulators for maintaining remission after tacrolimus therapy have not been sufficiently defined. This s…

The Inflammatory Bowel Disease Drug Azathioprine Induces Autophagy via mTORC1 a…

PMID: 30889246
Year: 2019
Relationship Type: Mechanism Score: 6.5

Riboflavin (RF), is essential for normal cellular metabolism/function. Intestinal RF absorption occurs via a specific carrier-mediated process that …

Mesalamine and azathioprine modulate junctional complexes and restore epithelia…

PMID: 30809073
Year: 2019
Relationship Type: Treatment Score: 6.5

The pathogenesis of inflammatory bowel disease (IBD) is linked to an intricate association of environmental, microbial, and host-related factors. Th…

Concerns and Side Effects of Azathioprine During Adalimumab Induction and Maint…

PMID: 30753377
Year: 2019
Relationship Type: Treatment Score: 6.5

Mutations in Wiskott-Aldrich syndrome protein (WASP) cause autoimmune sequelae including colitis. Yet, how WASP mediates mucosal homeostasis is not …

Acute pancreatitis and azathioprine in paediatric inflammatory bowel disease

PMID: 30685365
Year: 2019
Relationship Type: Association Score: 6.5

Withdrawal of Azathioprine in Inflammatory Bowel Disease Patients Who Sustain R…

PMID: 30604371
Year: 2019
Relationship Type: Treatment Score: 6.5

Arsenic trioxide (As2O3) is a trending subject in recent therapy approaches despite its described toxicity. In this work, we have investigated the u…

Red Blood cell IMPDH activity in adults and children with or without azathiopri…

PMID: 30451390
Year: 2019
Relationship Type: Treatment Score: 6.5

Total retocolectomy with ileal pouch-anal anastomosis (IPAA) is the surgery of choice for patients with ulcerative colitis (UC) that are refractory …

Thiopurine Methyltransferase Genetic Polymorphisms and Activity and Metabolic P…

PMID: 30451123
Year: 2019
Relationship Type: Association Score: 6.5

In recent years, acute severe outbreaks of infectious bursal disease (IBD) are frequently observed in commercial chicken populations of the North Ea…

Azathioprine-Induced Sweet Syndrome Treated With Infliximab

PMID: 30074533
Year: 2019
Relationship Type: Association Score: 6.5

BCL-2 levels do not predict azathioprine treatment response in inflammatory bow…

PMID: 29745420
Year: 2018
Relationship Type: Treatment Score: 6.3

Comment in Colorectal Dis. 2019 Oct;21(10):1212-1213. AIM: There is a requirement of an expansive and up to date review of surgical management …

NUDT15 R139C variation increases the risk of azathioprine-induced toxicity in C…

PMID: 29702976
Year: 2018
Relationship Type: Adverse Effect Score: 6.3

BACKGROUND: The human leukocyte antigen (HLA) region has been found to be involved in the pathogenesis of inflammatory bowel disease (IBD), which is…

Alopecia Universalis Associated with Ulcerative Colitis and The Role of Azathio…

PMID: 29682249
Year: 2018
Relationship Type: Treatment Score: 6.3

The two major forms of inflammatory bowel disease (IBD), encompassing Crohn's disease (CD) and ulcerative colitis (UC), are chronic immune-mediated …

[Role of Rac1 signaling pathway of azathioprine and peptidoglycan in the regula…

PMID: 29614587
Year: 2018
Relationship Type: Mechanism Score: 6.3

Objective: To evaluate the changes of macrophages and expression of Rac1 in the inflammatory site of Crohn's disease, and to investigate the effects …

Late-onset Rise of 6-MMP Metabolites in IBD Patients on Azathioprine or Mercapt…

PMID: 29522107
Year: 2018
Relationship Type: Treatment Score: 6.3

Therapeutic drug monitoring (TDM), or the measurement of drug concentrations in blood and antidrug antibodies, for biologic therapies used to treat …

Letter: predicting azathioprine-associated pancreatitis in IBD-phenotype or gen…

PMID: 29512918
Year: 2018
Relationship Type: Treatment Score: 6.3

Inflammatory bowel disease (IBD) involves chronic inflammation, loss of epithelial integrity, and gastrointestinal microbiota dysbiosis. Effective …

Letter: predicting azathioprine-associated pancreatitis in IBD-phenotype or gen…

PMID: 29512906
Year: 2018
Relationship Type: Association Score: 6.3

Comment in Am J Gastroenterol. 2017 Dec;112(12):1892-1893.

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