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

Nodular regenerative hyperplasia: a reversible entity associated with azathiopr…

PMID: 16607155
Year: 2006
Relationship Type: Treatment Score: 6.1

Emergency complications of IBD are rare, but may be life-threatening, require surgery, and result in permanent end organ damage. The most common com…

Inosine triphosphate pyrophosphatase and thiopurine s-methyltransferase genotyp…

PMID: 16431304
Year: 2006
Relationship Type: Association Score: 6.1

In the present study, the changes in circulating IGF-1 and its binding protein IGFBP-3 were determined in adult patients with active inflammatory bo…

On tolerability and safety of a maintenance treatment with 6-thioguanine in aza…

PMID: 16222751
Year: 2005
Relationship Type: Treatment Score: 6.1

Epithelial neutrophil-activating peptide-78 (ENA-78), a member of the CXC chemokine subfamily, is induced by inflammatory cytokines in human colonic…

A cost-effectiveness analysis of alternative disease management strategies in p…

PMID: 16181376
Year: 2005
Relationship Type: Treatment Score: 6.1

BACKGROUND: The aminosalicylates remain foundation therapy for mild-to-moderate ulcerative colitis. Pro-drug 5-aminosalicylic acid (5-ASA; mesalamin…

Effects of azathioprine and its metabolites on repair mechanisms of the intesti…

PMID: 16122821
Year: 2005
Relationship Type: Mechanism Score: 6.1

Interleukin (IL)-1 is a key mediator in the pathogenesis of inflammatory bowel disease (IBD). Naturally occurring IL-1 modulators include IL-1 recep…

Azathioprine and 6-mercaptopurine pharmacogenetics and metabolite monitoring in…

PMID: 16048561
Year: 2005
Relationship Type: Association Score: 6.1

INTRODUCTION: We sought to examine the relationship between C-reactive protein (CRP) and clinical, endoscopic, histologic, and radiographic activity…

Increased risk of lymphoma among inflammatory bowel disease patients treated wi…

PMID: 16009685
Year: 2005
Relationship Type: Mechanism Score: 6.1

BACKGROUND AND AIMS: The inflammatory bowel diseases (IBDs) Crohn's disease (CD) and ulcerative colitis are complex disorders with an important gene…

Azathioprine induced nodular regenerative hyperplasia in IBD patients

PMID: 15980758
Year: 2005
Relationship Type: Association Score: 6.1

Not found

Increased rates of early adverse reaction to azathioprine in patients with Croh…

PMID: 15842588
Year: 2005
Relationship Type: Adverse Effect Score: 6.1

BACKGROUND: Inflammatory bowel disease manifests throughout all ethnic groups. Antisaccharomyces cerevisiae (ASCA) and antineutrophil cytoplasmic an…

Thiopurine methyltransferase enzyme activity determination before treatment of …

PMID: 15776134
Year: 2005
Relationship Type: Treatment Score: 6.1

It has been proposed that defective activation of suppressor or regulatory T cells is one mechanism involved in the uncontrolled inflammatory proces…

Azathioprine, 6-mercaptopurine in inflammatory bowel disease: pharmacology, eff…

PMID: 15354273
Year: 2004
Relationship Type: Association Score: 6.1

BACKGROUND: Tissue inhibitors of metalloproteinases (TIMPs) play a key role in tissue degradation and remodeling. Since chronic inflammation is asso…

Clinical significance of azathioprine active metabolite concentrations in infla…

PMID: 15247179
Year: 2004
Relationship Type: Treatment Score: 6.1

OBJECTIVES: To assess the prevalence and determinants of alternative medicine (AM) use in gastroenterology outpatients and those with inflammatory b…

[Genetic polymorphism and treatment of chronic bowel inflammatory diseases: the…

PMID: 15199672
Year: 2004
Relationship Type: Treatment Score: 6.1

Dietary antigens may act as important stimuli of the mucosal immune system and have led to the study of nutritional therapy for IBD. Patients with a…

A prospective randomized observer-blind 2-year trial of azathioprine monotherap…

PMID: 15180735
Year: 2004
Relationship Type: Treatment Score: 6.1

Comment in J Pediatr Gastroenterol Nutr. 2003 Sep;37(3):228-9. BACKGROUND: Cytokines appear to play a significant role in the pathogenesis of i…

Treatment of inflammatory bowel disease with azathioprine and 6-mercaptopurine

PMID: 15177535
Year: 2004
Relationship Type: Treatment Score: 6.1

Not found

Thiopurine methyltransferase activity influences clinical response to azathiopr…

PMID: 15118980
Year: 2004
Relationship Type: Association Score: 6.1

INTRODUCTION: ALPHA-GAL is a glycoconjugate present on cell membranes of mammals and bacteria but not humans who display anti-Gal antibodies (AB) in…

Discordant erythrocyte sedimentation rate and C-reactive protein in children wi…

PMID: 15097439
Year: 2004
Relationship Type: Treatment Score: 6.1

A rabbit model of chronic ileitis has helped decipher the mechanism of alteration of multiple electrolyte and nutrient malabsorptions in inflammator…

Monitoring of azathioprine/6-mercaptopurine treatment in children with IBD is n…

PMID: 14671489
Year: 2003
Relationship Type: Treatment Score: 6.1

Dysregulated CD4(+) T cell responses and alterations in T regulatory cells (T(reg) cells) play a critical role in autoimmune diseases, including in…

Thioguanine: a potential alternate thiopurine for IBD patients allergic to 6-me…

PMID: 12809828
Year: 2003
Relationship Type: Association Score: 6.1

BACKGROUND & AIMS: There are few systematic studies on the natural history or immunogenetic associations of erythema nodosum (EN) or ocular inflamma…

6-Thioguanine seems promising in azathioprine- or 6-mercaptopurine-intolerant i…

PMID: 12544696
Year: 2003
Relationship Type: Treatment Score: 6.1

Comment in J Gastroenterol Hepatol. 2002 Mar;17(3):233-5. BACKGROUND AND AIM: Thalidomide is clinically effective in the treatment of graft ver…

Showing 461-480 of 497 articles