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

Finding Predictors of Azathioprine-Induced Pancreatitis in Patients With Inflam…

PMID: 35584388
Year: 2022
Relationship Type: Treatment Score: 9.5

OBJECTIVES: Azathioprine (AZA)-induced pancreatitis (AIP) is a common, idiosyncratic adverse effect whose incidence and risk factors data in inflamma…

Azathioprine and Acenocoumarol Drug Interaction in Patients with Crohn's Diseas…

PMID: 35469571
Year: 2023
Relationship Type: Association Score: 9.5

BACKGROUND: Acenocoumarol is an anticoagulant with numerous drug reactions. We report here, an unusual interaction between acenocoumarol and azathiop…

Gut Microbiota Metabolism of Azathioprine: A New Hallmark for Personalized Drug…

PMID: 35450035
Year: 2022
Relationship Type: Treatment Score: 9.5

Despite the growing number of new drugs approved for the treatment of inflammatory bowel disease (IBD), the long-term clinical use of thiopurine ther…

Mucosal healing with methotrexate versus azathioprine treatment in pediatric Cr…

PMID: 35373937
Year: 2022
Relationship Type: Treatment Score: 9.5

BACKGROUND/OBJECTIVES: The current treatment goal for inflammatory bowel disease (IBD) is achievement of mucosal healing (MH). While established with…

Persistently normal blood tests in patients taking methotrexate for RA or azath…

PMID: 35256384
Year: 2022
Relationship Type: Association Score: 9.5

BACKGROUND: Disease-modifying anti-rheumatic drugs (DMARDs), including methotrexate and azathioprine, are commonly used to treat rheumatoid arthritis…

HLA variants associated with azathioprine-induced pancreatitis in patients with…

PMID: 35120281
Year: 2022
Relationship Type: Association Score: 9.5

The immunosuppressant drug azathioprine is associated with a 4% risk of acute pancreatitis in patients with inflammatory bowel disease (IBD). Studies…

Parenteral Methotrexate Is Efficient in the Treatment of Azathioprine Refractor…

PMID: 35115294
Year: 2022
Relationship Type: Treatment Score: 9.5

BACKGROUND: There is limited data in the literature analyzing the efficacy of methotrexate in Crohn's disease used after thiopurine analogs. We aimed…

Sweet Syndrome Associated With Crohn's Disease Developed After a Combo Therapy …

PMID: 35111438
Year: 2021
Relationship Type: Treatment Score: 9.5

Sweet syndrome, also known as Acute Febrile Neutrophilic Dermatosis, is a rare inflammatory condition. The exact pathogenesis of Sweet syndrome is un…

NUDT15 intermediate metabolisers are associated with lower loss of response in …

PMID: 35032047
Year: 2022
Relationship Type: Treatment Score: 9.5

BACKGROUND: NUDT15 polymorphisms are associated with leukopenia during treatment with thiopurines. However, data regarding its effect on treatment ou…

Discontinuation of Azathioprine could be considered in pediatric patients with …

PMID: 35017546
Year: 2022
Relationship Type: Treatment Score: 9.5

Few studies have demonstrated treatment strategies about the duration and cessation of medications in patients with Crohn's disease (CD). We investig…

Azathioprine-induced alopecia: a rare adverse event, early marker of myelotoxic…

PMID: 34517716
Year: 2022
Relationship Type: Treatment Score: 9.5

Though not exempt from adverse events, azathioprine (AZA) is an inexpensive and effective drug in the induction and maintenance treatment of patients…

Simultaneous Monitoring of Azathioprine Metabolites in Erythrocytes of Crohn's …

PMID: 34159374
Year: 2022
Relationship Type: Treatment Score: 9.5

The conversion of azathioprine (AZA) to active 6-thioguanine nucleotides (6-TGN) is essential for its clinical efficacy; however, another metabolite …

Noninvasive Monitoring After Azathioprine Withdrawal in Patients With Inflammat…

PMID: 34139332
Year: 2021
Relationship Type: Treatment Score: 9.5

BACKGROUND & AIMS: There is uncertainty regarding the optimal duration of treatment with azathioprine (AZA) in ulcerative colitis (UC) and Crohn's di…

Ustekinumab is more effective than azathioprine to prevent endoscopic postopera…

PMID: 33951350
Year: 2021
Relationship Type: Treatment Score: 9.5

BACKGROUND: Preventing postoperative recurrence (POR) is a major concern in Crohn's disease (CD). While azathioprine is an option, no data is availab…

Azathioprine-induced toxoplasma gondii infection in a patient with Crohn's dise…

PMID: 33950972
Year: 2021
Relationship Type: Treatment Score: 9.5

INTRODUCTION: Azathioprine (AZA) has been widely used for the treatment of various immune-related diseases and has become a mainstay in the treatment…

CMV pneumonitis in a patient with Crohn's disease taking azathioprine

PMID: 33893128
Year: 2021
Relationship Type: Treatment Score: 9.5

This case report discusses the rare presentation of cytomegalovirus (CMV) pneumonitis in a young patient with moderately severe Crohn's disease manag…

Redox imbalance in Crohn's disease patients is modulated by Azathioprine

PMID: 33882797
Year: 2021
Relationship Type: Treatment Score: 9.5

BACKGROUND: Crohn's disease (CD) is a chronic inflammatory disease without a specific cause. Inflammation in these patients can disturb the oxidants/…

Development of a HPLC-DAD stability-indicating method and compatibility study o…

PMID: 33687392
Year: 2021
Relationship Type: Treatment Score: 9.5

Adherence in chronic diseases is a major problem which can be combated by prescribing fixed-dose combinations in the therapy of the disease. Thus, a …

Intrahepatic cholestasis of pregnancy associated with azathioprine: A case seri…

PMID: 33601075
Year: 2021
Relationship Type: Association Score: 9.5

BACKGROUND: Intrahepatic cholestasis of pregnancy (ICP) is characterised by otherwise unexplained maternal pruritus, increased serum bile acid concen…

Posterior Reversible Encephalopathy Syndrome After Azathioprine Administration …

PMID: 33532511
Year: 2021
Relationship Type: Treatment Score: 9.5

Posterior reversible encephalopathy syndrome is a rare syndrome characterized by brain edema and neurological symptoms, often resulting from several …

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