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

Azathioprine dose reduction in inflammatory bowel disease patients on combinati…

PMID: 28449228
Year: 2017
Relationship Type: Treatment Score: 6.3

Genome-wide association studies have identified autophagy-related susceptibility genes for inflammatory bowel disease (IBD); however, whether autoph…

Azathioprine, Mercaptopurine, and 5-Aminosalicylic Acid Affect the Growth of IB…

PMID: 28424670
Year: 2017
Relationship Type: Treatment Score: 6.3

The two main forms of intestinal bowel disease, namely ulcerative colitis and Crohn's disease, are not curable but can be controlled by various medi…

Safety of azathioprine and 6-mercaptopurine in patients with inflammatory bowel…

PMID: 28406092
Year: 2017
Relationship Type: Treatment Score: 6.3

Patients with inflammatory bowel disease [IBD] may develop, similarly to individuals from general population, rare cases of human papilloma virus […

Multicentric Case-Control Study on Azathioprine Dose and Pharmacokinetics in Ea…

PMID: 28296824
Year: 2017
Relationship Type: Pharmacology Score: 6.3

BACKGROUND AND AIM: There has been increased interest in sleep disorders in patients with inflammatory bowel disease (IBD). Studies in North America…

Azathioprine Therapy in a Pediatric TPMT-Deficient Patient-Still an Option

PMID: 28081040
Year: 2017
Relationship Type: Treatment Score: 6.3

Comment on Aliment Pharmacol Ther. 2019 Sep;50(6):675-683. Aliment Pharmacol Ther. 2019 Nov;50(9):1060-1061.

Endoscopic aspect of a severe CMV colitis induced by azathioprine in a patient …

PMID: 27981297
Year: 2016
Relationship Type: Association Score: 6.3

Blood group B is associated with azathioprine-induced acute pancreatitis in pat…

PMID: 27849560
Year: 2017
Relationship Type: Mechanism Score: 6.3

BACKGROUND: In active inflammatory bowel disease (IBD), microRNA expression profiling consistently features disease-specific signatures, and microRN…

Randomized clinical trial: a pilot study comparing efficacy of low-dose azathio…

PMID: 27686002
Year: 2016
Relationship Type: Treatment Score: 6.3

Serum level of IL-21 is increased in patients with inflammatory bowel diseases (IBD), suggesting that IL-21/IL-21 receptor (IL-21R) signaling may be…

Adalimumab Monotherapy and a Combination with Azathioprine for Crohn's Disease:…

PMID: 27566367
Year: 2016
Relationship Type: Treatment Score: 6.3

BACKGROUND AND AIMS: Toll-like receptors [TLRs] are potential drug targets for immunomodulation. We determined the safety and efficacy of the TLR-9 …

No Evidence That Azathioprine Increases Risk of Cholangiocarcinoma in Patients …

PMID: 27521513
Year: 2016
Relationship Type: Association Score: 6.3

Not found

Reassuring results on birth outcomes in children fathered by men treated with a…

PMID: 27456154
Year: 2017
Relationship Type: Mechanism Score: 6.3

Inflammatory bowel disease (IBD) arises when intestinal immune homeostasis is broken, the maintenance of such homeostasis is principally controlled …

Severe perianal shingles during azathioprine and budesonide treatment for Crohn…

PMID: 27440857
Year: 2016
Relationship Type: Treatment Score: 6.3

Infliximab (IFX) is commonly used to induce and maintain remission in inflammatory bowel disease (IBD). We report the first 2 cases of children with…

A Pitfall to Avoid: Hyperlipasemia, Azathioprine, and Autoimmune Pancreatitis

PMID: 27385401
Year: 2017
Relationship Type: Association Score: 6.3

Low-dose azathioprine is effective in maintaining remission in steroid-dependen…

PMID: 27366213
Year: 2016
Relationship Type: Treatment Score: 6.3

OBJECTIVE: To confirm the potential therapeutic efficacy of HAO472 against inflammatory bowel disease (IBD), we investigated the modulatory function…

Anaplastic lymphoma kinase (ALK)-positive large B-cell lymphoma in a patient tr…

PMID: 27311871
Year: 2016
Relationship Type: Association Score: 6.3

Use of azathioprine and corticosteroids during pregnancy and birth outcome in w…

PMID: 27301563
Year: 2016
Relationship Type: Treatment Score: 6.3

BACKGROUND: Inflammatory bowel diseases (IBD) are chronic relapsing inflammatory conditions of unknown cause and likely result from the loss of immu…

Effect of Early Versus Late Azathioprine Therapy in Pediatric Ulcerative Colitis

PMID: 27271489
Year: 2016
Relationship Type: Treatment Score: 6.3

Faecalibacterium prausnitzii strain A2-165 was previously reported to have anti-inflammatory properties and prevent colitis in a TNBS model. We comp…

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