Identification
NameAzathioprine
Accession NumberDB00993  (APRD00811)
TypeSmall Molecule
GroupsApproved
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.

Structure
Thumb
Synonyms
6-((1-Methyl-4-nitro-1H-imidazol-5-yl)thio)-1H-purine
6-(1'-Methyl-4'-nitro-5'-imidazolyl)-mercaptopurine
Imuran (tn)
External IDs BW-57-322 / NSC-39084
Product Ingredients
IngredientUNIICASInChI KeyDetails
Azathioprine SodiumAM94R510MS 55774-33-9WISNYKIQFMKSDQ-UHFFFAOYSA-NDetails
Product Images
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AzathioprineTablet50 mgOralSanis Health Inc2010-02-16Not applicableCanada
AzathioprineTablet50 mgOralBdh Inc.1998-10-082000-08-03Canada
Azathioprine Sodium for InjectionPowder, for solution100 mgIntravenousNovopharm LimitedNot applicableNot applicableCanada
Azathioprine-50Tablet50 mgOralPro Doc Limitee2009-06-10Not applicableCanada
ImuranTablet50 mg/1OralPrometheus Laboratories1968-03-20Not applicableUs
ImuranTablet50 mgOralAspen Pharmacare Canada Inc.1966-12-31Not applicableCanada
ImuranPowder, for solution50 mgIntravenousAspen Pharmacare Canada Inc.2001-12-20Not applicableCanada
Imuran Inj 100mgPowder, for solution100 mgIntravenousGlaxo Wellcome1976-12-312000-10-25Canada
Mylan-azathioprineTablet50 mgOralMylan Pharmaceuticals1997-06-19Not applicableCanada
Ntp-azathioprineTablet50 mgOralTevaNot applicableNot applicableCanada
Nu-azathioprineTablet50 mgOralNu Pharm IncNot applicableNot applicableCanada
Ratio-azathioprineTablet50 mgOralRatiopharm Inc Division Of Teva Canada Limited1998-02-232006-08-04Canada
Riva-azathioprine 50 mgTablet50 mgOralLaboratoire Riva Inc2000-05-122003-07-28Canada
Teva-azathioprineTablet50 mgOralTeva1998-02-02Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-azathioprineTablet50 mgOralApotex Corporation2000-10-17Not applicableCanada
AzasanTablet75 mg/1OralSalix Pharmaceuticals2003-04-01Not applicableUs
AzasanTablet100 mg/1OralSalix Pharmaceuticals2003-04-01Not applicableUs
AzathioprineTablet50 mg/1Oralbryant ranch prepack2008-02-22Not applicableUs
AzathioprineTablet50 mg/1OralAmneal Pharmaceuticals2015-02-02Not applicableUs
AzathioprineTablet50 mg/1OralMylan Pharmaceuticals2009-12-28Not applicableUs00378 1005 01 nlmimage10 7a45bd6d
AzathioprineTablet50 mg/1OralAmerincan Health Packaging2008-02-22Not applicableUs68382 0003 01 nlmimage10 011300e8
AzathioprineTablet50 mg/1OralAidarex Pharmaceuticals LLC2007-07-11Not applicableUs
AzathioprineTablet50 mg/1OralRoxane Laboratories1996-02-162017-04-01Us
AzathioprineTablet50 mg/1OralCadila Pharnmaceuticals2007-07-11Not applicableUs
AzathioprineTablet50 mg/1OralCardinal Health1996-02-16Not applicableUs
AzathioprineTablet50 1/1OralZydus Pharmaceuticals Usa, Inc.2007-07-11Not applicableUs
AzathioprineTablet50 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs1996-02-16Not applicableUs
AzathioprineTablet50 mg/1OralGlenmark Pharmaceuticals, Inc1999-08-01Not applicableUs
AzathioprineTablet50 mg/1OralAphena Pharma Solutions Tennessee, Inc.1996-02-16Not applicableUs
AzathioprineTablet50 mg/1OralRoxane Laboratories1996-02-162017-04-01Us
AzathioprineTablet50 mg/1OralCardinal Health1996-02-16Not applicableUs
AzathioprineTablet50 mg/1OralMylan Institutional2010-07-23Not applicableUs51079 0620 06 nlmimage10 973dcbee
AzathioprineTablet50 mg/1OralRebel Distributors2007-07-11Not applicableUs
AzathioprineTablet50 mg/1OralAmneal Pharmaceuticals of New York Llc2015-02-02Not applicableUs
AzathioprineTablet50 1/1OralAvera Mc Kennan Hospital2016-01-08Not applicableUs
AzathioprineTablet50 mg/1OralPhysicians Total Care, Inc.2005-05-23Not applicableUs
Azathioprine SodiumInjection, powder, lyophilized, for solution100 mg/10mLIntravenousWest Ward Pharmaceutical1995-05-01Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AzamunAscent
AzaninTanabe Mitsubishi Pharma
ImurekAspen
ImurelGlaxoSmithKline
Brand mixturesNot Available
Categories
UNIIMRK240IY2L
CAS number446-86-6
WeightAverage: 277.263
Monoisotopic: 277.038193193
Chemical FormulaC9H7N7O2S
InChI KeyLMEKQMALGUDUQG-UHFFFAOYSA-N
InChI
InChI=1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)
IUPAC Name
6-[(1-methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-7H-purine
SMILES
CN1C=NC(=C1SC1=NC=NC2=C1NC=N2)[N+]([O-])=O
Pharmacology
Indication

For use in rheumatoid arthritis, preventing renal transplant rejection, Crohn's disease, and colitis.

Structured Indications
Pharmacodynamics

Azathioprine is a chemotherapy drug, now rarely used for chemotherapy but more for immunosuppression in organ transplantation and autoimmune disease such as rheumatoid arthritis or inflammatory bowel disease or Crohn's disease. It is a pro-drug, converted in the body to the active metabolite 6-mercaptopurine. Azathioprine acts to inhibit purine synthesis necessary for the proliferation of cells, especially leukocytes and lymphocytes. It is a safe and effective drug used alone in certain autoimmune diseases, or in combination with other immunosuppressants in organ transplantation. Its most severe side effect is bone marrow suppression, and it should not be given in conjunction with purine analogues such as allopurinol. The enzyme thiopurine S-methyltransferase (TPMT) deactivates 6-mercaptopurine. Genetic polymorphisms of TPMT can lead to excessive drug toxicity, thus assay of serum TPMT may be useful to prevent this complication.

Mechanism of action

Azathioprine antagonizes purine metabolism and may inhibit synthesis of DNA, RNA, and proteins. It may also interfere with cellular metabolism and inhibit mitosis. Its mechanism of action is likely due to incorporation of thiopurine analogues into the DNA structure, causing chain termination and cytotoxicity.

TargetKindPharmacological actionActionsOrganismUniProt ID
Hypoxanthine-guanine phosphoribosyltransferaseProteinyes
inhibitor
HumanP00492 details
Ras-related C3 botulinum toxin substrate 1ProteinunknownNot AvailableHumanP63000 details
Related Articles
Absorption

Well absorbed following oral administration.

Volume of distributionNot Available
Protein binding

Azathioprine and the metabolite mercaptopurine are moderately bound to serum proteins (30%).

Metabolism

Primarily converted to the active metabolites 6-mercaptopurine and 6-thioinosinic acid via a non-enzymatica process and glutathione transferases. Activation of 6-mercaptopurine occurs via hypoxanthine-guanine phosphoribosyltransferase (HGPRT) and a series of multi-enzymatic processes involving kinases to form 6-thioguanine nucleotides (6-TGNs) as major metabolites

SubstrateEnzymesProduct
Azathioprine
S-methylazathioprineDetails
Azathioprine
Not Available
6-ThioguanineDetails
Azathioprine
6-MercaptopurineDetails
Azathioprine
Not Available
6-thioguanylic acidDetails
Azathioprine
Not Available
6-thioinosine triphosphateDetails
Azathioprine
Not Available
6-thioinosinic acidDetails
Azathioprine
Not Available
6-thioxanthylic acidDetails
Azathioprine
Not Available
8-hydroxythioguanineDetails
Azathioprine
Not Available
Thio-deoxyguanosine triphosphateDetails
Azathioprine
Not Available
Thioguanine diphosphateDetails
Azathioprine
Not Available
Thioguanine triphosphateDetails
Azathioprine
Not Available
6-thiouric acidDetails
Azathioprine
Not Available
6-Thioxanthine 5'-monophosphateDetails
Route of elimination

Both compounds are rapidly eliminated from blood and are oxidized or methylated in erythrocytes and liver; no azathioprine or mercaptopurine is detectable in urine after 8 hours.

Half lifeNot Available
ClearanceNot Available
Toxicity

The oral LD50 for single doses of azathioprine in mice and rats are 2500 mg/kg and 400 mg/kg, respectively. Very large doses of this antimetabolite may lead to marrow hypoplasia, bleeding, infection, and death.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Azathioprine Metabolism PathwayDrug metabolismSMP00645
Azathioprine Action PathwayDrug actionSMP00427
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Thiopurine S-methyltransferaseTPMT*2(G;G) / (C;G)G Allele ADR Directly StudiedPatients with this genotype have reduced metabolism of azathioprine resulting in increased toxicity. Details
Thiopurine S-methyltransferaseTPMT*3A(A;A) / (A;G)A Allele ADR Directly StudiedPatients with this genotype have reduced metabolism of azathioprine resulting in increased toxicity. Details
Thiopurine S-methyltransferaseTPMT*3C(G;G) / (A;G)G Allele ADR Directly StudiedPatients with this genotype have reduced metabolism of azathioprine resulting in increased toxicity. Details
Thiopurine S-methyltransferaseTPMT*3BNot Availablec.460G>A ADR InferredMyelosuppression Details
Thiopurine S-methyltransferaseTPMT*4ANot AvailableG > A ADR InferredMyelosuppression Details
Interactions
Drug Interactions
DrugInteractionDrug group
AcenocoumarolAzathioprine may decrease the anticoagulant activities of Acenocoumarol.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Azathioprine.Approved
AllopurinolThe serum concentration of the active metabolites of Azathioprine can be increased when Azathioprine is used in combination with Allopurinol.Approved
BalsalazideThe metabolism of Azathioprine can be decreased when combined with Balsalazide.Approved, Investigational
BCG vaccineThe therapeutic efficacy of Bcg can be decreased when used in combination with Azathioprine.Investigational
BenazeprilBenazepril may increase the myelosuppressive activities of Azathioprine.Approved, Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Azathioprine.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Azathioprine.Approved
CandoxatrilCandoxatril may increase the myelosuppressive activities of Azathioprine.Experimental
CaptoprilCaptopril may increase the myelosuppressive activities of Azathioprine.Approved
CilazaprilCilazapril may increase the myelosuppressive activities of Azathioprine.Approved
CyclophosphamideAzathioprine may increase the hepatotoxic activities of Cyclophosphamide.Approved, Investigational
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Azathioprine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Azathioprine.Approved
DicoumarolAzathioprine may decrease the anticoagulant activities of Dicoumarol.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Azathioprine.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Azathioprine.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Azathioprine.Approved, Investigational
EnalaprilEnalapril may increase the myelosuppressive activities of Azathioprine.Approved, Vet Approved
EnalaprilatEnalaprilat may increase the myelosuppressive activities of Azathioprine.Approved
Ethyl biscoumacetateAzathioprine may decrease the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FebuxostatThe serum concentration of Azathioprine can be increased when it is combined with Febuxostat.Approved
FingolimodAzathioprine may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
FluindioneAzathioprine may decrease the anticoagulant activities of Fluindione.Investigational
FosinoprilFosinopril may increase the myelosuppressive activities of Azathioprine.Approved
G17DTThe risk or severity of adverse effects can be increased when Azathioprine is combined with G17DT.Investigational
GI-5005The risk or severity of adverse effects can be increased when Azathioprine is combined with GI-5005.Investigational
ImidaprilImidapril may increase the myelosuppressive activities of Azathioprine.Investigational
INGN 201The risk or severity of adverse effects can be increased when Azathioprine is combined with INGN 201.Investigational
INGN 225The risk or severity of adverse effects can be increased when Azathioprine is combined with INGN 225.Investigational
LeflunomideThe risk or severity of adverse effects can be increased when Azathioprine is combined with Leflunomide.Approved, Investigational
LisinoprilLisinopril may increase the myelosuppressive activities of Azathioprine.Approved, Investigational
MercaptopurineAzathioprine may increase the myelosuppressive activities of Mercaptopurine.Approved
MesalazineThe metabolism of Azathioprine can be decreased when combined with Mesalazine.Approved
MoexiprilMoexipril may increase the myelosuppressive activities of Azathioprine.Approved
NatalizumabThe risk or severity of adverse effects can be increased when Azathioprine is combined with Natalizumab.Approved, Investigational
OleandrinAnvirzel may decrease the cardiotoxic activities of Azathioprine.Experimental
OlsalazineThe metabolism of Azathioprine can be decreased when combined with Olsalazine.Approved
OmapatrilatOmapatrilat may increase the myelosuppressive activities of Azathioprine.Investigational
OuabainOuabain may decrease the cardiotoxic activities of Azathioprine.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Azathioprine.Approved, Vet Approved
PerindoprilPerindopril may increase the myelosuppressive activities of Azathioprine.Approved
PhenindioneAzathioprine may decrease the anticoagulant activities of Phenindione.Approved
PhenprocoumonAzathioprine may decrease the anticoagulant activities of Phenprocoumon.Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Azathioprine.Approved, Investigational
QuinaprilQuinapril may increase the myelosuppressive activities of Azathioprine.Approved, Investigational
Rabies virus inactivated antigen, AThe risk or severity of adverse effects can be increased when Azathioprine is combined with Rabies vaccine.Approved
Rabies virus inactivated antigen, AThe therapeutic efficacy of Rabies vaccine can be decreased when used in combination with Azathioprine.Approved
RamiprilRamipril may increase the myelosuppressive activities of Azathioprine.Approved
RescinnamineRescinnamine may increase the myelosuppressive activities of Azathioprine.Approved
RibavirinThe serum concentration of the active metabolites of Azathioprine can be increased when Azathioprine is used in combination with Ribavirin.Approved
RindopepimutThe risk or severity of adverse effects can be increased when Azathioprine is combined with CDX-110.Investigational
RoflumilastRoflumilast may increase the immunosuppressive activities of Azathioprine.Approved
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Azathioprine.Approved
SpiraprilSpirapril may increase the myelosuppressive activities of Azathioprine.Approved
SRP 299The risk or severity of adverse effects can be increased when Azathioprine is combined with SRP 299.Investigational
SulfamethoxazoleSulfamethoxazole may increase the myelosuppressive activities of Azathioprine.Approved
SulfasalazineThe metabolism of Azathioprine can be decreased when combined with Sulfasalazine.Approved
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Azathioprine.Approved, Investigational
TemocaprilTemocapril may increase the myelosuppressive activities of Azathioprine.Experimental, Investigational
TG4010The risk or severity of adverse effects can be increased when Azathioprine is combined with TG4010.Investigational
TofacitinibAzathioprine may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TrandolaprilTrandolapril may increase the myelosuppressive activities of Azathioprine.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Azathioprine.Approved, Investigational
TrimethoprimTrimethoprim may increase the myelosuppressive activities of Azathioprine.Approved, Vet Approved
WarfarinAzathioprine may decrease the anticoagulant activities of Warfarin.Approved
Food Interactions
  • Take with food to reduce irritation.
References
Synthesis ReferenceNot Available
General References
  1. Konstantopoulou M, Belgi A, Griffiths KD, Seale JR, Macfarlane AW: Azathioprine-induced pancytopenia in a patient with pompholyx and deficiency of erythrocyte thiopurine methyltransferase. BMJ. 2005 Feb 12;330(7487):350-1. [PubMed:15705694 ]
  2. Woodroffe R, Yao GL, Meads C, Bayliss S, Ready A, Raftery J, Taylor RS: Clinical and cost-effectiveness of newer immunosuppressive regimens in renal transplantation: a systematic review and modelling study. Health Technol Assess. 2005 May;9(21):1-179, iii-iv. [PubMed:15899149 ]
  3. Gombar VK, Enslein K, Blake BW: Carcinogenicity of azathioprine: an S-AR investigation. Mutat Res. 1993 May;302(1):7-12. [PubMed:7683109 ]
External Links
ATC CodesL04AX01 — Azathioprine
AHFS Codes
  • 92:00.00
PDB EntriesNot Available
FDA labelDownload (212 KB)
MSDSDownload (75.4 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentInflammatory Bowel Diseases (IBD)1
1, 2CompletedTreatmentType 1 Mucopolysaccharidosis1
2CompletedPreventionChronic Lung Diseases1
2CompletedTreatmentAdult-Onset Still's Disease1
2CompletedTreatmentGranulomatosis With Polyangiitis / Microscopic Polyangiitis / Renal Limited Vasculitis1
2CompletedTreatmentHepatitis, Autoimmune1
2CompletedTreatmentIdiopathic Pulmonary Fibrosis (IPF)1
2CompletedTreatmentLupus Erythematosus, Systemic / Nephritis, Lupus1
2CompletedTreatmentNephritis, Lupus1
2CompletedTreatmentPemphigus Vulgaris (PV)1
2Not Yet RecruitingTreatmentNephritis, Lupus1
2RecruitingTreatmentCutaneous Polyarteritis Nodosa / Henoch-Schönlein Purpura / IgA Vasculitis / Primary Cutaneous Vasculitis1
2TerminatedPreventionAzathioprine / Crohn's Disease (CD) / Prevention / Recurrences1
2TerminatedTreatmentCrohn's Disease (CD)1
2WithdrawnTreatmentAnti-Neutrophil Cytoplasmic Antibody-Associated Vasculitis1
2WithdrawnTreatmentGranulomatous and Lymphocytic Interstitial Lung Disease1
2WithdrawnTreatmentSystemic Lupus Erythematosus (SLE)1
2, 3CompletedTreatmentGranulomatosis With Polyangiitis / Microscopic Polyangiitis / Vasculitis1
2, 3CompletedTreatmentNeuromyelitis Optica Spectrum Disorder1
3Active Not RecruitingTreatmentAnti-Neutrophil Cytoplasmic Antibody-Associated Vasculitis / Granulomatosis With Polyangiitis / Microscopic Polyangiitis1
3CompletedPreventionCrohn's Disease (CD)1
3CompletedTreatmentAt Diagnosis or Within the First 15 Days Following Initiation of Corticosteroids / MPA / PAN or EGPA With FFS=01
3CompletedTreatmentChronic Kidney Disease (CKD) / IgA Nephropathy1
3CompletedTreatmentCrohn's Disease (CD)2
3CompletedTreatmentGranulomatosis With Polyangiitis / Microscopic Polyangiitis1
3CompletedTreatmentHepatocellular,Carcinoma1
3CompletedTreatmentNephritis, Lupus2
3CompletedTreatmentRheumatoid Arthritis1
3CompletedTreatmentVasculitis1
3RecruitingPreventionCrohn's Disease (CD)1
3RecruitingTreatmentANCA-Associated Vasculitis (AAV)1
3RecruitingTreatmentColitis Ulcerative Exacerbation / Ulcerative Colitis (UC)1
3RecruitingTreatmentHand Eczema1
3RecruitingTreatmentThrombocytopenias1
3TerminatedNot AvailableCrohn's Disease (CD)1
3TerminatedTreatmentANCA Associated Systemic Vasculitis Including Wegener’s / Granulomatosis and Microscopic Polyangiitis and / Renal Limited Vasculitis1
3TerminatedTreatmentChronic Lung Diseases / Pulmonary Fibrosis1
3TerminatedTreatmentCrohn's Disease (CD)1
3TerminatedTreatmentNephritis, Lupus1
3TerminatedTreatmentSystemic Lupus Erythematosus (SLE)1
3TerminatedTreatmentUlcerative Colitis (UC)2
3Unknown StatusTreatmentCrohn's Disease (CD)1
3Unknown StatusTreatmentInflammatory Cardiomyopathy1
3Unknown StatusTreatmentMyasthenia Gravis1
4CompletedPreventionAcute Graft Rejection / Delayed Graft Function1
4CompletedTreatmentCrohn's Disease (CD)2
4CompletedTreatmentHepatitis, Autoimmune1
4CompletedTreatmentNephritis, Lupus1
4CompletedTreatmentSystemic Lupus Erythematosus (SLE)1
4CompletedTreatmentTransplant, Kidney1
4CompletedTreatmentUveitis1
4Enrolling by InvitationTreatmentCrohn's Disease (CD)1
4Not Yet RecruitingTreatmentEosinophilic Granulomatosis With Polyangiitis1
4Not Yet RecruitingTreatmentImmune Thrombocytopenia1
4Not Yet RecruitingTreatmentUlcerative Colitis (UC)1
4RecruitingTreatmentCrohn's Disease (CD)2
4RecruitingTreatmentHepatitis, Autoimmune1
4RecruitingTreatmentHepatocellular,Carcinoma1
4RecruitingTreatmentInflammatory Bowel Diseases (IBD) / Pancreatitis1
4RecruitingTreatmentUlcerative Colitis (UC)2
4TerminatedPreventionSkin Cancers / Transplantation, Kidney1
4TerminatedTreatmentCrohn's Disease (CD)1
4Unknown StatusTreatmentCardiac Transplant1
4Unknown StatusTreatmentChurg-Strauss Syndrome (CSS)1
4Unknown StatusTreatmentMicroscopic Polyangiitis / Polyarteritis Nodosa1
4Unknown StatusTreatmentVasculitis1
4WithdrawnTreatmentPediatric Crohn's Disease1
Not AvailableCompletedNot AvailableAzathioprine / Inosine Triphosphate Pyrophosphatase / Polymorphism, Genetic / Thiopurine Methyltransferase1
Not AvailableCompletedNot AvailableDermatomyositis / Polymyositis1
Not AvailableCompletedNot AvailableLiver Diseases2
Not AvailableCompletedScreeningRenal Failure, Chronic1
Not AvailableCompletedSupportive CareCrohn's Disease (CD) / Inflammatory Bowel Diseases (IBD) / Ulcerative Colitis (UC)1
Not AvailableCompletedTreatmentNephritis, Lupus1
Not AvailableCompletedTreatmentParthenium Dermatitis1
Not AvailableEnrolling by InvitationNot AvailableCrohn's Disease (CD)1
Not AvailableRecruitingNot AvailableCrohn's Disease (CD) / Inflammatory Bowel Diseases (IBD)1
Not AvailableRecruitingTreatmentCrohn's Disease (CD) / Inflammatory Bowel Diseases (IBD) / Ulcerative Colitis (UC)1
Not AvailableRecruitingTreatmentLupus / Nephritis1
Not AvailableUnknown StatusNot AvailableAcquired Haemophilia1
Not AvailableUnknown StatusNot AvailableScleritis / Uveitis1
Not AvailableUnknown StatusTreatmentCrohn's Disease (CD)2
Pharmacoeconomics
Manufacturers
  • Aaipharma llc
  • Mylan pharmaceuticals inc
  • Roxane laboratories inc
  • Zydus pharmaceuticals usa inc
  • Prometheus laboratories inc
  • Bedford laboratories div ben venue laboratories inc
Packagers
Dosage forms
FormRouteStrength
TabletOral100 mg/1
TabletOral75 mg/1
TabletOral50 mg/1
TabletOral50 1/1
Injection, powder, lyophilized, for solutionIntravenous100 mg/10mL
Powder, for solutionIntravenous50 mg
Powder, for solutionIntravenous100 mg
TabletOral50 mg
Prices
Unit descriptionCostUnit
Azathioprine sod 100 mg vial132.0USD vial
Azathioprine powder28.15USD g
Azasan 100 mg tablet5.8USD tablet
Azasan 75 mg tablet4.34USD tablet
Imuran 50 mg Tablet2.76USD tablet
Azathioprine 50 mg tablet0.94USD tablet
Apo-Azathioprine 50 mg Tablet0.57USD tablet
Mylan-Azathioprine 50 mg Tablet0.57USD tablet
Novo-Azathioprine 50 mg Tablet0.57USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)243.5 °CPhysProp
water solubilityInsoluble FDA label
logP0.10HANSCH,C ET AL. (1995)
pKa7.87 (at 25 °C)MITRA,AK & NARURKAR,MM (1986)
Predicted Properties
PropertyValueSource
Water Solubility1.07 mg/mLALOGPS
logP0.84ALOGPS
logP1.17ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)8.65ChemAxon
pKa (Strongest Basic)4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area118.1 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity70.95 m3·mol-1ChemAxon
Polarizability24.26 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9607
Blood Brain Barrier+0.9226
Caco-2 permeable+0.5057
P-glycoprotein substrateNon-substrate0.7766
P-glycoprotein inhibitor INon-inhibitor0.8049
P-glycoprotein inhibitor IINon-inhibitor0.6683
Renal organic cation transporterNon-inhibitor0.8493
CYP450 2C9 substrateNon-substrate0.7861
CYP450 2D6 substrateNon-substrate0.8273
CYP450 3A4 substrateNon-substrate0.5944
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9733
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7
Ames testAMES toxic0.9152
CarcinogenicityNon-carcinogens0.9182
BiodegradationNot ready biodegradable0.9576
Rat acute toxicity2.7519 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7434
hERG inhibition (predictor II)Non-inhibitor0.8449
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , PositiveNot Available
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , PositiveNot Available
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-0390000000-0d11d23373539cfb283cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000x-0950000000-b6de6073310270167ffbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001l-2950000000-4d3fb67844876c217814View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diarylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two aryl groups.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThioethers
Sub ClassAryl thioethers
Direct ParentDiarylthioethers
Alternative Parents6-thiopurines / Nitroimidazoles / Nitroaromatic compounds / Pyrimidines and pyrimidine derivatives / Imidolactams / N-substituted imidazoles / Heteroaromatic compounds / Sulfenyl compounds / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds
SubstituentsDiarylthioether / 6-thiopurine / Imidazopyrimidine / Purine / Nitroaromatic compound / Nitroimidazole / N-substituted imidazole / Imidolactam / Pyrimidine / Azole
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsC-nitro compound, aryl sulfide, imidazoles, thiopurine (CHEBI:2948 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Protein homodimerization activity
Specific Function:
Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway.
Gene Name:
HPRT1
Uniprot ID:
P00492
Uniprot Name:
Hypoxanthine-guanine phosphoribosyltransferase
Molecular Weight:
24579.155 Da
References
  1. Anstey A, Lear JT: Azathioprine: clinical pharmacology and current indications in autoimmune disorders. BioDrugs. 1998 Jan;9(1):33-47. [PubMed:18020555 ]
  2. Dubinsky MC: Azathioprine, 6-mercaptopurine in inflammatory bowel disease: pharmacology, efficacy, and safety. Clin Gastroenterol Hepatol. 2004 Sep;2(9):731-43. [PubMed:15354273 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Thioesterase binding
Specific Function:
Plasma membrane-associated small GTPase which cycles between active GTP-bound and inactive GDP-bound states. In its active state, binds to a variety of effector proteins to regulate cellular responses such as secretory processes, phagocytosis of apoptotic cells, epithelial cell polarization and growth-factor induced formation of membrane ruffles. Rac1 p21/rho GDI heterodimer is the active compo...
Gene Name:
RAC1
Uniprot ID:
P63000
Uniprot Name:
Ras-related C3 botulinum toxin substrate 1
Molecular Weight:
21449.895 Da
References
  1. Tiede I, Fritz G, Strand S, Poppe D, Dvorsky R, Strand D, Lehr HA, Wirtz S, Becker C, Atreya R, Mudter J, Hildner K, Bartsch B, Holtmann M, Blumberg R, Walczak H, Iven H, Galle PR, Ahmadian MR, Neurath MF: CD28-dependent Rac1 activation is the molecular target of azathioprine in primary human CD4+ T lymphocytes. J Clin Invest. 2003 Apr;111(8):1133-45. [PubMed:12697733 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Thiopurine s-methyltransferase activity
Specific Function:
Catalyzes the S-methylation of thiopurine drugs such as 6-mercaptopurine.
Gene Name:
TPMT
Uniprot ID:
P51580
Uniprot Name:
Thiopurine S-methyltransferase
Molecular Weight:
28180.09 Da
References
  1. Sahasranaman S, Howard D, Roy S: Clinical pharmacology and pharmacogenetics of thiopurines. Eur J Clin Pharmacol. 2008 Aug;64(8):753-67. doi: 10.1007/s00228-008-0478-6. Epub 2008 May 28. [PubMed:18506437 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Xanthine oxidase activity
Specific Function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Uniprot Name:
Xanthine dehydrogenase/oxidase
Molecular Weight:
146422.99 Da
References
  1. Dubinsky MC: Azathioprine, 6-mercaptopurine in inflammatory bowel disease: pharmacology, efficacy, and safety. Clin Gastroenterol Hepatol. 2004 Sep;2(9):731-43. [PubMed:15354273 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Glutathione transferase activity
Specific Function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTA1
Uniprot ID:
P08263
Uniprot Name:
Glutathione S-transferase A1
Molecular Weight:
25630.785 Da
References
  1. Link [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Glutathione transferase activity
Specific Function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTA2
Uniprot ID:
P09210
Uniprot Name:
Glutathione S-transferase A2
Molecular Weight:
25663.675 Da
References
  1. Link [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Protein homodimerization activity
Specific Function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTM1
Uniprot ID:
P09488
Uniprot Name:
Glutathione S-transferase Mu 1
Molecular Weight:
25711.555 Da
References
  1. Link [Link]
Drug created on June 13, 2005 07:24 / Updated on September 01, 2017 15:53