azathioprine indications/contra

Stem definitionDrug idCAS RN
269 446-86-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • BW 57-322
  • azathioprine sulfate
  • azathioprine
  • azamune
  • azanin
  • azathioprin
  • azathropine
  • azothioprine
  • azathioprine sodium
An immunosuppressive agent used in combination with cyclophosphamide and hydroxychloroquine in the treatment of rheumatoid arthritis. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance has been listed as a known carcinogen. (Merck Index, 11th ed)
  • Molecular weight: 277.26
  • Formula: C9H7N7O2S
  • CLOGP: 0.51
  • LIPINSKI: 0
  • HAC: 9
  • HDO: 1
  • TPSA: 115.42
  • ALOGS: -2.41
  • ROTB: 3

Drug dosage:

DoseUnitRoute
0.15 g O
0.15 g P

Approvals:

DateAgencyCompanyOrphan
March 20, 1968 FDA PROMETHEUS LABS

FDA Adverse Event Reporting System

scroll-->
MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Pancytopenia 907.72 30.26 306 6980 18514 3360059
Drug ineffective 800.99 30.26 481 6805 115609 3262964
Pyrexia 720.72 30.26 397 6889 80718 3297855
Leukopenia 640.49 30.26 226 7060 15597 3362976
Post transplant lymphoproliferative disorder 636.34 30.26 122 7164 646 3377927
Exposure during pregnancy 605.27 30.26 252 7034 27311 3351262
Sepsis 601.93 30.26 263 7023 32110 3346463
Epstein-Barr virus infection 600.05 30.26 133 7153 1565 3377008
Cytomegalovirus infection 591.59 30.26 159 7127 4348 3374225
Crohn's disease 526.13 30.26 165 7121 7851 3370722
Diffuse large B-cell lymphoma 478.69 30.26 106 7180 1239 3377334
Kaposi's sarcoma 466.55 30.26 96 7190 766 3377807
Pneumonia 466.05 30.26 285 7001 69858 3308715
Foetal exposure during pregnancy 436.84 30.26 170 7116 15381 3363192
Histiocytosis haematophagic 397.55 30.26 99 7187 1977 3376596
Hepatosplenic T-cell lymphoma 397.34 30.26 65 7221 101 3378472
Premature baby 384.44 30.26 127 7159 7126 3371447
Maternal exposure during pregnancy 374.55 30.26 136 7150 10135 3368438
Bone marrow failure 372.61 30.26 129 7157 8358 3370215
Squamous cell carcinoma 360.60 30.26 96 7190 2518 3376055
Pancreatitis 321.11 30.26 133 7153 14112 3364461
Drug intolerance 313.53 30.26 124 7162 11674 3366899
Off label use 311.56 30.26 201 7085 53776 3324797
Basal cell carcinoma 305.06 30.26 92 7194 3817 3374756
Epstein-Barr virus associated lymphoproliferative disorder 303.28 30.26 63 7223 528 3378045
Anaemia 302.96 30.26 198 7088 54135 3324438
Kidney transplant rejection 302.77 30.26 76 7210 1567 3377006
Renal impairment 295.64 30.26 135 7151 18126 3360447
Multiple organ dysfunction syndrome 289.55 30.26 124 7162 14286 3364287
Pneumocystis jirovecii pneumonia 277.76 30.26 85 7201 3705 3374868

Pharmacologic Action:

scroll-->
SourceCodeDescription
ATC L04AX01 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
IMMUNOSUPPRESSANTS
IMMUNOSUPPRESSANTS
Other immunosuppressants
FDA MoA N0000000233 Nucleic Acid Synthesis Inhibitors
FDA Chemical/Ingredient N0000175459 Nucleoside Analog
FDA EPC N0000175712 Purine Antimetabolite
FDA Chemical/Ingredient N0000008065 Purines
MeSH PA D000963 Antimetabolites
MeSH PA D000964 Antimetabolites, Antineoplastic
MeSH PA D000970 Antineoplastic Agents
MeSH PA D018501 Antirheumatic Agents
MeSH PA D007155 Immunologic Factors
MeSH PA D007166 Immunosuppressive Agents
MeSH PA D009676 Noxae

Drug Use (View source of the data)

scroll-->
DiseaseRelationSNOMED_IDDOID
Rheumatoid arthritis indication 69896004 DOID:7148
Prevention of Kidney Transplant Rejection indication
Mycosis contraindication 3218000 DOID:1564
Viral disease contraindication 34014006 DOID:934
Hepatic vein thrombosis contraindication 38739001 DOID:11512
Bacterial infectious disease contraindication 87628006 DOID:104
Malignant lymphoma contraindication 118600007 DOID:0060058
Liver function tests abnormal contraindication 166603001
Acute pancreatitis contraindication 197456007 DOID:2913
Impaired renal function disorder contraindication 197663003
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Bone marrow depression contraindication 307762000
Hepatosplenic T-cell lymphoma contraindication 445406001
Protozoal Infection contraindication
Severe Leukopenia contraindication
Thiopurine S-Methyltransferase Deficiency contraindication
Polymyositis off-label use 31384009
Crohn's disease off-label use 34000006
Systemic lupus erythematosus off-label use 55464009 DOID:9074
Ulcerative colitis off-label use 64766004 DOID:8577
Pemphigus off-label use 65172003 DOID:9182
Autoimmune hepatitis off-label use 408335007 DOID:2048
Systemic Dermatomyositis off-label use
Prevention of Cardiac Transplant Rejection off-label use
Prevention of Liver Transplant Rejection off-label use
Prevention of Lung Transplant Rejection off-label use

Acid dissociation constants calculated using MoKa v3.0.0

scroll-->
Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.28 acidic
pKa2 3.24 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

scroll-->
TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Thiopurine S-methyltransferase Enzyme WOMBAT-PK
Ras-related C3 botulinum toxin substrate 1 Unclassified WOMBAT-PK
Multidrug resistance-associated protein 4 Transporter WOMBAT-PK
Multidrug resistance-associated protein 5 Transporter WOMBAT-PK
ATP-binding cassette sub-family G member 2 Transporter WOMBAT-PK
DNA DNA OTHER DRUG LABEL SCIENTIFIC LITERATURE
RNA RNA OTHER DRUG LABEL SCIENTIFIC LITERATURE

External reference:

scroll-->
IDSource
4018766 VUID
N0000147069 NUI
C0004482 UMLSCUI
7120 IUPHAR_LIGAND_ID
D00238 KEGG_DRUG
DB00993 DRUGBANK_ID
2265 PUBCHEM_CID
4018766 VANDF
N0000005799 NDFRT
N0000147069 NDFRT
1256 RXNORM
6041 MMSL
d00024 MMSL
111165009 SNOMEDCT_US
372574004 SNOMEDCT_US
4234 MMSL
003419 NDDF
AM94R510MS UNII
55774-33-9 SECONDARY_CAS_RN
CHEMBL1542 ChEMBL_ID
CHEMBL1200400 ChEMBL_ID
1291 INN_ID
D001379 MESH_DESCRIPTOR_UI

Pharmaceutical products:

scroll-->
ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Azathioprine Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0143-9566 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 100 mg INTRAVENOUS ANDA 13 sections
Azathioprine HUMAN PRESCRIPTION DRUG LABEL 1 0378-1005 TABLET 50 mg ORAL ANDA 13 sections
Azathioprine HUMAN PRESCRIPTION DRUG LABEL 1 0615-7568 TABLET 50 mg ORAL ANDA 11 sections
Azathioprine HUMAN PRESCRIPTION DRUG LABEL 1 21695-484 TABLET 50 mg ORAL ANDA 14 sections
Azathioprine HUMAN PRESCRIPTION DRUG LABEL 1 33261-758 TABLET 50 mg ORAL ANDA 14 sections
Azathioprine HUMAN PRESCRIPTION DRUG LABEL 1 43353-686 TABLET 50 mg ORAL ANDA 13 sections
Azathioprine HUMAN PRESCRIPTION DRUG LABEL 1 43353-745 TABLET 50 mg ORAL ANDA 14 sections
Azathioprine HUMAN PRESCRIPTION DRUG LABEL 1 51079-620 TABLET 50 mg ORAL ANDA 13 sections
IMURAN HUMAN PRESCRIPTION DRUG LABEL 1 54766-590 TABLET 50 mg ORAL NDA 14 sections
Azathioprine HUMAN PRESCRIPTION DRUG LABEL 1 54868-5310 TABLET 50 mg ORAL ANDA 14 sections
Azathioprine HUMAN PRESCRIPTION DRUG LABEL 1 55154-4953 TABLET 50 mg ORAL ANDA 12 sections
AZATHIOPRINE HUMAN PRESCRIPTION DRUG LABEL 1 60219-1076 TABLET 50 mg ORAL ANDA 13 sections
IMURAN HUMAN PRESCRIPTION DRUG LABEL 1 65483-590 TABLET 50 mg ORAL NDA 14 sections
Azasan HUMAN PRESCRIPTION DRUG LABEL 1 65649-231 TABLET 75 mg ORAL ANDA 13 sections
Azasan HUMAN PRESCRIPTION DRUG LABEL 1 65649-241 TABLET 100 mg ORAL ANDA 13 sections
Azathioprine HUMAN PRESCRIPTION DRUG LABEL 1 65841-602 TABLET 50 mg ORAL ANDA 14 sections
Azathioprine HUMAN PRESCRIPTION DRUG LABEL 1 68084-229 TABLET 50 mg ORAL ANDA 14 sections
Azathioprine HUMAN PRESCRIPTION DRUG LABEL 1 68382-003 TABLET 50 1 ORAL ANDA 14 sections
Azathioprine HUMAN PRESCRIPTION DRUG LABEL 1 68382-120 TABLET 100 1 ORAL ANDA 14 sections
Azathioprine HUMAN PRESCRIPTION DRUG LABEL 1 68462-502 TABLET 50 mg ORAL ANDA 13 sections
Azathioprine HUMAN PRESCRIPTION DRUG LABEL 1 69189-0465 TABLET 50 1 ORAL ANDA 14 sections
AZATHIOPRINE HUMAN PRESCRIPTION DRUG LABEL 1 69238-1076 TABLET 50 mg ORAL ANDA 13 sections
Azathioprine HUMAN PRESCRIPTION DRUG LABEL 1 70771-1141 TABLET 100 1 ORAL ANDA 14 sections