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    Chemistry

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    Also known as: 446-86-6, Imuran, Azothioprine, Azathioprin, Azatioprin, Azamun
    Molecular Formula
    C9H7N7O2S
    Molecular Weight
    277.27  g/mol
    InChI Key
    LMEKQMALGUDUQG-UHFFFAOYSA-N
    FDA UNII
    MRK240IY2L
    Azathioprine
    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)
    Azathioprine is a Purine Antimetabolite. The mechanism of action of azathioprine is as a Nucleic Acid Synthesis Inhibitor.
    1 2D Structure

    Azathioprine

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    6-(3-methyl-5-nitroimidazol-4-yl)sulfanyl-7H-purine
    2.1.2 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)
    2.1.3 InChI Key
    LMEKQMALGUDUQG-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN1C=NC(=C1SC2=NC=NC3=C2NC=N3)[N+](=O)[O-]
    2.2 Other Identifiers
    2.2.1 UNII
    MRK240IY2L
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Azathioprine Sodium

    2. Azathioprine Sodium Salt

    3. Azathioprine Sulfate

    4. Azothioprine

    5. Immuran

    6. Imuran

    7. Imurel

    8. Sodium, Azathioprine

    2.3.2 Depositor-Supplied Synonyms

    1. 446-86-6

    2. Imuran

    3. Azothioprine

    4. Azathioprin

    5. Azatioprin

    6. Azamun

    7. Azanin

    8. Azasan

    9. Imurel

    10. Azathiopurine

    11. Ccucol

    12. Imurek

    13. Muran

    14. Rorasul

    15. Bw 57-322

    16. Azathioprinum

    17. Nsc-39084

    18. Bw-57-322

    19. 6-(1-methyl-4-nitroimidazol-5-yl)thiopurine

    20. Nci-c03474

    21. 6-[(1-methyl-4-nitro-1h-imidazol-5-yl)sulfanyl]-7h-purine

    22. Imuran (tn)

    23. Nsc 39084

    24. 6-(1-methyl-p-nitro-5-imidazolyl)-thiopurine

    25. 6-((1-methyl-4-nitroimidazol-5-yl)thio)purine

    26. 6-((1-methyl-4-nitro-1h-imidazol-5-yl)thio)-1h-purine

    27. 6-(1'-methyl-4'-nitro-5'-imidazolyl)-mercaptopurine

    28. 6-((1-methyl-4-nitro-1h-imidazol-5-yl)thio)-9h-purine

    29. Azathioprine (azasan, Imuran)

    30. 1h-purine, 6-((1-methyl-4-nitro-1h-imidazol-5-yl)thio)-

    31. Purine, 6-(1-methyl-4-nitro-5-imidazolylthio)-

    32. 6-(3-methyl-5-nitroimidazol-4-yl)sulfanyl-7h-purine

    33. 6-(methyl-p-nitro-5-imidazolyl)-thiopurine

    34. 1h-purine, 6-[(1-methyl-4-nitro-1h-imidazol-5-yl)thio]-

    35. Mrk240iy2l

    36. Bw 57322

    37. Azamun [czech]

    38. 6-((1-methyl-4-nitro-1h-imidazol-5-yl)thio)-7h-purine

    39. Chebi:2948

    40. B. W. 57-322

    41. Nsc39084

    42. 6-(1'-methyl-4'-nitro-5'-imidazolyl)mercaptopurine

    43. Purine, 6-((1-methyl-4-nitroimidazol-5-yl)thio)-

    44. 6-[(1-methyl-4-nitro-1h-imidazol-5-yl)thio]-7h-purine

    45. 6-[(1-methyl-4-nitro-1h-imidazol-5-yl)thio]-9h-purine

    46. Ncgc00015060-06

    47. Ncgc00015060-14

    48. Azatioprina

    49. Cas-446-86-6

    50. Dsstox_cid_119

    51. 6-[(1-methyl-4-nitroimidazol-5-yl)thio]purine

    52. Dsstox_rid_75381

    53. Dsstox_gsid_20119

    54. Azathioprinum [inn-latin]

    55. Azatioprina [inn-spanish]

    56. Azamune

    57. Methylnitroimidazolylmercaptopurine

    58. Ccris 62

    59. Azasan (tn)

    60. Hsdb 7084

    61. Sr-01000075537

    62. Purine, 6-[(1-methyl-4-nitroimidazol-5-yl)thio]-

    63. Einecs 207-175-4

    64. Mfcd00069203

    65. Unii-mrk240iy2l

    66. 6-(1-methyl-4-nitro-1h-imidazol-5-ylthio)-9h-purine

    67. 6-1'-methyl,4'-nitro,5'-imidazolyl Mercaptopurine

    68. Azanine

    69. 6-(1-methyl-4-nitroimidazol-5-ylthio)purin [czech]

    70. Azothioprin

    71. Jayempi

    72. Azoran

    73. Ai3-50290

    74. 6-(1-methyl-4-nitroimidazol-5-ylthio)purin

    75. Prestwick_41

    76. Azathiopurine,(s)

    77. [methyl(nitroimidazolyl)mercaptopurine]

    78. Azathioprine [usan:usp:inn:ban:jan]

    79. Spectrum_000064

    80. Azathioprine, >=98%

    81. 6-(methyl-p-nitro-5-imidazolyl)thiopurine

    82. Prestwick0_000094

    83. Prestwick1_000094

    84. Prestwick2_000094

    85. Prestwick3_000094

    86. Spectrum2_000068

    87. Spectrum3_000308

    88. Spectrum4_000243

    89. Spectrum5_000848

    90. Azathioprine [mi]

    91. Lopac-a-4638

    92. Chemdiv1_002659

    93. 6-(1-methyl-p-nitro-5-imidazolyl)thiopurine

    94. Azathioprine [inn]

    95. Azathioprine [jan]

    96. A 4638

    97. Azathioprine [hsdb]

    98. Azathioprine [iarc]

    99. Azathioprine [usan]

    100. Thiopurine 6-(1-methyl-4-nitroimidazol-5-yl)

    101. Schembl4278

    102. Azathioprine [vandf]

    103. Chembl1542

    104. Lopac0_000027

    105. Oprea1_375441

    106. Oprea1_533384

    107. Oprea1_633462

    108. Azathioprine [mart.]

    109. Bspbio_000048

    110. Bspbio_001876

    111. Cbdive_013132

    112. Kbiogr_000646

    113. Kbiogr_002427

    114. Kbioss_000464

    115. Kbioss_002433

    116. Ai-981/34845012

    117. Mls001049307

    118. Azathioprine [usp-rs]

    119. Azathioprine [who-dd]

    120. Azathioprine [who-ip]

    121. Divk1c_000586

    122. Spectrum1500133

    123. Spbio_000255

    124. Spbio_001987

    125. Bpbio1_000054

    126. Gtpl7120

    127. Dtxsid4020119

    128. Azathioprine (jp17/usp/inn)

    129. Hms501n08

    130. Hms594i19

    131. Kbio1_000586

    132. Kbio2_000464

    133. Kbio2_002427

    134. Kbio2_003032

    135. Kbio2_004995

    136. Kbio2_005600

    137. Kbio2_007563

    138. Kbio3_001376

    139. Kbio3_002906

    140. Cmap_000046

    141. Ninds_000586

    142. 6-({4-nitro-1-methyl-1h-imidazol-5-yl}sulfanyl)-7h-purine

    143. 6-[(1-methyl-4-nitro-1h-imidazol-5-yl)sulfanyl]-1h-purine

    144. Azathioprine [ep Impurity]

    145. Azathioprine [orange Book]

    146. Hms1568c10

    147. Hms1920e17

    148. Hms2091k19

    149. Hms2095c10

    150. Hms2802j03

    151. Hms3259p03

    152. Hms3260e15

    153. Hms3655m04

    154. Hms3712c10

    155. Pharmakon1600-01500133

    156. Azathioprine [ep Monograph]

    157. Act02232

    158. Bcp09492

    159. Hy-b0256

    160. Zinc4258316

    161. Azathioprine [usp Monograph]

    162. Tox21_110074

    163. Tox21_400024

    164. Tox21_500027

    165. Azathioprinum [who-ip Latin]

    166. Bdbm50373919

    167. Ccg-16168

    168. Ccg-39877

    169. Nsc755900

    170. S1721

    171. Stk831906

    172. Akos005609209

    173. Akos028108935

    174. Tox21_110074_1

    175. Ac-4230

    176. Ccg-220094

    177. Db00993

    178. Ks-1146

    179. Lp00027

    180. Nc00614

    181. Nsc-755900

    182. Sdccgmls-0065415.p001

    183. Sdccgsbi-0050016.p005

    184. Idi1_000586

    185. Ncgc00015060-01

    186. Ncgc00015060-02

    187. Ncgc00015060-03

    188. Ncgc00015060-04

    189. Ncgc00015060-05

    190. Ncgc00015060-07

    191. Ncgc00015060-08

    192. Ncgc00015060-09

    193. Ncgc00015060-10

    194. Ncgc00015060-11

    195. Ncgc00015060-12

    196. Ncgc00015060-13

    197. Ncgc00015060-15

    198. Ncgc00015060-16

    199. Ncgc00015060-18

    200. Ncgc00015060-19

    201. Ncgc00015060-29

    202. Ncgc00090836-01

    203. Ncgc00090836-02

    204. Ncgc00090836-03

    205. Ncgc00090836-04

    206. Ncgc00090836-05

    207. Ncgc00090836-06

    208. Ncgc00094593-01

    209. Ncgc00094593-02

    210. Ncgc00094593-03

    211. Ncgc00260712-01

    212. Ba166065

    213. Smr000427366

    214. 6-1'-methyl,5'-imidazolyl Mercaptopurine

    215. Sbi-0050016.p003

    216. Azathioprine 100 Microg/ml In Acetonitrile

    217. 6-(1-methyl-4-nitromidazol-5-ylthio)purine

    218. Ab00443544

    219. Eu-0100027

    220. Ft-0602904

    221. Ft-0662375

    222. Sw198560-2

    223. 6-(1-methyl-4-nitroimidazol-5-ylthio)purine

    224. Azathioprine, Meets Usp Testing Specifications

    225. C06837

    226. D00238

    227. D70170

    228. Q18939

    229. Ab00443544-03

    230. Ab00443544-11

    231. Ab00443544_12

    232. Ab00443544_13

    233. 055a974

    234. 446a866

    235. A826664

    236. Sr-01000762955

    237. 6-(1-methyl-4-nitro-5-imidazolythio)-9h-pur-ine

    238. Sr-01000075537-1

    239. Sr-01000075537-4

    240. Sr-01000762955-2

    241. Brd-k32821942-001-05-6

    242. Brd-k32821942-001-10-6

    243. Brd-k60324116-001-01-5

    244. Wln: T56 Bm Dn Fn Hnj Is- Et5n Cnj A1 Dnw

    245. Z57063156

    246. 6-((1-methyl-4-nitro-1h-imidazol-5-yl)thio)-1h-purin

    247. 6-(3-methyl-5-nitro-imidazol-4-yl)sulfanyl-9h-purine

    248. 6-[(1-methyl-4-nitro-1h-imidazol-5-yl)sulfanyl]-9h-purine

    249. 9h-purine, 6-[(1-methyl-4-nitro-1h-imidazol-5-yl)thio]-

    250. Azathioprine, European Pharmacopoeia (ep) Reference Standard

    251. 1h-purine, 6-((1-methyl-4-nitro-1h-imidazol-5-yl)thio)

    252. 6-[(1-methyl-4-nitro-1h-imidazol-5-yl)sulfanyl]-1h-purine #

    253. Azathioprine, United States Pharmacopeia (usp) Reference Standard

    254. Azathioprine, Pharmaceutical Secondary Standard; Certified Reference Material

    255. 6-((1-methyl-4-nitroimidazol-5-yl)thio)purine6-((1-methyl-4-nitro-1h-imidazol-5-yl)thio)-1h-purine

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 277.27 g/mol
    Molecular Formula C9H7N7O2S
    XLogP30.1
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count2
    Exact Mass277.03819367 g/mol
    Monoisotopic Mass277.03819367 g/mol
    Topological Polar Surface Area143 Ų
    Heavy Atom Count19
    Formal Charge0
    Complexity354
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 8  
    Drug NameAzasan
    PubMed HealthAzathioprine (By mouth)
    Drug ClassesAntirheumatic, Cytotoxic, Gastrointestinal Agent
    Drug LabelAZASAN, an immunosuppressive antimetabolite, is available in tablet form for oral administration. Each scored tablet contains75mg or 100 mg azathioprine and the inactive ingredients lactose monohydrate, pregelatinized starch,povidone, corn st...
    Active IngredientAzathioprine
    Dosage FormTablet
    RouteOral
    Strength75mg; 100mg; 25mg; 50mg
    Market StatusPrescription
    CompanyAaipharma

    2 of 8  
    Drug NameAzathioprine
    PubMed HealthAzathioprine
    Drug ClassesAntirheumatic, Cytotoxic, Gastrointestinal Agent
    Drug LabelAzathioprine is an immunosuppressive antimetabolite. Each uncoated azathioprine tablet intended for oral administration contains 50 mg of azathioprine. In addition, each tablet contains the following inactive ingredients: croscarmellose sodium, lacto...
    Active IngredientAzathioprine
    Dosage FormTablet
    RouteOral
    Strength75mg; 100mg; 25mg; 50mg
    Market StatusPrescription
    CompanyZydus Pharms Usa; Mylan; Roxane

    3 of 8  
    Drug NameAzathioprine sodium
    PubMed HealthAzathioprine
    Drug ClassesAntirheumatic, Cytotoxic, Gastrointestinal Agent
    Drug LabelIMURAN (azathioprine), an immunosuppressive antimetabolite, is available in tablet form for oral administration. Each scored tablet contains 50mg azathioprine and the inactive ingredients lactose, magnesium stearate, potato starch, povidone, and st...
    Active IngredientAzathioprine sodium
    Dosage FormInjectable
    RouteInjection
    Strengtheq 100mg base/vial
    Market StatusPrescription
    CompanyEurohlth Intl

    4 of 8  
    Drug NameImuran
    Active IngredientAzathioprine
    Dosage FormTablet
    RouteOral
    Strength50mg
    Market StatusPrescription
    CompanyPrometheus Labs

    5 of 8  
    Drug NameAzasan
    PubMed HealthAzathioprine (By mouth)
    Drug ClassesAntirheumatic, Cytotoxic, Gastrointestinal Agent
    Drug LabelAZASAN, an immunosuppressive antimetabolite, is available in tablet form for oral administration. Each scored tablet contains75mg or 100 mg azathioprine and the inactive ingredients lactose monohydrate, pregelatinized starch,povidone, corn st...
    Active IngredientAzathioprine
    Dosage FormTablet
    RouteOral
    Strength75mg; 100mg; 25mg; 50mg
    Market StatusPrescription
    CompanyAaipharma

    6 of 8  
    Drug NameAzathioprine
    PubMed HealthAzathioprine
    Drug ClassesAntirheumatic, Cytotoxic, Gastrointestinal Agent
    Drug LabelAzathioprine is an immunosuppressive antimetabolite. Each uncoated azathioprine tablet intended for oral administration contains 50 mg of azathioprine. In addition, each tablet contains the following inactive ingredients: croscarmellose sodium, lacto...
    Active IngredientAzathioprine
    Dosage FormTablet
    RouteOral
    Strength75mg; 100mg; 25mg; 50mg
    Market StatusPrescription
    CompanyZydus Pharms Usa; Mylan; Roxane

    7 of 8  
    Drug NameAzathioprine sodium
    PubMed HealthAzathioprine
    Drug ClassesAntirheumatic, Cytotoxic, Gastrointestinal Agent
    Drug LabelIMURAN (azathioprine), an immunosuppressive antimetabolite, is available in tablet form for oral administration. Each scored tablet contains 50mg azathioprine and the inactive ingredients lactose, magnesium stearate, potato starch, povidone, and st...
    Active IngredientAzathioprine sodium
    Dosage FormInjectable
    RouteInjection
    Strengtheq 100mg base/vial
    Market StatusPrescription
    CompanyEurohlth Intl

    8 of 8  
    Drug NameImuran
    Active IngredientAzathioprine
    Dosage FormTablet
    RouteOral
    Strength50mg
    Market StatusPrescription
    CompanyPrometheus Labs

    4.2 Therapeutic Uses

    Azathioprine also is indicated in the treatment of other immunological diseases including regional and ulcerative colitis, biliary cirrhosis, systemic dermatomyositis (polymyositis), glomerulonephritis, chronic active hepatitis, systemic lupus erythematosus (SLE), inflammatory myopathy, myasthenia gravis, nephrotic syndrome, pemphigus and pemphigoid. /NOT included in US product labeling/

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 509

    Azathioprine is indicated for the management of severe, active, and erosive rheumatoid arthritis unresponsive to rest or conventional medications. /Included in US product labeling/

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 509

    It /azathioprine/ is also also indicated in the prevention of rejection in cardiac, hepatic, and pancreatic transplantation. /NOT included in US product labeling/

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 509

    Azathioprine is indicated as an adjunct for prevention of rejection in renal homotransplantation. /Included in US product labeling/

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 509

    For more Therapeutic Uses (Complete) data for AZATHIOPRINE (12 total), please visit the HSDB record page.

    4.3 Drug Warning

    Azathioprine is a toxic drug and must be used only under close medical supervision. Other immunosuppressive therapy given concomitantly with azathioprine therapy may increase the toxic potential of the drug.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 3592

    Azathioprine may also cause rash, infection, drug fever, serum sickness, alopecia, arthralgia, retinopathy, Raynaud's disease, and pulmonary edema. Some of these adverse effects can occur as manifestations of rare hypersensitivity reactions. Azathioprine-induced hypersensitivity reactions are often characterized by a combination of symptoms, including fever, rigors, musculuskeletal symptoms (arthralgias, myalgias), and/or cutaneous effects (generalized erythematous or maculopapular rash with nonspecific inflammatory changes demonstrated on biopsy); pulmonary manifestations (eg, cough and/or dyspnea) and hypotension (which may be severe and, in the presence of fever, mimic septic shock) may also occur.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 3591

    Hepatotoxicity manifested by increased serum alkaline phosphatase, bilirubin, and/or aminotransferase concentrations may occur in patients receiving azathioprine, principally in allograft recipients. Azathioprine-induced hepatotoxicity following transplantation occurs most frequently within 6 months of transplantation and is generally reversible following discontinuance of the drug. Rare, but life-threatening hepatic veno-occlusive disease has occurred during chronic azathioprine therapy in several renal allograft recipients and in a patient with panuveitis; serious complications, including progressive portal hypertension, progressive liver failure requiring a portacaval shunt, progressive chronic liver failure with portal hypertension and esophageal varices, and/or rapid deterioration resulting in death, occurred in most of these patients. Veno-occlusive disease was associated with cytomegalovirus infection in some of these patients and with use of azathioprine but not with dosage of the drug, type or duration of renal allograft, or type of underlying renal disease. Reports to date suggest that the onset of hepatic veno-occlusive disease generally occurs after 1-2 years of therapy and that the disease occur principally in males. The clinical syndrome is usually manifested initially by jaundice, often followed by the development of ascites and other signs of partal hypertension. Serum alkaline phosphatase and bilirubin concentrations are usually elevated. Prognosis is poor. Because hepatic veno-occlusive disease may result in rapid clincial deterioration, prompt diagnosis and therapeutic intervention are necessary. Many clinicians suggest that liver biopsy to diagnose veno-occlusive disease should be performed in renal allograft recipients receiving azathioprine at the first sign of mild hepatic dysfunction. If veno-occlusive disease is evident, azathioprine therapy should be promptly and permanently discontinued; alternative immunosuppressive therapy should be considered and, if liver failure is progressive anticoagulation, a partacaval shunt, or hepatic allotransplantation should be considered. Hepatotoxicity occurs in less than 1% of patients with rheumatoid arthritis who receive azathioprine.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 3591

    Nausea, vomiting, anorexia, and diarrhea may occur in patients receiving large doses of azathioprine. Adverse GI effects may be minimized by giving the drug in divided doses and/or after meals. Vomiting with abdominal pain may occur rarely with a hypersensitivity pancreatitis. A GI hypersensitivity reaction characterized by severe nausea and vomiting has been reported. This reaction also may be accompanied by diarrhea, rash, fever, malaise, myalgias, elevations in liver enzymes, and, occasionally, hypotension. Symptoms of GI toxicity most often develop within the first several weeks of azathioprine therapy and are reversible upon discontinuance of the drug. The reaction can occur within several hours after rechallange with a single dose of the drug. Other adverse GI effects include ulceration of the mucous membranes of the mouth, esophagitis with possible ulceration, and steatorrhea.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 3591

    For more Drug Warnings (Complete) data for AZATHIOPRINE (33 total), please visit the HSDB record page.

    4.4 Drug Indication

    Azathioprine is indicated to treat rheumatoid arthritis and prevent renal transplant rejection.

    FDA Label

    Jayempi is indicated in combination with other immunosuppressive agents for the prophylaxis of transplant rejection in patients receiving allogenic kidney, liver, heart, lung or pancreas transplants. Azathioprine is indicated in immunosuppressive regimens as an adjunct to immunosuppressive agents that form the mainstay of treatment (basis immunosuppression).

    Jayempi is used as an immunosuppressant antimetabolite either alone or, more commonly, in combination with other agents (usually corticosteroids) and/ or procedures which influence the immune response.

    Jayempi is indicated in patients who are intolerant to glucocorticosteroids or if the therapeutic response is inadequate despite treatment with high doses of glucocorticosteroids, in the following diseases:

    - severe active rheumatoid arthritis (chronic polyarthritis ) that cannot be kept under control by less toxic agents (disease-modifying anti-rheumatic -medicinal products DMARDs)

    - auto-immune hepatitis

    - systemic lupus erythematosus

    - dermatomyositis

    - polyarteritis nodosa

    - pemphigus vulgaris and bullous pemphigoid

    - Behets disease

    - refractory auto-immune haemolytic anaemia, caused by warm IgG antibodies

    - chronic refractory idiopathic thrombocytopenic purpura

    Jayempi is used for the treatment of moderately severe to severe forms of chronic inflammatory bowel disease (IBD) (Crohns disease or ulcerative colitis) in patients in whom glucocorticosteroid therapy is necessary, but where glucocorticosteroids are not tolerated, or in whom the disease is untreatable with other common means of first choice.

    It is also indicated in adult patients in relapsing multiple sclerosis, if an immunomodulatory therapy is indicated but beta interferon therapy is not possible, or a stable course has been achieved with previous treatment with azathioprine. 3

    Jayempi is indicated for the treatment of generalised myasthenia gravis. Depending on the severity of the disease, Jayempi should be given in combination with glucocorticosteroids because of slow onset of action at the beginning of treatment and the glucocorticosteroid dose should be gradually reduced after several months of treatment.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Azathioprine is an immunosuppressive agent which functions through modulation of rac1 to induce T cell apoptosis, as well as other unknown immunosuppressive functions. It has a long duration of action as it is given daily, and has a narrow therapeutic index. Patients should be counselled regarding the risk of malignancies of the skin and lymphomas.

    5.2 MeSH Pharmacological Classification

    Antimetabolites

    Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Antimetabolites.)

    Antirheumatic Agents

    Drugs that are used to treat RHEUMATOID ARTHRITIS. (See all compounds classified as Antirheumatic Agents.)

    Antimetabolites, Antineoplastic

    Antimetabolites that are useful in cancer chemotherapy. (See all compounds classified as Antimetabolites, Antineoplastic.)

    Immunosuppressive Agents

    Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    AZATHIOPRINE
    5.3.2 FDA UNII
    MRK240IY2L
    5.3.3 Pharmacological Classes
    Nucleosides [CS]; Purine Antimetabolite [EPC]; Purines [CS]; Nucleic Acid Synthesis Inhibitors [MoA]
    5.4 ATC Code

    L04AX01

    L04AX01

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    L - Antineoplastic and immunomodulating agents

    L04 - Immunosuppressants

    L04A - Immunosuppressants

    L04AX - Other immunosuppressants

    L04AX01 - Azathioprine

    5.5 Absorption, Distribution and Excretion

    Absorption

    Oral azathioprine is well absorbed, with a Tmax of 1-2h. Further data regarding the absorption of azathioprine is not readily available.

    Route of Elimination

    Azathioprine and mercaptopurine are not detectable in urine after 8 hours. Further data regarding the route of elimination of azathioprine are not available.

    Volume of Distribution

    Data regarding the volume of distribution of azathioprine is not readily available.

    Clearance

    Data regarding the clearance of azathioprine is not readily available.

    Azathioprine and mercaptopurine are moderately bound to plasma proteins and are partially dialyzable. They are rapidly removed from the blood by oxidation or methylation in the liver and/or erythrocytes. Renal clearance is of little impact in biological effectiveness or toxicity, but dose reduction is practiced in patients with renal failure.

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1471

    Azathioprine is well absorbed orally and reaches maximum blood levels within 1 to 2 hours after administration.

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1471

    Azathioprine is well absorbed from the gastrointestinal tract and has an oral bioavailibility of approximately 60%.

    Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 778

    Azathioprine is rapidly cleared from the blood; both azathioprine and mercaptopurine are approximately 30% bound to serum proteins, both appear dialyzable, and both appear to cross the placenta.

    Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 778

    The metabolites are excreted in the urine, largely as 6-mercaptopurine. Less than 2% of azathioprine and 20 to 40% of 6-mercaptopurine are excreted as unchanged drugs in the urine.

    Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 778

    5.6 Metabolism/Metabolites

    Azathioprine is converted to 6-mercaptopurine nonenzymatically. 6-mercaptopurine is then metabolized to 6-methylmercaptopurine by thiopurine methyltransferase, 6-thiouric acid by xanthine oxidase, or 6-thiosine-5'-monophosphate by hypoxanthine phosphoribosyltransferase. 6-thiosine-5'-monophosphate is metabolized to 6-methylthiosine-5'-monophosphate by thiopurine methyltransferase or 6-thioxanthylic acid by inosine monophosphate dehydrogenase. 6-thioxanthylic acid is metabolized by guanosine monophosphate synthetase to 6-thioguanine monophosphate, the first of the 6-thioguanine nucleotides. 6-thioguanine monophosphate is phosphorylated to produce the remaining 6-thioguanine nucleotides, 6-thioguanine diphosphate and 6-thioguanine triphosphate.

    Orally administered azathioprine is rapidly divided in vivo to form 6-mercaptopurine.

    Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 778

    Metabolized in vivo to 6-mercaptopurine, q.v.

    O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 157

    Azathioprine is metabolized to 6-mercaptopurine.

    Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 777

    5.7 Biological Half-Life

    The half life of azathioprine is approximately 5 hours.

    The elimination half-life of azathioprine is approximately 12 to 15 minutes, and that of 6-mercaptopurine is approximately 30 minutes to 4 hours. The total boby clearance of azathioprine is 60 ml/min/kg, and that of 6-mercaptopurine, 10 ml/min/kg.

    Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 778

    The half-life of azathioprine itself is about 10 minutes, and that for mercaptopurine is about an hour.

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1471

    5.8 Mechanism of Action

    Azathioprine's mechanism of action is not entirely understood but it may be related to inhibition of purine synthesis, along with inhibition of B and T cells. 6-thioguanine triphosphate, a metabolite of azathioprine, modulates activation of rac1 when costimulated with CD28, inducing T cell apoptosis. This may be mediated through rac1's action on mitogen-activated protein kinase, NF-kappaB.

    Following exposure to nucleophiles ... azathioprine is cleaved to 6-mercaptopurine which, in turn, is converted to additional metabolites that inhibit de novo purine synthesis. 6-Thio-IMP, a fraudulent nucleotide, is converted to 6-thio-GMP and finally to 6-thio-GTP, which is incorporated into DNA and gene translation is inhibited. Cell proliferation is prevented, inhibiting a variety of lymphocyte functions.

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1471

    Azathioprine (AZA), one of the antimetabolite drugs, is a purine analog that is more potent than the prototype 6-mercaptopurine, as an inhibitor of cell replication. Immunosuppression likely occurs because of the ability of the drug to inhibit purine biosynthesis. ... Although T-cell functions are the primary targets for this drug, inhibition of /(natural killer cells)/ NK function and macrophage activities has also been reported.

    Klaassen, C.D. (ed). Casarett and Doull's Toxicology. The Basic Science of Poisons. 6th ed. New York, NY: McGraw-Hill, 2001., p. 447

    Azathioprine inhibits DNA synthesis and, as a purine antimetabolite, exerts its effect on activated lymphocytes, which requires purines during their proliferative phase. It inhibits both cellular and humoral responses, but does not interfere with phagocytosis or interferon production. It is a nonspecific cytotoxic agent. Its immunosuppressive effect is believed to be due to mercaptopurine, to which it is metabolized.

    Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 778

    The exact mechanism of immunosuppressive action is unknown since the exact mechanism of the immune response itself is complex and not completely understood. The immunosuppressive effects of azathioprine involve a greater suppression of delayed hypersensitivity and cellular cytotoxicity tests than of antibody responses. Azathioprine antagonizes purine metabolism and may inhibit synthesis of DNA, RNA, and proteins; it may also interfere with cellular metabolism and inhibit mitosis.

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 509

    For more Mechanism of Action (Complete) data for AZATHIOPRINE (6 total), please visit the HSDB record page.

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Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1722969000,"product":"AZATHIOPRINE BATCH NO-2097976 ( QTY 240 KGS)","address":"882\/1-871, NEAR KANKAVATI ,VILLAGE-","city":"AHMEDABAD, GUJARAT","supplier":"FERMION OY","supplierCountry":"FINLAND","foreign_port":"HELSINKI","customer":"AMNEAL PHARMACEUTICALS","customerCountry":"INDIA","quantity":"240.00","actualQuantity":"240","unit":"KGS","unitRateFc":"510","totalValueFC":"123452.8","currency":"USD","unitRateINR":"43146","date":"07-Aug-2024","totalValueINR":"10355040","totalValueInUsd":"123452.8","indian_port":"Ahmedabad Air","hs_no":"29335990","bill_no":"4930216","productDescription":"API","marketType":"REGULATED MARKET","country":"FINLAND","selfForZScoreResived":"Pharma Grade","supplierPort":"HELSINKI","supplierAddress":"KOIVU-MANKKAAN TIE 6A, PO BOX 28 FI-02101 ESPOO Helsinki, , FINLANDSDNF FINLAND","customerAddress":"882\/1-871, NEAR KANKAVATI ,VILLAGE-"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1723141800,"product":"AZATHIOPRINE","address":"SECOND FLOOR, BLOCK-III,MY HOME HUB","city":"HYDERABAD, AP","supplier":"ZHEJIANG CHENG YI PHARMACEUTICAL CO LTD","supplierCountry":"CHINA","foreign_port":"SHANGHAI","customer":"GRANULES INDIA LIMITED","customerCountry":"INDIA","quantity":"138.72","actualQuantity":"138.72","unit":"KGS","unitRateFc":"330","totalValueFC":"46171.3","currency":"USD","unitRateINR":"27918","date":"09-Aug-2024","totalValueINR":"3872784.96","totalValueInUsd":"46171.3","indian_port":"Hyderabad Air","hs_no":"29335990","bill_no":"4966177","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI","supplierAddress":"118 HUA GONG ROAD, DONGTOU DISTRICT, WENZHOU, ZHEJIANG PROVINCE 325700SDNF China","customerAddress":"SECOND FLOOR, BLOCK-III,MY HOME HUB"}]
    30-Jan-2021
    21-Aug-2024
    KGS
    overview
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    Average Price (USD/KGS)

    Number of Transactions

    Total Quantity (KGS)

    Total Value (USD)

    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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