Peringatan Keamanan

The oral LD50 in mice is 2500mg/kg and in rats is 400mg/kg.L11214

Patients experiencing an overdose may present with bone marrow hypoplasia, bleeding, and infection, which may progress to death.L11214 Patients should be treated with supportive and symptomatic treatments. 8 hour hemodialysis may remove 45% of a dose from serum.L11214

Azathioprine

DB00993

small molecule approved

Deskripsi

Azathioprine is a prodrug of 6-mercaptopurine, first synthesized in 1956 by Gertrude Elion, William Lange, and George Hitchings in an attempt to produce a derivative of 6-mercaptopurine with a better therapeutic index.A189678,A189687,A189690 Azathioprine is used to treat inflammatory conditions like rheumatoid arthritis and as an immunosuppressant in the prevention of renal transplant rejection.L11214

Azathiprine was granted FDA approval on 20 March 1968.L11214

Struktur Molekul 2D

Berat 277.263
Wujud solid

Peta Jejaring Molekuler
Legenda: Obat • Target • Gen • Enzim • (Panah → menunjukkan arah efek / relasi) • Transporter • Carrier

Profil Farmakokinetik

Waktu Paruh (Half-Life) The half life of azathioprine is approximately 5 hours.[L11214]
Volume Distribusi Data regarding the volume of distribution of azathioprine is not readily available.[A189657,A189663]
Klirens (Clearance) Data regarding the clearance of azathioprine is not readily available.[A189657,A189663]

Absorpsi

Oral azathioprine is well absorbed, with a Tmax of 1-2h.L11214 Further data regarding the absorption of azathioprine is not readily available.A189657,A189663

Metabolisme

Azathioprine is converted to 6-mercaptopurine nonenzymatically.A14289 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.A14289 6-thiosine-5'-monophosphate is metabolized to 6-methylthiosine-5'-monophosphate by thiopurine methyltransferase or 6-thioxanthylic acid by inosine monophosphate dehydrogenase.A14289 6-thioxanthylic acid is metabolized by guanosine monophosphate synthetase to 6-thioguanine monophosphate, the first of the 6-thioguanine nucleotides.A14289 6-thioguanine monophosphate is phosphorylated to produce the remaining 6-thioguanine nucleotides, 6-thioguanine diphosphate and 6-thioguanine triphosphate.A14289

Rute Eliminasi

Azathioprine and mercaptopurine are not detectable in urine after 8 hours.L11214 Further data regarding the route of elimination of azathioprine are not available.A189669

Farmakogenomik

3 Varian
TPMT (rs1800462)

Patients with this genotype have reduced metabolism of azathioprine resulting in increased toxicity.

TPMT (rs1800460)

Patients with this genotype have reduced metabolism of azathioprine resulting in increased toxicity.

TPMT (rs1142345)

Patients with this genotype have reduced metabolism of azathioprine resulting in increased toxicity.

Interaksi Makanan

1 Data
  • 1. Take with food. Food reduces irritation.

Interaksi Obat

1286 Data
Denosumab The risk or severity of adverse effects can be increased when Denosumab is combined with Azathioprine.
Peginterferon alfa-2a The risk or severity of adverse effects can be increased when Peginterferon alfa-2a is combined with Azathioprine.
Interferon alfa-n1 The risk or severity of adverse effects can be increased when Interferon alfa-n1 is combined with Azathioprine.
Interferon alfa-n3 The risk or severity of adverse effects can be increased when Interferon alfa-n3 is combined with Azathioprine.
Interferon gamma-1b The risk or severity of adverse effects can be increased when Interferon gamma-1b is combined with Azathioprine.
Interferon alfa-2a The risk or severity of adverse effects can be increased when Interferon alfa-2a is combined with Azathioprine.
Aldesleukin The risk or severity of adverse effects can be increased when Aldesleukin is combined with Azathioprine.
Gemtuzumab ozogamicin The risk or severity of adverse effects can be increased when Gemtuzumab ozogamicin is combined with Azathioprine.
Pegaspargase The risk or severity of adverse effects can be increased when Pegaspargase is combined with Azathioprine.
Interferon beta-1b The risk or severity of adverse effects can be increased when Interferon beta-1b is combined with Azathioprine.
Interferon alfacon-1 The risk or severity of adverse effects can be increased when Interferon alfacon-1 is combined with Azathioprine.
Rituximab The risk or severity of adverse effects can be increased when Rituximab is combined with Azathioprine.
Basiliximab The risk or severity of adverse effects can be increased when Basiliximab is combined with Azathioprine.
Muromonab The risk or severity of adverse effects can be increased when Muromonab is combined with Azathioprine.
Ibritumomab tiuxetan The risk or severity of adverse effects can be increased when Ibritumomab tiuxetan is combined with Azathioprine.
Tositumomab The risk or severity of adverse effects can be increased when Tositumomab is combined with Azathioprine.
Alemtuzumab The risk or severity of adverse effects can be increased when Alemtuzumab is combined with Azathioprine.
Alefacept The risk or severity of adverse effects can be increased when Alefacept is combined with Azathioprine.
Efalizumab The risk or severity of adverse effects can be increased when Efalizumab is combined with Azathioprine.
Antithymocyte immunoglobulin (rabbit) The risk or severity of adverse effects can be increased when Antithymocyte immunoglobulin (rabbit) is combined with Azathioprine.
Interferon alfa-2b The risk or severity of adverse effects can be increased when Interferon alfa-2b is combined with Azathioprine.
Daclizumab The risk or severity of adverse effects can be increased when Daclizumab is combined with Azathioprine.
Phenylalanine The risk or severity of adverse effects can be increased when Phenylalanine is combined with Azathioprine.
Flunisolide The risk or severity of adverse effects can be increased when Flunisolide is combined with Azathioprine.
Bortezomib The risk or severity of adverse effects can be increased when Bortezomib is combined with Azathioprine.
Cladribine Azathioprine may increase the immunosuppressive activities of Cladribine.
Carmustine The risk or severity of adverse effects can be increased when Carmustine is combined with Azathioprine.
Amsacrine The risk or severity of adverse effects can be increased when Amsacrine is combined with Azathioprine.
Bleomycin The risk or severity of adverse effects can be increased when Bleomycin is combined with Azathioprine.
Chlorambucil The risk or severity of adverse effects can be increased when Chlorambucil is combined with Azathioprine.
Raltitrexed The risk or severity of adverse effects can be increased when Raltitrexed is combined with Azathioprine.
Mitomycin The risk or severity of adverse effects can be increased when Mitomycin is combined with Azathioprine.
Bexarotene The risk or severity of adverse effects can be increased when Bexarotene is combined with Azathioprine.
Vindesine The risk or severity of adverse effects can be increased when Vindesine is combined with Azathioprine.
Floxuridine The risk or severity of adverse effects can be increased when Floxuridine is combined with Azathioprine.
Indomethacin The risk or severity of adverse effects can be increased when Indomethacin is combined with Azathioprine.
Tioguanine The risk or severity of adverse effects can be increased when Tioguanine is combined with Azathioprine.
Vinorelbine The risk or severity of adverse effects can be increased when Vinorelbine is combined with Azathioprine.
Dexrazoxane The risk or severity of adverse effects can be increased when Dexrazoxane is combined with Azathioprine.
Beclomethasone dipropionate The risk or severity of adverse effects can be increased when Beclomethasone dipropionate is combined with Azathioprine.
Sorafenib The risk or severity of adverse effects can be increased when Sorafenib is combined with Azathioprine.
Streptozocin The risk or severity of adverse effects can be increased when Streptozocin is combined with Azathioprine.
Trifluridine The risk or severity of adverse effects can be increased when Trifluridine is combined with Azathioprine.
Gemcitabine The risk or severity of adverse effects can be increased when Gemcitabine is combined with Azathioprine.
Betamethasone The risk or severity of adverse effects can be increased when Betamethasone is combined with Azathioprine.
Teniposide The risk or severity of adverse effects can be increased when Teniposide is combined with Azathioprine.
Epirubicin The risk or severity of adverse effects can be increased when Epirubicin is combined with Azathioprine.
Chloramphenicol The risk or severity of adverse effects can be increased when Chloramphenicol is combined with Azathioprine.
Lenalidomide The risk or severity of adverse effects can be increased when Lenalidomide is combined with Azathioprine.
Altretamine The risk or severity of adverse effects can be increased when Altretamine is combined with Azathioprine.
Zidovudine The risk or severity of adverse effects can be increased when Zidovudine is combined with Azathioprine.
Cisplatin The risk or severity of adverse effects can be increased when Cisplatin is combined with Azathioprine.
Oxaliplatin The risk or severity of adverse effects can be increased when Oxaliplatin is combined with Azathioprine.
Vincristine The risk or severity of adverse effects can be increased when Vincristine is combined with Azathioprine.
Fluorouracil The risk or severity of adverse effects can be increased when Fluorouracil is combined with Azathioprine.
Propylthiouracil The risk or severity of adverse effects can be increased when Propylthiouracil is combined with Azathioprine.
Pentostatin The risk or severity of adverse effects can be increased when Pentostatin is combined with Azathioprine.
Carbamazepine The risk or severity of adverse effects can be increased when Carbamazepine is combined with Azathioprine.
Vinblastine The risk or severity of adverse effects can be increased when Vinblastine is combined with Azathioprine.
Fluticasone propionate The risk or severity of adverse effects can be increased when Fluticasone propionate is combined with Azathioprine.
Fluocinolone acetonide The risk or severity of adverse effects can be increased when Fluocinolone acetonide is combined with Azathioprine.
Linezolid The risk or severity of adverse effects can be increased when Linezolid is combined with Azathioprine.
Imatinib The risk or severity of adverse effects can be increased when Imatinib is combined with Azathioprine.
Triamcinolone The risk or severity of adverse effects can be increased when Triamcinolone is combined with Azathioprine.
Clofarabine The risk or severity of adverse effects can be increased when Clofarabine is combined with Azathioprine.
Prednisone The risk or severity of adverse effects can be increased when Prednisone is combined with Azathioprine.
Pemetrexed The risk or severity of adverse effects can be increased when Pemetrexed is combined with Azathioprine.
Fludrocortisone The risk or severity of adverse effects can be increased when Fludrocortisone is combined with Azathioprine.
Mycophenolate mofetil The risk or severity of adverse effects can be increased when Mycophenolate mofetil is combined with Azathioprine.
Daunorubicin The risk or severity of adverse effects can be increased when Daunorubicin is combined with Azathioprine.
Irinotecan The risk or severity of adverse effects can be increased when Irinotecan is combined with Azathioprine.
Methimazole The risk or severity of adverse effects can be increased when Methimazole is combined with Azathioprine.
Etoposide The risk or severity of adverse effects can be increased when Etoposide is combined with Azathioprine.
Sulfasalazine The risk or severity of adverse effects can be increased when Sulfasalazine is combined with Azathioprine.
Dacarbazine The risk or severity of adverse effects can be increased when Dacarbazine is combined with Azathioprine.
Temozolomide The risk or severity of adverse effects can be increased when Temozolomide is combined with Azathioprine.
Penicillamine The risk or severity of adverse effects can be increased when Penicillamine is combined with Azathioprine.
Prednisolone The risk or severity of adverse effects can be increased when Prednisolone is combined with Azathioprine.
Sirolimus The risk or severity of adverse effects can be increased when Sirolimus is combined with Azathioprine.
Mechlorethamine The risk or severity of adverse effects can be increased when Mechlorethamine is combined with Azathioprine.
Azacitidine The risk or severity of adverse effects can be increased when Azacitidine is combined with Azathioprine.
Carboplatin The risk or severity of adverse effects can be increased when Carboplatin is combined with Azathioprine.
Methylprednisolone The risk or severity of adverse effects can be increased when Methylprednisolone is combined with Azathioprine.
Dactinomycin The risk or severity of adverse effects can be increased when Dactinomycin is combined with Azathioprine.
Cytarabine The risk or severity of adverse effects can be increased when Cytarabine is combined with Azathioprine.
Doxorubicin The risk or severity of adverse effects can be increased when Azathioprine is combined with Doxorubicin.
Hydroxyurea The risk or severity of adverse effects can be increased when Azathioprine is combined with Hydroxyurea.
Busulfan The risk or severity of adverse effects can be increased when Azathioprine is combined with Busulfan.
Mycophenolic acid The risk or severity of adverse effects can be increased when Azathioprine is combined with Mycophenolic acid.
Topotecan The risk or severity of adverse effects can be increased when Azathioprine is combined with Topotecan.
Mercaptopurine The risk or severity of adverse effects can be increased when Azathioprine is combined with Mercaptopurine.
Thalidomide The risk or severity of adverse effects can be increased when Azathioprine is combined with Thalidomide.
Melphalan The risk or severity of adverse effects can be increased when Azathioprine is combined with Melphalan.
Fludarabine The risk or severity of adverse effects can be increased when Azathioprine is combined with Fludarabine.
Flucytosine The risk or severity of adverse effects can be increased when Azathioprine is combined with Flucytosine.
Capecitabine The risk or severity of adverse effects can be increased when Azathioprine is combined with Capecitabine.
Trilostane The risk or severity of adverse effects can be increased when Azathioprine is combined with Trilostane.
Procarbazine The risk or severity of adverse effects can be increased when Azathioprine is combined with Procarbazine.
Arsenic trioxide The risk or severity of adverse effects can be increased when Azathioprine is combined with Arsenic trioxide.
Idarubicin The risk or severity of adverse effects can be increased when Azathioprine is combined with Idarubicin.

Target Protein

Amidophosphoribosyltransferase PPAT
Ras-related C3 botulinum toxin substrate 1 RAC1

Referensi & Sumber

Artikel (PubMed)
  • PMID: 25272656
    Sochacka J: Docking of thiopurine derivatives to human serum albumin and binding site analysis with Molegro Virtual Docker. Acta Pol Pharm. 2014 Mar-Apr;71(2):343-9.
  • PMID: 8881811
    Van Os EC, Zins BJ, Sandborn WJ, Mays DC, Tremaine WJ, Mahoney DW, Zinsmeister AR, Lipsky JJ: Azathioprine pharmacokinetics after intravenous, oral, delayed release oral and rectal foam administration. Gut. 1996 Jul;39(1):63-8. doi: 10.1136/gut.39.1.63.
  • PMID: 18020555
    Anstey A, Lear JT: Azathioprine: clinical pharmacology and current indications in autoimmune disorders. BioDrugs. 1998 Jan;9(1):33-47.
  • PMID: 15354273
    Dubinsky MC: Azathioprine, 6-mercaptopurine in inflammatory bowel disease: pharmacology, efficacy, and safety. Clin Gastroenterol Hepatol. 2004 Sep;2(9):731-43.
  • PMID: 12697733
    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.
  • PMID: 28296824
    Stocco G, Martelossi S, Arrigo S, Barabino A, Aloi M, Martinelli M, Miele E, Knafelz D, Romano C, Naviglio S, Favretto D, Cuzzoni E, Franca R, Decorti G, Ventura A: Multicentric Case-Control Study on Azathioprine Dose and Pharmacokinetics in Early-onset Pediatric Inflammatory Bowel Disease. Inflamm Bowel Dis. 2017 Apr;23(4):628-634. doi: 10.1097/MIB.0000000000001051.
  • PMID: 28811125
    Pelin M, Genova E, Fusco L, Marisat M, Hofmann U, Favretto D, Lucafo M, Taddio A, Martelossi S, Ventura A, Stocco G, Schwab M, Decorti G: Pharmacokinetics and pharmacodynamics of thiopurines in an in vitro model of human hepatocytes: Insights from an innovative mass spectrometry assay. Chem Biol Interact. 2017 Sep 25;275:189-195. doi: 10.1016/j.cbi.2017.08.009. Epub 2017 Aug 12.
  • PMID: 1002367
    Schusziarra V, Ziekursch V, Schlamp R, Siemensen HC: Pharmacokinetics of azathioprine under haemodialysis. Int J Clin Pharmacol Biopharm. 1976 Dec;14(4):298-302.
Menampilkan 8 dari 11 artikel.

Contoh Produk & Brand

Produk: 68 • International brands: 4
Produk
  • Apo-azathioprine
    Tablet • 50 mg • Oral • Canada • Generic • Approved
  • Azasan
    Tablet • 75 mg/1 • Oral • US • Generic • Approved
  • Azasan
    Tablet • 100 mg/1 • Oral • US • Generic • Approved
  • Azathioprine
    Tablet • 50 mg/1 • Oral • US • Generic • Approved
  • Azathioprine
    Tablet • 50 mg/1 • Oral • US • Generic • Approved
  • Azathioprine
    Tablet • 50 mg/1 • Oral • US • Generic • Approved
  • Azathioprine
    Tablet • 50 mg/1 • Oral • US • Generic • Approved
  • Azathioprine
    Tablet, film coated • 50 mg/1 • Oral • US • Generic • Approved
Menampilkan 8 dari 68 produk.
International Brands
  • Azamun — Ascent
  • Azanin — Tanabe Mitsubishi Pharma
  • Imurek — Aspen
  • Imurel — GlaxoSmithKline

Sekuens Gen/Protein (FASTA)

Sekuens dimuat saat dibutuhkan agar halaman tetap ringan.
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