Peringatan Keamanan

One case of overdose with azacitidine was reported during clinical trials. After receiving a single dose of 290 mg/m2 of azacitidine intravenously (almost 4 times the recommended starting dose), a patient experienced diarrhea, nausea, and vomiting. These adverse events resolved without sequelae, and the correct dose was resumed the following day. In case of overdose, patients should be monitored with appropriate blood counts and receive supportive treatment as necessary. There is no known specific antidote for azacitidine overdosage.L46861 In mice, the oral LD50 of azacitidine is 572 mg/kg, while the intravenous LD50 is approximately 117 mg/kg.L46871

Azacitidine

DB00928

small molecule approved investigational

Deskripsi

Azacitidine is a pyrimidine nucleoside analogue with anti-neoplastic activity. It differs from cytosine by the presence of nitrogen in the C5-position, key in its hypomethylating activity.A1406,A1413,A1415 Two main mechanisms of action have been proposed for azacitidine. One of them is the induction of cytotoxicity. As an analogue of cytidine, it is able to incorporate into RNA and DNA, disrupting RNA metabolism and inhibiting protein and DNA synthesis. The other one is through the inhibition of DNA methyltransferase, impairing DNA methylation.A1407 Due to its anti-neoplastic activity and its ability to inhibit methylation in replicating DNA, azacytidine has been used mainly used in the treatment of myelodysplastic syndromes (MDS) and acute myeloid leukemia (AML), two types of cancer characterized by the presence of aberrant DNA methylation.A1407,A1410,A1411,A1416,A1417

In May 2004, the FDA approved the use of azacitidine administered subcutaneously for the treatment of MDS of all French-American-British (FAB) subtypes. In January 2007, the FDA approved the intravenous administration of azacitidine.A1415 The use of oral azacitidine for the treatment of AML in patients in complete remission was approved by the FDA in September 2020.L35335

Struktur Molekul 2D

Berat 244.2047
Wujud solid

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

Profil Farmakokinetik

Waktu Paruh (Half-Life) The mean half-life of azacitidine after subcutaneous administration is 41 minutes. The mean elimination half-life of azacitidine and its metabolites was about 4 hours for intravenous and subcutaneous administrations.[L46861]
Volume Distribusi In patients given an intravenous dose of azacitidine, the volume of distribution is 76 L.[L46861]
Klirens (Clearance) Azacitidine has an apparent subcutaneous clearance of 167 L/hour in adults. In pediatric patients, the geometric mean clearance was 21.8 L/hour.[L46861]

Absorpsi

Azacitidine is rapidly absorbed after subcutaneous administration.A1414,L46861 In adult patients with myelodysplastic syndrome given a single subcutaneous dose of 75 mg/m2 of azacitidine, the Cmax and Tmax were 750 ng/ml and 0.5 hours, respectively. Based on the area under the curve, the bioavailability of subcutaneous azacitidine relative to intravenous azacitidine is approximately 89%. In 21 patients with cancer given subcutaneous azacitidine, the AUC and Cmax were approximately dose-proportional between 25 and 100 mg/m2. Multiple subcutaneous or intravenous doses of azacitidine are not expected to result in drug accumulation.L46861

Metabolisme

An in vitro study of azacitidine incubation in human liver fractions indicated that cytochrome P450 (CYP) enzymes do not participate in the metabolism of azacitidine. Azacitidine is metabolized through spontaneous hydrolysis and deamination mediated by cytidine deaminase.L46861

Rute Eliminasi

Azacitidine and its metabolites are mainly excreted through urine.A1414,L46861 In five cancer patients given radioactive azacitidine intravenously, the cumulative urinary excretion was 85% of the radioactive dose. Fecal excretion accounted for less than 1% of administered radioactivity over three days. Following the subcutaneous administration of 14C-azacitidine, the mean excretion of radioactivity in urine was 50%.L46861

Interaksi Obat

1168 Data
Denosumab The risk or severity of adverse effects can be increased when Denosumab is combined with Azacitidine.
Etanercept The risk or severity of adverse effects can be increased when Etanercept is combined with Azacitidine.
Peginterferon alfa-2a The risk or severity of adverse effects can be increased when Peginterferon alfa-2a is combined with Azacitidine.
Interferon alfa-n1 The risk or severity of adverse effects can be increased when Interferon alfa-n1 is combined with Azacitidine.
Interferon alfa-n3 The risk or severity of adverse effects can be increased when Interferon alfa-n3 is combined with Azacitidine.
Peginterferon alfa-2b The risk or severity of adverse effects can be increased when Peginterferon alfa-2b is combined with Azacitidine.
Anakinra The risk or severity of adverse effects can be increased when Anakinra is combined with Azacitidine.
Interferon gamma-1b The risk or severity of adverse effects can be increased when Interferon gamma-1b is combined with Azacitidine.
Interferon alfa-2a The risk or severity of adverse effects can be increased when Interferon alfa-2a is combined with Azacitidine.
Aldesleukin The risk or severity of adverse effects can be increased when Aldesleukin is combined with Azacitidine.
Adalimumab The risk or severity of adverse effects can be increased when Adalimumab is combined with Azacitidine.
Gemtuzumab ozogamicin The risk or severity of adverse effects can be increased when Gemtuzumab ozogamicin is combined with Azacitidine.
Pegaspargase The risk or severity of adverse effects can be increased when Pegaspargase is combined with Azacitidine.
Infliximab The risk or severity of adverse effects can be increased when Infliximab is combined with Azacitidine.
Interferon beta-1b The risk or severity of adverse effects can be increased when Interferon beta-1b is combined with Azacitidine.
Interferon alfacon-1 The risk or severity of adverse effects can be increased when Interferon alfacon-1 is combined with Azacitidine.
Rituximab The risk or severity of adverse effects can be increased when Rituximab is combined with Azacitidine.
Basiliximab The risk or severity of adverse effects can be increased when Basiliximab is combined with Azacitidine.
Muromonab The risk or severity of adverse effects can be increased when Muromonab is combined with Azacitidine.
Ibritumomab tiuxetan The risk or severity of adverse effects can be increased when Ibritumomab tiuxetan is combined with Azacitidine.
Tositumomab The risk or severity of adverse effects can be increased when Tositumomab is combined with Azacitidine.
Alemtuzumab The risk or severity of adverse effects can be increased when Alemtuzumab is combined with Azacitidine.
Alefacept The risk or severity of adverse effects can be increased when Alefacept is combined with Azacitidine.
Efalizumab The risk or severity of adverse effects can be increased when Efalizumab is combined with Azacitidine.
Antithymocyte immunoglobulin (rabbit) The risk or severity of adverse effects can be increased when Antithymocyte immunoglobulin (rabbit) is combined with Azacitidine.
Interferon alfa-2b The risk or severity of adverse effects can be increased when Interferon alfa-2b is combined with Azacitidine.
Daclizumab The risk or severity of adverse effects can be increased when Daclizumab is combined with Azacitidine.
Phenylalanine The risk or severity of adverse effects can be increased when Phenylalanine is combined with Azacitidine.
Flunisolide The risk or severity of adverse effects can be increased when Flunisolide is combined with Azacitidine.
Bortezomib The risk or severity of adverse effects can be increased when Bortezomib is combined with Azacitidine.
Cladribine Azacitidine may increase the immunosuppressive activities of Cladribine.
Carmustine The risk or severity of adverse effects can be increased when Carmustine is combined with Azacitidine.
Amsacrine The risk or severity of adverse effects can be increased when Amsacrine is combined with Azacitidine.
Bleomycin The risk or severity of adverse effects can be increased when Bleomycin is combined with Azacitidine.
Chlorambucil The risk or severity of adverse effects can be increased when Chlorambucil is combined with Azacitidine.
Raltitrexed The risk or severity of adverse effects can be increased when Raltitrexed is combined with Azacitidine.
Mitomycin The risk or severity of adverse effects can be increased when Mitomycin is combined with Azacitidine.
Bexarotene The risk or severity of adverse effects can be increased when Bexarotene is combined with Azacitidine.
Vindesine The risk or severity of adverse effects can be increased when Vindesine is combined with Azacitidine.
Floxuridine The risk or severity of adverse effects can be increased when Floxuridine is combined with Azacitidine.
Indomethacin The risk or severity of adverse effects can be increased when Indomethacin is combined with Azacitidine.
Tioguanine The risk or severity of adverse effects can be increased when Tioguanine is combined with Azacitidine.
Vinorelbine The risk or severity of adverse effects can be increased when Vinorelbine is combined with Azacitidine.
Dexrazoxane The risk or severity of adverse effects can be increased when Dexrazoxane is combined with Azacitidine.
Beclomethasone dipropionate The risk or severity of adverse effects can be increased when Beclomethasone dipropionate is combined with Azacitidine.
Sorafenib The risk or severity of adverse effects can be increased when Sorafenib is combined with Azacitidine.
Streptozocin The risk or severity of adverse effects can be increased when Streptozocin is combined with Azacitidine.
Trifluridine The risk or severity of adverse effects can be increased when Trifluridine is combined with Azacitidine.
Gemcitabine The risk or severity of adverse effects can be increased when Gemcitabine is combined with Azacitidine.
Betamethasone The risk or severity of adverse effects can be increased when Betamethasone is combined with Azacitidine.
Teniposide The risk or severity of adverse effects can be increased when Teniposide is combined with Azacitidine.
Epirubicin The risk or severity of adverse effects can be increased when Epirubicin is combined with Azacitidine.
Chloramphenicol The risk or severity of adverse effects can be increased when Chloramphenicol is combined with Azacitidine.
Lenalidomide The risk or severity of adverse effects can be increased when Lenalidomide is combined with Azacitidine.
Altretamine The risk or severity of adverse effects can be increased when Altretamine is combined with Azacitidine.
Zidovudine The risk or severity of adverse effects can be increased when Zidovudine is combined with Azacitidine.
Cisplatin The risk or severity of adverse effects can be increased when Cisplatin is combined with Azacitidine.
Oxaliplatin The risk or severity of adverse effects can be increased when Oxaliplatin is combined with Azacitidine.
Cyclophosphamide The risk or severity of adverse effects can be increased when Cyclophosphamide is combined with Azacitidine.
Vincristine The risk or severity of adverse effects can be increased when Vincristine is combined with Azacitidine.
Fluorouracil The risk or severity of adverse effects can be increased when Fluorouracil is combined with Azacitidine.
Propylthiouracil The risk or severity of adverse effects can be increased when Propylthiouracil is combined with Azacitidine.
Pentostatin The risk or severity of adverse effects can be increased when Pentostatin is combined with Azacitidine.
Methotrexate The risk or severity of adverse effects can be increased when Methotrexate is combined with Azacitidine.
Carbamazepine The risk or severity of adverse effects can be increased when Carbamazepine is combined with Azacitidine.
Vinblastine The risk or severity of adverse effects can be increased when Vinblastine is combined with Azacitidine.
Fluticasone propionate The risk or severity of adverse effects can be increased when Fluticasone propionate is combined with Azacitidine.
Fluocinolone acetonide The risk or severity of adverse effects can be increased when Fluocinolone acetonide is combined with Azacitidine.
Linezolid The risk or severity of adverse effects can be increased when Linezolid is combined with Azacitidine.
Imatinib The risk or severity of adverse effects can be increased when Imatinib is combined with Azacitidine.
Triamcinolone The risk or severity of adverse effects can be increased when Triamcinolone is combined with Azacitidine.
Clofarabine The risk or severity of adverse effects can be increased when Clofarabine is combined with Azacitidine.
Prednisone The risk or severity of adverse effects can be increased when Prednisone is combined with Azacitidine.
Pemetrexed The risk or severity of adverse effects can be increased when Pemetrexed is combined with Azacitidine.
Fludrocortisone The risk or severity of adverse effects can be increased when Fludrocortisone is combined with Azacitidine.
Mycophenolate mofetil The risk or severity of adverse effects can be increased when Mycophenolate mofetil is combined with Azacitidine.
Daunorubicin The risk or severity of adverse effects can be increased when Daunorubicin is combined with Azacitidine.
Irinotecan The risk or severity of adverse effects can be increased when Irinotecan is combined with Azacitidine.
Methimazole The risk or severity of adverse effects can be increased when Methimazole is combined with Azacitidine.
Etoposide The risk or severity of adverse effects can be increased when Etoposide is combined with Azacitidine.
Sulfasalazine The risk or severity of adverse effects can be increased when Sulfasalazine is combined with Azacitidine.
Dacarbazine The risk or severity of adverse effects can be increased when Dacarbazine is combined with Azacitidine.
Temozolomide The risk or severity of adverse effects can be increased when Temozolomide is combined with Azacitidine.
Penicillamine The risk or severity of adverse effects can be increased when Penicillamine is combined with Azacitidine.
Prednisolone The risk or severity of adverse effects can be increased when Prednisolone is combined with Azacitidine.
Sirolimus The risk or severity of adverse effects can be increased when Sirolimus is combined with Azacitidine.
Mechlorethamine The risk or severity of adverse effects can be increased when Mechlorethamine is combined with Azacitidine.
Carboplatin The risk or severity of adverse effects can be increased when Azacitidine is combined with Carboplatin.
Methylprednisolone The risk or severity of adverse effects can be increased when Azacitidine is combined with Methylprednisolone.
Dactinomycin The risk or severity of adverse effects can be increased when Azacitidine is combined with Dactinomycin.
Cytarabine The risk or severity of adverse effects can be increased when Azacitidine is combined with Cytarabine.
Azathioprine The risk or severity of adverse effects can be increased when Azacitidine is combined with Azathioprine.
Doxorubicin The risk or severity of adverse effects can be increased when Azacitidine is combined with Doxorubicin.
Hydroxyurea The risk or severity of adverse effects can be increased when Azacitidine is combined with Hydroxyurea.
Busulfan The risk or severity of adverse effects can be increased when Azacitidine is combined with Busulfan.
Mycophenolic acid The risk or severity of adverse effects can be increased when Azacitidine is combined with Mycophenolic acid.
Topotecan The risk or severity of adverse effects can be increased when Azacitidine is combined with Topotecan.
Mercaptopurine The risk or severity of adverse effects can be increased when Azacitidine is combined with Mercaptopurine.
Thalidomide The risk or severity of adverse effects can be increased when Azacitidine is combined with Thalidomide.
Melphalan The risk or severity of adverse effects can be increased when Azacitidine is combined with Melphalan.

Target Protein

DNA (cytosine-5)-methyltransferase 1 DNMT1
RNA
DNA

Referensi & Sumber

Synthesis reference: Lorenzo DE FERRA, Maurizio ZENONI, Stefano TURCHETTA, Mauro ANIBALDI, Ettore AMMIRATI, Paolo BRANDI, Giorgio BERARDI, "PROCESS FOR THE SYNTHESIS OF AZACITIDINE AND DECITABINE." U.S. Patent US20110245485, issued October 06, 2011.
Artikel (PubMed)
  • PMID: 4142650
    Cihak A: Biological effects of 5-azacytidine in eukaryotes. Oncology. 1974;30(5):405-22.
  • PMID: 15793220
    Kaminskas E, Farrell AT, Wang YC, Sridhara R, Pazdur R: FDA drug approval summary: azacitidine (5-azacytidine, Vidaza) for injectable suspension. Oncologist. 2005 Mar;10(3):176-82.
  • PMID: 14585280
    Leone G, Voso MT, Teofili L, Lubbert M: Inhibitors of DNA methylation in the treatment of hematological malignancies and MDS. Clin Immunol. 2003 Oct;109(1):89-102.
  • PMID: 17612710
    Ghoshal K, Bai S: DNA methyltransferases as targets for cancer therapy. Drugs Today (Barc). 2007 Jun;43(6):395-422.
  • PMID: 12011120
    Silverman LR, Demakos EP, Peterson BL, Kornblith AB, Holland JC, Odchimar-Reissig R, Stone RM, Nelson D, Powell BL, DeCastro CM, Ellerton J, Larson RA, Schiffer CA, Holland JF: Randomized controlled trial of azacitidine in patients with the myelodysplastic syndrome: a study of the cancer and leukemia group B. J Clin Oncol. 2002 May 15;20(10):2429-40.
  • PMID: 11700387
    Silverman LR: Targeting hypomethylation of DNA to achieve cellular differentiation in myelodysplastic syndromes (MDS). Oncologist. 2001;6 Suppl 5:8-14.
  • PMID: 15962522
    Issa JP, Kantarjian H: Azacitidine. Nat Rev Drug Discov. 2005 May;Suppl:S6-7.
  • PMID: 18627335
    O'Dwyer K, Maslak P: Azacitidine and the beginnings of therapeutic epigenetic modulation. Expert Opin Pharmacother. 2008 Aug;9(11):1981-6. doi: 10.1517/14656566.9.11.1981 .
Menampilkan 8 dari 12 artikel.

Contoh Produk & Brand

Produk: 65 • International brands: 2
Produk
  • Azacitidine
    Injection, powder, lyophilized, for solution • 100 mg/1 • Intravenous; Subcutaneous • US • Generic • Approved
  • Azacitidine
    Injection, powder, lyophilized, for solution • 100 mg/1 • Intravenous; Subcutaneous • US • Generic • Approved
  • Azacitidine
    Injection, powder, lyophilized, for solution • 100 mg/1 • Intravenous; Subcutaneous • US • Generic • Approved
  • Azacitidine
    Injection, powder, lyophilized, for solution • 100 mg/1 • Intravenous; Subcutaneous • US • Approved
  • Azacitidine
    Injection, powder, lyophilized, for solution • 100 mg/1 • Intravenous; Subcutaneous • US • Generic • Approved
  • Azacitidine
    Injection, powder, lyophilized, for solution • 100 mg/1 • Intravenous; Subcutaneous • US • Generic • Approved
  • Azacitidine
    Injection, powder, lyophilized, for solution • 100 mg/1 • Intravenous; Subcutaneous • US • Generic • Approved
  • Azacitidine
    Injection, powder, lyophilized, for solution • 100 mg/1 • Intravenous; Subcutaneous • US • Generic • Approved
Menampilkan 8 dari 65 produk.
International Brands
  • Ladakamycin
  • Mylosar

Sekuens Gen/Protein (FASTA)

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