Name: | Azacitidine |
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PubChem Compound ID: | 166731 |
Description: | A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent. |
Molecular formula: | C8H12N4O5 |
Molecular weight: | 244.205 g/mol |
Synonyms: |
Azacytidine; Amino-beta-D-ribofuranosyltriazinone; Triazinone, amino-beta-D-ribofuranosyl-; 12679-86-6
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Name: | Azacitidine |
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Name (isomeric): | DB00928 |
Drug Type: | small molecule |
Description: | A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent. |
Synonyms: |
Azacytidine; 5 AZC; Azacitidinum [INN-Latin]; Azacitidina [INN-Spanish]
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Brand: | Ladakamycin, Mylosar, Vidaza |
Category: | Antimetabolites, Antineoplastic, Enzyme Inhibitors |
CAS number: | 320-67-2 |
Indication: | For treatment of patients with the following French-American-British myelodysplastic syndrome subtypes: refractory anemia or refractory anemia with ringed sideroblasts (if accompanied by neutropenia or thrombocytopenia or requiring transfusions), refractory anemia with excess blasts, refractory anemia with excess blasts in transformation (now classified as acute myelogenous leukemia with multilineage dysplasia), and chronic myelomonocytic leukemia. |
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Pharmacology: |
Azacitidine is believed to exert its antineoplastic effects by causing hypomethylation of DNA and direct cytotoxicity on abnormal hematopoietic cells in the bone marrow. The concentration of azacitidine required for maximum inhibition of DNA methylation in vitro does not cause major suppression of DNA synthesis. Hypomethylation may restore normal f...
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Mechanism of Action: |
Azacitidine (5-azacytidine) is a chemical analogue of the cytosine nucleoside used in DNA and RNA. Azacitidine is thought to induce antineoplastic activity via two mechanisms; inhibition of DNA methyltransferase at low doses, causing hypomethylation of DNA, and direct cytotoxicity in abnormal hematopoietic cells in the bone marrow through its incor...
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Absorption: | Azacitidine is rapidly absorbed after subcutaneous administration. The bioavailability of subcutaneous azacitidine relative to IV azacitidine is approximately 89%, based on area under the curve. |
Biotransformation: | An in vitro study of azacitidine incubation in human liver fractions indicated that azacitidine may be metabolized by the liver. The potential of azacitidine to inhibit cytochrome P450 (CYP) enzymes is not known. |
Route of elimination: | Following IV administration of radioactive azacitidine to 5 cancer patients, the cumulative urinary excretion was 85% of the radioactive dose. Fecal excretion accounted for <1% of administered radioactivity over three days. Mean excretion of radioactivity in urine following SC administration of 14C-azacitidine was 50%. |
Half Life: | Mean elimination half-life is approximately 4 hours. |
Clearance: | 167 +/- 49 L/h |
Toxicity: | One case of overdose with azacitidine was reported during clinical trials. A patient experienced diarrhea, nausea, and vomiting after receiving a single IV dose of approximately 290 mg/m2, almost 4 times the recommended starting dose. |
Affected organisms: | Humans and other mammals |
Drug interaction: |
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