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Identification
NameAzacitidine
Accession NumberDB00928  (APRD00809)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionA pyrimidine nucleoside 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. [PubChem]
Structure
Thumb
Synonyms
4-Amino-1-beta-D-ribofuranosyl-S-triazin-2(1H)-one
5 AZC
5-Azacytidine
Azacitidina
Azacitidine
Azacitidinum
Azacytidine
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AzacitidineInjection, powder, lyophilized, for solution100 mg/1Intravenous; SubcutaneousActavis Pharma Company2016-08-16Not applicableUs
AzacitidineInjection, powder, lyophilized, for solution100 mg/1Intravenous; SubcutaneousSandoz2013-09-16Not applicableUs
AzacitidineInjection, powder, lyophilized, for solution100 mg/1Intravenous; SubcutaneousSandoz2014-03-27Not applicableUs
VidazaPowder, for suspension100 mgSubcutaneousCelgene2010-01-04Not applicableCanada
VidazaInjection, powder, lyophilized, for solution100 mg/1Intravenous; SubcutaneousCelgene2004-07-05Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AzacitidineInjection, powder, lyophilized, for solution100 mg/1Intravenous; SubcutaneousMylan Institutional2016-05-23Not applicableUs
AzacitidineInjection, powder, lyophilized, for solution100 mg/1Intravenous; SubcutaneousShilpa Medicare Limited2016-12-05Not applicableUs
AzacitidineInjection, powder, lyophilized, for solution100 mg/1Intravenous; SubcutaneousWockhardt2016-09-29Not applicableUs
AzacitidineInjection, powder, lyophilized, for solution100 mg/1Intravenous; SubcutaneousDr Reddy's Laboratories2013-09-19Not applicableUs
AzacitidineInjection, powder, lyophilized, for solution100 mg/1Intravenous; SubcutaneousDr Reddy's Laboratories2015-06-19Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
LadakamycinNot Available
MylosarNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIM801H13NRU
CAS number320-67-2
WeightAverage: 244.2047
Monoisotopic: 244.080769514
Chemical FormulaC8H12N4O5
InChI KeyNMUSYJAQQFHJEW-KVTDHHQDSA-N
InChI
InChI=1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5-,6-/m1/s1
IUPAC Name
4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one
SMILES
NC1=NC(=O)N(C=N1)[C@@H]1O[[email protected]](CO)[C@@H](O)[[email protected]]1O
Pharmacology
IndicationFor 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.
Structured Indications
Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentAcute Myelogenous Leukaemia (AML)1
1Active Not RecruitingTreatmentAcute Myeloid Leukaemias (AML) / Leukemia, Myelomonocytic, Chronic / Lymphoma NOS / Multiple Myeloma (MM) / Myelodysplastic Syndromes1
1Active Not RecruitingTreatmentAdult Acute Megakaryoblastic Leukemia (M7) / Adult Acute Monoblastic Leukemia (M5a) / Adult Acute Monocytic Leukemia (M5b) / Adult Acute Myeloblastic Leukemia With Maturation (M2) / Adult Acute Myeloblastic Leukemia Without Maturation (M1) / Adult Acute Myeloid Leukemia in Remission / Adult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Del(5q) / Adult Acute Myeloid Leukemia With Inv(16)(p13;q22) / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / Adult Acute Myelomonocytic Leukemia (M4) / Adult Erythroleukemia (M6a) / Adult Pure Erythroid Leukemia (M6b) / Recurrent Adult Acute Myeloid Leukemia / Secondary Acute Myeloid Leukemia / Untreated Adult Acute Myeloid Leukemia1
1Active Not RecruitingTreatmentAdult Acute Myeloid Leukemia With Inv(16)(p13.1q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With t(16;16)(p13.1;q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With t(8;21)(q22;q22); RUNX1-RUNX1T1 / Adult Acute Myeloid Leukemia With t(9;11)(p22;q23); MLLT3-MLL / Adult Acute Promyelocytic Leukemia With t(15;17)(q22;q12); PML-RARA / Alkylating Agent-Related Acute Myeloid Leukemia / Recurrent Adult Acute Myeloid Leukemia1
1Active Not RecruitingTreatmentAdult Nasal Type Extranodal NK/T-Cell Lymphoma / Recurrent Nasopharyngeal Keratinizing Squamous Cell Carcinoma / Recurrent Nasopharyngeal Undifferentiated Carcinoma / Stage IV Nasopharyngeal Keratinizing Squamous Cell Carcinoma / Stage IV Nasopharyngeal Undifferentiated Carcinoma1
1Active Not RecruitingTreatmentChronic Myelomonocytic Leukemia / De Novo Myelodysplastic Syndrome / Leukemias / Previously Treated Myelodysplastic Syndromes / Recurrent Adult Acute Myeloid Leukemia / Secondary Acute Myeloid Leukemia / Secondary Myelodysplastic Syndromes / Untreated Adult Acute Myeloid Leukemia1
1Active Not RecruitingTreatmentMelanoma (Skin)1
1Active Not RecruitingTreatmentMyelodysplastic Syndromes1
1CompletedNot AvailableAML / Hodgkins Disease (HD) / MDS / Multiple Myeloma (MM) / Non-Hodgkin's Lymphoma (NHL) / Tumors, Solid1
1CompletedNot AvailableMyelodysplastic Syndrome1
1CompletedTreatmentAccelerated Phase of Disease / Adult Acute Myeloid Leukemia With Inv(16)(p13.1q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With t(16;16)(p13.1;q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With t(8;21)(q22;q22); RUNX1-RUNX1T1 / Adult Acute Myeloid Leukemia With t(9;11)(p22;q23); MLLT3-MLL / Adult Acute Promyelocytic Leukemia With t(15;17)(q22;q12); PML-RARA / Atypical Chronic Myeloid Leukemia, BCR-ABL1 Negative / Blastic Phase / Chronic Myelogenous Leukemia, BCR-ABL1 Positive / Chronic Myelomonocytic Leukemia / De Novo Myelodysplastic Syndrome / Myelodysplastic/Myeloproliferative Neoplasm, Unclassifiable / Philadelphia Chromosome Negative, BCR-ABL1 Positive Chronic Myelogenous Leukemia / Previously Treated Myelodysplastic Syndromes / Primary Myelofibrosis / Recurrent Adult Acute Lymphoblastic Leukemia / Recurrent Adult Acute Myeloid Leukemia / Recurrent Disease / Secondary Acute Myeloid Leukemia / Secondary Myelodysplastic Syndromes1
1CompletedTreatmentAcute Lymphoblastic Leukaemias (ALL) / Acute Myelogenous Leukaemia (AML) / B-Cell Chronic Lymphocytic Leukemia / Chronic Myelogenous Leukemia (CML) / Myelodysplasia1
1CompletedTreatmentAcute Lymphoblastic Leukaemias (ALL) / Acute Myelogenous Leukaemia (AML) / Myelodysplastic Syndrome1
1CompletedTreatmentAcute Myelogenous Leukaemia (AML) / Chronic Myelomonocytic Leukemia (CMML) / Myelodysplastic Syndromes (MDS)1
1CompletedTreatmentAcute Myelogenous Leukaemia (AML) / Myelodysplastic Syndrome1
1CompletedTreatmentAdult Nasal Type Extranodal NK/T-Cell Lymphoma / Anaplastic Large Cell Lymphoma / Angioimmunoblastic T-Cell Lymphoma / Hepatosplenic T-Cell Lymphoma / Leukemia, Prolymphocytic / Peripheral T-Cell Lymphoma (PTCL) / Post-Transplant Lymphoproliferative Disorder / Recurrent Adult T-Cell Leukemia/Lymphoma / Recurrent Cutaneous T-Cell Non-Hodgkin Lymphoma / Recurrent Mycosis Fungoides/Sezary Syndrome / Small Intestine Lymphoma / T-Cell Large Granular Lymphocyte Leukemia1
1CompletedTreatmentAdult Solid Neoplasm / Hematopoietic and Lymphoid Cell Neoplasm1
1CompletedTreatmentAdvanced Cancers1
1CompletedTreatmentAdvanced Solid Tumor Malignancies1
1CompletedTreatmentChronic Lymphocytic Leukaemia (CLL) / Chronic Myeloid Leukemia (CML) / Myelodysplastic Syndrome / Myelofibrosis1
1CompletedTreatmentHead and Neck Cancers1
1CompletedTreatmentLeukemia, Myeloid, Acute / Myelodysplastic Syndromes1
1CompletedTreatmentLeukemia, Myelomonocytic, Chronic / Myelodysplastic Syndromes1
1CompletedTreatmentLeukemias / Myelodysplastic Syndrome1
1CompletedTreatmentLeukemias / Myelodysplastic Syndromes / Myelodysplastic/Myeloproliferative Diseases1
1CompletedTreatmentLymphoblastic Leukemia, Acute, Childhood / Myelogenous Leukemia, Acute, Childhood1
1CompletedTreatmentLymphoma NOS / Small Intestine Cancer / Unspecified Adult Solid Tumor, Protocol Specific1
1CompletedTreatmentMalignancies, Hematologic / Myelodysplastic Syndrome / Tumors, Solid1
1CompletedTreatmentRecurrent Melanoma / Recurrent Renal Cell Cancer / Stage III Melanoma / Stage IV Melanoma / Stage IV Renal Cell Cancer1
1CompletedTreatmentRelapsed Or Refractory Multiple Myeloma1
1CompletedTreatmentTumors, Solid1
1Not Yet RecruitingTreatmentChronic Myelomonocytic Leukemia / De Novo Myelodysplastic Syndrome / Previously Treated Myelodysplastic Syndromes / Refractory Anemia With Excess Blasts in Transformation / Secondary Myelodysplastic Syndromes1
1Not Yet RecruitingTreatmentMyelodysplastic Syndromes (MDS)1
1RecruitingBasic ScienceMyelodysplastic Syndromes1
1RecruitingTreatmentAcute Lymphocytic Leukemia (ALL) / Acute Myeloid Leukaemias (AML)1
1RecruitingTreatmentAcute Myelogenous Leukaemia (AML) / Acute Myeloid Leukaemias (AML) / Myelodysplastic Syndrome1
1RecruitingTreatmentAcute Myelogenous Leukaemia (AML) / Myelogenous Leukemia / Treatment Naive AML1
1RecruitingTreatmentAcute Myeloid Leukaemias (AML)1
1RecruitingTreatmentAcute Myeloid Leukaemias (AML) / Cancer, Breast / Genitourinary / Glioblastoma Multiforme / Hematological Neoplasms / Leukemias / Lymphoma NOS / Lymphoma, Hodgkins / Melanoma / Metastatic Breast Cancer (MBC) / Multiple Myeloma (MM) / Myelodysplastic Syndromes / Neoplasms / Non-Hodgkin's Lymphoma (NHL) / Non-Small-Cell Lung Carcinoma (NSCLC) / Osteosarcomas / Renal Cell Carcinoma (RCC) / Sarcomas / Small Cell Lung Cancer (SCLC) / Thyroid Cancers1
1RecruitingTreatmentCancer, Advanced1
1RecruitingTreatmentChronic Myelomonocytic Leukemia / De Novo Myelodysplastic Syndrome / Essential Thrombocythemia (ET) / Myelodysplastic Syndrome / Myelodysplastic/Myeloproliferative Neoplasms / Polycythemia Vera (PV) / Previously Treated Myelodysplastic Syndromes / Primary Myelofibrosis / Recurrent Adult Acute Myeloid Leukemia / Untreated Adult Acute Myeloid Leukemia1
1RecruitingTreatmentEsophageal Cancers / Malignant Neoplasm of Cardio-esophageal Junction of Stomach1
1RecruitingTreatmentLeukemia, Myelomonocytic, Chronic / Myelodysplastic Syndromes1
1RecruitingTreatmentLeukemias / Myelodysplastic Syndromes / Myelodysplastic/Myeloproliferative Neoplasms1
1RecruitingTreatmentMDS1
1RecruitingTreatmentMyelodysplastic Syndrome2
1RecruitingTreatmentMyelodysplastic Syndromes1
1RecruitingTreatmentRecurrent Non-Small Cell Lung Carcinoma / Stage IV Non-Small Cell Lung Cancer1
1RecruitingTreatmentTumors, Solid / Virally Mediated Cancers and Liposarcoma1
1TerminatedTreatmentAcute Myelogenous Leukaemia (AML) / Myelodysplastic Syndromes1
1TerminatedTreatmentAcute Myeloid Leukemia Arising From Previous Myelodysplastic Syndrome / Adult Acute Basophilic Leukemia / Adult Acute Eosinophilic Leukemia / Adult Acute Megakaryoblastic Leukemia / Adult Acute Monoblastic Leukemia / Adult Acute Monocytic Leukemia / Adult Acute Myeloid Leukemia in Remission / Adult Acute Myeloid Leukemia With Inv(16)(p13.1q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With Maturation / Adult Acute Myeloid Leukemia With Minimal Differentiation / Adult Acute Myeloid Leukemia With t(16;16)(p13.1;q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With t(8;21)(q22;q22); RUNX1-RUNX1T1 / Adult Acute Myeloid Leukemia With t(9;11)(p22;q23); MLLT3-MLL / Adult Acute Myeloid Leukemia Without Maturation / Adult Acute Myelomonocytic Leukemia / Adult Erythroleukemia / Adult Pure Erythroid Leukemia / Alkylating Agent-Related Acute Myeloid Leukemia / Recurrent Adult Acute Myeloid Leukemia / Secondary Acute Myeloid Leukemia / Untreated Adult Acute Myeloid Leukemia1
1TerminatedTreatmentAdvanced Cancers1
1TerminatedTreatmentCancer, Ovarian1
1TerminatedTreatmentLeukemias / Myelodysplastic Syndromes1
1TerminatedTreatmentNon-Small-Cell Lung Carcinoma (NSCLC) / Squamous Cell Carcinoma of the Head and Neck (SCCHN)1
1TerminatedTreatmentPancreatic Cancers1
1TerminatedTreatmentSquamous Cell Carcinoma (SCC)1
1TerminatedTreatmentStage IA Non-Small Cell Lung Carcinoma / Stage IB Non-Small Cell Lung Carcinoma / Stage IIA Non-Small Cell Lung Carcinoma / Stage IIB Non-Small Cell Lung Carcinoma / Stage IIIA Non-Small Cell Lung Cancer1
1, 2Active Not RecruitingTreatmentAcute Myeloid Leukaemias (AML) / Chronic Myelomonocytic Leukemia / Myelodysplastic Syndrome1
1, 2Active Not RecruitingTreatmentAdult Acute Megakaryoblastic Leukemia / Adult Acute Monoblastic Leukemia / Adult Acute Monocytic Leukemia / Adult Acute Myeloid Leukemia With Inv(16)(p13.1q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With Maturation / Adult Acute Myeloid Leukemia With Minimal Differentiation / Adult Acute Myeloid Leukemia With t(16;16)(p13.1;q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With t(8;21)(q22;q22); RUNX1-RUNX1T1 / Adult Acute Myeloid Leukemia With t(9;11)(p22;q23); MLLT3-MLL / Adult Acute Myeloid Leukemia Without Maturation / Adult Acute Myelomonocytic Leukemia / Adult Acute Promyelocytic Leukemia With t(15;17)(q22;q12); PML-RARA / Adult Erythroleukemia / Adult Pure Erythroid Leukemia / Chronic Myelomonocytic Leukemia / De Novo Myelodysplastic Syndrome / Previously Treated Myelodysplastic Syndromes / Recurrent Adult Acute Myeloid Leukemia / Refractory Anemia / Refractory Anemia With Excess Blasts / Refractory Anemia With Excess Blasts in Transformation / Refractory Anemia With Ring Sideroblasts / Secondary Acute Myeloid Leukemia / Secondary Myelodysplastic Syndromes / Untreated Adult Acute Myeloid Leukemia1
1, 2Active Not RecruitingTreatmentAdvanced Cancers / Lymphoma NOS1
1, 2Active Not RecruitingTreatmentAdvanced or Metastatic Breast Cancer / Advanced or Metastatic Solid Tumors1
1, 2Active Not RecruitingTreatmentHigh Grade Myelodysplastic Syndrome Lesions1
1, 2Active Not RecruitingTreatmentLeukemias3
1, 2Active Not RecruitingTreatmentMyelodysplastic Syndrome1
1, 2Active Not RecruitingTreatmentRenal Cell Carcinoma (RCC)1
1, 2CompletedTreatmentAcute Myelogenous Leukaemia (AML) / Leukemias / Myelodysplastic Syndrome1
1, 2CompletedTreatmentAcute Myeloid Leukaemias (AML) / Adult Acute Myeloblastic Leukemia1
1, 2CompletedTreatmentAdult Acute Megakaryoblastic Leukemia (M7) / Adult Acute Minimally Differentiated Myeloid Leukemia (M0) / Adult Acute Monoblastic Leukemia (M5a) / Adult Acute Monocytic Leukemia (M5b) / Adult Acute Myeloblastic Leukemia With Maturation (M2) / Adult Acute Myeloblastic Leukemia Without Maturation (M1) / Adult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Inv(16)(p13;q22) / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / Adult Acute Myelomonocytic Leukemia (M4) / Adult Erythroleukemia (M6a) / Adult Pure Erythroid Leukemia (M6b) / Recurrent Adult Acute Myeloid Leukemia1
1, 2CompletedTreatmentColorectal Cancers1
1, 2CompletedTreatmentDe Novo Myelodysplastic Syndromes / Previously Treated Myelodysplastic Syndromes / Secondary Myelodysplastic Syndromes1
1, 2CompletedTreatmentLeukemia, Myeloid, Acute1
1, 2CompletedTreatmentLeukemias3
1, 2CompletedTreatmentLeukemias / Myelodysplastic Syndromes1
1, 2CompletedTreatmentMyelodysplastic Syndrome1
1, 2CompletedTreatmentPain / Prostate Cancers1
1, 2CompletedTreatmentRecurrent Non-Small Cell Lung Carcinoma / Stage IIIA Non-Small Cell Lung Cancer / Stage IIIB Non-Small Cell Lung Cancer / Stage IV Non-Small Cell Lung Cancer1
1, 2Not Yet RecruitingTreatmentAdvanced Solid Tumors1
1, 2Not Yet RecruitingTreatmentLymphoma NOS1
1, 2RecruitingTreatmentAcute Myeloid Leukaemias (AML)2
1, 2RecruitingTreatmentDiffuse Large B Cell Lymphoma (DLBCL)1
1, 2RecruitingTreatmentLeukemia, Myeloid, Acute1
1, 2RecruitingTreatmentLeukemia, Myeloid, Acute / Myelodysplastic Syndromes / Precursor Cell Lymphoblastic Leukemia-Lymphoma1
1, 2RecruitingTreatmentLeukemias1
1, 2RecruitingTreatmentLymphoma NOS1
1, 2RecruitingTreatmentMDS1
1, 2RecruitingTreatmentMyelodysplastic Syndrome1
1, 2RecruitingTreatmentRefractory Multiple Myeloma1
1, 2RecruitingTreatmentUntreated Adult Acute Myeloid Leukemia1
1, 2WithdrawnTreatmentAcute Myeloid Leukaemias (AML)1
1, 2WithdrawnTreatmentMyelodysplastic Syndromes1
2Active Not RecruitingTreatmentAcute Myelogenous Leukaemia (AML) / Acute Myeloid Leukaemias (AML)1
2Active Not RecruitingTreatmentAcute Myeloid Leukaemias (AML)2
2Active Not RecruitingTreatmentAcute Myeloid Leukemia Arising From Previous Myelodysplastic Syndrome / Adult Acute Myeloid Leukemia in Remission / Adult Acute Myeloid Leukemia With Inv(16)(p13.1q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With t(16;16)(p13.1;q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With t(8;21)(q22;q22); RUNX1-RUNX1T1 / Adult Acute Myeloid Leukemia With t(9;11)(p22;q23); MLLT3-MLL / Adult Acute Promyelocytic Leukemia With t(15;17)(q22;q12); PML-RARA / Alkylating Agent-Related Acute Myeloid Leukemia / Chronic Myelomonocytic Leukemia / De Novo Myelodysplastic Syndrome / Previously Treated Myelodysplastic Syndromes / Recurrent Adult Acute Myeloid Leukemia / Secondary Acute Myeloid Leukemia / Secondary Myelodysplastic Syndromes / Untreated Adult Acute Myeloid Leukemia1
2Active Not RecruitingTreatmentAdult Acute Megakaryoblastic Leukemia / Adult Acute Monoblastic Leukemia / Adult Acute Monocytic Leukemia / Adult Acute Myeloid Leukemia in Remission / Adult Acute Myeloid Leukemia With Inv(16)(p13.1q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With Maturation / Adult Acute Myeloid Leukemia With Minimal Differentiation / Adult Acute Myeloid Leukemia With t(16;16)(p13.1;q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With t(8;21)(q22;q22); RUNX1-RUNX1T1 / Adult Acute Myeloid Leukemia With t(9;11)(p22;q23); MLLT3-MLL / Adult Acute Myeloid Leukemia Without Maturation / Adult Acute Myelomonocytic Leukemia / Adult Erythroleukemia / Adult Pure Erythroid Leukemia / Alkylating Agent-Related Acute Myeloid Leukemia / De Novo Myelodysplastic Syndrome / Previously Treated Myelodysplastic Syndromes / Recurrent Adult Acute Myeloid Leukemia / Refractory Anemia With Excess Blasts / Secondary Myelodysplastic Syndromes / Untreated Adult Acute Myeloid Leukemia1
2Active Not RecruitingTreatmentAdult Acute Megakaryoblastic Leukemia / Adult Acute Monoblastic Leukemia / Adult Acute Monocytic Leukemia / Adult Acute Myeloid Leukemia With Inv(16)(p13.1q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With Maturation / Adult Acute Myeloid Leukemia With t(16;16)(p13.1;q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With t(8;21)(q22;q22); RUNX1-RUNX1T1 / Adult Acute Myeloid Leukemia With t(9;11)(p22;q23); MLLT3-MLL / Adult Acute Myeloid Leukemia Without Maturation / Adult Acute Myelomonocytic Leukemia / Adult Erythroleukemia / Adult Pure Erythroid Leukemia / Secondary Acute Myeloid Leukemia / Untreated Adult Acute Myeloid Leukemia1
2Active Not RecruitingTreatmentEstrogen Receptor Negative / Estrogen Receptor Positive / HER2/Neu Negative / Male Breast Carcinoma / Progesterone Receptor Negative / Recurrent Breast Carcinoma / Stage IIIC Breast Cancer / Stage IV Breast Cancer / Triple-Negative Breast Carcinoma1
2Active Not RecruitingTreatmentLeukemias3
2Active Not RecruitingTreatmentMyelodysplastic Syndromes (MDS)1
2Active Not RecruitingTreatmentRecurrent Non-Small Cell Lung Carcinoma / Stage IV Non-Small Cell Lung Cancer1
2CompletedSupportive CareMDS / Myelodysplastic Syndromes / Thrombocytopenias1
2CompletedTreatmentAcute Myelogenous Leukaemia (AML) / Leukemias / Myelodysplastic Syndrome1
2CompletedTreatmentAcute Myelogenous Leukaemia (AML) / Myelodysplastic Syndrome1
2CompletedTreatmentAcute Myeloid Leukaemias (AML)2
2CompletedTreatmentAcute Myeloid Leukaemias (AML) / Myelodysplastic Syndrome2
2CompletedTreatmentAcute Myeloid Leukaemias (AML) / Myelodysplastic Syndromes (MDS)1
2CompletedTreatmentAdult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Del(5q) / Adult Acute Myeloid Leukemia With Inv(16)(p13;q22) / Adult Acute Myeloid Leukemia With T(15;17)(q22;q12) / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / Childhood Myelodysplastic Syndromes / Chronic Myelomonocytic Leukemia / Previously Treated Myelodysplastic Syndromes / Recurrent Adult Acute Myeloid Leukemia / Recurrent Childhood Acute Myeloid Leukemia / Secondary Myelodysplastic Syndromes1
2CompletedTreatmentBeta Thalassemia1
2CompletedTreatmentChronic Myelomonocytic Leukemia1
2CompletedTreatmentChronic Myelomonocytic Leukemia / Myelodysplastic Syndrome1
2CompletedTreatmentFollicular Lymphoma (FL) / Marginal Zone Lymphoma1
2CompletedTreatmentHigh Risk MDS1
2CompletedTreatmentLeukemias3
2CompletedTreatmentLeukemias / Lung Cancers / Lymphoma NOS / Multiple Myeloma and Plasma Cell Neoplasm / Myelodysplastic Syndromes / Prostate Cancers1
2CompletedTreatmentLeukemias / Myelodysplastic Syndromes1
2CompletedTreatmentLeukemias / Transplantation, Stem Cell1
2CompletedTreatmentMDS / Myelodysplastic Syndrome1
2CompletedTreatmentMyelodysplastic Syndrome3
2CompletedTreatmentMyelodysplastic Syndromes5
2CompletedTreatmentMyelodysplastic Syndromes (MDS)1
2CompletedTreatmentMyelofibrosis1
2CompletedTreatmentProstate Cancers1
2CompletedTreatmentRecurrent Colon Cancer / Recurrent Rectal Cancer / Stage IV Colon Cancer / Stage IV Rectal Cancer1
2Not Yet RecruitingTreatmentHead and Neck Squamous Cell Carcinoma (HNSCC)1
2Not Yet RecruitingTreatmentMyelodysplastic Syndrome2
2Not Yet RecruitingTreatmentMyelodysplastic Syndromes1
2RecruitingNot AvailableLeukemias1
2RecruitingTreatmentAcute Lymphoid Leukemia (ALL) / Acute Myelogenous Leukaemia (AML) / Juvenile Myelomonocytic Leukemia / Myelodysplastic Syndrome1
2RecruitingTreatmentAcute Myelocytic Leukemia / Myelodysplastic Syndrome1
2RecruitingTreatmentAcute Myelogenous Leukaemia (AML) / Myelodysplastic Syndrome2
2RecruitingTreatmentAcute Myelogenous Leukemia AML / Myelodysplastic Syndrome MDS1
2RecruitingTreatmentAcute Myeloid Leukaemias (AML)4
2RecruitingTreatmentAcute Myeloid Leukaemias (AML) / Chronic Myelomonocytic Leukemia / Myelodysplastic Syndromes1
2RecruitingTreatmentAcute Myeloid Leukaemias (AML) / Elderly1
2RecruitingTreatmentAcute Myeloid Leukaemias (AML) / Myelodysplastic Syndrome1
2RecruitingTreatmentAdult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Del(5q) / Adult Acute Myeloid Leukemia With Inv(16)(p13;q22) / Adult Acute Myeloid Leukemia With T(15;17)(q22;q12) / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / De Novo Myelodysplastic Syndromes / Myelodysplastic Syndrome With Isolated Del(5q) / Previously Treated Myelodysplastic Syndromes / Recurrent Adult Acute Myeloid Leukemia1
2RecruitingTreatmentChronic Myelomonocytic Leukemia / De Novo Myelodysplastic Syndrome / Secondary Myelodysplastic Syndromes1
2RecruitingTreatmentLeukemia, Erythroblastic, Acute / Myelodysplastic Syndromes1
2RecruitingTreatmentLeukemia, Myeloid, Acute2
2RecruitingTreatmentLeukemia, Myeloid, Acute / Leukemia, Myelomonocytic, Chronic / Myelodysplastic Syndromes2
2RecruitingTreatmentLeukemia, Myeloid, Acute / Myelodysplastic Syndromes1
2RecruitingTreatmentLeukemia, Myelomonocytic, Juvenile / Myelodysplastic Syndrome1
2RecruitingTreatmentLeukemias5
2RecruitingTreatmentLeukemias / Myelodysplastic Syndrome1
2RecruitingTreatmentMDS1
2RecruitingTreatmentMetastatic Colorectal Cancers1
2RecruitingTreatmentMyelodysplastic Syndrome2
2RecruitingTreatmentNon-Small Lung Cancer, Epigenetic Therapy1
2RecruitingTreatmentRecurrent Non-Small Cell Lung Carcinoma / Stage IIIA Non-Small Cell Lung Cancer / Stage IIIB Non-Small Cell Lung Cancer / Stage IV Non-Small Cell Lung Cancer1
2SuspendedTreatmentMyelodysplastic Syndrome1
2TerminatedTreatmentAcute Myeloid Leukaemias (AML)1
2TerminatedTreatmentAcute Myeloid Leukaemias (AML) / Leukemias / Myelodysplastic Syndromes (MDS)1
2TerminatedTreatmentAcute Myeloid Leukaemias (AML) / Myelodysplastic Syndromes (MDS)1
2TerminatedTreatmentChronic Lymphocytic Leukaemia (CLL) / Leukemias1
2TerminatedTreatmentChronic Lymphocytic Leukemia (CLL) and Small Lymphocytic Lymphoma (SLL)1
2TerminatedTreatmentChronic Myelomonocytic Leukemia (CMML) / Myelodysplastic Syndromes (MDS)1
2TerminatedTreatmentChronic Myeloproliferative Disorders / Secondary Myelofibrosis1
2TerminatedTreatmentLeukemia, Myelocytic, Acute / Myelodysplastic Syndromes1
2TerminatedTreatmentLeukemias1
2TerminatedTreatmentLeukemias / Myelodysplastic Syndromes1
2TerminatedTreatmentLymphoma, Hodgkins / Non-Hodgkin Lymphoma (Follicular or Large Diffuse B-cell Lymphoma or Mantle Cell Lymphoma)1
2TerminatedTreatmentMDS1
2TerminatedTreatmentMultiple Myeloma (MM)1
2TerminatedTreatmentMyelodysplastic Syndrome1
2TerminatedTreatmentMyelodysplastic Syndromes1
2TerminatedTreatmentStage IA Non-Small Cell Lung Carcinoma / Stage IB Non-Small Cell Lung Carcinoma1
2TerminatedTreatmentThalassemia Major (TM)1
2, 3Active Not RecruitingTreatmentAdult Myelodysplastic Syndrome / Chronic Myelomonocytic Leukemia / Chronic Myelomonocytic Leukemia-1 / Chronic Myelomonocytic Leukemia-2 / Previously Treated Myelodysplastic Syndromes / Refractory Anemia With Excess Blasts1
2, 3CompletedTreatmentLeukemias / Myelodysplastic Syndromes1
3Active Not RecruitingTreatmentAcute Myeloid Leukaemias (AML)1
3CompletedNot AvailableMyelodysplastic Syndromes1
3CompletedTreatmentMyelodysplastic Syndromes1
3RecruitingTreatmentAML / Leukemias / MDS1
3RecruitingTreatmentAcute Myeloid Leukaemias (AML)1
3RecruitingTreatmentIsocitrate Dehydrogenase / Myeloid Leukemias1
3RecruitingTreatmentLeukemia, Acute Myeloid (AML)1
3RecruitingTreatmentThrombocytopaenia1
3WithdrawnTreatmentAcute Myeloid Leukaemias (AML)1
4CompletedTreatmentMyelodysplastic Syndromes1
4TerminatedTreatmentMyelodysplastic Syndromes1
Not AvailableActive Not RecruitingNot AvailableMyelodysplastic Syndrome1
Not AvailableActive Not RecruitingTreatmentMultiple Myeloma (MM)1
Not AvailableCompletedNot AvailableMyelodysplastic Syndromes1
Not AvailableCompletedTreatmentHypermethylation / Lung Cancers / Non Small Cell Lung Carcinoma (NSCLC)1
Not AvailableCompletedTreatmentLeukemias1
Not AvailableNot Yet RecruitingDiagnosticMyelodysplastic Syndromes / Myeloid Leukemias1
Not AvailableNot Yet RecruitingTreatmentAcute Leukemias of Ambiguous Lineage / Childhood B Acute Lymphoblastic Leukemia / Mixed Phenotype Acute Leukemia (MPAL)1
Not AvailableWithdrawnTreatmentRecurrent Breast Cancer / Stage IA Breast Cancer / Stage IB Breast Cancer / Stage II Breast Cancer / Stage IIIA Breast Cancer / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer / Stage IV Breast Cancer / Triple-Negative Breast Cancer (TNBC)1
PharmacodynamicsAzacitidine 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 function to genes that are critical for differentiation and proliferation. The cytotoxic effects of azacitidine cause the death of rapidly dividing cells, including cancer cells that are no longer responsive to normal growth control mechanisms. Non-proliferating cells are relatively insensitive to azacitidine. Upon uptake into cells, azacitidine is phosphorylated to 5-azacytidine monophosphate by uridine-cytidine kinase, then to diphosphate by pyrimidine monophosphate kinases and triphosphate by diphosphate kinases. 5-Azacitidine triphosphate is incorporated into RNA, leading to the disruption of nuclear and cytoplasmic RNA metabolism and inhibition of protein synthesis. 5-Azacytidine diphosphate is reduced to 5-aza-deoxycytidine diphosphate by ribonucleotide reductase. The resultant metabolite is phosphorylated to 5-azadeoxycitidine triphosphate by nucleoside diphosphate kinases. 5-azadeoxycitidine triphosphate is then incoporated into DNA, leading to inhibition of DNA synthesis. Azacitidine is most toxic during the S-phase of the cell cycle.
Mechanism of actionAzacitidine (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 incorporation into DNA and RNA at high doses, resulting in cell death. As azacitidine is a ribonucleoside, it incoporates into RNA to a larger extent than into DNA. The incorporation into RNA leads to the dissembly of polyribosomes, defective methylation and acceptor function of transfer RNA, and inhibition of the production of protein. Its incorporation into DNA leads to a covalent binding with DNA methyltransferases, which prevents DNA synthesis and subsequent cytotoxicity.
TargetKindPharmacological actionActionsOrganismUniProt ID
DNA (cytosine-5)-methyltransferase 1Proteinyes
inhibitor
HumanP26358 details
RNANucleotideyes
other
Humannot applicabledetails
DNANucleotideyes
other
Humannot applicabledetails
Related Articles
AbsorptionAzacitidine is rapidly absorbed after subcutaneous administration. The bioavailability of subcutaneous azacitidine relative to IV azacitidine is approximately 89%, based on area under the curve.
Volume of distribution
  • 76 ± 26 L
Protein bindingNot Available
Metabolism

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 eliminationFollowing 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 lifeMean elimination half-life is approximately 4 hours.
Clearance
  • 167 +/- 49 L/h
ToxicityOne 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Azacitidine.Approved
ALT-110The risk or severity of adverse effects can be increased when Azacitidine is combined with ALT-110.Investigational
AnvirzelAnvirzel may decrease the cardiotoxic activities of Azacitidine.Investigational
BCGThe therapeutic efficacy of Bcg can be decreased when used in combination with Azacitidine.Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Azacitidine.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Azacitidine.Approved
CDX-110The risk or severity of adverse effects can be increased when Azacitidine is combined with CDX-110.Investigational
ClozapineThe risk or severity of adverse effects can be increased when Azacitidine is combined with Clozapine.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Azacitidine.Approved, Investigational
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Azacitidine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Azacitidine.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Azacitidine.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Azacitidine.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Azacitidine.Approved, Investigational
FingolimodAzacitidine may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
G17DTThe risk or severity of adverse effects can be increased when Azacitidine is combined with G17DT.Investigational
GI-5005The risk or severity of adverse effects can be increased when Azacitidine is combined with GI-5005.Investigational
INGN 201The risk or severity of adverse effects can be increased when Azacitidine is combined with INGN 201.Investigational
INGN 225The risk or severity of adverse effects can be increased when Azacitidine is combined with INGN 225.Investigational
LeflunomideThe risk or severity of adverse effects can be increased when Azacitidine is combined with Leflunomide.Approved, Investigational
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Azacitidine.Withdrawn
NatalizumabThe risk or severity of adverse effects can be increased when Azacitidine is combined with Natalizumab.Approved, Investigational
OuabainOuabain may decrease the cardiotoxic activities of Azacitidine.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Azacitidine.Approved, Vet Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Azacitidine.Approved, Investigational
Rabies vaccineThe risk or severity of adverse effects can be increased when Azacitidine is combined with Rabies vaccine.Approved
Rabies vaccineThe therapeutic efficacy of Rabies vaccine can be decreased when used in combination with Azacitidine.Approved
RoflumilastRoflumilast may increase the immunosuppressive activities of Azacitidine.Approved
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Azacitidine.Approved
SRP 299The risk or severity of adverse effects can be increased when Azacitidine is combined with SRP 299.Investigational
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Azacitidine.Approved, Investigational
TG4010The risk or severity of adverse effects can be increased when Azacitidine is combined with TG4010.Investigational
TofacitinibAzacitidine may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Azacitidine.Approved, Investigational
Food InteractionsNot Available
References
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.

US20110245485
General References
  1. Cihak A: Biological effects of 5-azacytidine in eukaryotes. Oncology. 1974;30(5):405-22. [PubMed:4142650 ]
  2. 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. [PubMed:15793220 ]
  3. 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. [PubMed:14585280 ]
  4. Ghoshal K, Bai S: DNA methyltransferases as targets for cancer therapy. Drugs Today (Barc). 2007 Jun;43(6):395-422. [PubMed:17612710 ]
  5. 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. [PubMed:12011120 ]
  6. Silverman LR: Targeting hypomethylation of DNA to achieve cellular differentiation in myelodysplastic syndromes (MDS). Oncologist. 2001;6 Suppl 5:8-14. [PubMed:11700387 ]
  7. Issa JP, Kantarjian H: Azacitidine. Nat Rev Drug Discov. 2005 May;Suppl:S6-7. [PubMed:15962522 ]
  8. 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 . [PubMed:18627335 ]
  9. Siddiqui MA, Scott LJ: Azacitidine: in myelodysplastic syndromes. Drugs. 2005;65(13):1781-9; discussion 1790-1. [PubMed:16114977 ]
  10. Abdulhaq H, Rossetti JM: The role of azacitidine in the treatment of myelodysplastic syndromes. Expert Opin Investig Drugs. 2007 Dec;16(12):1967-75. [PubMed:18042004 ]
  11. Keating GM: Azacitidine: a review of its use in higher-risk myelodysplastic syndromes/acute myeloid leukaemia. Drugs. 2009;69(17):2501-18. doi: 10.2165/11202840-000000000-00000. [PubMed:19911860 ]
  12. Sullivan M, Hahn K, Kolesar JM: Azacitidine: a novel agent for myelodysplastic syndromes. Am J Health Syst Pharm. 2005 Aug 1;62(15):1567-73. [PubMed:16030365 ]
  13. Dapp MJ, Clouser CL, Patterson S, Mansky LM: 5-Azacytidine can induce lethal mutagenesis in human immunodeficiency virus type 1. J Virol. 2009 Nov;83(22):11950-8. doi: 10.1128/JVI.01406-09. Epub 2009 Sep 2. [PubMed:19726509 ]
External Links
ATC CodesL01BC07
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (194 KB)
MSDSDownload (68.8 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9509
Blood Brain Barrier+0.8753
Caco-2 permeable-0.8715
P-glycoprotein substrateNon-substrate0.7879
P-glycoprotein inhibitor INon-inhibitor0.9591
P-glycoprotein inhibitor IINon-inhibitor0.9671
Renal organic cation transporterNon-inhibitor0.9355
CYP450 2C9 substrateNon-substrate0.8103
CYP450 2D6 substrateNon-substrate0.8572
CYP450 3A4 substrateNon-substrate0.6067
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9436
CYP450 2D6 inhibitorNon-inhibitor0.9438
CYP450 2C19 inhibitorNon-inhibitor0.9329
CYP450 3A4 inhibitorNon-inhibitor0.9617
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9839
Ames testAMES toxic0.8058
CarcinogenicityNon-carcinogens0.9182
BiodegradationNot ready biodegradable0.8432
Rat acute toxicity1.7991 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9794
hERG inhibition (predictor II)Non-inhibitor0.8996
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Celgene corp
Packagers
Dosage forms
FormRouteStrength
Injection, powder, lyophilized, for solutionIntravenous; Subcutaneous100 mg/1
Powder, for suspensionSubcutaneous100 mg
Prices
Unit descriptionCostUnit
Vidaza 100 mg vial588.23USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point229 °CPhysProp
water solubility8.9E+004 mg/LNot Available
logP-3.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility12.1 mg/mLALOGPS
logP-2.5ALOGPS
logP-3.1ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)12.55ChemAxon
pKa (Strongest Basic)-0.38ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area140.97 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52.19 m3·mol-1ChemAxon
Polarizability21.5 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as glycosylamines. These are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGlycosylamines
Alternative Parents
Substituents
  • N-glycosyl compound
  • Pentose monosaccharide
  • Amino-1,3,5-triazine
  • Aminotriazine
  • Triazinone
  • Monosaccharide
  • Triazine
  • 1,3,5-triazine
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Primary amine
  • Primary alcohol
  • Alcohol
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Zinc ion binding
Specific Function:
Methylates CpG residues. Preferentially methylates hemimethylated DNA. Associates with DNA replication sites in S phase maintaining the methylation pattern in the newly synthesized strand, that is essential for epigenetic inheritance. Associates with chromatin during G2 and M phases to maintain DNA methylation independently of replication. It is responsible for maintaining methylation patterns ...
Gene Name:
DNMT1
Uniprot ID:
P26358
Molecular Weight:
183163.635 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. 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. [PubMed:15793220 ]
  3. Cataldo VD, Cortes J, Quintas-Cardama A: Azacitidine for the treatment of myelodysplastic syndrome. Expert Rev Anticancer Ther. 2009 Jul;9(7):875-84. doi: 10.1586/era.09.61. [PubMed:19589026 ]
  4. 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. [PubMed:14585280 ]
  5. Ghoshal K, Bai S: DNA methyltransferases as targets for cancer therapy. Drugs Today (Barc). 2007 Jun;43(6):395-422. [PubMed:17612710 ]
  6. 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. [PubMed:12011120 ]
  7. Fenaux P: Inhibitors of DNA methylation: beyond myelodysplastic syndromes. Nat Clin Pract Oncol. 2005 Dec;2 Suppl 1:S36-44. [PubMed:16341239 ]
  8. Silverman LR: Targeting hypomethylation of DNA to achieve cellular differentiation in myelodysplastic syndromes (MDS). Oncologist. 2001;6 Suppl 5:8-14. [PubMed:11700387 ]
  9. 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 . [PubMed:18627335 ]
  10. Hollenbach PW, Nguyen AN, Brady H, Williams M, Ning Y, Richard N, Krushel L, Aukerman SL, Heise C, MacBeth KJ: A comparison of azacitidine and decitabine activities in acute myeloid leukemia cell lines. PLoS One. 2010 Feb 2;5(2):e9001. doi: 10.1371/journal.pone.0009001. [PubMed:20126405 ]
  11. Glover AB, Leyland-Jones B: Biochemistry of azacitidine: a review. Cancer Treat Rep. 1987 Oct;71(10):959-64. [PubMed:2443243 ]
2. RNA
Kind
Nucleotide
Organism
Human
Pharmacological action
yes
Actions
other
References
  1. Muller A, Florek M: 5-Azacytidine/Azacitidine. Recent Results Cancer Res. 2010;184:159-70. doi: 10.1007/978-3-642-01222-8_11. [PubMed:20072837 ]
  2. 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. [PubMed:15793220 ]
  3. Hollenbach PW, Nguyen AN, Brady H, Williams M, Ning Y, Richard N, Krushel L, Aukerman SL, Heise C, MacBeth KJ: A comparison of azacitidine and decitabine activities in acute myeloid leukemia cell lines. PLoS One. 2010 Feb 2;5(2):e9001. doi: 10.1371/journal.pone.0009001. [PubMed:20126405 ]
  4. Glover AB, Leyland-Jones B: Biochemistry of azacitidine: a review. Cancer Treat Rep. 1987 Oct;71(10):959-64. [PubMed:2443243 ]
  5. Cihak A, Vesely J, Skoda J: Azapyrimidine nucleosides: metabolism and inhibitory mechanisms. Adv Enzyme Regul. 1985;24:335-54. [PubMed:2424284 ]
  6. Dapp MJ, Clouser CL, Patterson S, Mansky LM: 5-Azacytidine can induce lethal mutagenesis in human immunodeficiency virus type 1. J Virol. 2009 Nov;83(22):11950-8. doi: 10.1128/JVI.01406-09. Epub 2009 Sep 2. [PubMed:19726509 ]
3. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
yes
Actions
other
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Allen A: Epigenetic alterations and cancer: new targets for therapy. IDrugs. 2007 Oct;10(10):709-12. [PubMed:17899489 ]
  4. 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. [PubMed:15793220 ]
  5. 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 . [PubMed:18627335 ]
  6. Muller A, Florek M: 5-Azacytidine/Azacitidine. Recent Results Cancer Res. 2010;184:159-70. doi: 10.1007/978-3-642-01222-8_11. [PubMed:20072837 ]
  7. Hollenbach PW, Nguyen AN, Brady H, Williams M, Ning Y, Richard N, Krushel L, Aukerman SL, Heise C, MacBeth KJ: A comparison of azacitidine and decitabine activities in acute myeloid leukemia cell lines. PLoS One. 2010 Feb 2;5(2):e9001. doi: 10.1371/journal.pone.0009001. [PubMed:20126405 ]
  8. Glover AB, Leyland-Jones B: Biochemistry of azacitidine: a review. Cancer Treat Rep. 1987 Oct;71(10):959-64. [PubMed:2443243 ]
  9. Cihak A, Vesely J, Skoda J: Azapyrimidine nucleosides: metabolism and inhibitory mechanisms. Adv Enzyme Regul. 1985;24:335-54. [PubMed:2424284 ]
  10. Dapp MJ, Clouser CL, Patterson S, Mansky LM: 5-Azacytidine can induce lethal mutagenesis in human immunodeficiency virus type 1. J Virol. 2009 Nov;83(22):11950-8. doi: 10.1128/JVI.01406-09. Epub 2009 Sep 2. [PubMed:19726509 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Zinc ion binding
Specific Function:
This enzyme scavenges exogenous and endogenous cytidine and 2'-deoxycytidine for UMP synthesis.
Gene Name:
CDA
Uniprot ID:
P32320
Molecular Weight:
16184.545 Da
References
  1. Garcia-Manero G, Stoltz ML, Ward MR, Kantarjian H, Sharma S: A pilot pharmacokinetic study of oral azacitidine. Leukemia. 2008 Sep;22(9):1680-4. doi: 10.1038/leu.2008.145. Epub 2008 Jun 12. [PubMed:18548103 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23