U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C8H12N4O5
Molecular Weight 244.205
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AZACITIDINE

SMILES

C([C@]1([H])[C@]([H])([C@]([H])([C@]([H])(n2cnc(=N)nc2O)O1)O)O)O

InChI

InChIKey=NMUSYJAQQFHJEW-KVTDHHQDSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15793220/ https://www.ncbi.nlm.nih.gov/pubmed/15962522

Azacitidine (Vidaza; Pharmion), an inhibitor of DNA methylation, was approved by the US FDA for the treatment of myelodysplastic syndromes in May 2004. It is the first drug to be approved by the FDA for treating this rare family of bone-marrow disorders, and has been given orphan-drug status. It is also a pioneering example of an agent that targets 'epigenetic' gene silencing, a mechanism that is exploited by cancer cells to inhibit the expression of genes that counteract the malignant phenotype. VIDAZA is used for the treatment of patients with the following FAB myelodysplastic syndrome (MDS) subtypes: Refractory anemia (RA) or refractory anemia with ringed sideroblasts (RARS), refractory anemia with excess blasts (RAEB), refractory anemia with excess blasts in transformation (RAEB-T), and chronic myelomonocytic leukemia (CMMoL). Azacitidine is a pyrimidine nucleoside analog of cytidine. It 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. As azacitidine is a ribonucleoside, it incorporates into RNA to a larger extent than into DNA. The incorporation into RNA leads to the dissemble 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. 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.

CNS Activity

Curator's Comment:: can cross the blood–brain barrier

Originator

Curator's Comment:: Pharmion acquired from Pharmacia Corp. the global rights to develop and commercialize 5-Azacitidine, a drug that has been studied for the treatment of myelodysplastic syndromes

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2311222
Target ID: CHEMBL2311221
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VIDAZA

Approved Use

Azacitidine for injection is a nucleoside metabolic inhibitor indicated for the treatment of patients with the following FAB myelodysplastic syndrome (MDS) subtypes: Refractory anemia (RA) or refractory anemia with ringed sideroblasts (RARS) (if accompanied by neutropenia or thrombocytopenia or requiring transfusions), refractory anemia with excess blasts (RAEB), refractory anemia with excess blasts in transformation (RAEB-T), and chronic myelomonocytic leukemia (CMMoL). 1.1 Myelodysplastic Syndromes (MDS) Azacitidine for injection is indicated for treatment of patients with the following French-American-British (FAB) myelodysplastic syndrome subtypes: refractory anemia (RA) or refractory anemia with ringed sideroblasts (if accompanied by neutropenia or thrombocytopenia or requiring transfusions), refractory anemia with excess blasts (RAEB), refractory anemia with excess blasts in transformation (RAEB-T), and chronic myelomonocytic leukemia (CMMoL).

Launch Date

1.08492482E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
121 ng/mL
200 mg 2 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
AZACITIDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1261.96 ng/mL
100 mg/m^2 single, subcutaneous
dose: 100 mg/m^2
route of administration: subcutaneous
experiment type: single
co-administered:
AZACITIDINE plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
1264.6 ng/mL
75 mg/m^2 1 times / day multiple, subcutaneous
dose: 75 mg/m^2
route of administration: subcutaneous
experiment type: multiple
co-administered:
AZACITIDINE plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
293.38 ng/mL
25 mg/m^2 single, subcutaneous
dose: 25 mg/m^2
route of administration: subcutaneous
experiment type: single
co-administered:
AZACITIDINE plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
745.5 ng/mL
75 mg/m^2 single, subcutaneous
dose: 75 mg/m^2
route of administration: subcutaneous
experiment type: single
co-administered:
AZACITIDINE plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
749.04 ng/mL
50 mg/m^2 single, subcutaneous
dose: 50 mg/m^2
route of administration: subcutaneous
experiment type: single
co-administered:
AZACITIDINE plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
184 ng × h/mL
200 mg 2 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
AZACITIDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1502.86 ng*h/mL
100 mg/m^2 single, subcutaneous
dose: 100 mg/m^2
route of administration: subcutaneous
experiment type: single
co-administered:
AZACITIDINE plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
1505.15999999999 ng*h/mL
100 mg/m^2 single, subcutaneous
dose: 100 mg/m^2
route of administration: subcutaneous
experiment type: single
co-administered:
AZACITIDINE plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
454.8 ng*h/mL
25 mg/m^2 single, subcutaneous
dose: 25 mg/m^2
route of administration: subcutaneous
experiment type: single
co-administered:
AZACITIDINE plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
455.86 ng*h/mL
25 mg/m^2 single, subcutaneous
dose: 25 mg/m^2
route of administration: subcutaneous
experiment type: single
co-administered:
AZACITIDINE plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
895.38 ng*h/mL
50 mg/m^2 single, subcutaneous
dose: 50 mg/m^2
route of administration: subcutaneous
experiment type: single
co-administered:
AZACITIDINE plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
897.43 ng*h/mL
50 mg/m^2 single, subcutaneous
dose: 50 mg/m^2
route of administration: subcutaneous
experiment type: single
co-administered:
AZACITIDINE plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
920.76 ng*h/mL
75 mg/m^2 single, subcutaneous
dose: 75 mg/m^2
route of administration: subcutaneous
experiment type: single
co-administered:
AZACITIDINE plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
921.87 ng*h/mL
75 mg/m^2 single, subcutaneous
dose: 75 mg/m^2
route of administration: subcutaneous
experiment type: single
co-administered:
AZACITIDINE plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
1533.37 ng*h/mL
100 mg/m^2 single, subcutaneous
dose: 100 mg/m^2
route of administration: subcutaneous
experiment type: single
co-administered:
AZACITIDINE plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
460.469999999999 ng*h/mL
25 mg/m^2 single, subcutaneous
dose: 25 mg/m^2
route of administration: subcutaneous
experiment type: single
co-administered:
AZACITIDINE plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
897.42 ng*h/mL
50 mg/m^2 single, subcutaneous
dose: 50 mg/m^2
route of administration: subcutaneous
experiment type: single
co-administered:
AZACITIDINE plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
945.5 ng*h/mL
75 mg/m^2 single, subcutaneous
dose: 75 mg/m^2
route of administration: subcutaneous
experiment type: single
co-administered:
AZACITIDINE plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.56 h
200 mg 2 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
AZACITIDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
41 min
75 mg/m² single, subcutaneous
dose: 75 mg/m²
route of administration: Subcutaneous
experiment type: SINGLE
co-administered:
AZACITIDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 68.0 years (range: 55- 86 years)
n = 236
Health Status: unhealthy
Condition: Acute Myeloid Leukemia
Age Group: 68.0 years (range: 55- 86 years)
Sex: M+F
Population Size: 236
Sources:
Disc. AE: Nausea, Diarrhea...
AEs leading to
discontinuation/dose reduction:
Nausea (2.1%)
Diarrhea (1.7%)
Vomiting (1.3%)
Neutropenia (20%)
Thrombocytopenia (8%)
Nausea (6%)
Neutropenia (6%)
Diarrhea (3.4%)
Thrombocytopenia (1.7%)
Nausea (1.7%)
Sources:
600 mg 1 times / day multiple, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unhealthy, 70 years (range: 31-91 years)
n = 3
Health Status: unhealthy
Condition: myelodysplastic syndromes | chronic myelomonocytic leukemia | acute myeloid leukemia
Age Group: 70 years (range: 31-91 years)
Sex: M+F
Population Size: 3
Sources:
DLT: Diarrhea...
Dose limiting toxicities:
Diarrhea (grade 3-4, 2 patients)
Sources:
480 mg 1 times / day multiple, oral
MTD
Dose: 480 mg, 1 times / day
Route: oral
Route: multiple
Dose: 480 mg, 1 times / day
Sources:
unhealthy, 70 years (range: 31-91 years)
n = 14
Health Status: unhealthy
Condition: myelodysplastic syndromes | chronic myelomonocytic leukemia | acute myeloid leukemia
Age Group: 70 years (range: 31-91 years)
Sex: M+F
Population Size: 14
Sources:
45 mg/m2 5 times / 2 weeks multiple, respiratory
Highest studied dose
Dose: 45 mg/m2, 5 times / 2 weeks
Route: respiratory
Route: multiple
Dose: 45 mg/m2, 5 times / 2 weeks
Sources:
unhealthy, adult
n = 8
Health Status: unhealthy
Condition: advanced non-small cell lung cancer
Age Group: adult
Population Size: 8
Sources:
290 mg/m2 single, intravenous
Overdose
Dose: 290 mg/m2
Route: intravenous
Route: single
Dose: 290 mg/m2
Sources:
unhealthy, adult
n = 1
Health Status: unhealthy
Age Group: adult
Population Size: 1
Sources:
Other AEs: Diarrhea, Nausea...
Other AEs:
Diarrhea (1 patient)
Nausea (1 patient)
Vomiting (1 patient)
Sources:
75 mg/m2 1 times / day multiple, intravenous (starting)
Recommended
Dose: 75 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 mg/m2, 1 times / day
Sources:
unhealthy, adult
Disc. AE: Leukopenia, Thrombocytopenia...
AEs leading to
discontinuation/dose reduction:
Leukopenia (>2)
Thrombocytopenia (>2)
Neutropenia (>2)
Sources:
75 mg/m2 1 times / day multiple, subcutaneous (starting)
Recommended
Dose: 75 mg/m2, 1 times / day
Route: subcutaneous
Route: multiple
Dose: 75 mg/m2, 1 times / day
Sources:
unhealthy, adult
Disc. AE: Leukopenia, Thrombocytopenia...
AEs leading to
discontinuation/dose reduction:
Leukopenia (>2)
Thrombocytopenia (>2)
Neutropenia (>2)
Sources:
AEs

AEs

AESignificanceDosePopulation
Vomiting 1.3%
Disc. AE
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 68.0 years (range: 55- 86 years)
n = 236
Health Status: unhealthy
Condition: Acute Myeloid Leukemia
Age Group: 68.0 years (range: 55- 86 years)
Sex: M+F
Population Size: 236
Sources:
Diarrhea 1.7%
Disc. AE
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 68.0 years (range: 55- 86 years)
n = 236
Health Status: unhealthy
Condition: Acute Myeloid Leukemia
Age Group: 68.0 years (range: 55- 86 years)
Sex: M+F
Population Size: 236
Sources:
Nausea 1.7%
Disc. AE
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 68.0 years (range: 55- 86 years)
n = 236
Health Status: unhealthy
Condition: Acute Myeloid Leukemia
Age Group: 68.0 years (range: 55- 86 years)
Sex: M+F
Population Size: 236
Sources:
Thrombocytopenia 1.7%
Disc. AE
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 68.0 years (range: 55- 86 years)
n = 236
Health Status: unhealthy
Condition: Acute Myeloid Leukemia
Age Group: 68.0 years (range: 55- 86 years)
Sex: M+F
Population Size: 236
Sources:
Nausea 2.1%
Disc. AE
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 68.0 years (range: 55- 86 years)
n = 236
Health Status: unhealthy
Condition: Acute Myeloid Leukemia
Age Group: 68.0 years (range: 55- 86 years)
Sex: M+F
Population Size: 236
Sources:
Neutropenia 20%
Disc. AE
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 68.0 years (range: 55- 86 years)
n = 236
Health Status: unhealthy
Condition: Acute Myeloid Leukemia
Age Group: 68.0 years (range: 55- 86 years)
Sex: M+F
Population Size: 236
Sources:
Diarrhea 3.4%
Disc. AE
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 68.0 years (range: 55- 86 years)
n = 236
Health Status: unhealthy
Condition: Acute Myeloid Leukemia
Age Group: 68.0 years (range: 55- 86 years)
Sex: M+F
Population Size: 236
Sources:
Nausea 6%
Disc. AE
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 68.0 years (range: 55- 86 years)
n = 236
Health Status: unhealthy
Condition: Acute Myeloid Leukemia
Age Group: 68.0 years (range: 55- 86 years)
Sex: M+F
Population Size: 236
Sources:
Neutropenia 6%
Disc. AE
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 68.0 years (range: 55- 86 years)
n = 236
Health Status: unhealthy
Condition: Acute Myeloid Leukemia
Age Group: 68.0 years (range: 55- 86 years)
Sex: M+F
Population Size: 236
Sources:
Thrombocytopenia 8%
Disc. AE
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 68.0 years (range: 55- 86 years)
n = 236
Health Status: unhealthy
Condition: Acute Myeloid Leukemia
Age Group: 68.0 years (range: 55- 86 years)
Sex: M+F
Population Size: 236
Sources:
Diarrhea grade 3-4, 2 patients
DLT
600 mg 1 times / day multiple, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unhealthy, 70 years (range: 31-91 years)
n = 3
Health Status: unhealthy
Condition: myelodysplastic syndromes | chronic myelomonocytic leukemia | acute myeloid leukemia
Age Group: 70 years (range: 31-91 years)
Sex: M+F
Population Size: 3
Sources:
Diarrhea 1 patient
290 mg/m2 single, intravenous
Overdose
Dose: 290 mg/m2
Route: intravenous
Route: single
Dose: 290 mg/m2
Sources:
unhealthy, adult
n = 1
Health Status: unhealthy
Age Group: adult
Population Size: 1
Sources:
Nausea 1 patient
290 mg/m2 single, intravenous
Overdose
Dose: 290 mg/m2
Route: intravenous
Route: single
Dose: 290 mg/m2
Sources:
unhealthy, adult
n = 1
Health Status: unhealthy
Age Group: adult
Population Size: 1
Sources:
Vomiting 1 patient
290 mg/m2 single, intravenous
Overdose
Dose: 290 mg/m2
Route: intravenous
Route: single
Dose: 290 mg/m2
Sources:
unhealthy, adult
n = 1
Health Status: unhealthy
Age Group: adult
Population Size: 1
Sources:
Leukopenia >2
Disc. AE
75 mg/m2 1 times / day multiple, intravenous (starting)
Recommended
Dose: 75 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 mg/m2, 1 times / day
Sources:
unhealthy, adult
Neutropenia >2
Disc. AE
75 mg/m2 1 times / day multiple, intravenous (starting)
Recommended
Dose: 75 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 mg/m2, 1 times / day
Sources:
unhealthy, adult
Thrombocytopenia >2
Disc. AE
75 mg/m2 1 times / day multiple, intravenous (starting)
Recommended
Dose: 75 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 mg/m2, 1 times / day
Sources:
unhealthy, adult
Leukopenia >2
Disc. AE
75 mg/m2 1 times / day multiple, subcutaneous (starting)
Recommended
Dose: 75 mg/m2, 1 times / day
Route: subcutaneous
Route: multiple
Dose: 75 mg/m2, 1 times / day
Sources:
unhealthy, adult
Neutropenia >2
Disc. AE
75 mg/m2 1 times / day multiple, subcutaneous (starting)
Recommended
Dose: 75 mg/m2, 1 times / day
Route: subcutaneous
Route: multiple
Dose: 75 mg/m2, 1 times / day
Sources:
unhealthy, adult
Thrombocytopenia >2
Disc. AE
75 mg/m2 1 times / day multiple, subcutaneous (starting)
Recommended
Dose: 75 mg/m2, 1 times / day
Route: subcutaneous
Route: multiple
Dose: 75 mg/m2, 1 times / day
Sources:
unhealthy, adult
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Unnatural enantiomers of 5-azacytidine analogues: syntheses and enzymatic properties.
2000 Nov
Comparative effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin on MCF-7, RL95-2, and LNCaP cells: role of target steroid hormones in cellular responsiveness to CYP1A1 induction.
2000 Sep
Targeting hypomethylation of DNA to achieve cellular differentiation in myelodysplastic syndromes (MDS).
2001
Hematologic malignancies: an opportunity for targeted drug therapy.
2001
Effects of simian virus 40 T-antigens on normal human mammary epithelial cells reveal evidence for spontaneous alterations in addition to loss of p16(INK4a) expression.
2001 Apr 15
Reversion of transcriptional repression of Sp1 by 5 aza-2' deoxycytidine restores TGF-beta type II receptor expression in the pancreatic cancer cell line MIA PaCa-2.
2001 Aug 15
5-azaC treatment enhances expression of transforming growth factor-beta receptors through down-regulation of Sp3.
2001 Aug 31
Effects of hydroxurea, stem cell factor, and erythropoietin in combination on fetal hemoglobin in the baboon.
2001 Feb
Identification of a novel member of the snail/Gfi-1 repressor family, mlt 1, which is methylated and silenced in liver tumors of SV40 T antigen transgenic mice.
2001 Feb 1
Evidence of abundant constitutive alkali-labile sites in human 5 bp classical satellite DNA loci by DBD-FISH.
2001 Feb 20
Anticancer drug-induced kidney disorders.
2001 Jan
Loss of mismatch repair activity in simian virus 40 large T antigen-immortalized BPH-1 human prostatic epithelial cell line.
2001 Jul
Decitabine with allogeneic peripheral blood stem cell transplantation in the therapy of leukemia relapse following a prior transplant: results of a phase I study.
2001 Jun
Overexpression of MnSOD protects murine fibrosarcoma cells (FSa-II) from apoptosis and promotes a differentiation program upon treatment with 5-azacytidine: involvement of MAPK and NFkappaB pathways.
2001 Jun
Increased sensitivity of transforming growth factor (TGF) beta 1 null cells to alkylating agents reveals a novel link between TGFbeta signaling and O(6)-methylguanine methyltransferase promoter hypermethylation.
2001 Jun 1
Silencing of the caspase-1 gene occurs in murine and human renal cancer cells and causes solid tumor growth in vivo.
2001 Mar 1
Association of deletions and translocation of the reduced folate carrier gene with profound loss of gene expression in methotrexate-resistant K562 human erythroleukemia cells.
2001 Mar 15
Two-dimensional database of a Burkitt lymphoma cell line (DG 75) proteins: protein pattern changes following treatment with 5'-azycytidine.
2001 May
Induction of Tax i expression in MT-4 cells by 5-azacytidine leads to protein binding in the HTLV-1 LTR in vivo.
2001 May 10
5-Azacytidine modulates the response of sensitive and multidrug-resistant K562 leukemic cells to cytostatic drugs.
2001 May-Jun
GSTP1 CpG island hypermethylation is responsible for the absence of GSTP1 expression in human prostate cancer cells.
2001 Nov
Inhibition of histone deacetylase activity causes cell type-specific induction of the PDGF-B promoter only in the absence of activation by its enhancer.
2001 Nov 1
E-cadherin expression is commonly downregulated by CpG island hypermethylation in esophageal carcinoma cells.
2001 Nov 8
Chondrocyte phenotype and cell survival are regulated by culture conditions and by specific cytokines through the expression of Sox-9 transcription factor.
2001 Oct
DNA hypermethylation is a mechanism for loss of expression of the HLA class I genes in human esophageal squamous cell carcinomas.
2001 Oct
Methylation changes in the human IGF2 p3 promoter parallel IGF2 expression in the primary tumor, established cell line, and xenograft of a human hepatoblastoma.
2001 Oct 15
CpG hypermethylation of the promoter region inactivates the estrogen receptor-beta gene in patients with prostate carcinoma.
2001 Oct 15
Glucocorticoid-mediated transrepression is regulated by histone acetylation and DNA methylation.
2001 Oct 19
Methylation in hMLH1 promoter interferes with its binding to transcription factor CBF and inhibits gene expression.
2001 Oct 25
Evolving treatment options of myelodysplastic syndromes.
2001 Sep
Selection of drug-resistant transduced cells with cytosine nucleoside analogs using the human cytidine deaminase gene.
2001 Sep
Molecular mechanisms mediating methylation-dependent silencing of ribosomal gene transcription.
2001 Sep
Hypermethylation of the tumor necrosis factor receptor superfamily 6 (APT1, Fas, CD95/Apo-1) gene promoter at rel/nuclear factor kappaB sites in prostatic carcinoma.
2001 Sep
Promoter hypermethylation of MGMT is associated with protein loss in gastric carcinoma.
2001 Sep
The E-cadherin gene is silenced by CpG methylation in human oral squamous cell carcinomas.
2001 Sep 1
Evaluation of pharmacological induction of fatty acid beta-oxidation in X-linked adrenoleukodystrophy.
2001 Sep-Oct
Patents

Sample Use Guides

The recommended starting dose for the first treatment cycle, for all patients regardless of baseline hematology laboratory values, is 75 mg/m2 subcutaneously or intravenously, daily for 7 days. Premedicate patients for nausea and vomiting. Repeat cycles every 4 weeks. After 2 cycles, may increase dose to 100 mg/m2 if no beneficial effect is seen and no toxicity other than nausea and vomiting has occurred.
Route of Administration: Other
5-AZA ( 5-azacytidine) exerted anti-myeloma activity in a time- and concentration-dependent manner. The IC(50) value of XG-7 cells treated with 5-AZA for 48 hours was 2.6 micromol/L. 1.0, 2.0, 2.5 and 5.0 micromol/L of 5-AZA treatment for 48 hours induced (34.3 +/- 8.0)%, (54.8 +/- 3.1)%, (64.1 +/- 3.4)%, (81.0 +/- 4.1)% apoptosis in XG-7 cell line respectively. 5-AZA treatment can induce the expression of XAF1 mRNA and protein in myeloma.
Name Type Language
AZACITIDINE
EMA EPAR   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
AZACITIDINE [ORANGE BOOK]
Common Name English
5-AZACYTIDINE
Systematic Name English
AZACITIDINE [VANDF]
Common Name English
ONUREG
Brand Name English
AZACITIDINE [INN]
Common Name English
AZACITIDINE [MI]
Common Name English
AZACITIDINE [HSDB]
Common Name English
AZACITIDINE [JAN]
Common Name English
VIDAZA
Brand Name English
AZACITIDINE [WHO-DD]
Common Name English
AZACITIDINE [IARC]
Common Name English
5-AZACITIDINE
Common Name English
4-AMINO-1-.BETA.-D-RIBOFURANOSYL-S-TRIAZIN-2(1H)-ONE
Common Name English
U-18,496
Code English
1,3,5-TRIAZIN-2(1H)-ONE, 4-AMINO-1-.BETA.-D-RIBOFURANOSYL-
Common Name English
AZACYTIDINE
Systematic Name English
AZACITIDINE [EMA EPAR]
Common Name English
AZACITIDINE [MART.]
Common Name English
NSC-102816
Code English
AZACITIDINE [USP-RS]
Common Name English
U-18496
Code English
AZACITIDINE [USAN]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 150101
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
WHO-ATC L01BC07
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
NDF-RT N0000000233
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
EMA ASSESSMENT REPORTS VIDAZA (AUTHORIZED: MYELODYPLASTIC SYNDROMES)
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
LIVERTOX 80
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
WHO-VATC QL01BC07
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
NCI_THESAURUS C2083
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
FDA ORPHAN DRUG 257008
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
NDF-RT N0000175595
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
NCI_THESAURUS C1557
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
EU-Orphan Drug EU/3/01/084
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL1489
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
PRIMARY
ECHA (EC/EINECS)
206-280-2
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
PRIMARY
IUPHAR
6796
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
PRIMARY
EPA CompTox
320-67-2
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
PRIMARY
RXCUI
1251
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
AZACITIDINE
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
PRIMARY
HSDB
6879
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
PRIMARY
PUBCHEM
9444
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
PRIMARY
INN
4520
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
PRIMARY
MESH
D001374
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
PRIMARY
EVMPD
SUB05624MIG
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
PRIMARY
MERCK INDEX
M2154
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
PRIMARY Merck Index
LACTMED
Azacitidine
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
PRIMARY
FDA UNII
M801H13NRU
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
PRIMARY
NCI_THESAURUS
C288
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
PRIMARY
USP_CATALOG
1045520
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
PRIMARY USP-RS
DRUG CENTRAL
25
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
PRIMARY
CAS
320-67-2
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
PRIMARY
DRUG BANK
DB00928
Created by admin on Sat Jun 26 07:17:46 UTC 2021 , Edited by admin on Sat Jun 26 07:17:46 UTC 2021
PRIMARY