AZACITIDINE

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 Search

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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050794s029lbl.pdf
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA (cytosine-5)-methyltransferase 3A 3 Target ID: CHEMBL1992 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20126405	Inhibitor 7728
RNA 17 Target ID: CHEMBL2311222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2443243	Binding Agent 996
DNA 232 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20126405	Binding Agent 996

Conditions

Condition	Modality	Targets	Highest Phase	Product
Myelodysplastic syndromes 50 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050794s029lbl.pdf	Primary		Approved 8043	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

C_max

Value	Dose	Analyte	Population
121 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26296092	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 Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00652626	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 Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01599325	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 Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00652626	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 Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00652626	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 Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00652626	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

Value	Dose	Analyte	Population
184 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26296092	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 Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00652626	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 Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00652626	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 Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00652626	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 Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00652626	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 Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00652626	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 Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00652626	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 Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00652626	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 Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00652626	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 Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00652626	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 Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00652626	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 Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00652626	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 Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00652626	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:

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.56 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26296092	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050794s011lbl.pdf	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

Dose	Population	Adverse 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf
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: https://pubmed.ncbi.nlm.nih.gov/21576646	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: https://pubmed.ncbi.nlm.nih.gov/21576646	DLT: Diarrhea... Dose limiting toxicities: Diarrhea (grade 3-4, 2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/21576646
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: https://pubmed.ncbi.nlm.nih.gov/21576646	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: https://pubmed.ncbi.nlm.nih.gov/21576646	Sources: https://pubmed.ncbi.nlm.nih.gov/21576646
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: https://pubmed.ncbi.nlm.nih.gov/33636454	unhealthy, adult n = 8 Health Status: unhealthy Condition: advanced non-small cell lung cancer Age Group: adult Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/33636454	Sources: https://pubmed.ncbi.nlm.nih.gov/33636454
290 mg/m2 single, intravenous Overdose Dose: 290 mg/m2 Route: intravenous Route: single Dose: 290 mg/m2 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208216s000lbl.pdf	unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Population Size: 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208216s000lbl.pdf	Other AEs: Diarrhea, Nausea... Other AEs: Diarrhea (1 patient) Nausea (1 patient) Vomiting (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208216s000lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208216s000lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208216s000lbl.pdf	Disc. AE: Leukopenia, Thrombocytopenia... AEs leading to discontinuation/dose reduction: Leukopenia (>2) Thrombocytopenia (>2) Neutropenia (>2) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208216s000lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208216s000lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208216s000lbl.pdf	Disc. AE: Leukopenia, Thrombocytopenia... AEs leading to discontinuation/dose reduction: Leukopenia (>2) Thrombocytopenia (>2) Neutropenia (>2) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208216s000lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1467	inhibitor 1604	inhibitor 1702

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1383 CYP2B6 717 CYP2C8 818 CYP2C19 1325 CYP2E1 790 P-gp 1330 BCRP 643 OAT1 554 OAT3 588 OATP1B1 733 OATP1B3 657 OCT2 594	P-gp 1400	CYP1A2 637 CYP2C19 269 CYP3A4/5 108

Drug as perpetrator

Target	Modality	Activity
BCRP 713	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
CYP1A2 1532	inducer 1440 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-794_Vidaza_BioPharmr.pdf#page=28 Page: 28.0	no
CYP1A2 1532	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
CYP2B6 884	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
CYP2C19 1392	inducer 1440 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-794_Vidaza_BioPharmr.pdf#page=28 Page: 28.0	no
CYP2C19 1392	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
CYP2C8 865	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
CYP2C9 1648	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
CYP2D6 1738	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
CYP2E1 871	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
CYP3A4 1772	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
CYP3A4/5 293	inducer 1440 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-794_Vidaza_BioPharmr.pdf#page=28 Page: 28.0	no
OAT1 558	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
OAT3 590	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
OATP1B1 748	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
OATP1B3 666	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
OCT2 595	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
P-gp 1514	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1400	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-001809	http://www.3bsc.com/index/pro_info.php?id=23700
AEchem Scientific Corp., USA	AE044605	http://www.aechemsc.com/info_products/AE044605.php
AHH Chemical co.,ltd	MT-01297	http://www.ahhchemical.com/product/MT-01297.html
AK Scientific, Inc. (AKSCI)	J10124	http://www.aksci.com/item_detail.php?cat=J10124
Aaron Chemicals	AR0038R4	http://www.aaronchem.com/320-67-2
AbMole Bioscience	M2291	http://www.abmole.com/products/azacitidine.html
Achemo Scientific Limited	AC-10247	http://www.achemo.com/search/?Keyword=320-67-2
Achemtek	0104-020045	http://www.achemtek.com/320-67-2
Acorn PharmaTech	ACN-038132	http://www.acornpharmatech.com/
Acros Organics	AC226620500	https://www.fishersci.com/shop/products/5-azacytidine-99-acros-organics-1/AC226620500
Acros Organics	AC226620010	https://www.fishersci.com/shop/products/5-azacytidine-99-acros-organics/AC226620010
Active Biopharma	ABP001093	http://www.activebiopharma.com/320-67-2
Adooq BioScience	A10105	https://www.adooq.com/azacitidine-vidaza.html
Alfa Chemistry	AP320672-B	https://reagents.alfa-chemistry.com/product/5-azacytidine-cas-320-67-2-9920.html
Alfa Chemistry	AP320672-A	https://reagents.alfa-chemistry.com/product/azacitidine-cas-320-67-2-9919.html
Alichem	490011277	http://www.alichem.com/en/products/320-67-2.html
Alsachim	944	http://www.alsachim.com/product-C2972-glo.bal-view.html
Ambeed	A386837	https://www.ambeed.com/products/320-67-2.html
Ambinter	Amb20240535	http://www.ambinter.com/reference/20240535
Anward	ANW-27256	http://www.anward.com/pro_result/18434
ApexBio Technology	A1907	http://www.apexbt.com/5-azacytidine.html
Aurora Fine Chemicals LLC	A17.876.741	http://online.aurorafinechemicals.com/info?ID=A17.876.741
AvaChem Scientific	2145	http://www.avachem.com/productSearch.asp?2145
BLD Pharm	BD8347	http://www.bldpharm.com/products/320-67-2.html
BioCrick	BCC1130	http://www.biocrick.com/5-Azacytidine-BCC1130.html
BioSynth	J-700085	https://www.biosynth.com/products/biochemistry/other-biochemicals/products/J-700085.html
BroadPharm	SL-000003	http://www.broadpharm.com/bykeyword.php?s=SL-000003
CSNpharm	CSN19354	https://www.csnpharm.com/products/5-azacytidine.html
Capot Chemical	14167	http://www.capotchem.com/en/14167.htm
Capot Chemical	PubChem14167	http://www.capotchem.com/en/14167.htm
Chem Scene	CS-1287	http://www.chemscene.com/320-67-2.html
ChemFish Tokyo co.,ltd	CF00118	http://www.chemfish.com/index.php?c=msg&id=4553&
Chemenu	CM110249	http://www.chemenu.com/products/CM110249
Chemodex	A0271	http://www.chemodex.com/products/A0271
Chemspace	CSSB00000015021	https://chem-space.com/CSSB00000015021
DAOGE BIOPHARMA	DG21-11136	https://www.daogechem.com/product/320-67-2.html
DC Chemicals	DCAPI1525	http://www.dcchemicals.com//product_show-5_Azacytidine.html
Debye Scientific	DB-006955	http://www.debyesci.com/DB-006955.html
Enamine	Z1522566611	https://www.enaminestore.com/catalog/Z1522566611
Glentham Life Sciences	GA4671	http://www.glentham.com/products/product/GA4671/
Hairui	HR127621	http://www.hairuichem.com/en/product/320-67-2.html
Hello Bio	HB1374	https://www.hellobio.com/5-azacytidine.html
LGC Standards	MM1259.00	https://www.lgcstandards.com/US/en/p/MM1259.00
Lab Network	LN01327044	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01327044
Matrix Scientific	146645	https://www.matrixscientific.com/146645.html
MedChem Express	HY-10586	https://www.medchemexpress.com/5-Azacytidine.html
OChem	328	http://www.ocheminc.com/index.php?act=psearch&pid=320A672
Parchem	28267	http://www.parchem.com/chemical-supplier-distributor/Azacitidine-018267.aspx
Parchem	28268	http://www.parchem.com/chemical-supplier-distributor/Azacitidine-018268.aspx
Renno Tech	RP28647	http://www.rennotech.com/product_show.asp?id=34258
Selleck Chemicals	S1782	http://www.selleckchem.com/products/Azacitidine(Vidaza).html
Sigma-Aldrich	PHR1911_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/phr1911?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	A1287_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/a1287?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	A2385_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/a2385?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1045520_USP	https://www.sigmaaldrich.com/catalog/product/usp/1045520?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S548716	http://www.smolecule.com/products/s548716
Synblock Inc	SB18981	http://www.synblock.com/product/320-67-2.html
THE BioTek	bt-288122	https://www.thebiotek.com/product/inhibitors/bt-288122
Tocris	3842	https://www.tocris.com/products/5-azacytidine_3842
VladaChem	VL263813-1G	https://www.vladachem.com/product.php?products=320-67-2
abcr GmbH	AB249589	http://www.abcr.com/shop/en/AB249589
abcr GmbH	AB353547	http://www.abcr.com/shop/en/AB353547
eNovation Chemicals	D488382	http://www.enovationchem.com/productDetails.asp?productID=D488382
iChemical	EBD145507	http://www.ichemical.com/products/320-67-2.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-8318770472	https://mcule.com/MCULE-8318770472/

PubMed

Title	Date	PubMed
Unnatural enantiomers of 5-azacytidine analogues: syntheses and enzymatic properties.	2000 Nov	11137229
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	11281733
Targeting hypomethylation of DNA to achieve cellular differentiation in myelodysplastic syndromes (MDS).	2001	11700387
Hematologic malignancies: an opportunity for targeted drug therapy.	2001	11700385
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	11281650
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	11507078
5-azaC treatment enhances expression of transforming growth factor-beta receptors through down-regulation of Sp3.	2001 Aug 31	11443124
Effects of hydroxurea, stem cell factor, and erythropoietin in combination on fetal hemoglobin in the baboon.	2001 Feb	11166454
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	11221845
Evidence of abundant constitutive alkali-labile sites in human 5 bp classical satellite DNA loci by DBD-FISH.	2001 Feb 20	11166034
Anticancer drug-induced kidney disorders.	2001 Jan	11219485
Loss of mismatch repair activity in simian virus 40 large T antigen-immortalized BPH-1 human prostatic epithelial cell line.	2001 Jul	11479923
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	11548839
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	11499385
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	11262404
Silencing of the caspase-1 gene occurs in murine and human renal cancer cells and causes solid tumor growth in vivo.	2001 Mar 1	11267979
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	11266651
Two-dimensional database of a Burkitt lymphoma cell line (DG 75) proteins: protein pattern changes following treatment with 5'-azycytidine.	2001 May	11425244
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	11336546
5-Azacytidine modulates the response of sensitive and multidrug-resistant K562 leukemic cells to cytostatic drugs.	2001 May-Jun	11482878
GSTP1 CpG island hypermethylation is responsible for the absence of GSTP1 expression in human prostate cancer cells.	2001 Nov	11696442
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	11640883
E-cadherin expression is commonly downregulated by CpG island hypermethylation in esophageal carcinoma cells.	2001 Nov 8	11578811
Chondrocyte phenotype and cell survival are regulated by culture conditions and by specific cytokines through the expression of Sox-9 transcription factor.	2001 Oct	11600745
DNA hypermethylation is a mechanism for loss of expression of the HLA class I genes in human esophageal squamous cell carcinomas.	2001 Oct	11577000
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	11597130
CpG hypermethylation of the promoter region inactivates the estrogen receptor-beta gene in patients with prostate carcinoma.	2001 Oct 15	11596023
Glucocorticoid-mediated transrepression is regulated by histone acetylation and DNA methylation.	2001 Oct 19	11698053
Methylation in hMLH1 promoter interferes with its binding to transcription factor CBF and inhibits gene expression.	2001 Oct 25	11704838
Evolving treatment options of myelodysplastic syndromes.	2001 Sep	11669297
Selection of drug-resistant transduced cells with cytosine nucleoside analogs using the human cytidine deaminase gene.	2001 Sep	11593336
Molecular mechanisms mediating methylation-dependent silencing of ribosomal gene transcription.	2001 Sep	11583633
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	11568974
Promoter hypermethylation of MGMT is associated with protein loss in gastric carcinoma.	2001 Sep	11519041
The E-cadherin gene is silenced by CpG methylation in human oral squamous cell carcinomas.	2001 Sep 1	11477576
Evaluation of pharmacological induction of fatty acid beta-oxidation in X-linked adrenoleukodystrophy.	2001 Sep-Oct	11592822

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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

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