AZACITIDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C8H12N4O5
Molecular Weight	244.2047
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC(=O)N(C=N1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O

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 8146
RNA 18 Target ID: CHEMBL2311222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2443243	Binding Agent 1037
DNA 241 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20126405	Binding Agent 1037

Conditions

Condition	Modality	Targets	Highest Phase	Product
Myelodysplastic syndromes 54 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050794s029lbl.pdf	Primary		Approved 8307	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 1532	inhibitor 1695	inhibitor 1789

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1463 CYP2B6 770 CYP2C8 869 CYP2C19 1410 CYP2E1 846 P-gp 1401 BCRP 678 OAT1 584 OAT3 625 OATP1B1 770 OATP1B3 691 OCT2 630	P-gp 1491	CYP1A2 671 CYP2C19 283 CYP3A4/5 112

Drug as perpetrator

Target	Modality	Activity
BCRP 751	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
CYP1A2 1620	inducer 1515 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-794_Vidaza_BioPharmr.pdf#page=28 Page: 28.0	no
CYP1A2 1620	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
CYP2B6 946	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
CYP2C19 1484	inducer 1515 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-794_Vidaza_BioPharmr.pdf#page=28 Page: 28.0	no
CYP2C19 1484	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
CYP2C8 923	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
CYP2C9 1747	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
CYP2D6 1826	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
CYP2E1 929	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
CYP3A4 1857	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
CYP3A4/5 314	inducer 1515 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/50-794_Vidaza_BioPharmr.pdf#page=28 Page: 28.0	no
OAT1 588	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
OAT3 627	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
OATP1B1 785	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
OATP1B3 700	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
OCT2 631	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/214120s000lbl.pdf#page=14 Page: 14.0	no
P-gp 1588	inhibitor 3185 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 1491	substrate 3264 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
Targeting hypomethylation of DNA to achieve cellular differentiation in myelodysplastic syndromes (MDS).	2001	11700387
Hematologic malignancies: an opportunity for targeted drug therapy.	2001	11700385
Demethylation by 5-aza-2'-deoxycytidine (5-azadC) of p16INK4A gene results in downregulation of vascular endothelial growth factor expression in human lung cancer cell lines.	2001	11589304
Autoreactive murine Th1 and Th2 cells kill syngeneic macrophages and induce autoantibodies.	2001	11530995
Unnatural enantiomers of 5-azacytidine analogues: syntheses and enzymatic properties.	2001 Apr-Jul	11563127
Zidovudine (AZT) resistance in H9 cells due to decreased TK expression is associated with hypermethylation of TK gene.	2001 Apr-Jul	11563064
6-azacytidine--compound with wide spectrum of antiviral activity.	2001 Apr-Jul	11562975
Inactivation of retinoic acid receptor beta by promoter CpG hypermethylation in gastric cancer.	2001 Aug	11683489
Cytogenetic responses in high-risk myelodysplastic syndrome following low-dose treatment with the DNA methylation inhibitor 5-aza-2'-deoxycytidine.	2001 Aug	11529854
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
Molecular mechanisms for aberrant expression of the human breast cancer specific gene 1 in breast cancer cells: control of transcription by DNA methylation and intronic sequences.	2001 Aug 23	11526506
Antineoplastic action of 5-aza-2'-deoxycytidine and histone deacetylase inhibitor and their effect on the expression of retinoic acid receptor beta and estrogen receptor alpha genes in breast carcinoma cells.	2001 Jul	11488527
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
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
CpG methylation as a basis for breast tumor-specific loss of NES1/kallikrein 10 expression.	2001 Nov 1	11691827
Diminished expression of S100A2, a putative tumor suppressor, at early stage of human lung carcinogenesis.	2001 Nov 1	11691825
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
Early detection of endogenous retroviruses in chemically induced mouse cells.	2001 Nov 5	11551644
E-cadherin expression is commonly downregulated by CpG island hypermethylation in esophageal carcinoma cells.	2001 Nov 8	11578811
5-Aza-2'-deoxycytidine induces histone hyperacetylation of mouse centromeric heterochromatin by a mechanism independent of DNA demethylation.	2001 Nov 9	11688997
Reduced expression of syndecan-1 affects metastatic potential and clinical outcome in patients with colorectal cancer.	2001 Oct	11676858
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
DNA hypomethylation of karyoplasts for bovine nuclear transplantation.	2001 Oct	11553920
Synergistic activation of functional estrogen receptor (ER)-alpha by DNA methyltransferase and histone deacetylase inhibition in human ER-alpha-negative breast cancer cells.	2001 Oct 1	11585728
Rexpression of HLA class I antigens and restoration of antigen-specific CTL response in melanoma cells following 5-aza-2'-deoxycytidine treatment.	2001 Oct 15	11668505
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
Methylation-dependent silencing of the reduced folate carrier gene in inherently methotrexate-resistant human breast cancer cells.	2001 Oct 26	11509559
Methylation of episomal plasmids as a barrier to transient gene expression via a synthetic delivery vector.	2001 Oct 31	11576873
Evolving treatment options of myelodysplastic syndromes.	2001 Sep	11669297
Alteration of DNA methylation in gastrointestinal carcinogenesis.	2001 Sep	11595058
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
Epigenetic regulation of the KAI1 metastasis suppressor gene in human prostate cancer cell lines.	2001 Sep	11572762
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
CpG methylation of promoter region inactivates E-cadherin gene in renal cell carcinoma.	2001 Sep	11568972
Promoter hypermethylation of MGMT is associated with protein loss in gastric carcinoma.	2001 Sep	11519041
Loss of annexin II heavy and light chains in prostate cancer and its precursors.	2001 Sep 1	11522620
The E-cadherin gene is silenced by CpG methylation in human oral squamous cell carcinomas.	2001 Sep 1	11477576
Sensitization for death receptor- or drug-induced apoptosis by re-expression of caspase-8 through demethylation or gene transfer.	2001 Sep 13	11593392
Hypermethylation of CpG islands in the mouse asparagine synthetase gene: relationship to asparaginase sensitivity in lymphoma cells. Partial methylation in normal cells.	2001 Sep 14	11556848
Histone deacetylase and DNA methyltransferase in human prostate cancer.	2001 Sep 28	11563853
Altered hox gene expression and cellular pathogenesis of 5-aza-2'-deoxycytidine-induced murine hindlimb dysmorphogenesis.	2001 Sep-Oct	11695566
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

Azacitidine [WHO-DD]

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 [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