DECITABINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C8H12N4O4
Molecular Weight	228.2056
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C1[C@@]([H])([C@@]([H])(CO)O[C@@]1([H])n2cnc(=N)nc2O)O

InChI

InChIKey=XAUDJQYHKZQPEU-KVQBGUIXSA-N

InChI=1S/C8H12N4O4/c9-7-10-3-12(8(15)11-7)6-1-4(14)5(2-13)16-6/h3-6,13-14H,1-2H2,(H2,9,11,15)/t4-,5+,6+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23369223
Curator's Comment:: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021790s018lbl.pdf, www.ncbi.nlm.nih.gov/pubmed/20501800

Decitabine was first synthesized by Pliml and Sorm in the Institute of Organic Chemistry, Czechoslovak Academy of Sciences in 1964. Later, the drug was approved by FDA for the treatment of myelodysplastic syndromes in patients with cancer. Upon administration the decitabine is metabolized to the active phosphorylated metabolite which is incorporated into DNA and thus inhibits DNA methyltransferase (decitabine deplete DNMT1).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 232 Target ID: CHEMBL2311221 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021790s018lbl.pdf	Binding Agent 996
DNA (cytosine-5)-methyltransferase 1 9 Target ID: CHEMBL1993 Sources: www.ncbi.nlm.nih.gov/pubmed/20501800	Inhibitor 7728

Conditions

Condition	Modality	Targets	Highest Phase	Product
Myelodysplastic syndromes 50 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021790s018lbl.pdf	Primary		Approved 8043	DACOGEN Approved Use Dacogen is a nucleoside metabolic inhibitor indicated for treatment of patients with myelodysplastic syndromes (MDS) including previously treated and untreated, de novo and secondary MDS of all French-American-British subtypes (refractory anemia, refractory anemia with ringed sideroblasts, refractory anemia with excess blasts, refractory anemia with excess blasts in transformation, and chronic myelomonocytic leukemia) and intermediate-1, intermediate -2, and high-risk International Prognostic Scoring System groups. Launch Date 1.14652794E12

C_max

Value	Dose	Co-administered	Analyte	Population
73.8 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17564707	15 mg/m² steady-state, intravenous dose: 15 mg/m² route of administration: Intravenous experiment type: STEADY-STATE co-administered:		DECITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
163 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17564707	15 mg/m² steady-state, intravenous dose: 15 mg/m² route of administration: Intravenous experiment type: STEADY-STATE co-administered:		DECITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.62 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17564707	15 mg/m² steady-state, intravenous dose: 15 mg/m² route of administration: Intravenous experiment type: STEADY-STATE co-administered:		DECITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
99% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/021790s021lbl.pdf			DECITABINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
100 mg/m2 2 times / day steady, intravenous Highest studied dose Dose: 100 mg/m2, 2 times / day Route: intravenous Route: steady Dose: 100 mg/m2, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9324279	unhealthy, 52 years (range: 23 - 78 years) n = 13 Health Status: unhealthy Condition: chronic myelogenous leukemia (CML) Age Group: 52 years (range: 23 - 78 years) Sex: M+F Population Size: 13 Sources: https://pubmed.ncbi.nlm.nih.gov/9324279	Sources: https://pubmed.ncbi.nlm.nih.gov/9324279
20 mg/m2 1 times / day steady, intravenous Recommended\|MTD Dose: 20 mg/m2, 1 times / day Route: intravenous Route: steady Dose: 20 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/30962963	unhealthy, 59 years (range: 42–79 years) n = 6 Health Status: unhealthy Condition: unresectable liver-predominant metastases Age Group: 59 years (range: 42–79 years) Sex: M+F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/30962963	Other AEs: Anaemia, Lymphopenia... Other AEs: Anaemia (grade 1, 17%) Lymphopenia (grade 2, 17%) Neutropenia (grade 2, 17%) Leucopenia (grade 1, 17%) Thrombocytopaenia (grade 1, 17%) Sources: https://pubmed.ncbi.nlm.nih.gov/30962963
15 mg/m2 1 times / day steady, intravenous Dose: 15 mg/m2, 1 times / day Route: intravenous Route: steady Dose: 15 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20456354	unhealthy, 61 years (range: 32–82 years) n = 16 Health Status: unhealthy Condition: CLL Age Group: 61 years (range: 32–82 years) Sex: M+F Population Size: 16 Sources: https://pubmed.ncbi.nlm.nih.gov/20456354	DLT: Hyperbilirubinemia, Thrombocytopenia... Dose limiting toxicities: Hyperbilirubinemia (grade 3, 2 patients) Thrombocytopenia (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/20456354
20 mg/m2 1 times / day multiple, subcutaneous Dose: 20 mg/m2, 1 times / day Route: subcutaneous Route: multiple Dose: 20 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16882708	unhealthy, 65 years n = 14 Health Status: unhealthy Condition: myelodysplastic syndrome Age Group: 65 years Sex: M+F Population Size: 14 Sources: https://pubmed.ncbi.nlm.nih.gov/16882708	Sources: https://pubmed.ncbi.nlm.nih.gov/16882708
15 mg/m2 3 times / day steady, intravenous Recommended Dose: 15 mg/m2, 3 times / day Route: intravenous Route: steady Dose: 15 mg/m2, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021790lbl.pdf	unhealthy, 70 years (range: 65-76 years) n = 81 Health Status: unhealthy Condition: myelodysplastic syndromes Age Group: 70 years (range: 65-76 years) Sex: M+F Population Size: 81 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021790lbl.pdf	Disc. AE: Anemia, Neutropenia... Other AEs: Neutropenia, Thrombocytopenia... AEs leading to discontinuation/dose reduction: Anemia (grade 5, 6 patients) Neutropenia (grade 5, 6 patients) Thrombocytopenia (grade 5, 6 patients) Other AEs: Neutropenia (grade 3-4, 87%) Thrombocytopenia (grade 3-4, 85%) Febrile neutropenia (grade 3-4, 23%) Leukopenia (grade 3-4, 22%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021790lbl.pdf
15 mg/m2 1 times / day steady, intravenous Dose: 15 mg/m2, 1 times / day Route: intravenous Route: steady Dose: 15 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20456354	unhealthy, 72 years (range: 68–75 years) n = 4 Health Status: unhealthy Condition: NHL Age Group: 72 years (range: 68–75 years) Sex: M+F Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/20456354	DLT: Febrile neutropenia... Dose limiting toxicities: Febrile neutropenia (grade 3-4, 2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/20456354
660 mg/m2 single, intravenous Highest studied dose Dose: 660 mg/m2 Route: intravenous Route: single Dose: 660 mg/m2 Sources: https://pubmed.ncbi.nlm.nih.gov/9180389	unhealthy n = 7 Health Status: unhealthy Condition: chronic myelogenous leukemia Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/9180389	Sources: https://pubmed.ncbi.nlm.nih.gov/9180389
15 mg/m2 3 times / day steady, intravenous Recommended Dose: 15 mg/m2, 3 times / day Route: intravenous Route: steady Dose: 15 mg/m2, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_MedR.pdf Page: p. 82	unhealthy n = 83 Health Status: unhealthy Population Size: 83 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_MedR.pdf Page: p. 82	Other AEs: Neutropenia, Thrombocytopenia... Other AEs: Neutropenia (all grades, 83%) Thrombocytopenia (all grades, 81%) Anemia (all grades, 54%) Splenomegaly (all grades, 2%) Thrombocythaemia (all grades, 4%) Tachycardia (all grades, 1%) Pulmonary edema (all grades, 1%) Nausea (all grades, 22%) Constipation (all grades, 8%) Diarrhea (all grades, 16%) Vomiting (all grades, 8%) Abdominal pain (all grades, 4%) Oral mucosal petechiae (all grades, 5%) Stomatitis (all grades, 7%) Loose stools (all grades, 2%) Tongue ulceration (all grades, 5%) Dysphagia (all grades, 2%) Pyrexia (all grades, 16%) Fatigue (all grades, 18%) Asthenia (all grades, 4%) Fall (all grades, 1%) Hyperbilirubinaemia (all grades, 4%) Hepatomegaly (all grades, 1%) Cellulitis (all grades, 2%) Urinary tract infection (all grades, 1%) Alanine aminotransferase increased (all grades, 1%) Aspartate aminotransferase increased (all grades, 1%) Alkaline phosphatase increased (all grades, 1%) Hypocalcemia (all grades, 7%) Hypoalbuminemia (all grades, 7%) Hypomagnesaemia (all grades, 2%) Hypokalemia (all grades, 4%) Decreased appetite (all grades, 4%) Anorexia (all grades, 6%) Dehydration (all grades, 1%) Arthralgia (all grades, 1%) Back pain (all grades, 1%) Headache (all grades, 10%) Dizziness (all grades, 2%) Hypoaesthesia (all grades, 1%) Insomnia (all grades, 5%) Depression (all grades, 2%) Cough (all grades, 6%) Dyspnea (all grades, 2%) Pharyngitis (all grades, 4%) Epistaxis (all grades, 4%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_MedR.pdf Page: p. 82

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1467	inhibitor 1604 inducer 355	inhibitor 1702	inhibitor 1475

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1383 CYP2C19 1325 P-gp 1330	P-gp 1400	CYP3A4/5 108 CYP2B6 501 CYP1A2 637 CYP2E1 117

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1532	inducer 1440 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=20 Page: 20.0	no
CYP1A2 1532	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
CYP2B6 884	inducer 1440 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
CYP2C19 1392	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
CYP2C9 1648	inducer 1440 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
CYP2C9 1648	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
CYP2D6 1738	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
CYP3A4 1772	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
CYP3A4/5 293	inducer 1440 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
P-gp 1514	inhibitor 3045 Sources: https://www.ema.europa.eu/en/documents/assessment-report/dacogen-epar-public-assessment-report_en.pdf#page=44 Page: 44.0	weak
CYP2E1 871	inducer 1440 Sources: https://pdf.hres.ca/dpd_pm/00049298.PDF#page=19 Page: 19.0	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1400	substrate 3113 Sources: https://www.ema.europa.eu/en/documents/assessment-report/dacogen-epar-public-assessment-report_en.pdf#page=44 Page: 44.0	weak

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1507	inhibitor 1489 Sources: https://www.ema.europa.eu/en/documents/assessment-report/dacogen-epar-public-assessment-report_en.pdf#page=22 Page: 22.0

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0249	http://www.3bsc.com/index/pro_info.php?id=19605
AEchem Scientific Corp., USA	AE067557	https://www.aechemsc.com/info_products/AE067557.php
AHH Chemical co.,ltd	API-1235	http://www.ahhchemical.com/product/API-1235.html
AK Scientific, Inc. (AKSCI)	J10097	http://www.aksci.com/item_detail.php?cat=J10097
AK Scientific, Inc. (AKSCI)	SYN3036	http://www.aksci.com/item_detail.php?cat=SYN3036
AK Scientific, Inc. (AKSCI)	V0702	http://www.aksci.com/item_detail.php?cat=V0702
Aaron Chemicals	AR002OAT	http://www.aaronchem.com/2353-33-5
AbMole Bioscience	M2052	http://www.abmole.com/products/decitabine.html
Achemtek	0102-022107	http://www.achemtek.com/2353-33-5
Acorn PharmaTech	ACN-034471	http://www.acornpharmatech.com/
Acros Organics	AC396810100	https://www.fishersci.com/shop/products/5-aza-2-deoxycytidine-98-acros-organics/AC396810100
Acros Organics	AC396810500	https://www.fishersci.com/shop/products/5-aza-2-deoxycytidine-98-acros-organics/AC396810500
Active Biopharma	ABP001084	http://www.activebiopharma.com/2353-33-5
Adooq BioScience	A10292	https://www.adooq.com/decitabine.html
Alfa Chemistry	AP2353335	https://reagents.alfa-chemistry.com/product/5-aza-2-deoxycytidine-cas-2353-33-5-8325.html
Alsachim	2335	http://www.alsachim.com/product-C3396-glo.bal-view.html
Ambeed	A156645	https://www.ambeed.com/products/2353-33-5.html
Ambinter	Amb20240580	http://www.ambinter.com/reference/20240580
Anward	ANW-25144	http://www.anward.com/pro_result/18433
ApexBio Technology	A1906	http://www.apexbt.com/decitabine-nsc127716-5aza-cdr-1767.html
Aurora Fine Chemicals LLC	A17.875.892	http://online.aurorafinechemicals.com/info?ID=A17.875.892
Aurum Pharmatech LLC	W-5049	http://www.Aurumpharmatech.com/Product/ProductDetails/W_5049
AvaChem Scientific	2564	http://www.avachem.com/productSearch.asp?2564
Avantor Inc	TCA2232-100MG	https://us.vwr.com/store/product/16808941/5-aza-2-deoxycytidine
Avantor Inc	TCA2232-20MG	https://us.vwr.com/store/product/16808941/5-aza-2-deoxycytidine
Axon MedChem	1590	https://www.axonmedchem.com/product/1590
BLD Pharm	BD00929245	http://www.bldpharm.com/products/22432-95-7.html
BLD Pharm	BD19549	http://www.bldpharm.com/products/2353-33-5.html
BioChemPartner	BCP02870	http://www.biochempartner.com/2353-33-5-BCP02870
BioSynth	J-700084	https://www.biosynth.com/products/biochemistry/other-biochemicals/products/J-700084.html
Boerchem	BC677683	http://www.boerchem.com/?product_39567.html
CSNpharm	CSN12608	https://www.csnpharm.com/products/decitabine.html
Calbiochem	189825	http://www.emdbiosciences.com/product/189825
Capot Chemical	19115	http://www.capotchem.com/en/19115.htm
Capot Chemical	PubChem19115	http://www.capotchem.com/en/19115.htm
Chem Scene	CS-0372	http://www.chemscene.com/2353-33-5.html
ChemFaces	CFN90007	http://www.chemfaces.com/natural/5-Aza-2--deoxycytidine-CFN90007.html
ChemMol	30108728	http://www.chemmol.com/chemmol/30108728.html
ChemMol	44009989	http://www.chemmol.com/chemmol/44009989.html
ChemMol	99060252	http://www.chemmol.com/chemmol/99060252.html
Chemenu	CM110244	http://www.chemenu.com/products/CM110244
Chemodex	A0563	http://www.chemodex.com/products/A0563
Chemspace	CSSB00000011658	https://chem-space.com/CSSB00000011658
DC Chemicals	DC4193	http://www.dcchemicals.com/product_show-Decitabine.html
Debye Scientific	DB-029060	http://www.debyesci.com/DB-029060.html
EMD Millipore	189825	http://www.emdbiosciences.com/product/189825
Excenen	EX-A961	http://www.excenen.com/searchresultlist.php?id=2353-33-5
Glentham Life Sciences	GP1241	http://www.glentham.com/products/product/GP1241/
Hairui	GUSA07401	http://www.hairuichem.com/en/product/2353-33-5.html
LGC Standards	MM3526.00	https://www.lgcstandards.com/US/en/p/MM3526.00
Lab Network	LN01254469	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01254469
Matrix Scientific	145268	https://www.matrixscientific.com/145268.html
MedChem Express	HY-A0004	https://www.medchemexpress.com/Decitabine.html
MuseChem	I002785	https://www.musechem.com/product/I002785.html
OChem	5173	http://www.ocheminc.com/index.php?act=psearch&pid=353A335
Parchem	51711	https://www.parchem.com/chemical-supplier-distributor/Decitabine-051711.aspx
Renno Tech	RL02744	http://www.rennotech.com/product_show.asp?id=2993
Selleck Chemicals	S1200	http://www.selleckchem.com/products/Decitabine.html
Sigma-Aldrich	A3656_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/a3656?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Synblock Inc	SB18982	http://www.synblock.com/product/2353-33-5.html
Tocris	2624	https://www.tocris.com/products/decitabine_2624
VladaChem	VL272247-100MG	https://www.vladachem.com/product.php?products=2353-33-5
Yuhao Chemical	LX2074	http://www.chemyuhao.com/2353-33-5.html
abcr GmbH	AB348661	http://www.abcr.com/shop/en/AB348661
eNovation Chemicals	D380365	http://www.enovationchem.com/productDetails.asp?productID=D380365
iChemical	EBD27248	http://www.ichemical.com/products/2353-33-5.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Targeting hypomethylation of DNA to achieve cellular differentiation in myelodysplastic syndromes (MDS).	2001	11700387
The E-cadherin/catenin complex: an important gatekeeper in breast cancer tumorigenesis and malignant progression.	2001	11597316
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
Cytogenetic responses in high-risk myelodysplastic syndrome following low-dose treatment with the DNA methylation inhibitor 5-aza-2'-deoxycytidine.	2001 Aug	11529854
Activation of the maternally preset program of apoptosis by microinjection of 5-aza-2'-deoxycytidine and 5-methyl-2'-deoxycytidine-5'-triphosphate in Xenopus laevis embryos.	2001 Aug	11473545
DNA methylation regulates placental lactogen I gene expression.	2001 Aug	11459782
Methylation of the E-cadherin gene promoter correlates with progression of prostate cancer.	2001 Aug	11458121
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
Identification and characterization of differentially methylated CpG islands in pancreatic carcinoma.	2001 Dec 1	11731440
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
Aberrant methylation of the adenomatous polyposis coli (APC) gene promoter 1A in breast and lung carcinomas.	2001 Jul	11448917
Promoter hypermethylation: a common cause of reduced p16(INK4a) expression in uveal melanoma.	2001 Jul 1	11431374
Hypermethylation leads to silencing of the SYK gene in human breast cancer.	2001 Jul 15	11454707
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
Cytosine methylation represses glutathione S-transferase P1 (GSTP1) gene expression in human prostate cancer cells.	2001 Jun 15	11406558
Glypican-3 expression is silenced in human breast cancer.	2001 Nov 1	11704870
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
Hypermethylation in human cancers of the RIZ1 tumor suppressor gene, a member of a histone/protein methyltransferase superfamily.	2001 Nov 15	11719434
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
Dynamic DNA methylation change in the CpG island region of p15 during human myeloid development.	2001 Oct	11602627
DNA hypermethylation is a mechanism for loss of expression of the HLA class I genes in human esophageal squamous cell carcinomas.	2001 Oct	11577000
Frequent epigenetic inactivation of RASSF1A by aberrant promoter hypermethylation in human gastric adenocarcinoma.	2001 Oct 1	11585730
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
Chloroplast DNA methylation and inheritance in Chlamydomonas.	2001 Oct 1	11581163
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
CpG hypermethylation of the promoter region inactivates the estrogen receptor-beta gene in patients with prostate carcinoma.	2001 Oct 15	11596023
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
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
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
Methylation status in the promoter region of the human PGP9.5 gene in cancer and normal tissues.	2001 Sep 10	11448537
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
Frequent epigenetic inactivation of RASSF1A in human bladder carcinoma.	2001 Sep 15	11559536
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
Methylation-mediated silencing of TMS1/ASC is accompanied by histone hypoacetylation and CpG island-localized changes in chromatin architecture.	2002 Feb 15	11733524
Reduced expression of insulin-like growth factor binding protein-3 and its promoter hypermethylation in human hepatocellular carcinoma.	2002 Feb 25	11804742
Combined restriction landmark genomic scanning and virtual genome scans identify a novel human homeobox gene, ALX3, that is hypermethylated in neuroblastoma.	2002 Mar	11807986

Patents

Sample Use Guides

In Vivo Use Guide

Regimen 1: administer decitabine (Dacogen) at a dose of 15 mg/m2 by continuous intravenous infusion over 3 hours repeated every 8 hours for 3 days. Repeat cycle every 6 weeks. Regimen 2: administer decitabine at a dose of 20 mg/m2 by continuous intravenous infusion over 1 hour repeated daily for 5 days. Repeat cycle every 4 weeks.

Route of Administration: Intravenous

In Vitro Use Guide

AML cells were treated daily with serial dilutions (0.02–50 uM) of freshlyprepared decitabine and incubated at 37 degree Celsius, 5% CO2 for 72 hours.

Name

Type

Language

DECITABINE

Official Name

English

1,3,5-TRIAZIN-2(1H)-ONE, 4-AMINO-1-(2-DEOXY-.BETA.-D-ERYTHRO-PENTOFURANOSYL)-

Common Name

English

ASTX-727 COMPONENT DECITABINE

Common Name

English

4-AMINO-1-(2-DEOXY-.BETA.-D-ERYTHRO-PENTOFURANOSYL)-S-TRIAZIN-2(1H)-ONE

Common Name

English

DACOGEN

Brand Name

English

DECITABINE [VANDF]

Common Name

English

ASTX727 COMPONENT DECITABINE

Common Name

English

NSC-127716

Code

English

5-AZA-2'-DEOXYCYTIDINE

Systematic Name

English

INQOVI COMPONENT DECITABINE

Brand Name

English

5-AZA-DEOXYCYTIDINE

Systematic Name

English

DECITABINE COMPONENT OF INQOVI

Brand Name

English

DECITABINE [WHO-DD]

Common Name

English

DECITABINE [INN]

Common Name

English

DAC

Common Name

English

2'-DEOXY-5-AZACYTIDINE

Common Name

English

DECITABINE [MART.]

Common Name

English

DECITABINE [USAN]

Common Name

English

DECITABINE [MI]

Common Name

English

DECITABINE [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

555916