Decitabine

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C8H12N4O4
Molecular Weight	228.2053
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC(=O)N(C=N1)[C@H]2C[C@H](O)[C@@H](CO)O2

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

Molecular Formula	C8H12N4O4
Molecular Weight	228.2053
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT02907359 | https://www.ncbi.nlm.nih.gov/pubmed/31060979 | https://clinicaltrials.gov/ct2/show/NCT02348489 | https://www.businesswire.com/news/home/20151006006636/en/Astex-Pharmaceuticals-Announces-Orphan-Drug-Designation-Guadecitabine | https://astx.com/research-development/clinical-pipeline/guadecitabine-sgi-110-dnmt-inhibitor-solid-tumors/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 282 Target ID: CHEMBL2311221 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021790s018lbl.pdf	Binding Agent 1076
DNA (cytosine-5)-methyltransferase 1 10 Target ID: CHEMBL1993 Sources: www.ncbi.nlm.nih.gov/pubmed/20501800	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Myelodysplastic syndromes 61 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021790s018lbl.pdf	Primary		Approved 8583	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 2006

C_max

Value	Dose	Co-administered	Analyte	Population
77 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17564707	15 mg/m² 3 times / day 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
155 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22816487/	20 mg/m² 1 times / day multiple, intravenous dose: 20 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:		DECITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status:

AUC

Value	Dose	Co-administered	Analyte	Population
158 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17564707	15 mg/m² 3 times / day 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
802.81 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32285126/	20 mg/m² 1 times / day multiple, intravenous dose: 20 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:		DECITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
750.82 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32285126/	35 mg 1 times / day multiple, oral dose: 35 mg route of administration: Oral experiment type: MULTIPLE co-administered: CEDAZURIDINE	CEDAZURIDINE	DECITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
150 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22816487/	20 mg/m² 1 times / day multiple, intravenous dose: 20 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:		DECITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status:

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.78 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17564707	15 mg/m² 3 times / day 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
0.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22816487/	20 mg/m² 1 times / day multiple, intravenous dose: 20 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:		DECITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status:

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) Health Status: unhealthy Age Group: 52 years (range: 23 - 78 years) Sex: M+F 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) Health Status: unhealthy Age Group: 59 years (range: 42–79 years) Sex: M+F 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) Health Status: unhealthy Age Group: 61 years (range: 32–82 years) Sex: M+F 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 Health Status: unhealthy Age Group: 65 years Sex: M+F 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) Health Status: unhealthy Age Group: 70 years (range: 65-76 years) Sex: M+F 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) Health Status: unhealthy Age Group: 72 years (range: 68–75 years) Sex: M+F 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 Health Status: unhealthy 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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_MedR.pdf	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

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438 inducer 440	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C19 2057 P-gp 1741	P-gp 2052	CYP3A4/5 133 CYP2B6 669 CYP1A2 832 CYP2E1 131

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=20 Page: 20.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
CYP2B6 1160	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
CYP2C9 2497	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
CYP3A4/5 357	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
P-gp 1932	inhibitor 4027 Sources: https://www.ema.europa.eu/en/documents/assessment-report/dacogen-epar-public-assessment-report_en.pdf#page=44 Page: 44.0	weak
CYP2E1 1146	inducer 1966 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 2052	substrate 4014 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 2263	inhibitor 2237 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
Aaron Chemicals	AR002OAT	http://www.aaronchem.com/2353-33-5
abcr GmbH	AB348661	http://www.abcr.com/shop/en/AB348661
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
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
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
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
BLD Pharm	BD00929245	http://www.bldpharm.com/products/22432-95-7.html
BLD Pharm	BD19549	http://www.bldpharm.com/products/2353-33-5.html
Boerchem	BC677683	http://www.boerchem.com/?product_39567.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
Chemenu	CM110244	http://www.chemenu.com/products/CM110244
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
Chemodex	A0563	http://www.chemodex.com/products/A0563
Chemspace	CSSB00000011658	https://chem-space.com/CSSB00000011658
CSNpharm	CSN12608	https://www.csnpharm.com/products/decitabine.html
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
eNovation Chemicals	D380365	http://www.enovationchem.com/productDetails.asp?productID=D380365
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
iChemical	EBD27248	http://www.ichemical.com/products/2353-33-5.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN01254469	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01254469
LGC Standards	MM3526.00	https://www.lgcstandards.com/US/en/p/MM3526.00
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

PubMed

Title	Date	PubMed
Targeting hypomethylation of DNA to achieve cellular differentiation in myelodysplastic syndromes (MDS).	2001	11700387
Hypermethylation of the cpG island of Ras association domain family 1A (RASSF1A), a putative tumor suppressor gene from the 3p21.3 locus, occurs in a large percentage of human breast cancers.	2001 Apr 1	11306494
Unnatural enantiomers of 5-azacytidine analogues: syntheses and enzymatic properties.	2001 Apr-Jul	11563127
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
[Chemotherapy and radiation therapy].	2001 Dec	11766340
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
Unbalanced expression of HLA-A and -B antigens: a specific feature of cutaneous melanoma and other non-hemopoietic malignancies reverted by IFN-gamma.	2001 Feb 15	11251973
Induction of MAGE-3 expression in lung and esophageal cancer cells.	2001 Jan	11216765
Hypermethylation leads to silencing of the SYK gene in human breast cancer.	2001 Jul 15	11454707
Transcriptional silencing of Cyclooxygenase-2 by hyper-methylation of the 5' CpG island in human gastric carcinoma cells.	2001 Jun 1	11389100
Pharmacologic induction of fetal hemoglobin: raising the therapeutic bar in sickle cell disease.	2001 Mar	11224687
Elevation of breast carcinoma Nm23-H1 metastasis suppressor gene expression and reduced motility by DNA methylation inhibition.	2001 Mar 1	11280805
Regulation of CD21 expression by DNA methylation and histone deacetylation.	2001 May	11312258
Methylation in hMLH1 promoter interferes with its binding to transcription factor CBF and inhibits gene expression.	2001 Oct 25	11704838
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
Altered hox gene expression and cellular pathogenesis of 5-aza-2'-deoxycytidine-induced murine hindlimb dysmorphogenesis.	2001 Sep-Oct	11695566
Frequent allelic losses on the short arm of chromosome 1 and decreased expression of the p73 gene at 1p36.3 in squamous cell carcinoma of the oral cavity.	2002 Feb	11788901
Reduced expression of insulin-like growth factor binding protein-3 and its promoter hypermethylation in human hepatocellular carcinoma.	2002 Feb 25	11804742
The 5-lipoxygenase promoter is regulated by DNA methylation.	2002 Feb 8	11706027
Novel agents for the therapy of acute leukemia.	2002 Jan	11790973
Characterization of XAGE-1b, a short major transcript of cancer/testis-associated gene XAGE-1, induced in melanoma metastasis.	2002 Jan 10	11774264
Aberrant methylation and histone deacetylation of cyclooxygenase 2 in gastric cancer.	2002 Jan 20	11774276
Combined restriction landmark genomic scanning and virtual genome scans identify a novel human homeobox gene, ALX3, that is hypermethylated in neuroblastoma.	2002 Mar	11807986
Immunomodulatory activity of SGI-110, a 5-aza-2'-deoxycytidine-containing demethylating dinucleotide.	2013 Mar	23138873
TGF-β induces global changes in DNA methylation during the epithelial-to-mesenchymal transition in ovarian cancer cells.	2014 Nov	25470663
Guadecitabine (SGI-110) in patients with intermediate or high-risk myelodysplastic syndromes: phase 2 results from a multicentre, open-label, randomised, phase 1/2 trial.	2019 Jun	31060979

Patents

Sample Use Guides

In Vivo Use Guide

Guadecitabine 60 mg/m2 given subcutaneously daily on Days 1-5 in 28-day cycles. The total amount (in mg) of guadecitabine to be administered is determined by body surface area.

Route of Administration: Other

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.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 07:04:39 GMT 2025` Edited by `admin` on `Wed Apr 02 07:04:39 GMT 2025`
Record UNII	776B62CQ27
Record Status	`Validated (UNII)`
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Name

Type

Language

DACOGEN

Preferred Name

English

Decitabine

Official Name

English

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

Common Name

English

Decitabine [WHO-DD]

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

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 [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