GUADECITABINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H24N9O10P
Molecular Weight	557.4112
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC(=O)C2=C(N1)N(C=N2)[C@H]3C[C@H](O)[C@@H](COP(O)(=O)O[C@H]4C[C@@H](O[C@@H]4CO)N5C=NC(N)=NC5=O)O3

InChI

InChIKey=GUWXKKAWLCENJA-WGWHJZDNSA-N

InChI=1S/C18H24N9O10P/c19-16-22-6-27(18(31)25-16)12-2-8(9(3-28)35-12)37-38(32,33)34-4-10-7(29)1-11(36-10)26-5-21-13-14(26)23-17(20)24-15(13)30/h5-12,28-29H,1-4H2,(H,32,33)(H2,19,25,31)(H3,20,23,24,30)/t7-,8-,9+,10+,11+,12+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C18H24N9O10P
Molecular Weight	557.4112
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
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 278 Target ID: CHEMBL2311221 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021790s018lbl.pdf	Binding Agent 1064
DNA (cytosine-5)-methyltransferase 1 10 Target ID: CHEMBL1993 Sources: www.ncbi.nlm.nih.gov/pubmed/20501800	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Myelodysplastic syndromes 58 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021790s018lbl.pdf	Primary		Approved 8429	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
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 1587	inhibitor 1767 inducer 389	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2C19 1478 P-gp 1461	P-gp 1537	CYP3A4/5 124 CYP2B6 547 CYP1A2 701 CYP2E1 128

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=20 Page: 20.0	no
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
CYP2B6 1001	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
CYP2C9 1819	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
CYP3A4/5 335	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021790s000_Dacogen_BioPharmR.pdf#page=6 Page: 6.0	no
P-gp 1650	inhibitor 3277 Sources: https://www.ema.europa.eu/en/documents/assessment-report/dacogen-epar-public-assessment-report_en.pdf#page=44 Page: 44.0	weak
CYP2E1 970	inducer 1573 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 1537	substrate 3367 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 1647	inhibitor 1626 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
Unnatural enantiomers of 5-azacytidine analogues: syntheses and enzymatic properties.	2001 Apr-Jul	11563127
[Chemotherapy and radiation therapy].	2001 Dec	11766340
Reexpression of a cluster of silenced transgenes is associated with their rearrangement.	2001 Dec	11746972
Potential of 5-aza-2'-deoxycytidine (Decitabine) a potent inhibitor of DNA methylation for therapy of advanced non-small cell lung cancer.	2001 Dec	11742714
Identification and characterization of differentially methylated CpG islands in pancreatic carcinoma.	2001 Dec 1	11731440
Expression of the Hypermethylated in Cancer gene (HIC-1) is associated with good outcome in human breast cancer.	2001 Dec 14	11747329
Reversal of GSTP1 CpG island hypermethylation and reactivation of pi-class glutathione S-transferase (GSTP1) expression in human prostate cancer cells by treatment with procainamide.	2001 Dec 15	11751372
Large scale mapping of methylcytosines in CTCF-binding sites in the human H19 promoter and aberrant hypomethylation in human bladder cancer.	2001 Nov 1	11726548
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
Reduced expression of intercellular adhesion molecule-1 in ovarian adenocarcinomas.	2001 Nov 2	11720474
Increased expression of unmethylated CDKN2D by 5-aza-2'-deoxycytidine in human lung cancer cells.	2001 Nov 22	11753657
Silencing of HTR1B and reduced expression of EDN1 in human lung cancers, revealed by methylation-sensitive representational difference analysis.	2001 Nov 8	11709722
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
Pharmacological reactivation of inactive genes: the fragile X experience.	2001 Oct-Nov 1	11719276
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
Sensitization for death receptor- or drug-induced apoptosis by re-expression of caspase-8 through demethylation or gene transfer.	2001 Sep 13	11593392
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
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
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
The 5-lipoxygenase promoter is regulated by DNA methylation.	2002 Feb 8	11706027
Novel agents for the therapy of acute leukemia.	2002 Jan	11790973
DNA methylation regulates the expression of Y chromosome specific genes in prostate cancer.	2002 Jan	11743352
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 `Fri Dec 15 19:46:44 GMT 2023` Edited by `admin` on `Fri Dec 15 19:46:44 GMT 2023`
Record UNII	2KT4YN1DP7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GUADECITABINE

Official Name

English

Guadecitabine [WHO-DD]

Common Name

English

((2R,3S,5R)-5-(2-AMINO-6-OXO-1,6-DIHYDRO-9H-PURIN-9-YL)-3- HYDROXYTETRAHYDROFURAN-2-YL)METHYL (2R,3S,5R)-5-(4-AMINO-2-OXO-1 ,3,5-TRIAZIN-1(2H)YL)- 2-(HYDROXYMETHYL)TETRAHYDROFURAN-3-YL HYDROGEN PHOSPHATE

Systematic Name

English

SGI-110 FREE ACID

Code

English

SGI-110

Code

English

GUADECITABINE [USAN]

Common Name

English

guadecitabine [INN]

Common Name

English

GUANOSINE, 2'-DEOXY-5-AZACYTIDYLYL-(3'-5')-2'-DEOXY-

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

627818