Details of the Drug

General Information of Drug (ID: DM9Y3EG)

Drug Name

Guadecitabine

Synonyms

UNII-2KT4YN1DP7; 929901-49-5; 2KT4YN1DP7; SGI-110 free acid; Guadecitabine [USAN:INN]; GuadecitabineSGI-110; Guadecitabine (USAN/INN); CHEMBL3544916; Guanosine, 2'-deoxy-5-azacytidylyl-(3'-5')-2'-deoxy-; ZINC43203165; AKOS027321496; AKOS030238181; DB11918; CS-3089; HY-13542; D10877; 2'-deoxy-5-azacytidylyl-(3'-5')-2'-deoxyguanosine

Indication

Disease Entry	ICD 11	Status	REF
Myelodysplastic syndrome	2A37	Phase 3	[1]

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 4

Molecular Weight (mw)

557.4

Topological Polar Surface Area (xlogp)

-4.6

Rotatable Bond Count (rotbonds)

8

Hydrogen Bond Donor Count (hbonddonor)

6

Hydrogen Bond Acceptor Count (hbondacc)

12

Chemical Identifiers

Formula: C18H24N9O10P
IUPAC Name: [(2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methyl [(2R,3S,5R)-5-(4-amino-2-oxo-1,3,5-triazin-1-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate
Canonical SMILES: C1[C@@H]([C@H](O[C@H]1N2C=NC3=C2N=C(NC3=O)N)COP(=O)(O)O[C@H]4C[C@@H](O[C@@H]4CO)N5C=NC(=NC5=O)N)O
InChI: 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
InChIKey: GUWXKKAWLCENJA-WGWHJZDNSA-N

Cross-matching ID

PubChem CID: 135564655
CAS Number: 929901-49-5
DrugBank ID: DB11918
TTD ID: D0VZ4N

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
DNA [cytosine-5]-methyltransferase 1 (DNMT1)	TT6S2FE	DNMT1_HUMAN	Inhibitor	[1]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Myelodysplastic syndrome

ICD Disease Classification

2A37

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
DNA [cytosine-5]-methyltransferase 1 (DNMT1)	DTT	DNMT1	0.00E+00	2.46	4.65

Molecular Expression Atlas (MEA)

MEA Detail

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References

1	Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
2	Efficacy and safety of extended dosing schedules of CC-486 (oral azacitidine) in patients with lower-risk myelodysplastic syndromes. Leukemia. 2016 Apr;30(4):889-96.
3	S110, a 5-Aza-2'-deoxycytidine-containing dinucleotide, is an effective DNA methylation inhibitor in vivo and can reduce tumor growth. Mol Cancer Ther. 2010 May;9(5):1443-50.
4	Immunomodulatory action of the DNA methyltransferase inhibitor SGI-110 in epithelial ovarian cancer cells and xenografts. Epigenetics. 2015;10(3):237-46.
5	Anticancer activity of stabilized palifosfamide in vivo: schedule effects, oral bioavailability, and enhanced activity with docetaxel and doxorubicin. Anticancer Drugs. 2012 Feb;23(2):173-84.
6	Metabolism, mechanism of action and sensitivity profile of fluorocyclopentenylcytosine (RX-3117; TV-1360). Invest New Drugs. 2013 Dec;31(6):1444-57.
7	Antroquinonol D, isolated from Antrodia camphorata, with DNA demethylation and anticancer potential. J Agric Food Chem. 2014 Jun 18;62(24):5625-35.
8	DNA methyltransferase inhibitors: an updated patent review (2012-2015).Expert Opin Ther Pat. 2016 Sep;26(9):1017-30.