Decitabine (CED0002294)

Record Information
Version1.0
Creation Date2016-05-22 04:14:05 UTC
Update Date2026-08-24 13:36:56 UTC
Accession NumberCHEM017309
Identification
Common NameDecitabine
ClassSmall Molecule
Description
Decitabine is an organic compound with the chemical formula C8H12N4O4 and an average molecular weight of 228.21 g/mol. Decitabine belongs to the triazinones, a subclass of triazines within the organic compounds. This compound is associated with three recorded sources, including healthcare, pharmaceuticals and veterinary products as antineoplastic agents, as well as electrical and electronic equipment such as antennas and amplifiers. Recorded exposure routes for the substance include oral and intravenous administration. Decitabine acts on 12 recorded protein targets, serving as an inhibitor of DNA (cytosine-5)-methyltransferase 1 (DNMT1), DNA (cytosine-5)-methyltransferase 3A (DNMT3A), and DNA (cytosine-5)-methyltransferase 3B (DNMT3B). Additionally, it targets histone deacetylase 3 (HDAC3) and eight other proteins.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-Amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-S-triazin-2(1H)-oneChEBI
5-AzadeoxycytidineChEBI
DacogenKegg
4-Amino-1-(2-deoxy-b-D-erythro-pentofuranosyl)-S-triazin-2(1H)-oneGenerator
4-Amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-S-triazin-2(1H)-oneGenerator
5-Aza-2'-deoxycytidineHMDB
AzadcHMDB
DezocitidineHMDB
5-DeoxyazacytidineHMDB
Decitabine mesylateHMDB
2'-Deoxy-5-azacytidineHMDB
AzadC compoundHMDB
2' Deoxy 5 azacytidineHMDB
5 Aza 2' deoxycytidineHMDB
5 AzadeoxycytidineHMDB
5 DeoxyazacytidineHMDB
5-AzadCHMDB
5AzadCHMDB
Compound, azadcHMDB
Mesylate, decitabineHMDB
DecitabineChEBI
Chemical FormulaC8H12N4O4
Average Molecular Mass228.205 g/mol
Monoisotopic Mass228.086 g/mol
CAS Registry Number2353-33-5
IUPAC Name4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one
Traditional Namedecitabine
SMILESNC1=NC(=O)N(C=N1)[C@H]1C[C@H](O)[C@@H](CO)O1
InChI IdentifierInChI=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
InChI KeyXAUDJQYHKZQPEU-KVQBGUIXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triazinones. Triazinones are compounds containing a triazine ring which bears a ketone group a carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTriazines
Sub ClassTriazinones
Direct ParentTriazinones
Alternative Parents
Substituents
  • Amino-1,3,5-triazine
  • Aminotriazine
  • Triazinone
  • 1,3,5-triazine
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.5 g/LALOGPS
logP-2ALOGPS
logP-2.2ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)13.89ChemAxon
pKa (Strongest Basic)-0.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area120.74 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity50.68 m³·mol⁻¹ChemAxon
Polarizability21.15 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9500000000-93e2d9110f2fded5b292Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0gi0-6792000000-f27b73769db73752ebdeNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0900000000-7976ff1b54184471f7f1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-5900000000-30985d6b34f33fc971bdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dl-9600000000-7eb826f89c6a9e79fd1aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-003r-4920000000-1d57eb49c2bfcee4a085Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9610000000-41445cf04cf3061ec547Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014l-9200000000-49c5c1822d5d6ef31f04Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0900000000-ad27e26e064f360f3006Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-4900000000-8baaf44cbb1e8b1eec0eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-7900000000-c1581650f477cf91f369Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ri-1940000000-983ffb62a26d8077f3b0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000x-8900000000-db8318379b860e59d087Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9300000000-8f2a29e2dd6708ebd1edNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2382.0Log mg/kg[1300:4200]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
358Antineoplastic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
Pathways
1 pathway
Decitabine Drug Metabolism Action Pathway
Decitabine Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Thymidine kinase, cytosolic structureClick to view 3D structureThymidine kinase, cytosolicP04183HumansPredicted (SEA)0.856341
Click to view 3D structureThymidine kinaseP06479Human herpesvirus 1 (strain SC16) (HHV-1) (Human herpes simplex virus1)Predicted (SEA)0.934191
Click to view 3D structureAdenosine receptor A1P25099Rattus norvegicusPredicted (SEA)64.8484
Reverse transcriptase/RNaseH structureClick to view 3D structureReverse transcriptase/RNaseHQ72547Human immunodeficiency virus 1Predicted (SEA)14.3243
Click to view 3D structureThymidine kinaseA3RLP8Macacine herpesvirus 1Predicted (SEA)0.544945
Ribonuclease pancreatic structureClick to view 3D structureRibonuclease pancreaticP07998HumansPredicted (SEA)7.00643
Non-secretory ribonuclease structureClick to view 3D structureNon-secretory ribonucleaseP10153HumansPredicted (SEA)7.00643
Click to view 3D structureAdenosine deaminaseP56658Bos taurusPredicted (SEA)13.7015
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)108.678
Click to view 3D structureAdenosine receptor A2aP30543Rattus norvegicusPredicted (SEA)82.9873
Adenosine deaminase structureClick to view 3D structureAdenosine deaminaseP00813HumansPredicted (SEA)7.55137
Thymidylate synthase structureClick to view 3D structureThymidylate synthaseP00469Lactobacillus caseiPredicted (SEA)11.5217
Click to view 3D structureAdenosine deaminaseQ86GS5Plasmodium falciparumPredicted (SEA)1.08989
DNA (cytosine-5)-methyltransferase 1 structureClick to view 3D structureDNA (cytosine-5)-methyltransferase 1P26358HumansPredicted (SEA)36.1999
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)121.367
Click to view 3D structureThymidylate synthase ThyAP9WFR9Mycobacterium tuberculosisPredicted (SEA)1.47914
Click to view 3D structureAdenosine receptor A3P28647Rattus norvegicusPredicted (SEA)57.6084
Adenosine receptor A1 structureClick to view 3D structureAdenosine receptor A1P30542HumansPredicted (SEA)117.864
Click to view 3D structureThymidylate synthaseP07607Mus musculusPredicted (SEA)9.809
Heat shock protein HSP 90-alpha structureClick to view 3D structureHeat shock protein HSP 90-alphaP07900HumansPredicted (SEA)53.3267
Endoplasmin structureClick to view 3D structureEndoplasminP14625HumansPredicted (SEA)37.5233
Click to view 3D structureAdenosine receptor A1P47745Cavia porcellusPredicted (SEA)39.5474
Thymidylate kinase structureClick to view 3D structureThymidylate kinaseP9WKE1Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)Predicted (SEA)2.33548
Click to view 3D structureThymidylate synthaseQ2TA32Bos taurusPredicted (SEA)3.58106
Click to view 3D structureThymidine kinaseP09250HHV-3Predicted (SEA)1.16774
Concentrations
Not Available
External Links
DrugBank IDDB01262
HMDB IDHMDB0015391
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDecitabine
Chemspider ID397844
ChEBI ID50131
PubChem Compound ID451668
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Saba HI, Wijermans PW: Decitabine in myelodysplastic syndromes. Semin Hematol. 2005 Jul;42(3 Suppl 2):S23-31.
2. Oki Y, Aoki E, Issa JP: Decitabine--bedside to bench. Crit Rev Oncol Hematol. 2007 Feb;61(2):140-52. Epub 2006 Oct 4.
3. Wijermans PW, Ruter B, Baer MR, Slack JL, Saba HI, Lubbert M: Efficacy of decitabine in the treatment of patients with chronic myelomonocytic leukemia (CMML). Leuk Res. 2008 Apr;32(4):587-91. Epub 2007 Sep 18.
4. Appleton K, Mackay HJ, Judson I, Plumb JA, McCormick C, Strathdee G, Lee C, Barrett S, Reade S, Jadayel D, Tang A, Bellenger K, Mackay L, Setanoians A, Schatzlein A, Twelves C, Kaye SB, Brown R: Phase I and pharmacodynamic trial of the DNA methyltransferase inhibitor decitabine and carboplatin in solid tumors. J Clin Oncol. 2007 Oct 10;25(29):4603-9.
5. Jabbour E, Issa JP, Garcia-Manero G, Kantarjian H: Evolution of decitabine development: accomplishments, ongoing investigations, and future strategies. Cancer. 2008 Jun;112(11):2341-51. doi: 10.1002/cncr.23463.
6. Stresemann C, Lyko F: Modes of action of the DNA methyltransferase inhibitors azacytidine and decitabine. Int J Cancer. 2008 Jul 1;123(1):8-13. doi: 10.1002/ijc.23607.
7. Daskalakis M, Blagitko-Dorfs N, Hackanson B: Decitabine. Recent Results Cancer Res. 2010;184:131-57. doi: 10.1007/978-3-642-01222-8_10.