DECITABINE

Search structure
Trade Names:
Synonyms:
DAC
Status: Approved (2006)
Entry Type: Small molecule
Molecule Category: UNKNOWN Prodrug
ATC: L01BC08
UNII: 776B62CQ27

Structure
InChI Key XAUDJQYHKZQPEU-KVQBGUIXSA-N
Smile Nc1ncn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)n1
InChI
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C8H12N4O4
Molecular Weight 228.21
AlogP -2.14
Hydrogen Bond Acceptor 8.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 2.0
Polar Surface Area 123.49
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 16.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR DNA (cytosine-5)-methyltransferase 1 inhibitor DailyMed Wikipedia
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Epigenetic regulator Writer DNA methyltransferase
- 30 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Myelodysplastic Syndromes 4 D009190 ClinicalTrials
Neoplasms 4 D009369 ClinicalTrials
Neoplasms 4 D009369 ClinicalTrials
Leukemia, Myeloid, Acute 3 D015470 ClinicalTrials
Leukemia 3 D007938 ClinicalTrials
Lymphoma, T-Cell, Peripheral 3 D016411 ClinicalTrials
Myeloproliferative Disorders 3 D009196 ClinicalTrials
Graft vs Host Disease 3 D006086 ClinicalTrials
Lymphoma, T-Cell, Peripheral 3 D016411 ClinicalTrials
Thrombocytopenia 3 D013921 ClinicalTrials
Purpura, Thrombocytopenic, Idiopathic 3 D016553 ClinicalTrials
Myeloproliferative Disorders 3 D009196 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Lymphoma 2 D008223 ClinicalTrials
Hodgkin Disease 2 D006689 ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL Positive 2 D015464 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 2 D016403 ClinicalTrials
Adenocarcinoma, Follicular 2 D018263 ClinicalTrials
Thyroid Neoplasms 2 D013964 ClinicalTrials
Carcinoma, Renal Cell 2 D002292 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Thalassemia 2 D013789 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Blast Crisis 2 D001752 ClinicalTrials
Peritoneal Neoplasms 2 D010534 ClinicalTrials
Fallopian Tube Neoplasms 2 D005185 ClinicalTrials
Lymphoma 2 D008223 ClinicalTrials
Lymphoma 2 D008223 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Granuloma, Lethal Midline 2 D006103 ClinicalTrials
Severe Acute Respiratory Syndrome 2 D045169 ClinicalTrials
Anemia, Aplastic 2 D000741 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 1 D054198 ClinicalTrials
Head and Neck Neoplasms 1 D006258 ClinicalTrials
Hematologic Neoplasms 1 D019337 ClinicalTrials
Leukemia, Promyelocytic, Acute 1 D015473 ClinicalTrials
Lymphoma, T-Cell, Cutaneous 1 D016410 ClinicalTrials
Medulloblastoma 1 D008527 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 1 D054198 ClinicalTrials
Glioma 1 D005910 ClinicalTrials
Multiple Myeloma 1 D009101 ClinicalTrials
Lymphoma, Non-Hodgkin 1 D008228 ClinicalTrials
Lymphoma, Mantle-Cell 1 D020522 ClinicalTrials
Precursor T-Cell Lymphoblastic Leukemia-Lymphoma 1 D054218 ClinicalTrials
Burkitt Lymphoma 1 D002051 ClinicalTrials
Anemia, Sickle Cell 1 D000755 ClinicalTrials
Prostatic Neoplasms 1 D011471 ClinicalTrials
Neuroblastoma 1 D009447 ClinicalTrials
Lymphoma, Follicular 0 D008224 ClinicalTrials

Related Entries

MCS

Scaffolds

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
12.58
Blood and lymphatic system disorders
12.48
Infections and infestations
11.03
Respiratory, thoracic and mediastinal disorders
8.15
Gastrointestinal disorders
7.9
Vascular disorders
6.49
Injury, poisoning and procedural complications
5.83
Cardiac disorders
5.54
Investigations
4.91
Nervous system disorders
4.52
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
3.77
Metabolism and nutrition disorders
3.34
Musculoskeletal and connective tissue disorders
2.53
Skin and subcutaneous tissue disorders
2.34

Cross References

Resources Reference
CAS NUMBER 2353-33-5
ChEBI 50131
ChEMBL CHEMBL1201129
DrugBank DB01262
DrugCentral 790
EPA CompTox DTXSID7030432
FDA SRS 776B62CQ27
Human Metabolome Database HMDB0015391
Guide to Pharmacology 6805
KEGG D03665
PharmGKB PA164749631
PubChem 451668
SureChEMBL SCHEMBL4006
ZINC ZINC000016929327
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