decitabine Indications/Contra | FAERs | Orange Book | BioActivity |

Stem definitionDrug idCAS RN
nucleosides antiviral or antineoplastic agents, cytarabine or azacitidine derivatives 790 2353-33-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • decitabine mesylate
  • decitabine mesilate
  • decitabine
  • dacogen
An azacitidine derivative and antineoplastic antimetabolite. It inhibits DNA methyltransferase to re-activate silent genes, limiting METASTASIS and NEOPLASM DRUG RESISTANCE. Decitabine is used in the treatment of MYELODISPLASTIC SYNDROMES, and ACUTE MYELOID LEUKEMIA.
  • Molecular weight: 228.21
  • Formula: C8H12N4O4
  • CLOGP: -1.90
  • LIPINSKI: 0
  • HAC: 8
  • HDO: 3
  • TPSA: 120.74
  • ALOGS: -1.62
  • ROTB: 2

Drug dosage:

None

Approvals:

DateAgencyCompanyOrphan
May 2, 2006 FDA OTSUKA PHARM CO LTD

FDA Adverse Event Reporting System

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Febrile neutropenia 839.66 51.89 203 1253 26109 4611427
Bone marrow failure 416.75 51.89 101 1355 12637 4624899
Acute myeloid leukaemia 402.51 51.89 88 1368 6957 4630579
Pneumonia 364.38 51.89 148 1308 102667 4534869
Sepsis 279.94 51.89 97 1359 42742 4594794
Haematotoxicity 222.05 51.89 47 1409 3142 4634394
Respiratory failure 187.22 51.89 66 1390 30260 4607276
Pyrexia 185.08 51.89 94 1362 107050 4530486
Thrombocytopenia 161.57 51.89 67 1389 47606 4589930
Neutropenia 161.19 51.89 67 1389 47883 4589653
Pancytopenia 156.71 51.89 55 1401 24798 4612738
Infection 154.23 51.89 60 1396 36082 4601454
Myelodysplastic syndrome 141.36 51.89 38 1418 7020 4630516
Acute myeloid leukaemia recurrent 116.56 51.89 21 1435 596 4636940
Platelet count decreased 114.31 51.89 48 1408 34954 4602582
Off label use 101.05 51.89 68 1388 129045 4508491
Colitis 100.98 51.89 32 1424 10467 4627069
Product use in unapproved indication 100.70 51.89 40 1416 25233 4612303
Anaemia 95.22 51.89 53 1403 71507 4566029
Cardiac failure 87.58 51.89 37 1419 27251 4610285
Chronic graft versus host disease 87.29 51.89 19 1437 1436 4636100
White blood cell count decreased 83.92 51.89 38 1418 33027 4604509
Hypotension 76.38 51.89 45 1411 67355 4570181
Disease progression 76.11 51.89 38 1418 40973 4596563
Neutrophil count decreased 73.57 51.89 27 1429 13696 4623840
Septic shock 71.84 51.89 28 1428 16738 4620798
Nausea 69.43 51.89 62 1394 177271 4460265
Hypoxia 67.33 51.89 25 1431 13096 4624440
Systemic inflammatory response syndrome 66.56 51.89 16 1440 1877 4635659
Chimerism 61.97 51.89 8 1448 18 4637518
Organising pneumonia 60.81 51.89 15 1441 1959 4635577
Extravasation 56.24 51.89 14 1442 1897 4635639
Haemoglobin decreased 55.73 51.89 30 1426 37627 4599909
Vomiting 55.11 51.89 46 1410 119653 4517883
Fatigue 55.07 51.89 50 1406 145516 4492020
Pneumonia fungal 53.98 51.89 12 1444 997 4636539
Pleural effusion 52.36 51.89 25 1431 24373 4613163
Bacterial infection 52.34 51.89 16 1440 4627 4632909
Escherichia bacteraemia 52.10 51.89 11 1445 717 4636819

Pharmacologic Action:

SourceCodeDescription
ATC L01BC08 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
ANTIMETABOLITES
Pyrimidine analogues
FDA MoA N0000000233 Nucleic Acid Synthesis Inhibitors
FDA EPC N0000175595 Nucleoside Metabolic Inhibitor
MeSH PA D000963 Antimetabolites
MeSH PA D000964 Antimetabolites, Antineoplastic
MeSH PA D000970 Antineoplastic Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D009676 Noxae

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Acute myeloid leukemia, disease indication 91861009
Myelodysplastic syndrome indication 109995007
Diabetes mellitus contraindication 73211009 DOID:9351
Kidney disease contraindication 90708001 DOID:557
Disease of liver contraindication 235856003 DOID:409
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Breastfeeding (mother) contraindication 413712001

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 12.94 acidic
pKa2 13.68 acidic
pKa3 4.39 Basic
pKa4 2.93 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
DNA (cytosine-5)-methyltransferase 1 Enzyme INHIBITOR WOMBAT-PK CHEMBL
DNA (cytosine-5)-methyltransferase 3A Enzyme INHIBITOR CHEMBL CHEMBL

External reference:

IDSource
D000077209 MESH_DESCRIPTOR_UI
4025438 VUID
N0000179023 NUI
C0049065 UMLSCUI
D03665 KEGG_DRUG
6U3LPL9PRN UNII
879492-57-6 SECONDARY_CAS_RN
6374 INN_ID
420759005 SNOMEDCT_US
420517007 SNOMEDCT_US
21366 MMSL
d05788 MMSL
15657 RXNORM
4025438 VANDF
203877 MMSL
011499 NDDF
451668 PUBCHEM_CID
CHEBI:50131 CHEBI
DB01262 DRUGBANK_ID
6805 IUPHAR_LIGAND_ID
CHEMBL1201129 ChEMBL_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 0781-3296 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 16714-749 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 16714-928 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 16729-224 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 18 sections
decitabine HUMAN PRESCRIPTION DRUG LABEL 1 25021-231 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 43598-348 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 43598-427 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
decitabine HUMAN PRESCRIPTION DRUG LABEL 1 47335-361 KIT 50 mg None NDA 17 sections
DECITABINE HUMAN PRESCRIPTION DRUG LABEL 1 50742-430 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 55111-556 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 16 sections
Dacogen HUMAN PRESCRIPTION DRUG LABEL 1 59148-046 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS NDA 18 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 63323-825 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 64679-067 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 67457-316 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 18 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 68001-347 INJECTION 50 mg INTRAVENOUS ANDA 17 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 68001-422 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 18 sections
decitabine HUMAN PRESCRIPTION DRUG LABEL 1 68180-738 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 69097-285 INJECTION 50 mg INTRAVENOUS ANDA 17 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 69539-115 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 70121-1644 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 72205-031 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 72205-036 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 17 sections