decitabine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | 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

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 4.87 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 4.60 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 130 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 1 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.58 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
May 2, 2006 FDA Astex Pharmaceuticals, Inc.

FDA Adverse Event Reporting System (Female)

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 234.94 34.17 107 2200 94520 46589235
Acute myeloid leukaemia 163.55 34.17 51 2256 15727 46668028
Bone marrow failure 77.76 34.17 35 2272 29634 46654121
Myelodysplastic syndrome 73.33 34.17 28 2279 15683 46668072
Neutropenia 55.24 34.17 50 2257 143154 46540601
Pancytopenia 54.61 34.17 40 2267 85018 46598737
Pneumonia 50.31 34.17 76 2231 376244 46307511
Haematotoxicity 49.78 34.17 17 2290 6916 46676839
Off label use 45.57 34.17 73 2234 379768 46303987
Acute myeloid leukaemia recurrent 44.89 34.17 11 2296 1385 46682370
Sepsis 43.81 34.17 43 2264 135971 46547784
Pyrexia 36.35 34.17 63 2244 348739 46335016
Product use in unapproved indication 35.68 34.17 32 2275 90241 46593514

FDA Adverse Event Reporting System (Male)

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 248.88 24.96 154 3337 106539 29842448
Acute myeloid leukaemia 236.44 24.96 86 3405 17920 29931067
Bone marrow failure 95.29 24.96 53 3438 29732 29919255
Pancytopenia 56.50 24.96 59 3432 84993 29863994
Pneumonia 53.76 24.96 119 3372 334187 29614800
Product use in unapproved indication 52.32 24.96 53 3438 73640 29875347
Off label use 50.89 24.96 98 3393 249192 29699795
Sepsis 46.28 24.96 70 3421 146325 29802662
Neutropenia 44.26 24.96 64 3427 128476 29820511
Infection 41.14 24.96 48 3443 78026 29870961
Acute myeloid leukaemia refractory 40.03 24.96 6 3485 18 29948969
Acute myeloid leukaemia recurrent 38.54 24.96 12 3479 1540 29947447
Aspergillus infection 37.67 24.96 20 3471 10194 29938793
Respiratory failure 35.91 24.96 51 3440 100591 29848396
Platelet count decreased 35.27 24.96 52 3439 106077 29842910
Myelodysplastic syndrome 31.02 24.96 22 3469 18756 29930231
Choroidal effusion 28.41 24.96 6 3485 161 29948826
Haematotoxicity 28.31 24.96 14 3477 6156 29942831
Mucormycosis 27.32 24.96 13 3478 5255 29943732
Pyrexia 26.78 24.96 85 3406 294404 29654583

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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
100MG;35MG INQOVI OTSUKA N212576 July 7, 2020 RX TABLET ORAL July 7, 2025 NEW CHEMICAL ENTITY
100MG;35MG INQOVI OTSUKA N212576 July 7, 2020 RX TABLET ORAL July 7, 2027 TREATMENT OF ADULT PATIENTS WITH MYELODYSPLASTIC SYNDROMES (MDS), INCLUDING PREVIOUSLY TREATED AND UNTREATED, DE NOVO AND SECONDARY MDS WITH THE FOLLOWING FRENCH-AMERICAN-BRITISH SUBTYPES (REFRACTORY ANEMIA, REFRACTORY ANEMIA WITH RINGED SIDEROBLASTS, REFRACTORY ANEMIA WITH EXCESS BLASTS, AND CHRONIC MYELOMONOCYTIC LEUKEMIA [CMML]) AND INTERMEDIATE-1, INTERMEDIATE-2, AND HIGH-RISK INTERNULLTIONULLL PROGNOSTIC SCORING SYSTEM GROUPS.

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
4025438 VUID
N0000179023 NUI
D03665 KEGG_DRUG
879492-57-6 SECONDARY_CAS_RN
4025438 VANDF
C1712036 UMLSCUI
CHEBI:50131 CHEBI
CHEMBL1201129 ChEMBL_ID
DB01262 DRUGBANK_ID
D000077209 MESH_DESCRIPTOR_UI
451668 PUBCHEM_CID
6805 IUPHAR_LIGAND_ID
6374 INN_ID
776B62CQ27 UNII
15657 RXNORM
203877 MMSL
21366 MMSL
81707 MMSL
d05788 MMSL
011499 NDDF
420517007 SNOMEDCT_US
420759005 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Decitabine Human Prescription Drug Label 1 0781-3296 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 27 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 16714-749 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 25 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 16714-928 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 27 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 16729-224 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 27 sections
decitabine HUMAN PRESCRIPTION DRUG LABEL 1 25021-231 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 27 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 43598-348 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 27 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 43598-427 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 27 sections
DECITABINE HUMAN PRESCRIPTION DRUG LABEL 1 50742-430 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 24 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 55111-556 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 27 sections
Dacogen HUMAN PRESCRIPTION DRUG LABEL 1 59148-046 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS NDA 30 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 63323-825 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 27 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 64679-067 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 24 sections
INQOVI HUMAN PRESCRIPTION DRUG LABEL 2 64842-0727 TABLET, FILM COATED 35 mg ORAL NDA 31 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 67184-0535 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 28 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 67457-316 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 27 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 68001-347 INJECTION 50 mg INTRAVENOUS ANDA 27 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 68001-422 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 27 sections
decitabine HUMAN PRESCRIPTION DRUG LABEL 1 68180-738 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 25 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 69097-285 INJECTION 50 mg INTRAVENOUS ANDA 24 sections
Decitabine Human Prescription Drug Label 1 69539-115 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 27 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 70121-1644 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 28 sections
Decitabine Human Prescription Drug Label 1 72205-031 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 27 sections
Decitabine Human Prescription Drug Label 1 72205-036 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 27 sections
Decitabine Human Prescription Drug Label 1 72603-107 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 27 sections
DECITABINE Human Prescription Drug Label 1 75834-190 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 27 sections