decitabine ๐Ÿถ Veterinary Use | 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 ยตM/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 295.51 31.20 131 2656 97536 50504801
Neutropenia 87.22 31.20 69 2718 147896 50454441
Bone marrow failure 82.83 31.20 37 2750 27587 50574750
Pneumonia 82.03 31.20 102 2685 378299 50224038
Acute myeloid leukaemia 67.97 31.20 27 2760 15047 50587290
Thrombocytopenia 59.44 31.20 52 2735 127621 50474716
Pancytopenia 57.75 31.20 43 2744 83987 50518350
Acute myeloid leukaemia recurrent 53.86 31.20 13 2774 1377 50600960
Sepsis 51.79 31.20 49 2738 132876 50469461
Off label use 48.18 31.20 90 2697 474336 50128001
Haematotoxicity 45.81 31.20 17 2770 7878 50594459
Pyrexia 38.34 31.20 72 2715 380131 50222206
Product use in unapproved indication 38.19 31.20 39 2748 115780 50486557
Myelosuppression 36.97 31.20 17 2770 13500 50588837
Splenic abscess 35.91 31.20 6 2781 95 50602242
Myelodysplastic syndrome 32.15 31.20 16 2771 15116 50587221

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 281.46 26.42 183 4054 112057 29458233
Acute myeloid leukaemia 127.09 26.42 57 4180 16456 29553834
Neutropenia 93.25 26.42 104 4133 131607 29438683
Bone marrow failure 89.07 26.42 53 4184 27396 29542894
Pneumonia 72.49 26.42 148 4089 320024 29250266
Pancytopenia 69.86 26.42 72 4165 83096 29487194
Off label use 62.10 26.42 134 4103 300666 29269624
Infection 56.54 26.42 62 4175 76689 29493601
Sepsis 48.65 26.42 79 4158 142603 29427687
Acute myeloid leukaemia recurrent 46.40 26.42 15 4222 1765 29568525
Acute myeloid leukaemia refractory 45.52 26.42 7 4230 20 29570270
Product use in unapproved indication 45.52 26.42 59 4178 86816 29483474
Aspergillus infection 41.12 26.42 23 4214 10558 29559732
Myelosuppression 38.03 26.42 23 4214 12204 29558086
Pyrexia 37.80 26.42 108 4129 287514 29282776
Thrombocytopenia 35.92 26.42 67 4170 134756 29435534
Platelet count decreased 35.67 26.42 58 4179 104614 29465676
Respiratory failure 29.32 26.42 51 4186 97080 29473210
Mucormycosis 27.94 26.42 14 4223 5144 29565146
Choroidal effusion 27.70 26.42 6 4231 147 29570143
Bacteraemia 27.48 26.42 21 4216 16302 29553988

FDA Adverse Event Reporting System (Geriatric)

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 541.41 26.96 297 6306 187360 64304769
Bone marrow failure 168.53 26.96 87 6516 47865 64444264
Pneumonia 163.68 26.96 240 6363 559336 63932793
Acute myeloid leukaemia 154.97 26.96 69 6534 27394 64464735
Neutropenia 149.17 26.96 151 6452 239473 64252656
Acute myeloid leukaemia recurrent 133.75 26.96 35 6568 2749 64489380
Product use in unapproved indication 116.56 26.96 115 6488 176503 64315626
Sepsis 101.18 26.96 121 6482 230220 64261909
Pancytopenia 90.19 26.96 91 6512 143218 64348911
Haematotoxicity 87.74 26.96 37 6566 12859 64479270
Thrombocytopenia 75.22 26.96 103 6500 223698 64268431
Off label use 73.95 26.96 184 6419 632622 63859507
Myelosuppression 68.88 26.96 38 6565 23792 64468337
Infection 58.94 26.96 83 6520 184797 64307332
Aspergillus infection 55.40 26.96 29 6574 16350 64475779
Pyrexia 53.47 26.96 151 6452 558493 63933636
Acute myeloid leukaemia refractory 49.52 26.96 8 6595 51 64492078
Platelet count decreased 48.61 26.96 72 6531 167639 64324490
Respiratory failure 46.43 26.96 69 6534 161114 64331015
Leukaemia recurrent 45.79 26.96 15 6588 2579 64489550
Bacteraemia 37.43 26.96 27 6576 26884 64465245
Mucormycosis 36.79 26.96 17 6586 7324 64484805
Gene mutation 36.59 26.96 12 6591 2070 64490059
Cardiac failure 34.33 26.96 54 6549 132319 64359810
Anaemia 33.81 26.96 100 6503 378580 64113549
Pneumonia fungal 33.72 26.96 17 6586 8860 64483269
Chronic graft versus host disease 32.92 26.96 15 6588 6261 64485868
Disease progression 31.61 26.96 54 6549 141626 64350503
Organising pneumonia 27.70 26.96 15 6588 9040 64483089

FDA Adverse Event Reporting System (Pediatric)

None

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 | Suggest Off label Use Form| |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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
100MG;35MG INQOVI OTSUKA N212576 July 7, 2020 RX TABLET ORAL 8618075 Oct. 16, 2028 METHOD FOR INHIBITING CYTIDINE DEAMINASE BY ADMINISTERING CEDAZURIDINE
100MG;35MG INQOVI OTSUKA N212576 July 7, 2020 RX TABLET ORAL 8618075 Oct. 16, 2028 METHOD FOR INHIBITING DEGRADATION OF A CDA SUBSTRATE BY ADMINISTERING CEDAZURIDINE
100MG;35MG INQOVI OTSUKA N212576 July 7, 2020 RX TABLET ORAL 8268800 Aug. 22, 2030 METHOD FOR INHIBITING CYTIDINE DEAMINASE BY ADMINISTERING CEDAZURIDINE
100MG;35MG INQOVI OTSUKA N212576 July 7, 2020 RX TABLET ORAL 8268800 Aug. 22, 2030 METHOD FOR INHIBITING DEGRADATION OF A CDA SUBSTRATE BY ADMINISTERING CEDAZURIDINE
100MG;35MG INQOVI OTSUKA N212576 July 7, 2020 RX TABLET ORAL 8268800 Aug. 22, 2030 TREATMENT OF CHRONIC MYELOMONOCYTIC LEUKEMIA
100MG;35MG INQOVI OTSUKA N212576 July 7, 2020 RX TABLET ORAL 8268800 Aug. 22, 2030 TREATMENT OF MYELODYSPLASTIC SYNDROME

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 INTERNATIONAL PROGNOSTIC SCORING SYSTEM GROUPS.

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
DNA (cytosine-5)-methyltransferase 1 Enzyme INHIBITOR IC50 7.52 CHEMBL 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
15657 RXNORM
4025438 VANDF
C0049065 UMLSCUI
CHEBI:50131 CHEBI
CHEMBL1201129 ChEMBL_ID
DB01262 DRUGBANK_ID
D000077209 MESH_DESCRIPTOR_UI
451668 PUBCHEM_CID
6374 INN_ID
6805 IUPHAR_LIGAND_ID
776B62CQ27 UNII
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 0143-9385 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 28 sections
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 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
Decitabine Human Prescription Drug Label 1 55150-376 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
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 68001-422 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 27 sections
decitabine Human Prescription Drug Label 1 68083-528 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 69097-905 INJECTION 50 mg INTRAVENOUS ANDA 21 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 70860-219 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 28 sections
Decitabine HUMAN PRESCRIPTION DRUG LABEL 1 71288-119 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 27 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