azacitidine indications/contra

Stem definitionDrug idCAS RN
nucleosides antiviral or antineoplastic agents, cytarabine or azacitidine derivatives 25 320-67-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • 5-azacytidine
  • azacitidine
  • azacytidine
  • ladakamycin
  • ledakamycin
  • vidaza
  • U-18496
A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent.
  • Molecular weight: 244.21
  • Formula: C8H12N4O5
  • CLOGP: -2.20
  • LIPINSKI: 0
  • HAC: 9
  • HDO: 4
  • TPSA: 140.97
  • ALOGS: -1.30
  • ROTB: 2

Drug dosage:

None

Approvals:

DateAgencyCompanyOrphan
May 19, 2004 FDA CELGENE

FDA Adverse Event Reporting System

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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
Acute myeloid leukaemia 3115.67 64.25 614 5916 4559 3374770
Febrile neutropenia 3078.66 64.25 767 5763 18208 3361121
Death 2080.69 64.25 949 5581 151375 3227954
Pneumonia 1774.72 64.25 682 5848 69461 3309868
Sepsis 1561.17 64.25 510 6020 31863 3347466
Myelodysplastic syndrome 1423.27 64.25 328 6202 5319 3374010
Thrombocytopenia 1047.61 64.25 388 6142 34880 3344449
Neutropenia 1016.01 64.25 374 6156 33012 3346317
Infection 904.70 64.25 320 6210 25082 3354247
Platelet count decreased 880.25 64.25 320 6210 27148 3352181
Anaemia 810.58 64.25 365 6165 53968 3325361
Pyrexia 757.02 64.25 395 6135 80720 3298609
Neutrophil count decreased 726.38 64.25 218 6312 10055 3369274
Pancytopenia 676.12 64.25 239 6291 18581 3360748
White blood cell count decreased 635.37 64.25 246 6284 24701 3354628
Myelodysplastic syndrome transformation 532.95 64.25 91 6439 245 3379084
Septic shock 519.27 64.25 176 6354 12008 3367321
Constipation 470.11 64.25 211 6319 30601 3348728
Therapy non-responder 444.19 64.25 152 6378 10657 3368672
Acute myeloid leukaemia recurrent 438.09 64.25 80 6450 352 3378977
Disease progression 356.50 64.25 177 6353 32082 3347247
Blast cell count increased 304.71 64.25 55 6475 223 3379106
General physical health deterioration 272.58 64.25 128 6402 20461 3358868
Nausea 238.14 64.25 235 6295 129410 3249919
Haemoglobin decreased 228.60 64.25 129 6401 30165 3349164
Cerebral haemorrhage 224.73 64.25 90 6440 9764 3369565
Diarrhoea 221.45 64.25 205 6325 104143 3275186
Cardiac failure 208.96 64.25 106 6424 19999 3359330
Bone marrow failure 205.66 64.25 81 6449 8406 3370923
Pneumonia fungal 196.34 64.25 45 6485 695 3378634

Pharmacologic Action:

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SourceCodeDescription
ATC L01BC07 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)

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DiseaseRelationSNOMED_IDDOID
Myelodysplastic syndrome indication 109995007
Hepatic failure contraindication 59927004
Kidney disease contraindication 90708001 DOID:2527
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Breastfeeding (mother) contraindication 413712001
Advanced Malignant Neoplasm of Liver contraindication

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 12.32 acidic
pKa2 12.92 acidic
pKa3 13.79 acidic
pKa4 4.43 Basic
pKa5 2.98 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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

External reference:

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IDSource
4021468 VUID
N0000148852 NUI
C0004475 UMLSCUI
6796 IUPHAR_LIGAND_ID
D03021 KEGG_DRUG
DB00928 DRUGBANK_ID
9444 PUBCHEM_CID
1251 RXNORM
4021468 VANDF
18639 MMSL
N0000010550 NDFRT
N0000148852 NDFRT
d05293 MMSL
008661 NDDF
412328000 SNOMEDCT_US
412329008 SNOMEDCT_US
88551000 SNOMEDCT_US
205981 MMSL
CHEMBL1489 ChEMBL_ID
CHEBI:2038 CHEBI
M801H13NRU UNII
4520 INN_ID
D001374 MESH_DESCRIPTOR_UI
5AE PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Azacitidine HUMAN PRESCRIPTION DRUG LABEL 1 0591-2897 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 100 mg INTRAVENOUS NDA 16 sections
Azacitidine HUMAN PRESCRIPTION DRUG LABEL 1 0781-3253 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 100 mg SUBCUTANEOUS NDA authorized generic 17 sections
Azacitidine HUMAN PRESCRIPTION DRUG LABEL 1 0781-9253 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 100 mg SUBCUTANEOUS NDA authorized generic 17 sections
Azacitidine HUMAN PRESCRIPTION DRUG LABEL 1 43598-305 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 100 mg SUBCUTANEOUS ANDA 16 sections
Azacitidine HUMAN PRESCRIPTION DRUG LABEL 1 43598-465 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 100 mg SUBCUTANEOUS ANDA 17 sections
AZACITIDINE HUMAN PRESCRIPTION DRUG LABEL 1 43598-678 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 100 mg INTRAVENOUS ANDA 17 sections
Azacitidine HUMAN PRESCRIPTION DRUG LABEL 1 51991-797 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 100 mg SUBCUTANEOUS ANDA 18 sections
VIDAZA HUMAN PRESCRIPTION DRUG LABEL 1 59572-102 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 100 mg INTRAVENOUS NDA 17 sections
Azacitidine HUMAN PRESCRIPTION DRUG LABEL 1 63323-771 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 100 mg INTRAVENOUS ANDA 17 sections
AZACITIDINE HUMAN PRESCRIPTION DRUG LABEL 1 63759-0003 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 100 mg INTRAVENOUS ANDA 17 sections
AZACITIDINE HUMAN PRESCRIPTION DRUG LABEL 1 64679-096 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 100 mg INTRAVENOUS ANDA 17 sections
Azacitidine HUMAN PRESCRIPTION DRUG LABEL 1 67457-254 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 100 mg INTRAVENOUS ANDA 17 sections
Azacitidine HUMAN PRESCRIPTION DRUG LABEL 1 68001-313 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 100 mg INTRAVENOUS NDA 16 sections