Azacitidine
Highest phase reached
Approved
Drug type
Small molecule
First approval year
2004
- First approval year
- 2004
- Listing at source
- Listed
- Highest phase reached
- Approved
- Drug type
- Small molecule
- Drug name
- Azacitidine
- Molecular weight
- 244.21
- Structure (SMILES)
- Nc1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)n1
- azacitidine
- Azacitidine
- azacitidine accord
- Azacitidine accord
- azacitidine betapharm
- Azacitidine betapharm
- azacitidine celgene
- Azacitidine celgene
- azacitidine kabi
- Azacitidine kabi
- azacitidine mylan
- Azacitidine mylan
- onureg
- Onureg
- vidaza
- Vidaza
- 1 3 5 triazin 2 1h one 4 amino 1 beta d ribofuranosyl
- 1,3,5-TRIAZIN-2(1H)-ONE, 4-AMINO-1-.BETA.-D-RIBOFURANOSYL-
- 4 amino 1 beta d ribofuranosyl s triazin 2 1h one
- 4-AMINO-1-.BETA.-D-RIBOFURANOSYL-S-TRIAZIN-2(1H)-ONE
- 5 azacitidine
- 5-azacitidine
- 5-Azacitidine
- 5' Azacitidine
- azacitidina
- Azacitidina
- azacitidine
- Azacitidine
- Azacitidine (AZA)
- Azacitidine (AZC)
- Azacitidine (BAML-16-001-S12 Arm A)
- Azacitidine (BAML-16-001-S12 Arm B)
- Azacitidine (BAML-16-001-S16)
- Azacitidine (BAML-16-001-S17)
- Azacitidine (BAML-16-001-S18)
- Azacitidine (BAML-16-001-S2)
- Azacitidine (BAML-16-001-S24)
- Azacitidine (BAML-16-001-S3)
- Azacitidine (BAML-16-001-S4)
- Azacitidine (BAML-16-001-S9)
- Azacitidine (Monotherapy)
And 53 more, listed on the interactive page.
- ATC classification codes
- L01BC07
Sources for recorded values
- CAS registry numbers
- 320-67-2
- ChEMBL ID
- CHEMBL1489
- InChIKey
- NMUSYJAQQFHJEW-KVTDHHQDSA-N
- PubChem compound IDs
- 9444
- RxNorm IDs (RxCUI)
- 1251
- FDA ingredient codes (UNII)
- M801H13NRU
- Applicant
- BRISTOL-MYERS
- Approval date
- 19 May 2004
- Application number
- NDA050794
- Status
- Authorised
- Status date
- 17 Dec 2008
- Authorisation date
- 17 Dec 2008
- Approved indications
- Vidaza is indicated for the treatment of adult patients who are not eligible for haematopoietic stem cell transplantation (HSCT) with: intermediate 2 and high-risk myelodysplastic syndromes (MDS) according to the International Prognostic Scoring System (IPSS), chronic myelomonocytic leukaemia (CMML) with 10 29 % marrow blasts without myeloproliferative disorder, acute myeloid leukaemia (AML) with 20 30 % blasts and multi-lineage dysplasia, according to World Health Organisation (WHO) classification. Vidaza is indicated for the treatment of adult patients aged 65 years or older who are not eligible for HSCT with AML with >30% marrow blasts according to the WHO classification.
- Product number
- EMEA/H/C/000978
- Authorisation holder
- Bristol-Myers Squibb Pharma EEIG
- Priority medicines scheme
- No
- Generic
- No
- Biosimilar
- No
- Generic medicines
- 4
- Biosimilar medicines
- 0
- Advanced therapy
- No
- Conditional approval
- No
- Additional monitoring
- No
- Accelerated assessment
- Yes
- Exceptional circumstances
- No
Therapeutic areas
- Leukemia, Myeloid, Acute
- Leukemia, Myelomonocytic, Chronic
- Myelodysplastic Syndromes
European medicines record
- Patents
- 3
- Designations
- 5
- Earliest recorded loss of exclusivity
- 3 Jun 2030
- First in class
- No
- Fast track
- Yes
- Breakthrough designation
- Yes
- Orphan designation
- No
- Priority review
- Yes
- Orphan exclusivity
- No
- Accelerated approval
- No
- Availability
- Prescription only
- Pharmacology name
- azacitidine
- Type
- Synthetic organic
- Drug name stem
- -tidine
- Approval recorded by Guide to Pharmacology
- Yes
Administration routes
- Oral
- Parenteral
- Mechanism
- DNA (cytosine-5)-methyltransferase 1 inhibitor
- Action type
- Inhibitor
- Target
- DNA (cytosine-5)-methyltransferase 1
- Protein identifier
- P26358
- Mechanism
- DNA (cytosine-5)-methyltransferase 3A inhibitor
- Action type
- Inhibitor
- Target
- DNA (cytosine-5)-methyltransferase 3A
- Protein identifier
- Q9Y6K1
- Mechanism
- DNA inhibitor
- Action type
- Inhibitor
- Target
- DNA
- Mechanism
- RNA inhibitor
- Action type
- Inhibitor
- Target
- RNA
- Mechanism
- DNA (cytosine-5)-methyltransferase 1 inhibitor
- Action type
- Inhibitor
- Target
- DNA (cytosine-5)-methyltransferase 1
- Mechanism
- DNA (cytosine-5)-methyltransferase 3A inhibitor
- Action type
- Inhibitor
- Target
- DNA (cytosine-5)-methyltransferase 3A
- Action type
- Inhibitor
- Gene symbol
- DNMT1
- Protein identifier
- P26358
- Organism
- Homo sapiens
- Target development level
- Clinical
- Action type
- Inhibitor
- Gene symbol
- DNMT3A
- Protein identifier
- Q9Y6K1
- Organism
- Homo sapiens
- Target development level
- Clinical
- Condition
- Leukemia, Lymphocytic, Chronic, B-Cell
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000095
- Subject identifier
- D015451
- Condition
- Carcinoma, Squamous Cell
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000181
- Subject identifier
- D002294
- Condition
- Hodgkin Disease
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000183
- Subject identifier
- D006689
- Condition
- Myelodysplastic Syndromes
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000198
- Subject identifier
- D009190
- Condition
- Lymphoma, T-Cell, Peripheral
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000211
- Subject identifier
- D016411
- Condition
- Precursor Cell Lymphoblastic Leukemia-Lymphoma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000220
- Subject identifier
- D054198
- Condition
- Leukemia, Monocytic, Acute
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000221
- Subject identifier
- D007948
- Condition
- Leukemia, Myeloid, Acute
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000222
- Subject identifier
- D015470
- Condition
- Immunoblastic Lymphadenopathy
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000255
- Subject identifier
- D007119
- Condition
- Glioma
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000326
- Subject identifier
- D005910
- Condition
- Leukemia, Myelogenous, Chronic, BCR-ABL Positive
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000339
- Subject identifier
- D015464
- Condition
- Melanoma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000389
- Subject identifier
- D008545
- Condition
- Lymphoma, Large B-Cell, Diffuse
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000403
- Subject identifier
- D016403
- Condition
- Leukemia
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000565
- Subject identifier
- D007938
- Condition
- Liposarcoma
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000569
- Subject identifier
- D008080
- Condition
- Lymphoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000574
- Subject identifier
- D008223
- Condition
- Neoplasms
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000616
- Subject identifier
- D009369
- Condition
- Osteosarcoma
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000637
- Subject identifier
- D012516
- Condition
- Prostatic Neoplasms
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000673
- Subject identifier
- D011471
- Condition
- Carcinoma, Renal Cell
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000681
- Subject identifier
- D002292
- Condition
- Sarcoma
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000691
- Subject identifier
- D012509
- Condition
- Carcinoma, Squamous Cell
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000707
- Subject identifier
- D002294
- Condition
- Multiple Myeloma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0001378
- Subject identifier
- D009101
- Condition
- Hematologic Neoplasms
- Highest recorded phase
- 2
- Condition identifier
- EFO:0001642
- Subject identifier
- D019337
- Condition
- Melanoma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0002617
- Subject identifier
- D008545
And 43 more, listed on the interactive page.
- Condition identifier
- EFO_0000183
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000198
- Condition identifier
- EFO_0000211
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000220
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000221
- Condition identifier
- EFO_0000222
- Condition identifier
- EFO_0000255
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000326
- Highest recorded phase
- 1
- Condition identifier
- EFO_0000330
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000339
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000389
- Highest recorded phase
- 1
- Condition identifier
- EFO_0000565
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000569
- Highest recorded phase
- 1
- Condition identifier
- EFO_0000574
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000616
- Condition identifier
- EFO_0000681
- Condition identifier
- EFO_0001378
- Highest recorded phase
- 2
- Condition identifier
- EFO_0002427
- Highest recorded phase
- 2
- Condition identifier
- EFO_0002618
- Highest recorded phase
- 2
- Condition identifier
- EFO_0003060
- Highest recorded phase
- 2
- Condition identifier
- EFO_0003811
- Condition identifier
- EFO_0003833
- Condition identifier
- EFO_0003869
- Highest recorded phase
- 2
- Condition identifier
- EFO_0004251
- Highest recorded phase
- 2
- Condition identifier
- EFO_0004252
- Highest recorded phase
- 2
And 124 more, listed on the interactive page.
- Event
- acute febrile neutrophilic dermatosis
- Reports
- 46
- Reporting signal score
- 111.665
- Event
- acute myeloid leukaemia
- Reports
- 195
- Reporting signal score
- 506.244
- Event
- acute myeloid leukaemia recurrent
- Reports
- 52
- Reporting signal score
- 190.609
- Event
- anaemia
- Reports
- 392
- Reporting signal score
- 216.27
- Event
- blast cell count increased
- Reports
- 43
- Reporting signal score
- 145.822
- Event
- bronchopulmonary aspergillosis
- Reports
- 63
- Reporting signal score
- 127.176
- Event
- cytopenia
- Reports
- 120
- Reporting signal score
- 247.869
- Event
- differentiation syndrome
- Reports
- 28
- Reporting signal score
- 95.4096
- Event
- drug hypersensitivity
- Reports
- 11
- Reporting signal score
- 89.8764
- Event
- febrile neutropenia
- Reports
- 1,034
- Reporting signal score
- 2,465.83
- Event
- headache
- Reports
- 46
- Reporting signal score
- 115.254
- Event
- myelodysplastic syndrome
- Reports
- 111
- Reporting signal score
- 195.043
- Event
- myelosuppression
- Reports
- 83
- Reporting signal score
- 130.429
- Event
- neutropenia
- Reports
- 386
- Reporting signal score
- 292.67
- Event
- neutrophil count decreased
- Reports
- 166
- Reporting signal score
- 183.443
- Event
- pancytopenia
- Reports
- 226
- Reporting signal score
- 247.616
- Event
- platelet count decreased
- Reports
- 259
- Reporting signal score
- 192.028
- Event
- pneumonia
- Reports
- 416
- Reporting signal score
- 207.446
- Event
- pneumonia fungal
- Reports
- 45
- Reporting signal score
- 124.961
- Event
- pyrexia
- Reports
- 451
- Reporting signal score
- 163.363
- Event
- sepsis
- Reports
- 250
- Reporting signal score
- 254.79
- Event
- thrombocytopenia
- Reports
- 365
- Reporting signal score
- 292.271
- Event
- transformation to acute myeloid leukaemia
- Reports
- 43
- Reporting signal score
- 182.146
- Event
- white blood cell count decreased
- Reports
- 192
- Reporting signal score
- 97.1438
- NCT00004062
- NCT00004871
- NCT00005598
- NCT00071799
- NCT00102687
- NCT00118287
- NCT00326170
- NCT00339196
- NCT00379912
- NCT00382590
- NCT00384956
- NCT00439673
- NCT00446303
- NCT00495547
- NCT00569010
- NCT00666497
- NCT00704704
- NCT00721214
- NCT00741234
- NCT00761722
- NCT00795548
- NCT00887068
- NCT00897130
- NCT00915785
- NCT00923234
And 384 more, listed on the interactive page.
- Dose
- 300 mg
- Route
- Oral
- How often
- Once daily on Days 1 through 14 of each 28-day cycle
- Do not take 2 doses on the same day if a dose is vomited
- If a dose is missed, take as soon as possible on the same day, then resume normal schedule
- Swallow tablets whole, do not cut, crush, or chew
- Take doses at about the same time each day
- Take with or without food
- Hydrogen bond acceptors
- 9
- Hydrogen bond donors
- 4
- Polar surface area
- 143.72
- Calculated partition coefficient (ALogP)
- -3.17
- Calculated partition coefficient (XLogP)
- -2.2
- Prodrug
- Yes
- Chirality
- Single enantiomer
- Inorganic
- No
- Rule-of-five violations
- 0
- Rotatable bonds
- 2
- Heavy atoms
- 17
- Molecular formula
- C8H12N4O5
- Monoisotopic mass
- 244.08076950
- Natural product
- Yes
- 0143-9606
- 0781-3491
- 16714-927
- 16729-306
- 31722-365
- 43598-305
- 43598-465
- 43598-678
- 43817-906
- 55150-393
- 58458-002
- 59572-102
- 59572-730
- 59572-740
- 63323-771
- 68001-313
- 68001-527
- 68001-620
- 69539-112
- 70069-857
- 71288-115
- 71288-153
- 72485-201
- 72572-020
- 75907-225
And 3 more, listed on the interactive page.
- Recorded assays
- 3,307
- Active assays
- 470
- Confirmatory
- Other
- Screening
- Summary
- Antimetabolites, Antineoplastic
- Enzyme Inhibitors
Distribution coefficient (LogD)
- Median
- -2.17
- Mean
- -2.17
- Minimum
- -2.17
- Maximum
- -2.17
- Unit
- unitless
- Assays
- 1
- Standard deviation
- 0
- Summary method
- median
- Censored results excluded
- 0
- Other units excluded
- 0
- Unknown units excluded
- 0
Measurement types
- LogD
Related records
Trials (700)
- 5 Day Versus 7 Day Azacitidine in Lower Risk Myelodysplastic Syndrome
- A Biomarker-Directed Phase 2 Trial of Tamibarotene (SY-1425) in Participants With Acute Myeloid Leukemia or Myelodysplastic Syndrome
- A Clinical Trial of Cidabenamine Plus Azacitidine to Prevent Post-Transplant Progression in High-Risk Peripheral T-Cell Lymphoma
- A Clinical Trial of Omacetaxine, Azacitidine, and Growth-Colony Stimulating Factor (G-CSF) for Myelodysplastic Syndromes (MDS)
- A Clinical Trial of TQB3455 Tablets in Patients With Hematological Malignancies
- A Clinical Trial of TQB3909 Tablets in Combination With Azacitidine for the Treatment of Myeloid Malignancies
- A Clinical Trial to Learn About the Study Medicine Called Maplirpacept (PF-07901801), Alone and When Used in Combination With Other Medicines to Treat Participants With Advanced Hematological Malignancies, Including Lymphoma, Leukemia and Multiple Myeloma
- A Combination Study of PF-04449913 (Glasdegib) and Azacitidine In Untreated MDS, AML and CMML Patients
- A Dose-Finding and Efficacy Study of Venetoclax, CC-486, and Obinutuzumab in Follicular Lymphoma
- A Multi-phase Study of ASTX030 (Azacitidine and Cedazuridine) in Myeloid Neoplasm Alone or in Combination With Venetoclax in AML (AZTOUND Study)
- A Multi-Site Break Through Cancer Trial: Targeting Measurable Residual Disease in Patients With Acute Myeloid Leukemia: A Phase 1/2 Study of Tagraxofusp, Azacitidine, and Venetoclax
- A Multicenter Study on the Treatment of MDS/MPN Overlap Syndrome With AZA or Rux Combined With Selinexor
- A Multicenter Trial Evaluating Efficacy and Safety of A Reduced Venetoclax Exposure To Seven Days Versus Standard Continuous Venetoclax Exposure Combined With Azacitidine in Treatment Naïve Subjects With Acute Myeloid Leukemia Who Are Ineligible for Intensive Induction
- a New Treatment of Newly Diagnosed IDH1 Mutation Acute Myeloid Leukemia
- A Novel Conditioning Regimen for Myelodysplastic Syndrome With Moderate High IPSS-M Score
- A Phase 1 Protocol of 5-Azacytidine and Erlotinib in Advanced Solid Tumor Malignancies
- A Phase 1 Study of AOH1996 in Patients With Relapsed/Refractory Acute Myeloid Leukemia
- A Phase 1 Study of CC-486 as a Single Agent and in Combination With Carboplatin or ABI-007 in Subjects With Relapsed or Refractory Solid Tumors
- A Phase 1 Study to Evaluate the Pharmacokinetics and Tolerability of Oral Azacitidine in Japanese Patients With Myelodysplastic Syndromes
- A Phase 1 Study With LYT-200 in Patients With Relapsed/Refractory Acute Myeloid Leukemia (AML), or With Relapsed/Refractory, High-risk Myelodysplastic Syndrome (MDS)
Approved for (6)
- Acute myeloid leukemia
- Cancer
- Chronic myelomonocytic leukemia
- Myelodysplastic syndrome
- Myelodysplastic syndrome with excess blasts
- Neoplasm
In development for (68)
- Acute erythroid leukemia Phase 2
- Acute kidney injury Phase 1
- Acute leukemia of ambiguous lineage Phase 1
- Acute lymphoblastic leukemia Phase 2
- Acute monocytic leukemia Phase 2
- Angioimmunoblastic T-cell lymphoma Phase 3
- B-cell chronic lymphocytic leukemia Phase 2
- Beta thalassemia Phase 2
- Beta-thalassemia major Phase 2
- Bone marrow neoplasm Phase 2
- Brain neoplasm Early phase 1
- Breast cancer Phase 2
- Breast neoplasm Phase 2
- CD4+/CD56+ hematodermic neoplasm Phase 1
- Central nervous system cancer Phase 1
- Childhood acute myeloid leukemia Phase 2
- Childhood ependymoma Phase 1
- Chronic myeloid leukemia Phase 1
- Classic Hodgkin lymphoma Phase 2
- Colorectal cancer Phase 1
Other linked conditions (1)
- T-cell non-Hodgkin lymphoma