Cytarabine
Highest phase reached
Approved
Drug type
Small molecule
First approval year
1969
- First approval year
- 1969
- Listing at source
- Listed
- Highest phase reached
- Approved
- Drug type
- Small molecule
- Drug name
- Cytarabine
- Molecular weight
- 243.22
- Structure (SMILES)
- Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1
- alexan
- Alexan
- alexan 100
- Alexan 100
- cytarabine
- Cytarabine
- cytarabine component of vyxeos
- Cytarabine component of vyxeos
- cytosar
- Cytosar
- cytosar u
- Cytosar-u
- depocyt
- Depocyt
- depocyte
- Depocyte
- tarabine pfs
- Tarabine pfs
- 1 beta d arabinofuranosylcytosine
- 1-.BETA.-D-ARABINOFURANOSYLCYTOSINE
- 2 1h pyrimidinone 4 amino 1 beta d arabinofuranosyl
- 2(1H)-PYRIMIDINONE, 4-AMINO-1-.BETA.-D-ARABINOFURANOSYL-
- alexan
- ara c
- Ara C
- ARA C
- ara cytidine
- ara-C
- Ara-c
- Ara-C
- ARA-C
- ARA-C:
- Ara-cytidine
- arabinocytosine
- Arabinocytosine
- arabinosyl cytosine
- Arabinosyl cytosine
- arac
- Arac
- AraC
- arac intrathecal
- aracytidine
- Aracytidine
And 78 more, listed on the interactive page.
- ATC classification codes
- L01BC01
Sources for recorded values
- CAS registry numbers
- 147-94-4
- ChEMBL ID
- CHEMBL803
- InChIKey
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N
- PubChem compound IDs
- 6253
- FDA ingredient codes (UNII)
- 04079A1RDZ
- 3041
- 968804
- Applicant
- JAZZ PHARMS THERAP
- Approval date
- 3 Aug 2017
- Application number
- NDA209401
- Status
- Withdrawn
- Authorisation date
- 11 Jul 2001
- Approved indications
- Intrathecal treatment of lymphomatous meningitis. In the majority of patients such treatment will be part of symptomatic palliation of the disease.
- Product number
- EMEA/H/C/000317
- Authorisation holder
- Pacira Limited
- Priority medicines scheme
- No
- Generic
- No
- Biosimilar
- No
- Generic medicines
- 0
- Biosimilar medicines
- 0
- Advanced therapy
- No
- Conditional approval
- No
- Additional monitoring
- No
- Accelerated assessment
- No
- Exceptional circumstances
- No
Therapeutic areas
- Meningeal Neoplasms
European medicines record
- Patents
- 0
- Designations
- 1
- First in class
- No
- Fast track
- No
- Breakthrough designation
- No
- Orphan designation
- No
- Priority review
- No
- Orphan exclusivity
- No
- Accelerated approval
- No
- Availability
- Prescription only
- Boxed warning
- Yes
- United States (FDA)
- Approved
- European Union (EMA)
- Withdrawn
- Pharmacology name
- cytarabine
- Type
- Synthetic organic
- Drug name stem
- -arabine
- Approval recorded by Guide to Pharmacology
- Yes
Administration routes
- Parenteral
- Mechanism
- DNA inhibitor
- Action type
- Inhibitor
- Target
- DNA
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- P09884
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- P28340
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- P49005
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- P49642
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- P49643
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- P56282
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- Q07864
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- Q14181
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- Q15054
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- Q9HCU8
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- Q9NRF9
- Mechanism
- RNA inhibitor
- Action type
- Inhibitor
- Target
- RNA
Open Targets mechanisms
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
DrugCentral mechanisms
- Action type
- Inhibitor
- Gene symbol
- POLA1|POLD1|POLE
- Protein identifier
- P09884|P28340|Q07864
- Organism
- Homo sapiens
- Target development level
- Clinical
- Condition
- Leukemia, Biphenotypic, Acute
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000094
- Subject identifier
- D015456
- Condition
- Leukemia, Lymphocytic, Chronic, B-Cell
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000095
- Subject identifier
- D015451
- Condition
- Lymphoma, Follicular
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000096
- Subject identifier
- D008224
- Condition
- Hodgkin Disease
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000183
- Subject identifier
- D006689
- Condition
- Myelodysplastic Syndromes
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000198
- Subject identifier
- D009190
- Condition
- Neoplasms, Plasma Cell
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000200
- Subject identifier
- D054219
- Condition
- Leukemia, Biphenotypic, Acute
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000209
- Subject identifier
- D015456
- Condition
- Lymphoma, T-Cell, Peripheral
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000211
- Subject identifier
- D016411
- Condition
- Leukemia, Erythroblastic, Acute
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000218
- Subject identifier
- D004915
- Condition
- Precursor Cell Lymphoblastic Leukemia-Lymphoma
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000220
- Subject identifier
- D054198
- Condition
- Leukemia, Monocytic, Acute
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000221
- Subject identifier
- D007948
- Condition
- Leukemia, Myeloid, Acute
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000222
- Subject identifier
- D015470
- Condition
- Leukemia, Myelomonocytic, Acute
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000223
- Subject identifier
- D015479
- Condition
- Leukemia, Promyelocytic, Acute
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000224
- Subject identifier
- D015473
- Condition
- Burkitt Lymphoma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000309
- Subject identifier
- D002051
- Condition
- Leukemia, Myelogenous, Chronic, BCR-ABL Positive
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000339
- Subject identifier
- D015464
- Condition
- Lymphoma, Large B-Cell, Diffuse
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000403
- Subject identifier
- D016403
- Condition
- Thrombocythemia, Essential
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000479
- Subject identifier
- D013920
- Condition
- Glioblastoma
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000519
- Subject identifier
- D005909
- Condition
- Leukemia
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000565
- Subject identifier
- D007938
- 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
- Sarcoma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000691
- Subject identifier
- D012509
- Condition
- Melanoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000756
- Subject identifier
- D008545
- Condition
- Malaria
- Highest recorded phase
- 3
- Condition identifier
- EFO:0001068
- Subject identifier
- D008288
And 55 more, listed on the interactive page.
- Condition identifier
- EFO_0000094
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000096
- Condition identifier
- EFO_0000183
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000198
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000211
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000220
- Condition identifier
- EFO_0000222
- Condition identifier
- EFO_0000224
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000339
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000403
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000565
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000574
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000616
- Condition identifier
- EFO_0000691
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000756
- Highest recorded phase
- 3
- Condition identifier
- EFO_0001068
- Highest recorded phase
- 3
- Condition identifier
- EFO_0001378
- Highest recorded phase
- 3
- Condition identifier
- EFO_0003851
- Condition identifier
- EFO_0003929
- Highest recorded phase
- 2
- Condition identifier
- EFO_0004251
- Highest recorded phase
- 2
- Condition identifier
- EFO_0004289
- Condition identifier
- EFO_0004952
- Highest recorded phase
- 2
- Condition identifier
- EFO_0005952
- Highest recorded phase
- 3
- Condition identifier
- EFO_0803536
- Highest recorded phase
- 2
- Condition identifier
- EFO_1000157
- Highest recorded phase
- 2
And 100 more, listed on the interactive page.
- Warning
- Black Box Warning
- Effect
- gastrointestinal toxicity
- Warning
- Black Box Warning
- Effect
- hematological toxicity
- Warning
- Black Box Warning
- Effect
- hepatotoxicity
- Warning
- Black Box Warning
- Effect
- gastrointestinal toxicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- hematological toxicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- hepatotoxicity
- Country
- United States
- Event
- acute lymphocytic leukaemia recurrent
- Reports
- 137
- Reporting signal score
- 375.238
- Event
- acute myeloid leukaemia
- Reports
- 254
- Reporting signal score
- 449.12
- Event
- aplasia
- Reports
- 124
- Reporting signal score
- 296.756
- Event
- arachnoiditis
- Reports
- 87
- Reporting signal score
- 280.45
- Event
- bacteraemia
- Reports
- 250
- Reporting signal score
- 396.213
- Event
- bone marrow failure
- Reports
- 608
- Reporting signal score
- 998.178
- Event
- bronchopulmonary aspergillosis
- Reports
- 208
- Reporting signal score
- 433.812
- Event
- diffuse large b-cell lymphoma recurrent
- Reports
- 129
- Reporting signal score
- 349.965
- Event
- dizziness
- Reports
- 115
- Reporting signal score
- 303.33
- Event
- fatigue
- Reports
- 267
- Reporting signal score
- 298.145
- Event
- febrile bone marrow aplasia
- Reports
- 596
- Reporting signal score
- 1,872.09
- Event
- febrile neutropenia
- Reports
- 3,376
- Reporting signal score
- 8,254.08
- Event
- haematotoxicity
- Reports
- 397
- Reporting signal score
- 847.478
- Event
- hyperbilirubinaemia
- Reports
- 211
- Reporting signal score
- 300.967
- Event
- hypofibrinogenaemia
- Reports
- 138
- Reporting signal score
- 418.701
- Event
- injection site pain
- Reports
- 3
- Reporting signal score
- 292.923
- Event
- leukoencephalopathy
- Reports
- 161
- Reporting signal score
- 303.489
- Event
- mucosal inflammation
- Reports
- 734
- Reporting signal score
- 1,237.78
- Event
- myelodysplastic syndrome
- Reports
- 377
- Reporting signal score
- 698
- Event
- myelopathy
- Reports
- 125
- Reporting signal score
- 319.077
- Event
- neutropenia
- Reports
- 1,349
- Reporting signal score
- 1,167.03
- Event
- neutropenic colitis
- Reports
- 159
- Reporting signal score
- 459.572
- Event
- pancytopenia
- Reports
- 797
- Reporting signal score
- 967.453
- Event
- posterior reversible encephalopathy syndrome
- Reports
- 260
- Reporting signal score
- 411.459
- Event
- pyrexia
- Reports
- 1,470
- Reporting signal score
- 588.941
And 5 more, listed on the interactive page.
- NCT00000658
- NCT00367497
- NCT00384553
- NCT01178645
- NCT01178658
- NCT01516580
- NCT01840566
- NCT01969435
- NCT02371161
- NCT03892421
- NCT00002471
- NCT00002481
- NCT00002494
- NCT00002552
- NCT00002565
- NCT00002578
- NCT00002590
- NCT00002618
- NCT00002657
- NCT00002676
- NCT00002691
- NCT00002700
- NCT00002718
- NCT00002757
- NCT00002766
And 714 more, listed on the interactive page.
- Dose
- 100 mg/m2 (cytarabine) in induction, 65 mg/m2 in consolidation
- Route
- Intravenous
- How often
- Days 1, 3, and 5 for first induction; days 1 and 3 for second induction; days 1 and 3 for consolidation
- Administer over 90 minutes
- Reconstitute before infusion
- Use immediately after reconstitution or store for up to 4 hours at 2-8°C
- Hydrogen bond acceptors
- 8
- Hydrogen bond donors
- 4
- Polar surface area
- 130.83
- Calculated partition coefficient (ALogP)
- -2.56
- Calculated partition coefficient (XLogP)
- -2.1
- Prodrug
- No
- Chirality
- Single enantiomer
- Inorganic
- No
- Rule-of-five violations
- 0
- Rotatable bonds
- 2
- Heavy atoms
- 17
- Molecular formula
- C9H13N3O5
- Monoisotopic mass
- 243.08552052
- Natural product
- Yes
- 25021-223
- 25021-229
- 61703-155
- 61703-303
- 61703-304
- 61703-305
- 61703-319
- 63323-120
- 68083-337
- 68083-343
- 68727-745
- 71288-108
- 71288-109
- 71288-168
- 71288-169
- Recorded assays
- 5,003
- Active assays
- 830
- Confirmatory
- Other
- Screening
- Summary
- Antimetabolites, Antineoplastic
- Antiviral Agents
- Immunosuppressive Agents
Distribution coefficient (LogD)
- Median
- -2.13
- Mean
- -2.13
- Minimum
- -2.13
- Maximum
- -2.13
- Unit
- unitless
- Assays
- 2
- Standard deviation
- 0
- Summary method
- median
- Censored results excluded
- 0
- Other units excluded
- 0
- Unknown units excluded
- 0
Measurement types
- LogD
Oral bioavailability
- Median
- 20
- Mean
- 20
- Minimum
- 20
- Maximum
- 20
- Unit
- %
- Assays
- 1
- Standard deviation
- 0
- Summary method
- median
- Censored results excluded
- 0
- Other units excluded
- 0
- Unknown units excluded
- 0
Measurement types
- F
Related records
Trials (1,201)
- [CREMA]Combination of R-M Followed by R-A in Elderly Patients With Primary CNS Lymphoma
- 05-001: Treatment of Acute Lymphoblastic Leukemia in Children
- 2-Chlorodeoxyadenosine and Cytarabine in Patients With Idiopathic Hypereosinophilic Syndrome (HES)
- 3 Anthracyclines, 2 Types of Consolidation With Different ARA-C Doses and Maintenance in Adult Acute Myeloid Leukemia
- 3-AP and Cytarabine in Treating Patients With Hematologic Cancer
- 3-AP and High-Dose Cytarabine in Treating Patients With Advanced Hematologic Malignancies
- 506U78 in Treating Patients With Refractory Hematologic Cancer
- 6,8-Bis(Benzylthio)Octanoic Acid, Cytarabine, and Daunorubicin Hydrochloride in Treating Older Patients With Newly Diagnosed Acute Myeloid Leukemia
- A 5 Day Course of Fludarabine and Cytarabine Followed by Full Intensity Allogeneic Stem Cell Transplantation (FA5-Bucy) in Treating Patients With High-risk, Recurrent or Refractory Acute Leukemia and Advanced Myelodysplastic Syndrome
- A Bioequivalence Study of (Cytarabine: Daunorubicin) Liposome for Injection
- A Clinical Trail of Demethylation Drug Combined With Chemotherapy in Intermediate-risk AML
- A Clinical Trial of Decitabine in Relapsed or Refractory T-lymphoblastic Lymphoma
- A Clinical Trial to Assess the Efficacy and Safety of the Combination of a Drug Call Quizartinib With Chemotherapy (FLAG-IDA) in Patients With Acute Myeloid Leukemia That Has Not Responded to the First Treatment or That Has Returned After the First Treatment
- A Clinical Trial to Assess the Safety & Efficacy of the Treatment of Patients With Metastasis From Malignant Melanoma - Treatment Consists of the Substances Lomustine (Capsules) & Cytarabine (Injected Into an Area Near the Spinal Cord), Accompanied by Radiotherapy of the Brain
- A Combination of Vemurafenib, Cytarabine and 2-chlorodeoxyadenosine in Children With LCH and BRAF V600E Mutation
- A Comparison of Three Chemotherapy Regimens for the Treatment of Patients With Newly Diagnosed Mantle Cell Lymphoma
- A Global Study of Midostaurin in Combination With Chemotherapy to Evaluate Safety, Efficacy and Pharmacokinetics in Newly Diagnosed Pediatric Patients With FLT3 Mutated AML
- A Multicenter Prospective Cohort Study Study of CLAG Regimen in Acute Myeloid Leukemia Patients With First-induction Failure
- A Novel "Pediatric-Inspired" Regimen With Reduced Myelosuppressive Drugs for Adults (Aged 18-60) With Newly Diagnosed Ph Negative Acute Lymphoblastic Leukemia
- A Pharmacokinetic and Efficacy Study of Amonafide L-malate (AS1413) in Combination With Cytarabine in Patients With Acute Myeloid Leukemia (AML)
Approved for (10)
- Acute lymphoblastic leukemia
- Acute myeloblastic leukemia with maturation
- Acute myeloblastic leukemia without maturation
- Acute myeloid leukemia
- Cancer
- Childhood acute lymphoblastic leukemia
- Lymphoblastic lymphoma
- Lymphoid leukemia
- Neoplasm
- Tumor of meninges
In development for (104)
- Acquired polycythemia vera Phase 1
- Acute basophilic leukemia Phase 3
- Acute erythroid leukemia Phase 3
- Acute leukemia Phase 3
- Acute leukemia of ambiguous lineage Phase 3
- Acute megakaryoblastic leukemia Phase 3
- Acute monocytic leukemia Phase 3
- Acute myeloid leukemia by FAB classification Phase 3
- Acute myelomonocytic leukemia M4 Phase 3
- Acute promyelocytic leukemia Phase 3
- Adult T-cell leukemia/lymphoma Phase 2
- Anaplastic large cell lymphoma Phase 2
- Aplastic anemia Phase 2
- Aseptic meningitis Phase 2
- Atypical teratoid rhabdoid tumor Phase 2
- Autoimmune disorder of the nervous system Phase 2
- B-cell acute lymphoblastic leukemia Phase 3
- B-cell adult acute lymphocytic leukemia Phase 2
- B-cell childhood acute lymphoblastic leukemia Phase 2
- B-cell chronic lymphocytic leukemia Phase 2
Other linked conditions (2)
- Retinoblastoma
- Sickle cell disease
Targets (11)
- POLA1 DNA polymerase (alpha/delta/epsilon) inhibitor
- POLA2 DNA polymerase (alpha/delta/epsilon) inhibitor
- POLD1 DNA polymerase (alpha/delta/epsilon) inhibitor
- POLD2 DNA polymerase (alpha/delta/epsilon) inhibitor
- POLD3 DNA polymerase (alpha/delta/epsilon) inhibitor
- POLD4 DNA polymerase (alpha/delta/epsilon) inhibitor
- POLE DNA polymerase (alpha/delta/epsilon) inhibitor
- POLE2 DNA polymerase (alpha/delta/epsilon) inhibitor
- POLE3 DNA polymerase (alpha/delta/epsilon) inhibitor
- PRIM1 DNA polymerase (alpha/delta/epsilon) inhibitor
- PRIM2 DNA polymerase (alpha/delta/epsilon) inhibitor