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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13N3O5.ClH
Molecular Weight 279.678
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYTARABINE HYDROCHLORIDE

SMILES

Cl.NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O

InChI

InChIKey=KCURWTAZOZXKSJ-JBMRGDGGSA-N
InChI=1S/C9H13N3O5.ClH/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8;/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16);1H/t4-,6-,7+,8-;/m1./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C9H13N3O5
Molecular Weight 243.2166
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Sources: www.accessdata.fda.gov/drugsatfda_docs/label/2011/021041s023lbl.pdf
Curator's Comment: Description was created using several sources including: http://www.ebi.ac.uk/chebi/searchId.do?chebiId=28680 http://www.tandfonline.com/doi/abs/10.1517/17425247.2010.527330

Cytarabine is a pyrimidine nucleoside analog. Cytarabine or cytosine arabinoside (Cytosar-U or Depocyt) is a chemotherapy agent used mainly in the treatment of cancers of white blood cells such as acute myeloid leukemia (AML) and non-Hodgkin lymphoma. It also has antiviral and immunosuppressant properties. Cytarabine is an antimetabolite antineoplastic agent that inhibits the synthesis of DNA. It is a cell cycle phase-specific, affecting cells only during the S phase of cell division. Intracellularly, cytarabine is converted into cytarabine-5-triphosphate (ara-CTP), which is the active metabolite. The mechanism of action is not completely understood, but it appears that ara-CTP acts primarily through inhibition of DNA polymerase. Incorporation into DNA and RNA may also contribute to cytarabine cytotoxicity. Cytarabine is cytotoxic to a wide variety of proliferating mammalian cells in culture.The drug has a short plasma half-life, low stability and limited bioavailability. Overdosing of patients with continuous infusions may lead to side effects. Thus, various prodrug strategies and delivery systems have been explored extensively to enhance the half-life, stability and delivery of cytarabine. Alternative, delivery systems of cytarabine have emerged for the treatment of different cancers. The liposomal-cytarabine formulation has been approved for the treatment of lymphomatous meningitis.

CNS Activity

Originator

Curator's Comment: Cytarabine was first synthesized in 1959 by Richard Walwick, Walden Roberts, and Charles Dekker at the University of California, Berkeley. It was approved by the United States Food and Drug Administration in June 1969, and was initially marketed in the U.S. by Upjohn under the trade name Cytosar-U and is at present manufactured by Pfizer, Sicor Pharmaceuticals and Teva. CYTOSAR (cytarabine injection) was developed in September 1994 Dana-­Farber Cancer Institute and is manufactured by Pfizer and Perrigo. DEPOCYT - (cytarabine injection, lipid complex) manufactured by Manufactured by: Pacira Pharmaceuticals Inc., distributed by Sigma-Tau Pharmaceutical, Inc. is an intrathecal cancer chemotherapeutic agent approved by FDA is used for the treatment of lymphomatous meningitis.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Sources: www.accessdata.fda.gov/drugsatfda_docs/label/2011/021041s023lbl.pdf
Primary
CYTARABINE

Approved Use

Cytarabine in combination with other approved anticancer drugs is indicated for remission induction in acute non-lymphocytic leukemia of adults and children. It has also been found useful in the treatment of acute lymphocytic leukemia and the blast phase of chronic myelocytic leukemia. Intrathecal administration of cytarabine injection (preservative-free only) is indicated for the prophylaxis and treatment of meningeal leukemia.

Launch Date

1969
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
62.2 μg/mL
100 mg/m² 1 times / day multiple, intravenous
dose: 100 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: DAUNORUBICIN
CYTARABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1900 μg × h/mL
100 mg/m² 1 times / day multiple, intravenous
dose: 100 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: DAUNORUBICIN
CYTARABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
40.4 h
100 mg/m² 1 times / day multiple, intravenous
dose: 100 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: DAUNORUBICIN
CYTARABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
80 h
50 mg single, intrathecal
dose: 50 mg
route of administration: Intrathecal
experiment type: SINGLE
co-administered:
CYTARABINE cerebrospinal fluid
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
4.5 g/m2 2 times / day multiple, intravenous
Highest studied dose
Dose: 4.5 g/m2, 2 times / day
Route: intravenous
Route: multiple
Dose: 4.5 g/m2, 2 times / day
Sources:
unhealthy, 16-76
Health Status: unhealthy
Age Group: 16-76
Sex: M+F
Sources:
Disc. AE: Cerebellar disorder NOS, Diarrhea...
AEs leading to
discontinuation/dose reduction:
Cerebellar disorder NOS (grade 4, 66.7%)
Diarrhea (grade 3, 66.7%)
Sources:
4.5 g/m2 2 times / day multiple, intravenous
Highest studied dose
Dose: 4.5 g/m2, 2 times / day
Route: intravenous
Route: multiple
Dose: 4.5 g/m2, 2 times / day
Sources:
unhealthy, 16-76
Health Status: unhealthy
Age Group: 16-76
Sex: M+F
Sources:
Disc. AE: Cerebellar disorder NOS, Cerebellar disorder NOS...
AEs leading to
discontinuation/dose reduction:
Cerebellar disorder NOS (grade 4, 33.3%)
Cerebellar disorder NOS (grade 5, 16.7%)
Sources:
3 g/m2 2 times / day multiple, intravenous
MTD
Dose: 3 g/m2, 2 times / day
Route: intravenous
Route: multiple
Dose: 3 g/m2, 2 times / day
Sources:
unhealthy, 16-76
Health Status: unhealthy
Age Group: 16-76
Sex: M+F
Sources:
100 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 100 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / day
Sources:
unhealthy
Disc. AE: Bone marrow depression, Leukopenia...
AEs leading to
discontinuation/dose reduction:
Bone marrow depression
Leukopenia
Thrombocytopenia
Anemia
Nausea
Vomiting
Diarrhea
Abdominal pain
Oral ulceration
Hepatic dysfunction NOS
Sources:
AEs

AEs

AESignificanceDosePopulation
Diarrhea grade 3, 66.7%
Disc. AE
4.5 g/m2 2 times / day multiple, intravenous
Highest studied dose
Dose: 4.5 g/m2, 2 times / day
Route: intravenous
Route: multiple
Dose: 4.5 g/m2, 2 times / day
Sources:
unhealthy, 16-76
Health Status: unhealthy
Age Group: 16-76
Sex: M+F
Sources:
Cerebellar disorder NOS grade 4, 66.7%
Disc. AE
4.5 g/m2 2 times / day multiple, intravenous
Highest studied dose
Dose: 4.5 g/m2, 2 times / day
Route: intravenous
Route: multiple
Dose: 4.5 g/m2, 2 times / day
Sources:
unhealthy, 16-76
Health Status: unhealthy
Age Group: 16-76
Sex: M+F
Sources:
Cerebellar disorder NOS grade 4, 33.3%
Disc. AE
4.5 g/m2 2 times / day multiple, intravenous
Highest studied dose
Dose: 4.5 g/m2, 2 times / day
Route: intravenous
Route: multiple
Dose: 4.5 g/m2, 2 times / day
Sources:
unhealthy, 16-76
Health Status: unhealthy
Age Group: 16-76
Sex: M+F
Sources:
Cerebellar disorder NOS grade 5, 16.7%
Disc. AE
4.5 g/m2 2 times / day multiple, intravenous
Highest studied dose
Dose: 4.5 g/m2, 2 times / day
Route: intravenous
Route: multiple
Dose: 4.5 g/m2, 2 times / day
Sources:
unhealthy, 16-76
Health Status: unhealthy
Age Group: 16-76
Sex: M+F
Sources:
Abdominal pain Disc. AE
100 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 100 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / day
Sources:
unhealthy
Anemia Disc. AE
100 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 100 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / day
Sources:
unhealthy
Bone marrow depression Disc. AE
100 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 100 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / day
Sources:
unhealthy
Diarrhea Disc. AE
100 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 100 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / day
Sources:
unhealthy
Hepatic dysfunction NOS Disc. AE
100 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 100 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / day
Sources:
unhealthy
Leukopenia Disc. AE
100 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 100 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / day
Sources:
unhealthy
Nausea Disc. AE
100 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 100 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / day
Sources:
unhealthy
Oral ulceration Disc. AE
100 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 100 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / day
Sources:
unhealthy
Thrombocytopenia Disc. AE
100 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 100 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / day
Sources:
unhealthy
Vomiting Disc. AE
100 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 100 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / day
Sources:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 6.6 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Differential p53 phosphorylation and activation of apoptosis-promoting genes Bax and Fas/APO-1 by irradiation and ara-C treatment.
1998 Jul
Protection by short-chain fatty acids against 1-beta-D-arabinofuranosylcytosine-induced intestinal lesions in germfree mice.
1999 Apr
Pseudotumor cerebri secondary to intermediate-dose cytarabine HCl.
1999 May
Contribution of single-photon emission computed tomography in the diagnosis and follow-up of CNS toxicity of a cytarabine-containing regimen in pediatric leukemia.
1999 Sep
Efficacy and toxicity of IFN-alpha2b combined with cytarabine in chronic myelogenous leukaemia.
1999 Sep
Differential transport of cytosine-containing nucleosides by recombinant human concentrative nucleoside transporter protein hCNT1.
2000 Jan-Feb
Oxidative stress interferes with cancer chemotherapy: inhibition of lymphoma cell apoptosis and phagocytosis.
2000 Jul 1
A phase-II trial of all trans retinoic acid and low-dose cytosine arabinoside for the treatment of high-risk myelodysplastic syndromes.
2000 Mar
2'-C-cyano-2'-deoxy-1-beta-D-arabino-pentofuranosylcytosine: a novel anticancer nucleoside analog that causes both DNA strand breaks and G(2) arrest.
2001 Apr
Cell cycle-related changes in regulatory volume decrease and volume-sensitive chloride conductance in mouse fibroblasts.
2001 Apr
Involvement of oxygen radicals in cytarabine-induced apoptosis in human polymorphonuclear cells.
2001 Apr 15
Chemotherapy for acute myelogenous leukemia in the elderly with cytarabine, mitoxantrone, and granulocyte-macrophage colony-stimulating factor.
2001 Feb
Temporary response of localized intracranial mast cell sarcoma to combination chemotherapy.
2001 Feb
Bilateral breast relapse in acute myelogenous leukemia.
2001 Feb
Bone marrow involvement by nasal NK cell lymphoma at diagnosis is uncommon.
2001 Feb
Mutations in ras proto-oncogenes are associated with lower mdr1 gene expression in adult acute myeloid leukaemia.
2001 Feb
Allogeneic bone marrow transplantation in children failing prior autologous bone marrow transplantation.
2001 Jan
[Outcome of acute myelogenous leukemia in 41 patients treated with idarubicin: the prognosis of t(8;21) cases].
2001 Jan
Intrathecal treatment of neoplastic meningitis due to breast cancer with a slow-release formulation of cytarabine.
2001 Jan
Fludarabine, cytarabine and topotecan (FLAT) as induction therapy for acute myeloid leukemia in the elderly: a preliminary report.
2001 Jan
De novo acute myeloid leukemia in the elderly; a consistent fraction of long-term survivors by standard-dose chemotherapy.
2001 Jan
Induction of differentiation of acute promyelocytic leukemia cells by a cytidine deaminase-resistant analogue of 1-beta-D-arabinofuranosylcytosine, 1-(2-deoxy-2-methylene-beta-D-erythro-pentofuranosyl)cytidine.
2001 Jan 1
Simultaneous treatment with 1-beta-D-arabinofuranosylcytosine and daunorubicin induces cross-resistance to both drugs due to a combination-specific mechanism in HL60 cells.
2001 Jan 1
Reduced cellular transport and activation of fluoropyrimidine nucleosides and resistance in human lymphocytic cell lines selected for arabinosylcytosine resistance.
2001 Jan 1
Targeting and anti-tumor efficacy of liposomal 5'-O-dipalmitoylphosphatidyl 2'-C-cyano-2'-deoxy-1-beta-D-arabino-pentofuranosylcytosine in mice lung bearing B16BL6 melanoma.
2001 Jan 10
Activation of deoxycytidine kinase by inhibition of DNA synthesis in human lymphocytes.
2001 Jan 15
JP-8 jet fuel-induced DNA damage in H4IIE rat hepatoma cells.
2001 Jan 25
Upregulation of preprodynorphin and preproenkephalin mRNA expression by selective activation of group I metabotropic glutamate receptors in characterized primary cultures of rat striatal neurons.
2001 Jan 31
Results of IDA-FLAG programme in the treatment of recurrent acute myeloblastic leukaemia--preliminary report.
2001 Jan-Feb
Toxic epidermal necrolysis after the use of high-dose cytosine arabinoside.
2001 Jan-Feb
Therapy of acute myeloid leukemia.
2001 Jan-Feb
[All-trans retinoic acid combined with low-dose cytosine arabinoside treatment for acute myelogenous leukemia with trilineage myelodysplasia--a case report].
2001 Mar
Cytogenetic subgroups in acute myeloid leukemia differ in proliferative activity and response to GM-CSF.
2001 Mar
Idarubicin improves blast cell clearance during induction therapy in children with AML: results of study AML-BFM 93. AML-BFM Study Group.
2001 Mar
Synergistic activity of the new ABL-specific tyrosine kinase inhibitor STI571 and chemotherapeutic drugs on BCR-ABL-positive chronic myelogenous leukemia cells.
2001 Mar
Total body irradiation before allogeneic bone marrow transplantation: is more dose better?
2001 Mar 15
Patents

Sample Use Guides

Induction therapy: DepoCyt (cytarabine liposome injection), 50 mg, administered intrathecally (intraventricular or lumbar puncture) every 14 days for 2 doses (weeks 1 and 3). Consolidation therapy: DepoCyt, 50 mg, administered intrathecally (intraventricular or lumbar puncture) every 14 days for 3 doses (weeks 5, 7 and 9) followed by 1 additional dose at week 13. Maintenance: DepoCyt, 50 mg, administered intrathecally (intraventricular or lumbar puncture) every 28 days for 4 doses (weeks 17, 21, 25 and 29).
Route of Administration: Intratracheal
In Vitro Use Guide
Curator's Comment: The effect of Ara-C (0.1 μM) treatment on HUVEC proliferation alone or in drug combinations compared to drug-free control cultures. Results are expressed as mean percentage ± SEM from three independent experiments (six replicates per condition) relative to corresponding untreated control cultures.
Human umbilical vein endothelial cells (HUVECs) and human osteosarcoma cell line (Cal72) were incubated with various concentrations of Cytarabine (Ara-C) (0.01–20 μM) for 3 days
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:50:19 GMT 2025
Edited
by admin
on Mon Mar 31 17:50:19 GMT 2025
Record UNII
33K3DB6591
Record Status Validated (UNII)
Record Version
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Name Type Language
CYTARABINE HYDROCHLORIDE
USAN   WHO-DD  
USAN  
Official Name English
NSC-63878
Preferred Name English
2(1H)-PYRIMIDINONE, 4-AMINO-1-.BETA.-D-ARABINOFURANOSYL-, MONOHYDROCHLORIDE
Common Name English
U-19920A
Code English
Cytarabine hydrochloride [WHO-DD]
Common Name English
CYTARABINE HYDROCHLORIDE [USAN]
Common Name English
1-.BETA.-D-ARABINOFURANOSYLCYTOSINE MONOHYDROCHLORIDE
Common Name English
CYTARABINE HCL
Common Name English
CYTOSINE ARABINOSIDE HYDROCHLORIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1557
Created by admin on Mon Mar 31 17:50:19 GMT 2025 , Edited by admin on Mon Mar 31 17:50:19 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID5024891
Created by admin on Mon Mar 31 17:50:19 GMT 2025 , Edited by admin on Mon Mar 31 17:50:19 GMT 2025
PRIMARY
ChEMBL
CHEMBL803
Created by admin on Mon Mar 31 17:50:19 GMT 2025 , Edited by admin on Mon Mar 31 17:50:19 GMT 2025
PRIMARY
CAS
69-74-9
Created by admin on Mon Mar 31 17:50:19 GMT 2025 , Edited by admin on Mon Mar 31 17:50:19 GMT 2025
PRIMARY
PUBCHEM
6252
Created by admin on Mon Mar 31 17:50:19 GMT 2025 , Edited by admin on Mon Mar 31 17:50:19 GMT 2025
PRIMARY
EVMPD
SUB13523MIG
Created by admin on Mon Mar 31 17:50:19 GMT 2025 , Edited by admin on Mon Mar 31 17:50:19 GMT 2025
PRIMARY
SMS_ID
100000092040
Created by admin on Mon Mar 31 17:50:19 GMT 2025 , Edited by admin on Mon Mar 31 17:50:19 GMT 2025
PRIMARY
DRUG BANK
DBSALT002381
Created by admin on Mon Mar 31 17:50:19 GMT 2025 , Edited by admin on Mon Mar 31 17:50:19 GMT 2025
PRIMARY
NCI_THESAURUS
C71603
Created by admin on Mon Mar 31 17:50:19 GMT 2025 , Edited by admin on Mon Mar 31 17:50:19 GMT 2025
PRIMARY
FDA UNII
33K3DB6591
Created by admin on Mon Mar 31 17:50:19 GMT 2025 , Edited by admin on Mon Mar 31 17:50:19 GMT 2025
PRIMARY
NSC
63878
Created by admin on Mon Mar 31 17:50:19 GMT 2025 , Edited by admin on Mon Mar 31 17:50:19 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-713-9
Created by admin on Mon Mar 31 17:50:19 GMT 2025 , Edited by admin on Mon Mar 31 17:50:19 GMT 2025
PRIMARY
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ACTIVE MOIETY