CYTARABINE HYDROCHLORIDE

First approved in 1969

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 Search

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA polymerase lambda 4 Target ID: CHEMBL5367 Sources: http://www.drugbank.ca/drugs/DB00987	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic myelogenous leukemia 21 Sources: https://clinicaltrials.gov/ct2/show/NCT00333840	Primary		Phase III 665	Unknown Approved Use Unknown
Lymphomatous meningitis 3 Sources: www.accessdata.fda.gov/drugsatfda_docs/label/2011/021041s023lbl.pdf	Primary		Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
62.2 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209401s000lbl.pdf	100 mg/m² 1 times / day multiple, intravenous dose: 100 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: DAUNORUBICIN	DAUNORUBICIN	CYTARABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
1900 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209401s000lbl.pdf	100 mg/m² 1 times / day multiple, intravenous dose: 100 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: DAUNORUBICIN	DAUNORUBICIN	CYTARABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
40.4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209401s000lbl.pdf	100 mg/m² 1 times / day multiple, intravenous dose: 100 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: DAUNORUBICIN	DAUNORUBICIN	CYTARABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
80 h REVIEW https://www.ncbi.nlm.nih.gov/pubmed/12162758	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/6223674	unhealthy, 16-76 Health Status: unhealthy Age Group: 16-76 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6223674	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: https://pubmed.ncbi.nlm.nih.gov/6223674
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: https://pubmed.ncbi.nlm.nih.gov/7306918	unhealthy, 16-76 Health Status: unhealthy Age Group: 16-76 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/7306918	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: https://pubmed.ncbi.nlm.nih.gov/7306918
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: https://pubmed.ncbi.nlm.nih.gov/6223674	unhealthy, 16-76 Health Status: unhealthy Age Group: 16-76 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6223674	Sources: https://pubmed.ncbi.nlm.nih.gov/6223674
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/6223674	unhealthy, 16-76 Health Status: unhealthy Age Group: 16-76 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6223674
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: https://pubmed.ncbi.nlm.nih.gov/6223674	unhealthy, 16-76 Health Status: unhealthy Age Group: 16-76 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6223674
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: https://pubmed.ncbi.nlm.nih.gov/7306918	unhealthy, 16-76 Health Status: unhealthy Age Group: 16-76 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/7306918
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: https://pubmed.ncbi.nlm.nih.gov/7306918	unhealthy, 16-76 Health Status: unhealthy Age Group: 16-76 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/7306918
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/071868s032lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15204103/ Page: 4.0	yes [IC50 6.6 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15204103/ Page: 4.0	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:28680	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28680
eMolecules	1012736	https://www.emolecules.com/cgi-bin/more?vid=1012736
MolPort	MolPort-001-792-509	https://www.molport.com/shop/molecule-link/MolPort-001-792-509
Selleck Chemicals	Cytarabine(Cytosar-U)	http://www.selleckchem.com/products/Cytarabine(Cytosar-U).html
ZINC	ZINC000003795098	http://zinc15.docking.org/substances/ZINC000003795098

PubMed

Title	Date	PubMed
Differential p53 phosphorylation and activation of apoptosis-promoting genes Bax and Fas/APO-1 by irradiation and ara-C treatment.	1998 Jul	10200513
Protection by short-chain fatty acids against 1-beta-D-arabinofuranosylcytosine-induced intestinal lesions in germfree mice.	1999 Apr	10103207
Pseudotumor cerebri secondary to intermediate-dose cytarabine HCl.	1999 May	10369621
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	10561356
Efficacy and toxicity of IFN-alpha2b combined with cytarabine in chronic myelogenous leukaemia.	1999 Sep	10520005
Differential transport of cytosine-containing nucleosides by recombinant human concentrative nucleoside transporter protein hCNT1.	2000 Jan-Feb	10772724
Oxidative stress interferes with cancer chemotherapy: inhibition of lymphoma cell apoptosis and phagocytosis.	2000 Jul 1	10891466
A phase-II trial of all trans retinoic acid and low-dose cytosine arabinoside for the treatment of high-risk myelodysplastic syndromes.	2000 Mar	10803936
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	11259616
Cell cycle-related changes in regulatory volume decrease and volume-sensitive chloride conductance in mouse fibroblasts.	2001 Apr	11241350
Involvement of oxygen radicals in cytarabine-induced apoptosis in human polymorphonuclear cells.	2001 Apr 15	11286995
Chemotherapy for acute myelogenous leukemia in the elderly with cytarabine, mitoxantrone, and granulocyte-macrophage colony-stimulating factor.	2001 Feb	11232951
Temporary response of localized intracranial mast cell sarcoma to combination chemotherapy.	2001 Feb	11216707
Bilateral breast relapse in acute myelogenous leukemia.	2001 Feb	11216705
Bone marrow involvement by nasal NK cell lymphoma at diagnosis is uncommon.	2001 Feb	11211616
Mutations in ras proto-oncogenes are associated with lower mdr1 gene expression in adult acute myeloid leukaemia.	2001 Feb	11167822
Allogeneic bone marrow transplantation in children failing prior autologous bone marrow transplantation.	2001 Jan	11281384
[Outcome of acute myelogenous leukemia in 41 patients treated with idarubicin: the prognosis of t(8;21) cases].	2001 Jan	11235129
Intrathecal treatment of neoplastic meningitis due to breast cancer with a slow-release formulation of cytarabine.	2001 Jan	11161370
Fludarabine, cytarabine and topotecan (FLAT) as induction therapy for acute myeloid leukemia in the elderly: a preliminary report.	2001 Jan	11146581
De novo acute myeloid leukemia in the elderly; a consistent fraction of long-term survivors by standard-dose chemotherapy.	2001 Jan	11137558
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	11196157
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	11196156
Reduced cellular transport and activation of fluoropyrimidine nucleosides and resistance in human lymphocytic cell lines selected for arabinosylcytosine resistance.	2001 Jan 1	11137707
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	11121862
Activation of deoxycytidine kinase by inhibition of DNA synthesis in human lymphocytes.	2001 Jan 15	11163333
JP-8 jet fuel-induced DNA damage in H4IIE rat hepatoma cells.	2001 Jan 25	11152973
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	11165379
Results of IDA-FLAG programme in the treatment of recurrent acute myeloblastic leukaemia--preliminary report.	2001 Jan-Feb	11208507
Toxic epidermal necrolysis after the use of high-dose cytosine arabinoside.	2001 Jan-Feb	11207969
Therapy of acute myeloid leukemia.	2001 Jan-Feb	11176038
[All-trans retinoic acid combined with low-dose cytosine arabinoside treatment for acute myelogenous leukemia with trilineage myelodysplasia--a case report].	2001 Mar	11265415
Cytogenetic subgroups in acute myeloid leukemia differ in proliferative activity and response to GM-CSF.	2001 Mar	11237060
Idarubicin improves blast cell clearance during induction therapy in children with AML: results of study AML-BFM 93. AML-BFM Study Group.	2001 Mar	11237056
Synergistic activity of the new ABL-specific tyrosine kinase inhibitor STI571 and chemotherapeutic drugs on BCR-ABL-positive chronic myelogenous leukemia cells.	2001 Mar	11237055
Total body irradiation before allogeneic bone marrow transplantation: is more dose better?	2001 Mar 15	11240249

Patents

Sample Use Guides

In Vivo Use Guide

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

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)`
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Name

Type

Language

CYTARABINE HYDROCHLORIDE

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