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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H43N3O6
Molecular Weight 481.6254
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYTARABINE-5'-PALMITATE

SMILES

CCCCCCCCCCCCCCCC(=O)OC[C@H]1O[C@H]([C@@H](O)[C@@H]1O)N2C=CC(N)=NC2=O

InChI

InChIKey=SHBAKEKBTCPUFI-OUJCMCIWSA-N
InChI=1S/C25H43N3O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-21(29)33-18-19-22(30)23(31)24(34-19)28-17-16-20(26)27-25(28)32/h16-17,19,22-24,30-31H,2-15,18H2,1H3,(H2,26,27,32)/t19-,22-,23+,24-/m1/s1

HIDE SMILES / InChI

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
CYTARABINE

Cmax

ValueDoseCo-administeredAnalytePopulation
62.2 μg/mL
100 mg/m² 1 times / day multiple, intravenous
CYTARABINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1900 μg × h/mL
100 mg/m² 1 times / day multiple, intravenous
CYTARABINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
40.4 h
100 mg/m² 1 times / day multiple, intravenous
CYTARABINE plasma
Homo sapiens
80 h
50 mg single, intrathecal
CYTARABINE cerebrospinal fluid
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as victim

PubMed

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