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Identification
NameCytarabine
Accession NumberDB00987  (APRD00499)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionA pyrimidine nucleoside analog that is used mainly in the treatment of leukemia, especially acute non-lymphoblastic leukemia. Cytarabine is an antimetabolite antineoplastic agent that inhibits the synthesis of DNA. Its actions are specific for the S phase of the cell cycle. It also has antiviral and immunosuppressant properties. (From Martindale, The Extra Pharmacopoeia, 30th ed, p472)
Structure
Thumb
Synonyms
1-beta-D-Arabinofuranosylcytosine
4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinone
Ara-C
Arabinofuranosyl Cytidine
Citarabina
Cytarabine
Cytarabinum
Cytosine arabinoside
Cytosine-1-beta-D-arabinofuranoside
Cytosine-beta-D-arabinofuranoside
cytosine-β-D-arabinofuranoside
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Aj-cytarabineSolution100 mgIntrathecal; Intravenous; SubcutaneousAgila Jamp Canada IncNot applicableNot applicableCanada
CytarabineSolution100 mgIntrathecal; Intravenous; SubcutaneousPfizer Canada Inc2014-01-16Not applicableCanada
CytarabineSolution20 mgIntrathecal; Intravenous; SubcutaneousPfizer Canada Inc2014-01-16Not applicableCanada
Cytarabine - Pws 1gn/vialPowder, for solution1 gIntrathecal; Intravenous; SubcutaneousNovopharm Limited1995-12-312015-10-26Canada
Cytarabine - Pws 2gm/vialPowder, for solution2 gIntrathecal; Intravenous; SubcutaneousNovopharm Limited1995-12-312015-10-26Canada
Cytarabine - Pws 500mg/vialPowder, for solution500 mgIntrathecal; Intravenous; SubcutaneousNovopharm Limited1995-12-312015-10-26Canada
Cytarabine Inj 100mg/mlLiquid100 mgIntravenous; SubcutaneousDavid Bull Laboratories (Pty) Ltd.1992-12-311998-08-13Canada
Cytarabine InjectionSolution100 mgIntrathecal; Intravenous; SubcutaneousHospira Healthcare Corporation1996-09-23Not applicableCanada
Cytarabine Injection BPSolution100 mgIntrathecal; Intravenous; SubcutaneousSandoz Canada IncorporatedNot applicableNot applicableCanada
Cytarabine Injection, Mylan Std.Solution100 mgIntrathecal; Intravenous; SubcutaneousMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Cytarabine-pws 100mg/vialPowder, for solution100 mgIntrathecal; Intravenous; SubcutaneousNovopharm Limited1995-12-31Not applicableCanada
CytosarPowder, for solution1 gIntrathecal; Intravenous; SubcutaneousPfizer Canada Inc1986-12-31Not applicableCanada
CytosarSolution20 mgIntrathecal; Intravenous; SubcutaneousPfizer Canada IncNot applicableNot applicableCanada
CytosarPowder, for solution2 gIntrathecal; Intravenous; SubcutaneousPfizer Canada Inc1986-12-31Not applicableCanada
CytosarPowder, for solution500 mgIntrathecal; Intravenous; SubcutaneousPfizer Canada Inc1977-12-312006-08-02Canada
CytosarPowder, for solution100 mgIntrathecal; Intravenous; SubcutaneousPfizer Canada Inc1977-12-31Not applicableCanada
CytosarSolution100 mgIntrathecal; Intravenous; SubcutaneousPfizer Canada IncNot applicableNot applicableCanada
DepocytInjection, lipid complex50 mg/5mLIntrathecalSigma Tau Pharmaceuticals, Inc.2010-10-22Not applicableUs
DepocytSuspension10 mgIntrathecalSkyepharma Inc.2000-12-29Not applicableCanada
DepocyteInjection, suspension50 mgIntrathecalPacira Limited2001-07-11Not applicableEu
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CytarabineInjection2 g/20mLIntrathecal; Intravenous; SubcutaneousMylan Institutional LLC2012-01-31Not applicableUs
CytarabineInjection100 mg/5mLIntrathecal; Intravenous; SubcutaneousPfizer Laboratories Div Pfizer Inc.2011-12-14Not applicableUs
CytarabineInjection, solution20 mg/mLIntravenous; SubcutaneousHospira, Inc.1994-02-28Not applicableUs
CytarabineInjection2 g/20mLIntrathecal; Intravenous; SubcutaneousMylan Institutional LLC2012-01-31Not applicableUs
CytarabineInjection, solution100 mg/mLIntrathecal; Intravenous; SubcutaneousFresenius Kabi USA, LLC2004-11-29Not applicableUs
CytarabineInjection20 mg/mLIntravenous; SubcutaneousPfizer Laboratories Div Pfizer Inc.2011-12-14Not applicableUs
CytarabineInjection, solution20 mg/mLIntrathecal; Intravenous; SubcutaneousHospira Worldwide, Inc.1990-06-04Not applicableUs
CytarabineInjection20 mg/mLIntravenous; SubcutaneousMylan Institutional LLC2011-12-14Not applicableUs
CytarabineInjection, solution100 mg/mLIntrathecal; Intravenous; SubcutaneousHospira, Inc.1999-11-22Not applicableUs
CytarabineInjection20 mg/mLIntravenous; SubcutaneousPfizer Laboratories Div Pfizer Inc.2011-12-14Not applicableUs
CytarabineInjection100 mg/5mLIntrathecal; Intravenous; SubcutaneousMylan Institutional LLC2011-12-14Not applicableUs
CytarabineInjection, solution20 mg/mLIntravenousHospira, Inc.1990-08-31Not applicableUs
CytarabineInjection2 g/20mLIntrathecal; Intravenous; SubcutaneousPfizer Laboratories Div Pfizer Inc.2012-01-31Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Ara-CGobbi
Cytosar-UPfizer
Brand mixturesNot Available
SaltsNot Available
Categories
UNII04079A1RDZ
CAS number147-94-4
WeightAverage: 243.2166
Monoisotopic: 243.085520541
Chemical FormulaC9H13N3O5
InChI KeyUHDGCWIWMRVCDJ-CCXZUQQUSA-N
InChI
InChI=1S/C9H13N3O5/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)/t4-,6-,7+,8-/m1/s1
IUPAC Name
4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
SMILES
NC1=NC(=O)N(C=C1)[C@@H]1O[[email protected]](CO)[C@@H](O)[C@@H]1O
Pharmacology
IndicationFor the treatment of acute non-lymphocytic leukemia, acute lymphocytic leukemia and blast phase of chronic myelocytic leukemia.
Structured Indications
PharmacodynamicsCytarabine is an antineoplastic anti-metabolite used in the treatment of several forms of leukemia including acute myelogenous leukemia and meningeal leukemia. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances becoming incorporated in to DNA during the "S" phase (of the cell cycle), stopping normal development and division. Cytarabine is metabolized intracellularly into its active triphosphate form (cytosine arabinoside triphosphate). This metabolite then damages DNA by multiple mechanisms, including the inhibition of alpha-DNA polymerase, inhibition of DNA repair through an effect on beta-DNA polymerase, and incorporation into DNA. The latter mechanism is probably the most important. Cytotoxicity is highly specific for the S phase of the cell cycle.
Mechanism of actionCytarabine acts through direct DNA damage and incorporation into DNA. Cytarabine is cytotoxic to a wide variety of proliferating mammalian cells in culture. It exhibits cell phase specificity, primarily killing cells undergoing DNA synthesis (S-phase) and under certain conditions blocking the progression of cells from the G1 phase to the S-phase. Although the mechanism of action is not completely understood, it appears that cytarabine acts through the inhibition of DNA polymerase. A limited, but significant, incorporation of cytarabine into both DNA and RNA has also been reported.
TargetKindPharmacological actionActionsOrganismUniProt ID
DNANucleotideyes
cross-linking/alkylation
Humannot applicabledetails
DNA polymerase betaProteinyes
inhibitor
HumanP06746 details
Related Articles
AbsorptionLess than 20% of the orally administered dose is absorbed from the gastrointestinal tract.
Volume of distributionNot Available
Protein binding13%
Metabolism

Hepatic.

Route of eliminationThe primary route of elimination of cytarabine is metabolism to the inactive compound ara-U, followed by urinary excretion of ara-U.
Half life10 minutes
ClearanceNot Available
ToxicityCytarabine syndrome may develop - it is characterized by fever, myalgia, bone pain, occasionally chest pain, maculopapular rash, conjunctivitis, and malaise.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Cytarabine.Approved
ALT-110The risk or severity of adverse effects can be increased when Cytarabine is combined with ALT-110.Investigational
AmiodaroneThe metabolism of Cytarabine can be decreased when combined with Amiodarone.Approved, Investigational
AnvirzelAnvirzel may decrease the cardiotoxic activities of Cytarabine.Investigational
AprepitantThe serum concentration of Cytarabine can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe metabolism of Cytarabine can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Cytarabine can be decreased when combined with Atomoxetine.Approved
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Cytarabine.Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Cytarabine.Approved, Investigational
BexaroteneThe serum concentration of Cytarabine can be decreased when it is combined with Bexarotene.Approved, Investigational
BoceprevirThe metabolism of Cytarabine can be decreased when combined with Boceprevir.Approved
BortezomibThe metabolism of Cytarabine can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Cytarabine can be decreased when it is combined with Bosentan.Approved, Investigational
BupropionThe serum concentration of Cytarabine can be increased when it is combined with Bupropion.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Cytarabine.Approved
CarbamazepineThe metabolism of Cytarabine can be increased when combined with Carbamazepine.Approved, Investigational
CDX-110The risk or severity of adverse effects can be increased when Cytarabine is combined with CDX-110.Investigational
CeritinibThe serum concentration of Cytarabine can be increased when it is combined with Ceritinib.Approved
ClarithromycinThe metabolism of Cytarabine can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Cytarabine can be decreased when combined with Clemastine.Approved
ClotrimazoleThe metabolism of Cytarabine can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe risk or severity of adverse effects can be increased when Cytarabine is combined with Clozapine.Approved
CobicistatThe metabolism of Cytarabine can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Cytarabine can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Cytarabine can be decreased when combined with Crizotinib.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Cytarabine.Approved, Investigational
CyclosporineThe metabolism of Cytarabine can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Cytarabine can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe metabolism of Cytarabine can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Cytarabine can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Cytarabine can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Cytarabine can be decreased when combined with Delavirdine.Approved
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Cytarabine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Cytarabine.Approved
DexamethasoneThe serum concentration of Cytarabine can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Cytarabine.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Cytarabine.Approved
DihydroergotamineThe metabolism of Cytarabine can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Cytarabine can be decreased when combined with Diltiazem.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Cytarabine.Approved, Investigational
DoxycyclineThe metabolism of Cytarabine can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Cytarabine can be decreased when combined with Dronedarone.Approved
EfavirenzThe serum concentration of Cytarabine can be decreased when it is combined with Efavirenz.Approved, Investigational
EnzalutamideThe serum concentration of Cytarabine can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Cytarabine can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Cytarabine can be decreased when it is combined with Eslicarbazepine acetate.Approved
EtravirineThe serum concentration of Cytarabine can be decreased when it is combined with Etravirine.Approved
FingolimodCytarabine may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
FluconazoleThe metabolism of Cytarabine can be decreased when combined with Fluconazole.Approved
FlucytosineThe therapeutic efficacy of Flucytosine can be decreased when used in combination with Cytarabine.Approved
FluvoxamineThe metabolism of Cytarabine can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Cytarabine can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Cytarabine can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Cytarabine can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Cytarabine can be increased when it is combined with Fusidic Acid.Approved
G17DTThe risk or severity of adverse effects can be increased when Cytarabine is combined with G17DT.Investigational
GI-5005The risk or severity of adverse effects can be increased when Cytarabine is combined with GI-5005.Investigational
IdelalisibThe serum concentration of Cytarabine can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Cytarabine can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Cytarabine can be decreased when combined with Indinavir.Approved
INGN 201The risk or severity of adverse effects can be increased when Cytarabine is combined with INGN 201.Investigational
INGN 225The risk or severity of adverse effects can be increased when Cytarabine is combined with INGN 225.Investigational
IsavuconazoniumThe metabolism of Cytarabine can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Cytarabine can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Cytarabine can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Cytarabine can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Cytarabine can be decreased when combined with Ketoconazole.Approved, Investigational
LeflunomideThe risk or severity of adverse effects can be increased when Cytarabine is combined with Leflunomide.Approved, Investigational
LopinavirThe metabolism of Cytarabine can be decreased when combined with Lopinavir.Approved
LovastatinThe metabolism of Cytarabine can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Cytarabine can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Cytarabine can be increased when combined with Lumacaftor.Approved
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Cytarabine.Withdrawn
MifepristoneThe serum concentration of Cytarabine can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Cytarabine can be decreased when it is combined with Mitotane.Approved
ModafinilThe serum concentration of Cytarabine can be decreased when it is combined with Modafinil.Approved, Investigational
NafcillinThe serum concentration of Cytarabine can be decreased when it is combined with Nafcillin.Approved
NatalizumabThe risk or severity of adverse effects can be increased when Cytarabine is combined with Natalizumab.Approved, Investigational
NefazodoneThe metabolism of Cytarabine can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Cytarabine can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Cytarabine can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Cytarabine can be increased when combined with Nevirapine.Approved
NilotinibThe metabolism of Cytarabine can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Cytarabine can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Cytarabine can be increased when it is combined with Osimertinib.Approved
OuabainOuabain may decrease the cardiotoxic activities of Cytarabine.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Cytarabine.Approved, Vet Approved
PalbociclibThe serum concentration of Cytarabine can be increased when it is combined with Palbociclib.Approved
PentobarbitalThe metabolism of Cytarabine can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenobarbitalThe metabolism of Cytarabine can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Cytarabine can be increased when combined with Phenytoin.Approved, Vet Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Cytarabine.Approved, Investigational
PosaconazoleThe metabolism of Cytarabine can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Cytarabine can be increased when combined with Primidone.Approved, Vet Approved
Rabies vaccineThe risk or severity of adverse effects can be increased when Cytarabine is combined with Rabies vaccine.Approved
RanolazineThe metabolism of Cytarabine can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Cytarabine can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Cytarabine can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Cytarabine can be increased when combined with Rifapentine.Approved
RitonavirThe metabolism of Cytarabine can be decreased when combined with Ritonavir.Approved, Investigational
RoflumilastRoflumilast may increase the immunosuppressive activities of Cytarabine.Approved
SaquinavirThe metabolism of Cytarabine can be decreased when combined with Saquinavir.Approved, Investigational
SildenafilThe metabolism of Cytarabine can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Cytarabine can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Cytarabine can be increased when it is combined with Simeprevir.Approved
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Cytarabine.Approved
SRP 299The risk or severity of adverse effects can be increased when Cytarabine is combined with SRP 299.Investigational
St. John's WortThe serum concentration of Cytarabine can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Cytarabine can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Cytarabine can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Cytarabine.Approved, Investigational
TelaprevirThe metabolism of Cytarabine can be decreased when combined with Telaprevir.Approved
TelithromycinThe metabolism of Cytarabine can be decreased when combined with Telithromycin.Approved
TG4010The risk or severity of adverse effects can be increased when Cytarabine is combined with TG4010.Investigational
TiclopidineThe metabolism of Cytarabine can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Cytarabine can be decreased when it is combined with Tocilizumab.Approved
TofacitinibCytarabine may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Cytarabine.Approved, Investigational
VenlafaxineThe metabolism of Cytarabine can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Cytarabine can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Cytarabine can be decreased when combined with Voriconazole.Approved, Investigational
ZiprasidoneThe metabolism of Cytarabine can be decreased when combined with Ziprasidone.Approved
Food InteractionsNot Available
References
Synthesis Reference

Michael Kluge, Herbert Schott, “Cytarabine derivatives, the preparation and use thereof.” U.S. Patent US5641758, issued August, 1992.

US5641758
General ReferencesNot Available
External Links
ATC CodesL01BC01
AHFS Codes
  • 10:00.00
PDB Entries
FDA labelDownload (49.8 KB)
MSDSDownload (36.8 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9623
Blood Brain Barrier+0.9465
Caco-2 permeable-0.8887
P-glycoprotein substrateNon-substrate0.798
P-glycoprotein inhibitor INon-inhibitor0.9686
P-glycoprotein inhibitor IINon-inhibitor0.9532
Renal organic cation transporterNon-inhibitor0.9519
CYP450 2C9 substrateNon-substrate0.793
CYP450 2D6 substrateNon-substrate0.8613
CYP450 3A4 substrateNon-substrate0.6203
CYP450 1A2 substrateNon-inhibitor0.9543
CYP450 2C9 inhibitorNon-inhibitor0.9638
CYP450 2D6 inhibitorNon-inhibitor0.9497
CYP450 2C19 inhibitorNon-inhibitor0.9489
CYP450 3A4 inhibitorNon-inhibitor0.9609
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.981
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9158
BiodegradationNot ready biodegradable0.7807
Rat acute toxicity1.7184 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.983
hERG inhibition (predictor II)Non-inhibitor0.911
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Pacira pharmaceuticals inc
  • App pharmaceuticals llc
  • Bedford laboratories div ben venue laboratories inc
  • Hospira inc
  • Teva parenteral medicines inc
Packagers
Dosage forms
FormRouteStrength
InjectionIntrathecal; Intravenous; Subcutaneous100 mg/5mL
InjectionIntrathecal; Intravenous; Subcutaneous2 g/20mL
InjectionIntravenous; Subcutaneous20 mg/mL
Injection, solutionIntrathecal; Intravenous; Subcutaneous100 mg/mL
Injection, solutionIntrathecal; Intravenous; Subcutaneous20 mg/mL
Injection, solutionIntravenous20 mg/mL
Injection, solutionIntravenous; Subcutaneous20 mg/mL
SolutionIntrathecal; Intravenous; Subcutaneous20 mg
LiquidIntravenous; Subcutaneous100 mg
SolutionIntrathecal; Intravenous; Subcutaneous100 mg
Powder, for solutionIntrathecal; Intravenous; Subcutaneous100 mg
Powder, for solutionIntrathecal; Intravenous; Subcutaneous1 g
Powder, for solutionIntrathecal; Intravenous; Subcutaneous2 g
Powder, for solutionIntrathecal; Intravenous; Subcutaneous500 mg
Injection, lipid complexIntrathecal50 mg/5mL
SuspensionIntrathecal10 mg
Injection, suspensionIntrathecal50 mg
Prices
Unit descriptionCostUnit
Depocyt 50 mg/5 ml vial588.0USD ml
Cytarabine 2 gm vial48.0USD vial
Cytarabine 1 gm vial24.0USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5455044 No1993-05-142013-05-14Us
US5723147 No1995-03-032015-03-03Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point186-188Hunter, J.H.; U S . Patent 3,116,282; December 31,1963; assigned to The Upjohn Company.
water solubilityFreely solubleNot Available
logP-2.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility43.8 mg/mLALOGPS
logP-2.2ALOGPS
logP-2.8ChemAxon
logS-0.74ALOGPS
pKa (Strongest Acidic)12.55ChemAxon
pKa (Strongest Basic)-0.55ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area128.61 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.54 m3·mol-1ChemAxon
Polarizability22.21 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyrimidine nucleosides. These are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleosides
Sub ClassNot Available
Direct ParentPyrimidine nucleosides
Alternative Parents
Substituents
  • Pyrimidine nucleoside
  • N-glycosyl compound
  • Glycosyl compound
  • Pyrimidone
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Primary aromatic amine
  • Monosaccharide
  • Hydropyrimidine
  • Heteroaromatic compound
  • Oxolane
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
yes
Actions
cross-linking/alkylation
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Prakasha Gowda AS, Polizzi JM, Eckert KA, Spratt TE: Incorporation of gemcitabine and cytarabine into DNA by DNA polymerase beta and ligase III/XRCC1. Biochemistry. 2010 Jun 15;49(23):4833-40. doi: 10.1021/bi100200c. [PubMed:20459144 ]
  2. Foti M, Omichinski JG, Stahl S, Maloney D, West J, Schweitzer BI: Effects of nucleoside analog incorporation on DNA binding to the DNA binding domain of the GATA-1 erythroid transcription factor. FEBS Lett. 1999 Feb 5;444(1):47-53. [PubMed:10037146 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Microtubule binding
Specific Function:
Repair polymerase that plays a key role in base-excision repair. Has 5'-deoxyribose-5-phosphate lyase (dRP lyase) activity that removes the 5' sugar phosphate and also acts as a DNA polymerase that adds one nucleotide to the 3' end of the arising single-nucleotide gap. Conducts 'gap-filling' DNA synthesis in a stepwise distributive fashion rather than in a processive fashion as for other DNA po...
Gene Name:
POLB
Uniprot ID:
P06746
Molecular Weight:
38177.34 Da
References
  1. Angeli JP, Ribeiro LR, Bellini MF, Mantovanil: Anti-clastogenic effect of beta-glucan extracted from barley towards chemically induced DNA damage in rodent cells. Hum Exp Toxicol. 2006 Jun;25(6):319-24. [PubMed:16866189 ]
  2. Miura S, Izuta S: DNA polymerases as targets of anticancer nucleosides. Curr Drug Targets. 2004 Feb;5(2):191-5. [PubMed:15011952 ]
  3. Krynetskaia NF, Phadke MS, Jadhav SH, Krynetskiy EY: Chromatin-associated proteins HMGB1/2 and PDIA3 trigger cellular response to chemotherapy-induced DNA damage. Mol Cancer Ther. 2009 Apr;8(4):864-72. doi: 10.1158/1535-7163.MCT-08-0695. [PubMed:19372559 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Zinc ion binding
Specific Function:
This enzyme scavenges exogenous and endogenous cytidine and 2'-deoxycytidine for UMP synthesis.
Gene Name:
CDA
Uniprot ID:
P32320
Molecular Weight:
16184.545 Da
References
  1. Ohta T, Hori H, Ogawa M, Miyahara M, Kawasaki H, Taniguchi N, Komada Y: Impact of cytidine deaminase activity on intrinsic resistance to cytarabine in carcinoma cells. Oncol Rep. 2004 Nov;12(5):1115-20. [PubMed:15492802 ]
  2. Lamba JK: Genetic factors influencing cytarabine therapy. Pharmacogenomics. 2009 Oct;10(10):1657-74. doi: 10.2217/pgs.09.118. [PubMed:19842938 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Protein homodimerization activity
Specific Function:
Required for the phosphorylation of the deoxyribonucleosides deoxycytidine (dC), deoxyguanosine (dG) and deoxyadenosine (dA). Has broad substrate specificity, and does not display selectivity based on the chirality of the substrate. It is also an essential enzyme for the phosphorylation of numerous nucleoside analogs widely employed as antiviral and chemotherapeutic agents.
Gene Name:
DCK
Uniprot ID:
P27707
Molecular Weight:
30518.315 Da
References
  1. Ohta T, Hori H, Ogawa M, Miyahara M, Kawasaki H, Taniguchi N, Komada Y: Impact of cytidine deaminase activity on intrinsic resistance to cytarabine in carcinoma cells. Oncol Rep. 2004 Nov;12(5):1115-20. [PubMed:15492802 ]
  2. Lamba JK: Genetic factors influencing cytarabine therapy. Pharmacogenomics. 2009 Oct;10(10):1657-74. doi: 10.2217/pgs.09.118. [PubMed:19842938 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Nucleotide binding
Specific Function:
Hydrolyzes extracellular nucleotides into membrane permeable nucleosides. Exhibits AMP-, NAD-, and NMN-nucleosidase activities.
Gene Name:
NT5E
Uniprot ID:
P21589
Molecular Weight:
63367.255 Da
References
  1. Lamba JK: Genetic factors influencing cytarabine therapy. Pharmacogenomics. 2009 Oct;10(10):1657-74. doi: 10.2217/pgs.09.118. [PubMed:19842938 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Zinc ion binding
Specific Function:
Supplies the nucleotide substrate for thymidylate synthetase.
Gene Name:
DCTD
Uniprot ID:
P32321
Molecular Weight:
20015.805 Da
References
  1. Lamba JK: Genetic factors influencing cytarabine therapy. Pharmacogenomics. 2009 Oct;10(10):1657-74. doi: 10.2217/pgs.09.118. [PubMed:19842938 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Quaternary ammonium group transmembrane transporter activity
Specific Function:
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridiniu...
Gene Name:
SLC22A2
Uniprot ID:
O15244
Molecular Weight:
62579.99 Da
References
  1. Chen R, Nelson JA: Role of organic cation transporters in the renal secretion of nucleosides. Biochem Pharmacol. 2000 Jul 15;60(2):215-9. [PubMed:10825466 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Secondary active organic cation transmembrane transporter activity
Specific Function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine...
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular Weight:
61153.345 Da
References
  1. Chen R, Nelson JA: Role of organic cation transporters in the renal secretion of nucleosides. Biochem Pharmacol. 2000 Jul 15;60(2):215-9. [PubMed:10825466 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Atpase activity, coupled to transmembrane movement of substances
Specific Function:
ATP-dependent transporter probably involved in cellular detoxification through lipophilic anion extrusion.
Gene Name:
ABCC10
Uniprot ID:
Q5T3U5
Molecular Weight:
161627.375 Da
References
  1. Hopper-Borge E, Xu X, Shen T, Shi Z, Chen ZS, Kruh GD: Human multidrug resistance protein 7 (ABCC10) is a resistance factor for nucleoside analogues and epothilone B. Cancer Res. 2009 Jan 1;69(1):178-84. doi: 10.1158/0008-5472.CAN-08-1420. [PubMed:19118001 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Nucleoside transmembrane transporter activity
Specific Function:
Mediates both influx and efflux of nucleosides across the membrane (equilibrative transporter). It is sensitive (ES) to low concentrations of the inhibitor nitrobenzylmercaptopurine riboside (NBMPR) and is sodium-independent. It has a higher affinity for adenosine. Inhibited by dipyridamole and dilazep (anticancer chemotherapeutics drugs).
Gene Name:
SLC29A1
Uniprot ID:
Q99808
Molecular Weight:
50218.805 Da
References
  1. Santini D, Vincenzi B, Fratto ME, Perrone G, Lai R, Catalano V, Cass C, Ruffini PA, Spoto C, Muretto P, Rizzo S, Muda AO, Mackey JR, Russo A, Tonini G, Graziano F: Prognostic role of human equilibrative transporter 1 (hENT1) in patients with resected gastric cancer. J Cell Physiol. 2010 May;223(2):384-8. doi: 10.1002/jcp.22045. [PubMed:20082300 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23