Cytarabine

Identification

Summary

Cytarabine is a pyrimidine nucleoside analogue used to treat acute non-lymphocytic leukemia, lymphocytic leukemia, and the blast phase of chronic myelocytic leukemia.

Brand Names
Cytosar, Vyxeos
Generic Name
Cytarabine
DrugBank Accession Number
DB00987
Background

A 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)

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 243.2166
Monoisotopic: 243.085520541
Chemical Formula
C9H13N3O5
Synonyms
  • 1-beta-D-Arabinofuranosylcytosine
  • 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinone
  • Citarabina
  • Cytarabine
  • Cytarabine liposome
  • Cytarabinum
  • Cytosine arabinoside
  • Cytosine-1-beta-D-arabinofuranoside
  • cytosine-β-D-arabinofuranoside
External IDs
  • NSC-287459
  • U 19920A
  • U-19,920
  • U-19920

Pharmacology

Indication

For the treatment of acute non-lymphocytic leukemia, acute lymphocytic leukemia and blast phase of chronic myelocytic leukemia.

Cytarabine is indicated in combination with daunorubicin for the treatment of newly-diagnosed therapy-related acute myeloid leukemia (t-AML) or AML with myelodysplasia-related changes (AML-MRC) in adults and pediatric patients 1 year and older.2

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAcute lymphocytic leukemia•••••••••••••••••••••• •••••••••• ••••• •••••••• •••••••••• ••••••••• •••••••••• ••••••••••
Treatment ofAcute myeloid leukemia•••••••••••••••••••••• •••••••••• ••••• •••••••• •••••••••• ••••••••• •••••••••• ••••••••••
Used in combination to treatAcute myeloid leukemia with myelodysplasia-related changesCombination Product in combination with: Daunorubicin (DB00694)••••••••••••••••••••••• •••••• •••••••••••••• •••••••••
Used in combination to treatAcute promyelocytic leukemia••• •••••
Treatment ofLymphomatous meningitis•••••••••••••••••••••
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Cytarabine 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 action

Cytarabine 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.

TargetActionsOrganism
ADNA polymerase beta
inhibitor
Humans
ADNA
cross-linking/alkylation
Humans
Absorption

Less than 20% of the orally administered dose is absorbed from the gastrointestinal tract.

Volume of distribution

Not Available

Protein binding

13%

Metabolism

Hepatic.

Route of elimination

The primary route of elimination of cytarabine is metabolism to the inactive compound ara-U, followed by urinary excretion of ara-U.

Half-life

10 minutes

Clearance

Not Available

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Cytarabine syndrome may develop - it is characterized by fever, myalgia, bone pain, occasionally chest pain, maculopapular rash, conjunctivitis, and malaise.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbataceptThe risk or severity of adverse effects can be increased when Cytarabine is combined with Abatacept.
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Cytarabine.
AcenocoumarolThe risk or severity of bleeding can be increased when Acenocoumarol is combined with Cytarabine.
Acetylsalicylic acidThe risk or severity of bleeding can be increased when Acetylsalicylic acid is combined with Cytarabine.
AcipimoxThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Cytarabine is combined with Acipimox.
Food Interactions
No interactions found.

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Product Ingredients
IngredientUNIICASInChI Key
Cytarabine hydrochloride33K3DB659169-74-9KCURWTAZOZXKSJ-JBMRGDGGSA-N
International/Other Brands
Ara-C (Gobbi) / Cytosar-U (Pfizer)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CytarabineInjection100 mg/5mLIntrathecal; Intravenous; SubcutaneousGland Pharma Limited2018-02-14Not applicableUS flag
CytarabineInjection20 mg/1mLIntravenous; SubcutaneousGland Pharma Limited2011-12-14Not applicableUS flag
Cytarabine - Pws 1gn/vialPowder, for solution1 g / vialIntrathecal; Intravenous; SubcutaneousNovopharm Limited1995-12-312015-10-26Canada flag
Cytarabine - Pws 2gm/vialPowder, for solution2 g / vialIntrathecal; Intravenous; SubcutaneousNovopharm Limited1995-12-312015-10-26Canada flag
Cytarabine - Pws 500mg/vialPowder, for solution500 mg / vialIntrathecal; Intravenous; SubcutaneousNovopharm Limited1995-12-312015-10-26Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Aj-cytarabineSolution100 mg / mLIntrathecal; Intravenous; SubcutaneousAgila Jamp Canada IncNot applicableNot applicableCanada flag
CytarabineInjection, solution20 mg/1mLIntrathecal; Intravenous; SubcutaneousHospira, Inc.1990-06-04Not applicableUS flag
CytarabineInjection, solution100 mg/1mLIntrathecal; Intravenous; SubcutaneousHospira, Inc.1999-11-22Not applicableUS flag
CytarabineInjection20 mg/1mLIntravenous; SubcutaneousPfizer Laboratories Div Pfizer Inc.2014-06-302014-06-30US flag
CytarabineInjection2 g/20mLIntrathecal; Intravenous; SubcutaneousMylan Institutional LLC2012-01-312022-12-31US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
VyxeosCytarabine (100 mg) + Daunorubicin (44 mg)PowderIntravenousJazz Pharmaceuticals Ireland Limited2021-07-06Not applicableCanada flag
VyxeosCytarabine (100 mg/20mL) + Daunorubicin (44 mg/20mL)Injection, powder, lyophilized, for suspensionIntravenousJazz Pharmaceuticals, Inc.2017-08-03Not applicableUS flag
Vyxeos LiposomalCytarabine (5 mg/ml) + Daunorubicin hydrochloride (2.2 mg/ml)Injection, powder, for solutionIntravenousJazz Pharmaceuticals Ireland Limited2020-12-16Not applicableEU flag
VYXEOS LIPOSOMALCytarabine (5 MG/ML) + Daunorubicin (2.2 MG/ML)PowderIntravenous; ParenteralJazz Pharmaceuticals Ireland Limited2019-01-29Not applicableItaly flag
Vyxeos LiposomalCytarabine (5 mg/ml) + Daunorubicin hydrochloride (2.2 mg/ml)Injection, powder, for solutionIntravenousJazz Pharmaceuticals Ireland Limited2020-12-16Not applicableEU flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
CYTARABINE DBL 10 ML 1 GR FLAKON, 1 ADETCytarabine (100 mg/5ml)SolutionIntrathecal; Intravenous; SubcutaneousORNA İLAÇ TEKSTİL KİMYEVİ MAD. SAN. VE DIŞ TİC. LTD. ŞTİ.2018-12-25Not applicableTurkey flag

Categories

ATC Codes
L01BC01 — CytarabineL01XY01 — Cytarabine and daunorubicin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleosides
Sub Class
Not Available
Direct Parent
Pyrimidine nucleosides
Alternative Parents
Glycosylamines / Pentoses / Pyrimidones / Aminopyrimidines and derivatives / Imidolactams / Hydropyrimidines / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Azacyclic compounds
show 6 more
Substituents
Alcohol / Amine / Aminopyrimidine / Aromatic heteromonocyclic compound / Azacycle / Glycosyl compound / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Imidolactam
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
monosaccharide derivative, beta-D-arabinoside, pyrimidine nucleoside (CHEBI:28680)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
04079A1RDZ
CAS number
147-94-4
InChI Key
UHDGCWIWMRVCDJ-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[C@H](CO)[C@@H](O)[C@@H]1O

References

Synthesis Reference

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

US5641758
General References
  1. Health Canada Product Monograph: Cytarabine injection [Link]
  2. FDA Approved Drug Products: VYXEOS (daunorubicin and cytarabine) liposome for injection, for intravenous use [Link]
Human Metabolome Database
HMDB0015122
KEGG Drug
D00168
KEGG Compound
C02961
PubChem Compound
6253
PubChem Substance
46505879
ChemSpider
6017
BindingDB
50087289
RxNav
3041
ChEBI
28680
ChEMBL
CHEMBL803
ZINC
ZINC000003795098
Therapeutic Targets Database
DNC001551
PharmGKB
PA449177
PDBe Ligand
AR3
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Cytarabine
PDB Entries
1p5z / 5y9a
FDA label
Download (49.8 KB)
MSDS
Download (36.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingPreventionAcute Myeloid Leukemia1
4CompletedTreatmentAcute Lymphobkastic Leukemia1
4CompletedTreatmentAcute Lymphoblastic Leukemia (ALL)6
4CompletedTreatmentAcute Myeloid Leukemia3
4CompletedTreatmentAcute Myeloid Leukemia / Myelodysplastic Syndrome1

Pharmacoeconomics

Manufacturers
  • Pacira pharmaceuticals inc
  • App pharmaceuticals llc
  • Bedford laboratories div ben venue laboratories inc
  • Hospira inc
  • Teva parenteral medicines inc
Packagers
  • APP Pharmaceuticals
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Enzon Inc.
  • Hospira Inc.
  • Pacira Pharmaceuticals Inc.
  • Pharmacia Inc.
  • Teva Pharmaceutical Industries Ltd.
Dosage Forms
FormRouteStrength
Injection, powder, lyophilized, for solutionIntrathecal; Intravenous; Subcutaneous1000 mg
SolutionIntramuscular; Intrathecal; Intravenous; Subcutaneous100 mg
SolutionIntramuscular; Intrathecal; Intravenous; Subcutaneous500 mg
Injection, solutionIntrathecal; Intravenous; Subcutaneous100 mg/5ml
Injection, solution, concentrateIntravenous100 mg/ml
SolutionIntravenous; Subcutaneous1000 mg
Injection, solutionIntrathecal; Intravenous; Subcutaneous1000 mg/20ml
InjectionParenteral20 mg/ml
Injection, solutionIntrathecal; Intravenous; Subcutaneous40 mg/2ml
SolutionParenteral40 mg
InjectionParenteral50 mg/ml
InjectionIntravenous100 mg/5ml
InjectionIntravenous1000 mg
Injection, powder, for solutionParenteral100 MG/5ML
Injection, powder, for solutionParenteral500 MG/10ML
Injection, powder, for solutionParenteral; Subcutaneous500 MG/10ML
Injection, solution100 mg/1ml
Injection, powder, lyophilized, for solutionIntrathecal; Intravenous; Subcutaneous100 mg
SolutionIntrathecal; Intravenous; Subcutaneous100 mg
SolutionIntravenous10000000 mg
Injection, powder, for solutionIntrathecal; Intravenous; Subcutaneous1000 mg
SolutionParenteral100 mg
SolutionIntravenous; Subcutaneous1 g
Injection, powder, for solutionIntrathecal; Intravenous; Subcutaneous500 mg
SolutionIntravenous; Subcutaneous500 mg
SolutionIntravenous; Subcutaneous50000000 mg
Injection, powder, lyophilized, for solutionIntravenous500 mg
SolutionIntrathecal; Intravenous; Subcutaneous50000000 mg
Injection, solutionParenteral100 MG/ML
Injection, powder, for solution
Injection, solutionParenteral1 G/50ML
Injection, solutionParenteral1 G/10ML
Injection, solutionParenteral100 MG/5ML
Injection, solutionParenteral2 G/20ML
Injection, solutionParenteral500 MG/5ML
SolutionIntravenous100 mg
SolutionIntrathecal; Intravenous; Subcutaneous500 mg
Injection, solutionParenteral
Injection, solution, concentrateIntrathecal; Intravenous; Subcutaneous100 mg/ml
SolutionIntravenous500.00 mg
SolutionIntravenous50000000 mg
SolutionIntravenous; Subcutaneous100 mg
Injection, solution100 mg/ml
Injection, solutionParenteral20 mg/ml
InjectionIntrathecal; Intravenous; Subcutaneous100 mg/5mL
InjectionIntrathecal; Intravenous; Subcutaneous2 g/20mL
InjectionIntravenous; Subcutaneous20 mg/1mL
Injection, powder, lyophilized, for solutionIntrathecal; Intravenous; Subcutaneous1 g/10mL
Injection, powder, lyophilized, for solutionIntrathecal; Intravenous; Subcutaneous100 mg/5mL
Injection, powder, lyophilized, for solutionIntrathecal; Intravenous; Subcutaneous2 g/20mL
Injection, powder, lyophilized, for solutionIntrathecal; Intravenous; Subcutaneous500 mg/10mL
Injection, solutionIntrathecal; Intravenous; Subcutaneous100 mg/1mL
Injection, solutionIntrathecal; Intravenous; Subcutaneous2 g/20mL
Injection, solutionIntrathecal; Intravenous; Subcutaneous20 mg/1mL
Injection, solutionIntravenous20 mg/1mL
Injection, solutionIntravenous; Subcutaneous20 mg/1mL
Powder, for solutionIntrathecal; Intravenous; Subcutaneous1 g / vial
Powder, for solutionIntrathecal; Intravenous; Subcutaneous2 g / vial
Powder, for solutionIntrathecal; Intravenous; Subcutaneous500 mg / vial
SolutionIntrathecal; Intravenous; Subcutaneous100 mg/5ml
InjectionIntrathecal; Intravenous; Subcutaneous
InjectionIntradermal; Intravenous; Subcutaneous100 mg/ml
SolutionIntravenous; Subcutaneous100 mg/1ml
LiquidIntravenous; Subcutaneous100 mg / mL
SolutionIntravenous1000 mg
SolutionIntravenous500 mg
SolutionIntrathecal; Intravenous; Subcutaneous100 mg / mL
Injection, powder, lyophilized, for solutionParenteral100 mg
Injection, solutionIntravenous100 mg/ml
SolutionSubcutaneous100.000 mg
Powder, for solutionIntrathecal; Intravenous; Subcutaneous100 mg / vial
Solution100 mg/1ml
Solution20 mg/1ml
SolutionParenteral500.000 mg
Injection, solution
Injection, solution1000 mg/10ml
Injection
InjectionIntravenous; Subcutaneous100 mg/ml
Injection1 g/10ml
Injection, lipid complexIntrathecal50 mg/5mL
SuspensionIntrathecal10 mg / mL
Injection, suspensionIntrathecal50 mg
Injection100 mg/ml
Injection, solutionIntrathecal; Intravenous; Subcutaneous
Injection, solutionIntrathecal; Intravenous; Subcutaneous500 mg/25ml
SolutionIntrathecal; Intravenous500 mg
SolutionIntravenous500.000 mg
SolutionIntrathecal; Intravenous; Subcutaneous20 mg / mL
Injection, powder, lyophilized, for suspensionIntravenous
PowderIntravenous
Injection, powder, for solutionIntravenous
PowderIntravenous; Parenteral
SolutionIntravenous100000000 mg
SolutionParenteral500.00 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)Region
US5723147No1998-03-032015-03-03US flag
US5455044No1995-10-032013-05-14US flag
US7850990No2010-12-142027-01-23US flag
US8022279No2011-09-202027-09-14US flag
US8431806No2013-04-302025-04-22US flag
US8092828No2012-01-102029-04-01US flag
US8518437No2013-08-272026-06-07US flag
US9271931No2016-03-012027-01-23US flag
US10028912No2018-07-242034-09-29US flag
US10166184No2019-01-012032-10-15US flag
US10835492No2020-11-172032-10-15US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)186-188Hunter, 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)4.19Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area128.61 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity54.54 m3·mol-1Chemaxon
Polarizability22.53 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-08ml-9320000000-b032ad2c3dbed3face55
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-0190000000-eff861edb69ddab2c195
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-0900000000-4b5b14f0a5467db173b6
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-3900000000-d85ae6c771dd9206c4c2
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-06sl-9600000000-b154ca170372bcbf8a4a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00lu-9200000000-840df44a2d1149f4a7f7
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-01ox-0790000000-270551529aa609aa9ce8
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-0900000000-855a7f8775ed4351b290
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-0900000000-50671582f88f6b4d8cee
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-1900000000-54269291900f80d353c3
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-7900000000-ae3ff52581cbe6141064
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-03di-0900000000-9f3ae8e87da22e4e2e82
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-36f9a180589f056704d4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03xu-8910000000-30bf98db3fdebc89779c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-1900000000-947a2c9db175f3b5e8ac
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-9400000000-c8ab640ca9f4ecd057ba
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0jba-9300000000-5f2cecdc7876a62d826d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kg-9400000000-405e4172bd08c2393dbb
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-161.0166385
predicted
DarkChem Lite v0.1.0
[M-H]-161.0579385
predicted
DarkChem Lite v0.1.0
[M-H]-161.3619385
predicted
DarkChem Lite v0.1.0
[M-H]-151.58852
predicted
DeepCCS 1.0 (2019)
[M+H]+161.6367385
predicted
DarkChem Lite v0.1.0
[M+H]+161.3019385
predicted
DarkChem Lite v0.1.0
[M+H]+161.1363385
predicted
DarkChem Lite v0.1.0
[M+H]+153.98409
predicted
DeepCCS 1.0 (2019)
[M+Na]+160.5224385
predicted
DarkChem Lite v0.1.0
[M+Na]+160.8809385
predicted
DarkChem Lite v0.1.0
[M+Na]+161.1688385
predicted
DarkChem Lite v0.1.0
[M+Na]+160.96428
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Humans
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...
Gene Name
POLB
Uniprot ID
P06746
Uniprot Name
DNA polymerase beta
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. [Article]
  2. Miura S, Izuta S: DNA polymerases as targets of anticancer nucleosides. Curr Drug Targets. 2004 Feb;5(2):191-5. [Article]
  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. [Article]
Kind
Nucleotide
Organism
Humans
Pharmacological action
Yes
Actions
Cross-linking/alkylation
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
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. [Article]
  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. [Article]

Enzymes

Kind
Protein
Organism
Humans
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Colburn DE, Giles FJ, Oladovich D, Smith JA: In vitro evaluation of cytochrome P450-mediated drug interactions between cytarabine, idarubicin, itraconazole and caspofungin. Hematology. 2004 Jun;9(3):217-21. doi: 10.1080/10245330410001701585. [Article]
  2. Su M, Chang YT, Hernandez D, Jones RJ, Ghiaur G: Regulation of drug metabolizing enzymes in the leukaemic bone marrow microenvironment. J Cell Mol Med. 2019 Jun;23(6):4111-4117. doi: 10.1111/jcmm.14298. Epub 2019 Mar 28. [Article]
Kind
Protein
Organism
Humans
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...
Gene Name
DCK
Uniprot ID
P27707
Uniprot Name
Deoxycytidine kinase
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. [Article]
  2. Lamba JK: Genetic factors influencing cytarabine therapy. Pharmacogenomics. 2009 Oct;10(10):1657-74. doi: 10.2217/pgs.09.118. [Article]
Kind
Protein
Organism
Humans
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
Uniprot Name
5'-nucleotidase
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. [Article]
Kind
Protein
Organism
Humans
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
Uniprot Name
Deoxycytidylate deaminase
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. [Article]
Kind
Protein
Organism
Humans
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
Uniprot Name
Cytidine deaminase
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. [Article]
  2. Lamba JK: Genetic factors influencing cytarabine therapy. Pharmacogenomics. 2009 Oct;10(10):1657-74. doi: 10.2217/pgs.09.118. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Symporter activity
Specific Function
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without...
Gene Name
SLC22A4
Uniprot ID
Q9H015
Uniprot Name
Solute carrier family 22 member 4
Molecular Weight
62154.48 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. [Article]
  2. Drenberg CD, Gibson AA, Pounds SB, Shi L, Rhinehart DP, Li L, Hu S, Du G, Nies AT, Schwab M, Pabla N, Blum W, Gruber TA, Baker SD, Sparreboom A: OCTN1 Is a High-Affinity Carrier of Nucleoside Analogues. Cancer Res. 2017 Apr 15;77(8):2102-2111. doi: 10.1158/0008-5472.CAN-16-2548. Epub 2017 Feb 16. [Article]
Kind
Protein
Organism
Humans
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
Uniprot Name
Multidrug resistance-associated protein 7
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. [Article]
Kind
Protein
Organism
Humans
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...
Gene Name
SLC29A1
Uniprot ID
Q99808
Uniprot Name
Equilibrative nucleoside transporter 1
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. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48