Identification

Name
Cytarabine
Accession Number
DB00987
Description

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
Thumb
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
  • 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.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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
Learn about our commercial Adverse Effects data.
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Toxicity

Cytarabine 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
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.
AcyclovirThe risk or severity of adverse effects can be increased when Acyclovir is combined with Cytarabine.
AdalimumabThe risk or severity of adverse effects can be increased when Adalimumab is combined with Cytarabine.
Adenovirus type 7 vaccine liveThe risk or severity of infection can be increased when Adenovirus type 7 vaccine live is combined with Cytarabine.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Cytarabine.
AlefaceptThe risk or severity of adverse effects can be increased when Alefacept is combined with Cytarabine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

Products

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 solutionIntrathecal; Intravenous; SubcutaneousNovopharm Limited1995-12-312015-10-26Canada flag
Cytarabine - Pws 2gm/vialPowder, for solutionIntrathecal; Intravenous; SubcutaneousNovopharm Limited1995-12-312015-10-26Canada flag
Cytarabine - Pws 500mg/vialPowder, for solutionIntrathecal; Intravenous; SubcutaneousNovopharm Limited1995-12-312015-10-26Canada flag
Cytarabine Inj 100mg/mlLiquidIntravenous; SubcutaneousDavid Bull Laboratories (Pty) Ltd.1992-12-311998-08-13Canada flag
Cytarabine InjectionSolutionIntrathecal; Intravenous; SubcutaneousPfizer Canada Ulc1996-09-23Not applicableCanada flag
Cytarabine Injection BPSolutionIntrathecal; Intravenous; SubcutaneousSandoz Canada IncorporatedNot applicableNot applicableCanada flag
Cytarabine Injection, Mylan Std.SolutionIntrathecal; Intravenous; SubcutaneousMylan PharmaceuticalsNot applicableNot applicableCanada flag
Cytarabine-pws 100mg/vialPowder, for solutionIntrathecal; Intravenous; SubcutaneousNovopharm Limited1995-12-312018-05-07Canada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Aj-cytarabineSolutionIntrathecal; Intravenous; SubcutaneousAgila Jamp Canada IncNot applicableNot applicableCanada flag
CytarabineInjection2 g/20mLIntrathecal; Intravenous; SubcutaneousMylan Institutional LLC2012-01-31Not applicableUS flag
CytarabineInjection, powder, lyophilized, for solution1 g/10mLIntrathecal; Intravenous; SubcutaneousBedford Pharmaceuticals1996-06-282014-08-31US flag
CytarabineInjection, powder, lyophilized, for solution2 g/20mLIntrathecal; Intravenous; SubcutaneousBedford Pharmaceuticals1996-05-012011-03-31US flag
CytarabineInjection, solution20 mg/1mLIntrathecal; Intravenous; SubcutaneousGland Pharma Limited2019-12-23Not applicableUS flag
CytarabineInjection20 mg/1mLIntravenous; SubcutaneousPfizer Laboratories Div Pfizer Inc.2014-06-302014-06-30US flag
CytarabineInjection, solution20 mg/1mLIntravenousHospira, Inc.1990-08-31Not applicableUS flag
CytarabineInjection, powder, lyophilized, for solution100 mg/5mLIntrathecal; Intravenous; SubcutaneousBedford Pharmaceuticals1996-05-012014-04-30US flag
CytarabineInjection20 mg/1mLIntravenous; SubcutaneousMylan Institutional LLC2011-12-14Not applicableUS flag
CytarabineInjection100 mg/5mLIntrathecal; Intravenous; SubcutaneousPfizer Laboratories Div Pfizer Inc.2011-12-142017-12-31US flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
VyxeosCytarabine (100 mg/20mL) + Daunorubicin (44 mg/20mL)Injection, powder, lyophilized, for suspensionIntravenousJazz Pharmaceuticals, Inc.2017-08-03Not applicableUS 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)

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

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]
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
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
PDB Entries
1p5z / 5y9a
FDA label
Download (49.8 KB)
MSDS
Download (36.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingPreventionAcute Myeloid Leukemia (AML)1
4Active Not RecruitingTreatmentAcute Promyelocytic Leukemia (APL)1
4CompletedTreatmentAcute Lymphobkastic Leukemia1
4CompletedTreatmentAcute Lymphoblastic Leukaemias (ALL)6
4CompletedTreatmentAcute Myeloblastic Leukemia1
4CompletedTreatmentAcute Myeloblastic Leukemia / Myelodysplastic Syndrome1
4CompletedTreatmentAcute Myeloid Leukemia (AML)1
4CompletedTreatmentAcute Promyelocytic Leukemia (APL)1
4CompletedTreatmentAdult Acute Lymphocytic Leukemia4
4CompletedTreatmentBurkitt's Lymphoma / Large Cell Anaplastic Lymphoma / Lymphoma, Lymphoblastic / Mediastinal Neoplasms1

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
SolutionIntramuscular; Intrathecal; Intravenous; Subcutaneous100 mg
SolutionIntramuscular; Intrathecal; Intravenous; Subcutaneous500 mg
Injection, solutionIntrathecal; Intravenous; Subcutaneous100 mg/5ml
Injection, solutionIntrathecal; Intravenous; Subcutaneous1000 mg/20ml
Injection, solutionIntrathecal; Intravenous; Subcutaneous40 mg/2ml
InjectionIntravenous1000 mg
Injection, powder, for solutionCutaneous; Parenteral500 MG/10ML
Injection, powder, for solutionParenteral100 MG/5ML
Injection, powder, for solutionParenteral500 MG/10ML
Injection
Injection, powder, lyophilized, for solutionIntrathecal; Intravenous; Subcutaneous100 mg
Injection, powder, for solutionIntrathecal; Intravenous; Subcutaneous1000 mg
Injection, powder, for solutionIntrathecal; Intravenous; Subcutaneous500 mg
SolutionIntrathecal; Intravenous; Subcutaneous500 mg
Injection, solutionParenteral1 G/50ML
Injection, solutionParenteral1 G/10ML
Injection, solutionParenteral100 MG/5ML
Injection, solutionParenteral2 G/20ML
Injection, solutionParenteral500 MG/5ML
Injection, solutionParenteral100 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; Subcutaneous
SolutionIntrathecal; Intravenous; Subcutaneous100 mg/5ml
SolutionIntravenous; Subcutaneous100 mg/1ml
LiquidIntravenous; Subcutaneous
Injection40 mg
SolutionIntrathecal; Intravenous; Subcutaneous
Injection, solution100 mg/ml
Injection, solution1000 mg/10ml
Injection, solution500 mg/5ml
Injection, lipid complexIntrathecal50 mg/5mL
SuspensionIntrathecal10 mg
Injection, suspensionIntrathecal50 mg
Injection, solutionIntrathecal; Intravenous; Subcutaneous500 mg/25ml
Injection, powder, lyophilized, for suspensionIntravenous
SolutionIntravenous1000 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
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

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)-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 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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
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

Targets

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. [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]
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. [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]

Enzymes

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. [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
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. [PubMed:15204103]
  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. [PubMed:30920135]
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. [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
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. [PubMed:19842938]
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. [PubMed:19842938]

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. [PubMed:10825466]
  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. [PubMed:28209616]
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. [PubMed:19118001]
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. [PubMed:20082300]

Drug created on June 13, 2005 07:24 / Updated on September 24, 2020 02:08

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