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
Structure for Cytarabine (DB00987)
- 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.
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
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- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- 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.
Target Actions Organism ADNA polymerase beta inhibitorHumans ADNA cross-linking/alkylationHumans - 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
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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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbatacept The risk or severity of adverse effects can be increased when Cytarabine is combined with Abatacept. Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with Cytarabine. Acenocoumarol The risk or severity of bleeding can be increased when Acenocoumarol is combined with Cytarabine. Acetylsalicylic acid The risk or severity of bleeding can be increased when Acetylsalicylic acid is combined with Cytarabine. Acipimox The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Cytarabine is combined with Acipimox. Acyclovir The risk or severity of adverse effects can be increased when Acyclovir is combined with Cytarabine. Adalimumab The risk or severity of adverse effects can be increased when Adalimumab is combined with Cytarabine. Adenovirus type 7 vaccine live The risk or severity of infection can be increased when Adenovirus type 7 vaccine live is combined with Cytarabine. Aldesleukin The risk or severity of adverse effects can be increased when Aldesleukin is combined with Cytarabine. Alefacept The risk or severity of adverse effects can be increased when Alefacept is combined with Cytarabine. 
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- No interactions found.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- Product Ingredients
Ingredient UNII CAS InChI Key Cytarabine hydrochloride 33K3DB6591 69-74-9 KCURWTAZOZXKSJ-JBMRGDGGSA-N - International/Other Brands
- Ara-C (Gobbi) / Cytosar-U (Pfizer)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cytarabine Injection 20 mg/1mL Intravenous; Subcutaneous Gland Pharma Limited 2011-12-14 Not applicable US 
Cytarabine Injection 100 mg/5mL Intrathecal; Intravenous; Subcutaneous Gland Pharma Limited 2018-02-14 Not applicable US Cytarabine - Pws 1gn/vial Powder, for solution 1 g / vial Intrathecal; Intravenous; Subcutaneous Novopharm Limited 1995-12-31 2015-10-26 Canada 
Cytarabine - Pws 2gm/vial Powder, for solution 2 g / vial Intrathecal; Intravenous; Subcutaneous Novopharm Limited 1995-12-31 2015-10-26 Canada Cytarabine - Pws 500mg/vial Powder, for solution 500 mg / vial Intrathecal; Intravenous; Subcutaneous Novopharm Limited 1995-12-31 2015-10-26 Canada Cytarabine Inj 100mg/ml Liquid 100 mg / mL Intravenous; Subcutaneous David Bull Laboratories (Pty) Ltd. 1992-12-31 1998-08-13 Canada Cytarabine Injection Solution 100 mg / mL Intrathecal; Intravenous; Subcutaneous Pfizer Canada Ulc 1996-09-23 Not applicable Canada Cytarabine Injection Solution 100 mg / mL Intrathecal; Intravenous; Subcutaneous Sterimax Inc Not applicable Not applicable Canada Cytarabine Injection BP Solution 100 mg / mL Intrathecal; Intravenous; Subcutaneous Sandoz Canada Incorporated Not applicable Not applicable Canada Cytarabine Injection, Mylan Std. Solution 100 mg / mL Intrathecal; Intravenous; Subcutaneous Mylan Pharmaceuticals Not applicable Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Aj-cytarabine Solution 100 mg / mL Intrathecal; Intravenous; Subcutaneous Agila Jamp Canada Inc Not applicable Not applicable Canada Cytarabine Injection 20 mg/1mL Intravenous; Subcutaneous Pfizer Laboratories Div Pfizer Inc. 2014-06-30 2014-06-30 US Cytarabine Injection, solution 100 mg/1mL Intrathecal; Intravenous; Subcutaneous Hospira, Inc. 1999-11-22 Not applicable US Cytarabine Injection 2 g/20mL Intrathecal; Intravenous; Subcutaneous Mylan Institutional LLC 2012-01-31 2022-12-31 US Cytarabine Injection 100 mg/5mL Intrathecal; Intravenous; Subcutaneous Pfizer Laboratories Div Pfizer Inc. 2011-12-14 2017-12-31 US Cytarabine Injection, powder, lyophilized, for solution 1 g/10mL Intrathecal; Intravenous; Subcutaneous Bedford Pharmaceuticals 1996-06-28 2014-08-31 US Cytarabine Injection, solution 20 mg/1mL Intrathecal; Intravenous; Subcutaneous Gland Pharma Limited 2019-12-23 Not applicable US Cytarabine Injection, powder, lyophilized, for solution 2 g/20mL Intrathecal; Intravenous; Subcutaneous Bedford Pharmaceuticals 1996-05-01 2011-03-31 US Cytarabine Injection, solution 20 mg/1mL Intravenous Hospira, Inc. 1990-08-31 Not applicable US Cytarabine Injection 20 mg/1mL Intravenous; Subcutaneous Mylan Institutional LLC 2011-12-14 2021-12-31 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Vyxeos Cytarabine (100 mg/20mL) + Daunorubicin (44 mg/20mL) Injection, powder, lyophilized, for suspension Intravenous Jazz Pharmaceuticals, Inc. 2017-08-03 Not applicable US Vyxeos Cytarabine (100 mg) + Daunorubicin (44 mg) Powder Intravenous Jazz Pharmaceuticals Ireland Limited Not applicable Not applicable Canada Vyxeos Liposomal Cytarabine (5 mg/ml) + Daunorubicin hydrochloride (2.2 mg/ml) Injection, powder, for solution Intravenous Jazz Pharmaceuticals Ireland Limited 2020-12-16 Not applicable EU 
Vyxeos Liposomal Cytarabine (5 mg/ml) + Daunorubicin hydrochloride (2.2 mg/ml) Injection, powder, for solution Intravenous Jazz Pharmaceuticals Ireland Limited 2020-12-16 Not applicable EU Vyxeos Liposomal Cytarabine (5 mg/ml) + Daunorubicin hydrochloride (2.2 mg/ml) Injection, powder, for solution Intravenous Jazz Pharmaceuticals Ireland Limited 2020-12-16 Not applicable EU - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image CYTARABINE DBL 10 ML 1 GR FLAKON, 1 ADET Cytarabine (100 mg/5ml) Solution Intrathecal; Intravenous; Subcutaneous ORNA İLAÇ TEKSTİL KİMYEVİ MAD. SAN. VE DIŞ TİC. LTD. ŞTİ. 2020-08-14 Not applicable Turkey 
Categories
- ATC Codes
- L01BC01 — Cytarabine
- L01BC — Pyrimidine analogues
- L01B — ANTIMETABOLITES
- L01 — ANTINEOPLASTIC AGENTS
- L — ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
- Drug Categories
- Agents Causing Muscle Toxicity
- Anti-Infective Agents
- Antimetabolites
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Arabinonucleosides
- Carbohydrates
- Cardiotoxic antineoplastic agents
- Cytidine Deaminase Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index
- Cytochrome P-450 Substrates
- Glycosides
- Immunologic Factors
- Immunosuppressive Agents
- Myelosuppressive Agents
- Narrow Therapeutic Index Drugs
- Noxae
- Nucleic Acid Synthesis Inhibitors
- Nucleic Acids, Nucleotides, and Nucleosides
- Nucleoside Metabolic Inhibitor
- Nucleosides
- OCT1 substrates
- Pyrimidine Analogues
- Pyrimidine Nucleosides
- Pyrimidines
- Ribonucleosides
- Toxic Actions
- 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
- External Links
- Human Metabolome Database
- HMDB0015122
- KEGG Drug
- D00168
- KEGG Compound
- C02961
- PubChem Compound
- 6253
- PubChem Substance
- 46505879
- ChemSpider
- 6017
- BindingDB
- 50087289
- 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
Phase Status Purpose Conditions Count 4 Active Not Recruiting Prevention Acute Myeloid Leukemia (AML) 1 4 Active Not Recruiting Treatment Acute Promyelocytic Leukemia (APL) 1 4 Completed Treatment Acute Lymphobkastic Leukemia 1 4 Completed Treatment Acute Lymphoblastic Leukaemias (ALL) 6 4 Completed Treatment Acute Myeloblastic Leukemia 1 4 Completed Treatment Acute Myeloblastic Leukemia / Myelodysplastic Syndrome 1 4 Completed Treatment Acute Myeloid Leukemia (AML) 1 4 Completed Treatment Acute Promyelocytic Leukemia (APL) 1 4 Completed Treatment Adult Acute Lymphocytic Leukemia 4 4 Completed Treatment Burkitt's Lymphoma / Large Cell Anaplastic Lymphoma / Lymphoma, Lymphoblastic / Mediastinal Neoplasms 1
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
Form Route Strength Solution Intramuscular; Intrathecal; Intravenous; Subcutaneous 100 mg Solution Intramuscular; Intrathecal; Intravenous; Subcutaneous 500 mg Injection, solution Intrathecal; Intravenous; Subcutaneous Injection, solution, concentrate Intravenous Solution Intravenous; Subcutaneous 1000 mg Injection Parenteral Solution Parenteral 40 mg Injection Intravenous Injection, powder, for solution Parenteral Injection, powder, for solution Parenteral; Subcutaneous Injection, solution 100 mg/1ml Injection, powder, lyophilized, for solution Intrathecal; Intravenous; Subcutaneous 100 mg Solution Intrathecal; Intravenous; Subcutaneous 100 mg Injection, powder, for solution Intrathecal; Intravenous; Subcutaneous 1000 mg Solution Parenteral 100 mg Injection, powder, for solution Intrathecal; Intravenous; Subcutaneous 500 mg Solution Intravenous; Subcutaneous 500 mg Injection, powder, lyophilized, for solution Intravenous 500 mg Solution Intrathecal; Intravenous; Subcutaneous 500 mg Injection, powder, for solution Solution Intravenous 100 mg Solution Intravenous 500 mg Solution Intravenous; Subcutaneous 100 mg Injection, solution Injection, solution Parenteral Injection Intrathecal; Intravenous; Subcutaneous 100 mg/5mL Injection Intrathecal; Intravenous; Subcutaneous 2 g/20mL Injection Intravenous; Subcutaneous 20 mg/1mL Injection, powder, lyophilized, for solution Intrathecal; Intravenous; Subcutaneous 1 g/10mL Injection, powder, lyophilized, for solution Intrathecal; Intravenous; Subcutaneous 100 mg/5mL Injection, powder, lyophilized, for solution Intrathecal; Intravenous; Subcutaneous 2 g/20mL Injection, powder, lyophilized, for solution Intrathecal; Intravenous; Subcutaneous 500 mg/10mL Injection, solution Intrathecal; Intravenous; Subcutaneous 100 mg/1mL Injection, solution Intrathecal; Intravenous; Subcutaneous 2 g/20mL Injection, solution Intrathecal; Intravenous; Subcutaneous 20 mg/1mL Injection, solution Intravenous 20 mg/1mL Injection, solution Intravenous; Subcutaneous 20 mg/1mL Powder, for solution Intrathecal; Intravenous; Subcutaneous 1 g / vial Powder, for solution Intrathecal; Intravenous; Subcutaneous 2 g / vial Powder, for solution Intrathecal; Intravenous; Subcutaneous 500 mg / vial Solution Intrathecal; Intravenous; Subcutaneous Injection Intrathecal; Intravenous; Subcutaneous Solution Intravenous; Subcutaneous Liquid Intravenous; Subcutaneous 100 mg / mL Solution Intravenous 1000 mg Solution Intrathecal; Intravenous; Subcutaneous 100 mg / mL Injection, powder, lyophilized, for solution Parenteral 100 mg Powder, for solution Intrathecal; Intravenous; Subcutaneous 100 mg / vial Solution 100 mg/1ml Solution 20 mg/1ml Injection Injection, lipid complex Intrathecal 50 mg/5mL Suspension Intrathecal 10 mg / mL Injection, suspension Intrathecal Injection, suspension Intrathecal 50 mg Solution Intrathecal; Intravenous 500 mg Solution Intrathecal; Intravenous; Subcutaneous 20 mg / mL Injection, powder, lyophilized, for suspension Intravenous Powder Intravenous Injection, powder, for solution Intravenous Powder Intravenous; Parenteral - Prices
Unit description Cost Unit Depocyt 50 mg/5 ml vial 588.0USD ml Cytarabine 2 gm vial 48.0USD vial Cytarabine 1 gm vial 24.0USD vial DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5723147 No 1998-03-03 2015-03-03 US US5455044 No 1995-10-03 2013-05-14 US US7850990 No 2010-12-14 2027-01-23 US US8022279 No 2011-09-20 2027-09-14 US US8431806 No 2013-04-30 2025-04-22 US US8092828 No 2012-01-10 2029-04-01 US US8518437 No 2013-08-27 2026-06-07 US US9271931 No 2016-03-01 2027-01-23 US US10028912 No 2018-07-24 2034-09-29 US US10166184 No 2019-01-01 2032-10-15 US US10835492 No 2012-10-15 2032-10-15 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 186-188 Hunter, J.H.; U S . Patent 3,116,282; December 31,1963; assigned to The Upjohn Company. water solubility Freely soluble Not Available logP -2.8 Not Available - Predicted Properties
Property Value Source Water Solubility 43.8 mg/mL ALOGPS logP -2.2 ALOGPS logP -2.8 ChemAxon logS -0.74 ALOGPS pKa (Strongest Acidic) 12.55 ChemAxon pKa (Strongest Basic) -0.55 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 128.61 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 54.54 m3·mol-1 ChemAxon Polarizability 22.21 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9623 Blood Brain Barrier + 0.9465 Caco-2 permeable - 0.8887 P-glycoprotein substrate Non-substrate 0.798 P-glycoprotein inhibitor I Non-inhibitor 0.9686 P-glycoprotein inhibitor II Non-inhibitor 0.9532 Renal organic cation transporter Non-inhibitor 0.9519 CYP450 2C9 substrate Non-substrate 0.793 CYP450 2D6 substrate Non-substrate 0.8613 CYP450 3A4 substrate Non-substrate 0.6203 CYP450 1A2 substrate Non-inhibitor 0.9543 CYP450 2C9 inhibitor Non-inhibitor 0.9638 CYP450 2D6 inhibitor Non-inhibitor 0.9497 CYP450 2C19 inhibitor Non-inhibitor 0.9489 CYP450 3A4 inhibitor Non-inhibitor 0.9609 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.981 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.9158 Biodegradation Not ready biodegradable 0.7807 Rat acute toxicity 1.7184 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.983 hERG inhibition (predictor II) Non-inhibitor 0.911
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
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- 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
- 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]
- Miura S, Izuta S: DNA polymerases as targets of anticancer nucleosides. Curr Drug Targets. 2004 Feb;5(2):191-5. [Article]
- 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]
Yes
Cross-linking/alkylation
References
- 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]
- 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
- 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
- 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]
- 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
- 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
- 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]
- 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
- 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]
- 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
- 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
- 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
- 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]
- 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
- 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
- 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 on June 13, 2005 13:24 / Updated on July 23, 2021 16:02