Cytarabine
Overview
Description
Cytarabine, also known as cytosine arabinoside, is a chemotherapy medication primarily used to treat various forms of leukemia, including acute myeloid leukemia, acute lymphocytic leukemia, and chronic myelogenous leukemia. It is also used in the treatment of non-Hodgkin’s lymphoma. This compound is a pyrimidine nucleoside analog that inhibits DNA synthesis, making it effective in targeting rapidly dividing cancer cells .
Scientific Research Applications
Mechanism of Action
Target of Action
Cytarabine, also known as cytosine arabinoside (ara-C), is a pyrimidine nucleoside analogue . Its primary target is the DNA synthesis process . It acts specifically during the S phase of the cell cycle, which is the period during which DNA replication occurs .
Mode of Action
This compound exerts its effects through direct DNA damage and incorporation into DNA . It is cytotoxic to a wide variety of proliferating mammalian cells in culture . Under certain conditions, it can block the progression of cells from the G1 phase to the S-phase . The primary action of this compound is the inhibition of DNA polymerase , resulting in decreased DNA synthesis and repair .
Biochemical Pathways
This compound affects the DNA synthesis pathway by inhibiting the function of DNA polymerase . This results in the disruption of normal cell cycle progression, primarily affecting cells undergoing DNA synthesis (S-phase) and potentially blocking the progression of cells from the G1 phase to the S-phase .
Pharmacokinetics
This compound is administered via injection into a vein, under the skin, or into the cerebrospinal fluid . It has a bioavailability of 20% when taken orally . It is metabolized in the liver and has a biphasic elimination half-life of 10 minutes to 1-3 hours . The primary route of excretion is through the kidneys .
Result of Action
The result of this compound’s action is the inhibition of DNA synthesis , leading to cell death . It is cytotoxic to a wide variety of proliferating mammalian cells in culture . It primarily kills cells undergoing DNA synthesis (S-phase) and under certain conditions, blocks the progression of cells from the G1 phase to the S-phase .
Action Environment
The efficacy and stability of this compound can be influenced by various environmental factors For instance, the drug’s effectiveness can be affected by the presence of other medications, the patient’s overall health status, and specific genetic factors.
Safety and Hazards
Cytarabine can cause a severe decrease in the number of blood cells in your bone marrow. This may cause certain symptoms and may increase the risk that you will develop a serious infection or bleeding . Common side effects include bone marrow suppression, vomiting, diarrhea, liver problems, rash, ulcer formation in the mouth, and bleeding . Other serious side effects include loss of consciousness, lung disease, and allergic reactions . Use during pregnancy may harm the baby .
Future Directions
Since 2017, nine agents have been approved for various indications in AML. These included several targeted therapies like venetoclax, FLT3 inhibitors, IDH inhibitors, and others . The management of AML is complicated, highlighting the need for expertise in order to deliver optimal therapy and achieve optimal outcomes . The multiple subentities in AML require very different therapies . In this review, we summarize the important pathophysiologies driving AML, review current therapies in standard practice, and address present and future research directions .
Biochemical Analysis
Biochemical Properties
Cytarabine is a pyrimidine nucleoside analogue 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 . This compound is metabolized intracellularly into its active triphosphate form (cytosine arabinoside triphosphate) .
Cellular Effects
This compound 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 . The mechanisms that critically determine resistance to this compound appear to be related to a deficiency of this compound cellular uptake and retention, overexpression of enzymes inactivating this compound, increased cellular dCTP pools, and increased DNA repair .
Molecular Mechanism
This compound acts through direct DNA damage and incorporation into DNA . This metabolite 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 .
Temporal Effects in Laboratory Settings
This compound’s effects can change over time in laboratory settings. For instance, chemotherapy regimens can induce a suboptimal clinical outcome in a fraction of patients . The individual variability in clinical response to treatments among patients is associated with intracellular accumulation of Ara-CTP due to genetic variants related to metabolic enzymes .
Dosage Effects in Animal Models
The effects of this compound can vary with different dosages in animal models . For instance, a higher dose of this compound leads to toxicity to normal organs and tissues . This toxicity and nonspecific distribution often lead to chemotherapeutic failure and noncompliance .
Metabolic Pathways
This compound is involved in several metabolic pathways. It 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 .
Transport and Distribution
This compound is transported and distributed within cells and tissuesSome studies suggest that lipophilic conjugates, including in combination with delivery vehicles, can be used to control drug delivery, distribution, and therapeutic profiles .
Subcellular Localization
It is known that this compound primarily acts in the S phase of the cell cycle, suggesting that it localizes to the nucleus where DNA replication occurs .
Preparation Methods
Synthetic Routes and Reaction Conditions
Cytarabine is synthesized from cytidine through a series of chemical reactions. The traditional preparation method involves the use of polyphosphoric acid to synthesize this compound from cytidine. The reaction conditions typically include heating and the use of solvents such as water and alcohol. The yield of this process ranges from 29% to 40% .
Industrial Production Methods
In industrial settings, this compound is produced in large quantities using similar synthetic routes but with optimized reaction conditions to maximize yield and purity. The process involves the use of advanced purification techniques to ensure the final product meets pharmaceutical standards .
Chemical Reactions Analysis
Types of Reactions
Cytarabine undergoes various chemical reactions, including:
Oxidation: this compound can be oxidized to form different derivatives.
Reduction: Reduction reactions can modify the functional groups on the this compound molecule.
Substitution: Substitution reactions can replace specific atoms or groups within the this compound structure.
Common Reagents and Conditions
Common reagents used in these reactions include oxidizing agents like hydrogen peroxide, reducing agents like sodium borohydride, and various catalysts to facilitate substitution reactions. The reaction conditions often involve controlled temperatures and pH levels to ensure the desired chemical transformations .
Major Products
The major products formed from these reactions include various this compound derivatives, which can have different pharmacological properties and applications .
Comparison with Similar Compounds
Similar Compounds
Fludarabine: Another nucleoside analog used in the treatment of leukemia.
Cladribine: Used to treat hairy cell leukemia and multiple sclerosis.
Gemcitabine: Employed in the treatment of various cancers, including pancreatic and breast cancer.
Uniqueness of Cytarabine
This compound is unique due to its specific mechanism of action, targeting DNA polymerase and its incorporation into DNA. This specificity makes it highly effective in treating certain types of leukemia. Additionally, its use in liposomal formulations has shown reduced cardiotoxicity compared to other chemotherapeutic agents .
Properties
IUPAC Name |
4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
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 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
UHDGCWIWMRVCDJ-CCXZUQQUSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Isomeric SMILES |
C1=CN(C(=O)N=C1N)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C9H13N3O5 |
Source
|
| Record name | CYTARABINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20078 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Related CAS |
69-74-9 (hydrochloride) |
Source
|
| Record name | Cytarabine [USAN:USP:INN:BAN:JAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000147944 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
DSSTOX Substance ID |
DTXSID3022877 |
Source
|
| Record name | Cytarabine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID3022877 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
243.22 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Cytarabine appears as colorless crystals. Used as an antiviral agent., Solid |
Source
|
| Record name | CYTARABINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20078 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Cytarabine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015122 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Solubility |
>36.5 [ug/mL] (The mean of the results at pH 7.4), Freely soluble, 1 G IN ABOUT 5 ML WATER & 500 ML ALC; 1 G IN ABOUT 1000 ML CHLOROFORM & 300 ML METHANOL, Soluble in water, 4.38e+01 g/L |
Source
|
| Record name | SID47193873 | |
| Source | Burnham Center for Chemical Genomics | |
| URL | https://pubchem.ncbi.nlm.nih.gov/bioassay/1996#section=Data-Table | |
| Description | Aqueous solubility in buffer at pH 7.4 | |
| Record name | Cytarabine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00987 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | CYTARABINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3049 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Cytarabine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015122 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
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., Cytarabine is converted intracellularly to the nucleotide, cytarabine triphosphate (ara-CTP, cytosine arabinoside triphosphate). Although the exact mechanism(s) of action of cytarabine has not been fully elucidated, cytarabine triphosphate appears to inhibit DNA polymerase by competing with the physiologic substrate, deoxycytidine triphosphate, resulting in the inhibition of DNA synthesis. Although limited, incorporation of cytarabine triphosphate into DNA and RNA may also contribute to the cytotoxic effects of the drug., Cytarabine is a potent immunosuppressant which can suppress humoral and/or cellular immune responses; however, the drug does not decrease preexisting antibody titers and has no effect on established delayed hypersensitivity reactions., Cytarabine liposome injection is a sustained-release formulation of the active ingredient cytarabine designed for direct administration into the cerebrospinal fluid (CSF). Cytarabine is a cell cycle phase-specific antineoplastic agent, affecting cells only during the S-phase of cell division. Intracellularly, cytarabine is converted into cytarabine-5'-triphosphate (ara-CTP), which is the active metabolite. The mechanism of action is not completely understood, but it appears that ara-CTP acts primarily through inhibition of DNA polymerase. Incorporation into DNA and RNA may also contribute to cytarabine cytotoxicity. Cytarabine is cytotoxic to a wide variety of proliferating mammalian cells in culture. /Cytarabine liposome injection/ |
Source
|
| Record name | Cytarabine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00987 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
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| Record name | CYTARABINE | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3049 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Color/Form |
Prisms from 50% ethanol, WHITE TO OFF-WHITE CRYSTALLINE POWDER | |
CAS No. |
147-94-4 |
Source
|
| Record name | CYTARABINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20078 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Cytarabine | |
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| URL | https://commonchemistry.cas.org/detail?cas_rn=147-94-4 | |
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| Record name | Cytarabine [USAN:USP:INN:BAN:JAN] | |
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| Record name | CYTARABINE | |
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| Record name | Cytarabine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015122 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Melting Point |
414 to 415 °F (NTP, 1992), 186-188, 212-213 °C, 212 - 213 °C |
Source
|
| Record name | CYTARABINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20078 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Cytarabine | |
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| URL | https://www.drugbank.ca/drugs/DB00987 | |
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| Record name | CYTARABINE | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3049 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Cytarabine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015122 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
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| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
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