Cytarabine
Vue d'ensemble
Description
Cytarabine, également connue sous le nom d’arabinoside de cytosine, est un médicament de chimiothérapie principalement utilisé pour traiter diverses formes de leucémie, notamment la leucémie aiguë myéloïde, la leucémie aiguë lymphoblastique et la leucémie myéloïde chronique. Il est également utilisé dans le traitement du lymphome non hodgkinien. La this compound est un analogue nucléosidique de la pyrimidine qui inhibe la synthèse de l’ADN, ce qui la rend efficace pour cibler les cellules cancéreuses qui se divisent rapidement .
Mécanisme D'action
La cytarabine exerce ses effets en inhibant l’ADN polymérase, une enzyme essentielle à la synthèse de l’ADN. Elle est incorporée à l’ADN pendant la phase S du cycle cellulaire, ce qui entraîne la terminaison de l’élongation de la chaîne d’ADN et, finalement, la mort cellulaire. Ce mécanisme rend la this compound particulièrement efficace contre les cellules cancéreuses qui se divisent rapidement .
Applications De Recherche Scientifique
Pharmacokinetics
Cytarabine is poorly absorbed when taken orally due to extensive first-pass metabolism; therefore, it is typically administered via intravenous or subcutaneous routes. Its pharmacokinetic properties include:
- Bioavailability: High when administered intravenously.
- Volume of Distribution: High due to low plasma protein binding.
- Metabolism: Primarily occurs in the liver with renal excretion of metabolites .
Clinical Applications
This compound has a wide range of applications in oncology, particularly for treating different types of leukemia. Below are some key indications:
Liposomal Formulations
Recent advancements have led to the development of liposomal formulations of this compound, which improve its pharmacokinetic profile and reduce systemic toxicity. Liposomal this compound has shown efficacy in treating CNS relapses in ALL and has been compared favorably to traditional therapies .
Efficacy Studies
A study evaluating liposomal this compound for CNS relapse in ALL demonstrated comparable safety and efficacy profiles to methotrexate and traditional this compound formulations. The European Working Group for Adult ALL initiated trials to further explore this application .
Case Studies
-
Case Study: Liposomal this compound in CNS Relapse
- Patient Profile: Adult patient with recurrent ALL.
- Treatment Regimen: Administered liposomal this compound.
- Outcome: Achieved significant CNS response after one cycle; tolerated well without severe adverse effects.
-
Case Study: Differentiation Induction
- Patient Profile: AML patient receiving low-dose this compound.
- Treatment Regimen: Low-dose this compound combined with differentiation agents.
- Outcome: Induced maturation of leukemic cells without significant toxicity, suggesting potential as a differentiation therapy.
Analyse Biochimique
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 .
Méthodes De Préparation
Voies de synthèse et conditions de réaction
La cytarabine est synthétisée à partir de la cytidine par une série de réactions chimiques. La méthode de préparation traditionnelle implique l’utilisation d’acide polyphosphorique pour synthétiser la this compound à partir de la cytidine. Les conditions de réaction comprennent généralement un chauffage et l’utilisation de solvants tels que l’eau et l’alcool. Le rendement de ce processus varie de 29 % à 40 % .
Méthodes de production industrielle
Dans les milieux industriels, la this compound est produite en grandes quantités en utilisant des voies de synthèse similaires, mais avec des conditions de réaction optimisées pour maximiser le rendement et la pureté. Le processus implique l’utilisation de techniques de purification avancées pour garantir que le produit final répond aux normes pharmaceutiques .
Analyse Des Réactions Chimiques
Types de réactions
La cytarabine subit diverses réactions chimiques, notamment :
Oxydation : La this compound peut être oxydée pour former différents dérivés.
Réduction : Les réactions de réduction peuvent modifier les groupes fonctionnels de la molécule de this compound.
Substitution : Les réactions de substitution peuvent remplacer des atomes ou des groupes spécifiques dans la structure de la this compound.
Réactifs et conditions courants
Les réactifs courants utilisés dans ces réactions comprennent des agents oxydants comme le peroxyde d’hydrogène, des agents réducteurs comme le borohydrure de sodium et divers catalyseurs pour faciliter les réactions de substitution. Les conditions de réaction impliquent souvent des températures et des niveaux de pH contrôlés pour assurer les transformations chimiques souhaitées .
Principaux produits
Les principaux produits formés à partir de ces réactions comprennent divers dérivés de la this compound, qui peuvent avoir des propriétés pharmacologiques et des applications différentes .
Applications de la recherche scientifique
La this compound a un large éventail d’applications de recherche scientifique :
Comparaison Avec Des Composés Similaires
Composés similaires
Fludarabine : Un autre analogue nucléosidique utilisé dans le traitement de la leucémie.
Cladribine : Utilisé pour traiter la leucémie à tricholeucocytes et la sclérose en plaques.
Gémcitabine : Employée dans le traitement de divers cancers, notamment le cancer du pancréas et le cancer du sein.
Unicité de la cytarabine
La this compound est unique en raison de son mécanisme d’action spécifique, ciblant l’ADN polymérase et son incorporation dans l’ADN. Cette spécificité la rend très efficace dans le traitement de certains types de leucémie. De plus, son utilisation dans des formulations liposomales a montré une cardiotoxicité réduite par rapport à d’autres agents chimiothérapeutiques .
Activité Biologique
Cytarabine, also known as cytosine β-D-arabinofuranoside, is a pyrimidine nucleoside analog primarily used in the treatment of acute myeloid leukemia (AML) and other hematological malignancies. Its biological activity is characterized by its ability to inhibit DNA synthesis, thereby exerting cytotoxic effects on rapidly dividing cells. This article explores the mechanisms of action, pharmacokinetics, clinical efficacy, and recent advancements in drug formulations related to this compound.
This compound's primary mechanism involves its conversion into this compound triphosphate (Ara-CTP) within the cell. This active form competes with deoxycytidine triphosphate (dCTP) for incorporation into DNA during replication. The incorporation of Ara-CTP results in the termination of DNA chain elongation, leading to cell cycle arrest at the S-phase and subsequent apoptosis of malignant cells.
- Key Enzymes Involved :
- Deoxycytidine kinase (DCK) activates this compound by phosphorylating it to Ara-CTP.
- Cytidine deaminase (CDA) is responsible for the catabolism of this compound, influencing its bioavailability and efficacy.
Pharmacokinetics
This compound has a short plasma half-life, typically around 1 to 3 hours, necessitating continuous infusion or frequent dosing to maintain therapeutic levels. Its pharmacokinetic profile can be affected by various factors including patient genetics and concurrent medications.
| Parameter | Value |
|---|---|
| Half-life | 1-3 hours |
| Peak plasma levels | ~0.5 hours post-infusion |
| Bioavailability | Variable (due to CDA activity) |
Clinical Efficacy
This compound is a cornerstone in the treatment regimens for AML and is often used in combination with other agents such as anthracyclines. The efficacy varies among patients due to genetic polymorphisms affecting drug metabolism.
Case Studies
- Ewing Sarcoma : A Phase II study demonstrated that intermediate doses of this compound significantly reduced EWS/FLI1 protein levels in Ewing sarcoma cells both in vitro and in vivo, indicating potential utility beyond traditional leukemias .
- Acute Myeloid Leukemia : Clinical trials have shown that high-dose this compound regimens improve remission rates in patients with AML, particularly those with favorable cytogenetics .
Recent Advancements
Recent research has focused on enhancing the delivery and efficacy of this compound through novel drug formulations:
- Cholic Acid-Cytarabine Conjugates : These liver-targeting conjugates have shown improved absorption and specificity for hepatic tissues, potentially reducing systemic toxicity while maintaining antitumor activity .
- Pharmacogenomic Biomarkers : Studies are exploring genetic markers that predict patient response to this compound therapy, aiming to tailor treatments based on individual metabolic profiles .
Propriétés
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. | |
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| 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 | |
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| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| 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. | |
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 | |
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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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| Record name | Cytarabine [USAN:USP:INN:BAN:JAN] | |
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| Record name | Cytarabine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00987 | |
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| Record name | Cytarabine | |
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| Record name | CYTARABINE | |
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| Record name | CYTARABINE | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3049 | |
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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. | |
Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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Veuillez noter que tous les articles et informations sur les produits présentés sur BenchChem sont destinés uniquement à des fins informatives. Les produits disponibles à l'achat sur BenchChem sont spécifiquement conçus pour des études in vitro, qui sont réalisées en dehors des organismes vivants. Les études in vitro, dérivées du terme latin "in verre", impliquent des expériences réalisées dans des environnements de laboratoire contrôlés à l'aide de cellules ou de tissus. Il est important de noter que ces produits ne sont pas classés comme médicaments et n'ont pas reçu l'approbation de la FDA pour la prévention, le traitement ou la guérison de toute condition médicale, affection ou maladie. Nous devons souligner que toute forme d'introduction corporelle de ces produits chez les humains ou les animaux est strictement interdite par la loi. Il est essentiel de respecter ces directives pour assurer la conformité aux normes légales et éthiques en matière de recherche et d'expérimentation.
