Méthotrexate
Vue d'ensemble
Description
Le méthotrexate, anciennement connu sous le nom d'améthoptérine, est un agent chimiothérapeutique et un immunosuppresseur. Il est largement utilisé pour traiter divers types de cancer, les maladies auto-immunes et les grossesses extra-utérines. Le composé est particulièrement efficace contre le cancer du sein, la leucémie, le cancer du poumon, le lymphome, la maladie trophoblastique gestationnelle et l'ostéosarcome . De plus, il est utilisé pour gérer les affections auto-immunes telles que le psoriasis, la polyarthrite rhumatoïde et la maladie de Crohn .
Mécanisme D'action
- MTX primarily targets enzymes involved in nucleotide synthesis. These include:
- Dihydrofolate reductase (DHFR) : MTX competitively inhibits DHFR, an enzyme essential for tetrahydrofolate synthesis. By blocking this step, MTX disrupts the production of folate derivatives needed for DNA synthesis and cell proliferation .
- Thymidylate synthase : MTX inhibits thymidylate synthase, which catalyzes the conversion of deoxyuridine monophosphate (dUMP) to deoxythymidine monophosphate (dTMP). This affects DNA synthesis and repair .
- Aminoimidazole carboxamide ribonucleotide transformylase (AICART) : MTX inhibits AICART, an enzyme involved in purine biosynthesis. Reduced purine availability impacts cell division, especially in T-lymphocytes .
- Amido phosphoribosyltransferase : MTX also inhibits this enzyme, further disrupting purine synthesis .
- MTX affects several pathways:
Target of Action
Mode of Action
Biochemical Pathways
Pharmacokinetics
Applications De Recherche Scientifique
Methotrexate has a wide range of applications in scientific research:
Analyse Biochimique
Biochemical Properties
Methotrexate plays a significant role in biochemical reactions. It interacts with enzymes, proteins, and other biomolecules. For instance, it is known to inhibit the enzyme dihydrofolate reductase (DHFR), which is involved in the synthesis of tetrahydrofolate, a cofactor required for the synthesis of nucleotides .
Cellular Effects
Methotrexate has profound effects on various types of cells and cellular processes. It influences cell function by impacting cell signaling pathways, gene expression, and cellular metabolism. For example, by inhibiting DHFR, Methotrexate disrupts the synthesis of nucleotides, thereby affecting DNA replication and cell division .
Molecular Mechanism
Methotrexate exerts its effects at the molecular level through binding interactions with biomolecules, enzyme inhibition, and changes in gene expression. Its primary mechanism of action is the competitive inhibition of DHFR, which leads to a decrease in the synthesis of nucleotides and subsequently affects DNA replication .
Temporal Effects in Laboratory Settings
The effects of Methotrexate change over time in laboratory settings. Information on the product’s stability, degradation, and any long-term effects on cellular function observed in in vitro or in vivo studies is crucial. For instance, a study using high-performance liquid chromatography–selected reaction monitoring– mass spectrometry (HPLC-SRM-MS) based biochemical analysis of drug levels was conducted to monitor Methotrexate adherence .
Dosage Effects in Animal Models
The effects of Methotrexate vary with different dosages in animal models. High doses of Methotrexate can lead to toxic or adverse effects. The specific threshold effects observed in these studies are beyond the scope of this article .
Metabolic Pathways
Methotrexate is involved in various metabolic pathways. It interacts with enzymes or cofactors, and it can affect metabolic flux or metabolite levels. For example, by inhibiting DHFR, Methotrexate disrupts the folate metabolic pathway .
Transport and Distribution
Methotrexate is transported and distributed within cells and tissues. It can interact with various transporters or binding proteins, and it can affect its localization or accumulation .
Subcellular Localization
The subcellular localization of Methotrexate and its effects on its activity or function are crucial. Methotrexate primarily localizes in the cytoplasm where it exerts its inhibitory effects on DHFR .
Méthodes De Préparation
Voies de synthèse et conditions de réaction : Le méthotrexate est synthétisé par un processus en plusieurs étapes impliquant la réaction de l'acide 4-aminobenzoïque avec la 2,4-diamino-6-hydroxypyrimidine pour former l'acide 4-amino-4-désoxy-N10-méthylptéroïque. Cet intermédiaire est ensuite couplé à l'acide L-glutamique pour produire du this compound .
Méthodes de production industrielle : La production industrielle de this compound implique une synthèse à grande échelle utilisant des conditions de réaction similaires à celles de la synthèse en laboratoire, mais optimisées pour des rendements et une pureté plus élevés. Le processus comprend des étapes de purification rigoureuses telles que la cristallisation et la chromatographie pour garantir que le produit final répond aux normes pharmaceutiques .
Analyse Des Réactions Chimiques
Types de réactions : Le méthotrexate subit diverses réactions chimiques, notamment l'oxydation, la réduction et la substitution.
Réactifs et conditions courantes :
Oxydation : Le this compound peut être oxydé en utilisant des agents comme le peroxyde d'hydrogène en conditions acides.
Réduction : Les réactions de réduction impliquent l'utilisation d'agents réducteurs tels que le borohydrure de sodium.
Substitution : Les réactions de substitution peuvent se produire avec des nucléophiles comme les amines en conditions basiques.
Principaux produits : Les principaux produits formés à partir de ces réactions comprennent le 7-hydroxythis compound et d'autres métabolites qui conservent une certaine activité biologique .
4. Applications de la recherche scientifique
Le this compound a une large gamme d'applications dans la recherche scientifique :
Chimie : Utilisé comme composé modèle pour étudier le métabolisme des folates et l'inhibition enzymatique.
Biologie : Étudié pour ses effets sur la prolifération cellulaire et l'apoptose dans diverses lignées cellulaires.
5. Mécanisme d'action
Le this compound exerce ses effets en inhibant plusieurs enzymes responsables de la synthèse des nucléotides, notamment la dihydrofolate réductase, la thymidylate synthase et l'aminoimidazolecarboxamide ribonucléotide transformylase . Cette inhibition conduit à la suppression de la synthèse de l'ADN et de la division cellulaire, ce qui la rend efficace contre les cellules cancéreuses à division rapide . De plus, le this compound favorise la libération d'adénosine, qui a des effets anti-inflammatoires .
Comparaison Avec Des Composés Similaires
Le méthotrexate est structurellement similaire à l'acide folique et à l'aminoptérine. Il est unique dans sa forme N-méthylée, ce qui améliore sa puissance en tant qu'antimetabolite . Des composés similaires comprennent :
Aminoptérine : Un agent antifolate antérieur avec des mécanismes similaires mais une toxicité plus élevée.
Pemetrexed : Un autre antifolate utilisé dans le traitement du cancer, avec un spectre d'activité plus large.
Raltitrexed : Un inhibiteur de la thymidylate synthase utilisé dans le cancer colorectal.
La structure unique du this compound et son mécanisme d'action en font un agent thérapeutique précieux avec des applications diverses en médecine et en recherche.
Propriétés
IUPAC Name |
(2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C20H22N8O5/c1-28(9-11-8-23-17-15(24-11)16(21)26-20(22)27-17)12-4-2-10(3-5-12)18(31)25-13(19(32)33)6-7-14(29)30/h2-5,8,13H,6-7,9H2,1H3,(H,25,31)(H,29,30)(H,32,33)(H4,21,22,23,26,27)/t13-/m0/s1 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
FBOZXECLQNJBKD-ZDUSSCGKSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Isomeric SMILES |
CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)O)C(=O)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C20H22N8O5 |
Source
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| Record name | METHOTREXATE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20602 | |
| 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 |
15475-56-6 (hydrochloride salt), 7413-34-5 (di-hydrochloride salt) |
Source
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| Record name | Methotrexate [USAN:USP:INN:BAN:JAN] | |
| Source | ChemIDplus | |
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DSSTOX Substance ID |
DTXSID4020822 |
Source
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| Record name | Methotrexate | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID4020822 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
454.4 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Methotrexate is an odorless yellow to orange-brown crystalline powder. (NTP, 1992) It is a chemotherapy drug that interferes with DNA and RNA synthesis., Solid, Bright yellow-orange, odorless, crystalline powder. |
Source
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| Record name | METHOTREXATE | |
| Source | CAMEO Chemicals | |
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| 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 | Methotrexate | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014703 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
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| Record name | METHOTREXATE | |
| Source | Occupational Safety and Health Administration (OSHA) | |
| URL | https://www.osha.gov/chemicaldata/874 | |
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Solubility |
less than 1 mg/mL at 66 °F (NTP, 1992), Insoluble in water , alcohol, chloroform, ether; slightly soluble in dilute hydrochloric acid; soluble in dil solns of alkali hydroxides and carbonates., Practically insoluble in water and in alcohol., In water, 2.6X10+3 mg/L at 25 °C /Estimated/, 1.71e-01 g/L |
Source
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| Record name | METHOTREXATE | |
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| 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 | METHOTREXATE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3123 | |
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| Record name | Methotrexate | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014703 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
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Vapor Pressure |
2.1X10-19 mm Hg at 25 °C /Estimated/ |
Source
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| Record name | METHOTREXATE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3123 | |
| 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. | |
Mechanism of Action |
Methotrexate enters tissues and is converted to a methotrexate polyglutamate by folylpolyglutamate. Methotrexate's mechanism of action is due to its inhibition of enzymes responsible for nucleotide synthesis including dihydrofolate reductase, thymidylate synthase, aminoimidazole caboxamide ribonucleotide transformylase (AICART), and amido phosphoribosyltransferase. Inhibtion of nucleotide synthesis prevents cell division. In rheumatoid arthritis, methotrexate polyglutamates inhibit AICART more than methotrexate. This inhibition leads to accumulation of AICART ribonucleotide, which inhibits adenosine deaminase, leading to an accumulation of adenosine triphosphate and adenosine in the extracellular space, stimulating adenosine receptors, leading to anti-inflammatory action., Methotrexate and its polyglutanate metabolites reversibly inhibits dihydrofolate reductase, the enzyme that reduces folic acid to tetrahydrofolic acid. Inhibition of tetrahydrofolate formation limits the availability of one-carbon fragments necessary for synthesis of purines and the conversion of deoxyuridylate to thymidylate in the synthesis of DNA and cell reproduction. The affinity of dihydrofolate reductase for methotrexate is far greater than its affinity for folic acid or dihydrofolic acid. and, therefore, even very large doses of folic acid given simultaneously will not reverse the effects of methotrexate. Leucovorin calcium, a derivative of tetrahydrofolic acid, may block the effects of methotrexate if given shortly after the antineoplastic agent. Results of one study indicate that methotrexate also causes an increase in intracellular deoxyadenosine triphosphate, which is thought to inhibit ribonucleotide reduction, and polynucleotide ligase, an enzyme concerned in DNA synthesis and repair. Tissues with high rates of cellular proliferation such as neoplasms, psoriatic epidermis, bone marrow, the lining of the GI tract, hair matrix, and fetal cells are most sensitive to the effects of methotrexate., Methotrexate ... has immunosuppressive activity, in part possibly as a result of inhibition of lymphocyte multiplication. The mechanism(s) of action in the management of rheumatoid arthritis of the drug is not known, although suggested mechanisms have included immunosuppressive and/or antiinflammatory effects. |
Source
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| Record name | Methotrexate | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00563 | |
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| Record name | METHOTREXATE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3123 | |
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Color/Form |
Orange-brown, crystalline powder | |
CAS No. |
59-05-2 |
Source
|
| Record name | METHOTREXATE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20602 | |
| 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 | Methotrexate | |
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| Record name | Methotrexate [USAN:USP:INN:BAN:JAN] | |
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| Record name | L-Glutamic acid, N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]- | |
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| Record name | Methotrexate | |
| Source | Human Metabolome Database (HMDB) | |
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| Explanation | Materials created by the federal government are generally part of the public domain and may be used, reproduced and distributed without permission. Therefore, content on this website which is in the public domain may be used without the prior permission of the U.S. Department of Labor (DOL). Warning: Some content - including both images and text - may be the copyrighted property of others and used by the DOL under a license. | |
Melting Point |
365 to 399 °F (decomposes) (NTP, 1992), Melting point: 185-204 °C. /Methotrexate monohydrate/, 195 °C, 356-399 °F |
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| Record name | METHOTREXATE | |
| Source | CAMEO Chemicals | |
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| Record name | Methotrexate | |
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| Record name | METHOTREXATE | |
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| Record name | Methotrexate | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014703 | |
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| Record name | METHOTREXATE | |
| Source | Occupational Safety and Health Administration (OSHA) | |
| URL | https://www.osha.gov/chemicaldata/874 | |
| Description | The OSHA Occupational Chemical Database contains over 800 entries with information such as physical properties, exposure guidelines, etc. | |
| Explanation | Materials created by the federal government are generally part of the public domain and may be used, reproduced and distributed without permission. Therefore, content on this website which is in the public domain may be used without the prior permission of the U.S. Department of Labor (DOL). Warning: Some content - including both images and text - may be the copyrighted property of others and used by the DOL under a license. | |
Retrosynthesis Analysis
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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.
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