Methotrexat
Übersicht
Beschreibung
Methotrexate, formerly known as amethopterin, is a chemotherapy agent and immune-system suppressant. It is widely used to treat various types of cancer, autoimmune diseases, and ectopic pregnancies. The compound is particularly effective against breast cancer, leukemia, lung cancer, lymphoma, gestational trophoblastic disease, and osteosarcoma . Additionally, it is used to manage autoimmune conditions such as psoriasis, rheumatoid arthritis, and Crohn’s disease .
Wirkmechanismus
- 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
Wissenschaftliche Forschungsanwendungen
Methotrexat hat eine breite Palette von Anwendungen in der wissenschaftlichen Forschung:
5. Wirkmechanismus
This compound übt seine Wirkung aus, indem es verschiedene Enzyme hemmt, die für die Nukleotidsynthese verantwortlich sind, darunter Dihydrofolat-Reduktase, Thymidylat-Synthase und Aminoimidazol-Carboxamid-Ribonukleotid-Transformylase . Diese Hemmung führt zur Unterdrückung der DNS-Synthese und Zellteilung, wodurch es gegen schnell wachsende Krebszellen wirksam ist . Darüber hinaus fördert this compound die Freisetzung von Adenosin, das entzündungshemmende Wirkungen hat .
Biochemische Analyse
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 .
Vorbereitungsmethoden
Synthetische Wege und Reaktionsbedingungen: Methotrexat wird durch einen mehrstufigen Prozess synthetisiert, der die Reaktion von 4-Aminobenzoesäure mit 2,4-Diamino-6-hydroxypyrimidin zur Bildung von 4-Amino-4-desoxy-N10-methylpteroinsäure beinhaltet. Dieser Zwischenstoff wird dann mit L-Glutaminsäure gekoppelt, um this compound zu erhalten .
Industrielle Produktionsmethoden: Die industrielle Produktion von this compound beinhaltet die großtechnische Synthese unter ähnlichen Reaktionsbedingungen wie die Laborsynthese, jedoch optimiert für höhere Ausbeuten und Reinheit. Der Prozess umfasst strenge Reinigungsschritte wie Kristallisation und Chromatographie, um sicherzustellen, dass das Endprodukt pharmazeutische Standards erfüllt .
Analyse Chemischer Reaktionen
Arten von Reaktionen: Methotrexat unterliegt verschiedenen chemischen Reaktionen, einschließlich Oxidation, Reduktion und Substitution.
Häufige Reagenzien und Bedingungen:
Oxidation: this compound kann mit Oxidationsmitteln wie Wasserstoffperoxid unter sauren Bedingungen oxidiert werden.
Reduktion: Reduktionsreaktionen beinhalten die Verwendung von Reduktionsmitteln wie Natriumborhydrid.
Substitution: Substitutionsreaktionen können mit Nukleophilen wie Aminen unter basischen Bedingungen auftreten.
Hauptprodukte: Zu den Hauptprodukten, die aus diesen Reaktionen entstehen, gehören 7-Hydroxythis compound und andere Metaboliten, die eine gewisse biologische Aktivität behalten .
Vergleich Mit ähnlichen Verbindungen
Methotrexat ist strukturell ähnlich wie Folsäure und Aminopterin. Es ist einzigartig in seiner N-methylierten Form, die seine Potenz als Antimetabolit erhöht . Ähnliche Verbindungen umfassen:
Aminopterin: Ein früheres Antifolatmittel mit ähnlichen Mechanismen, aber höherer Toxizität.
Pemetrexed: Ein weiteres Antifolat, das in der Krebstherapie eingesetzt wird, mit einem breiteren Wirkungsspektrum.
Raltitrexed: Ein Thymidylat-Synthase-Inhibitor, der bei Darmkrebs eingesetzt wird.
Die einzigartige Struktur und der Wirkmechanismus von this compound machen es zu einem wertvollen therapeutischen Mittel mit vielfältigen Anwendungen in Medizin und Forschung.
Eigenschaften
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
|
| Record name | Methotrexate | |
| Source | EPA DSSTox | |
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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) | |
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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 |
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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 | |
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| 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
|
| 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 | |
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| Record name | METHOTREXATE | |
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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 | 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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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 | |
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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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| Source | Occupational Safety and Health Administration (OSHA) | |
| URL | https://www.osha.gov/chemicaldata/874 | |
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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. | |
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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