molecular formula C20H22N8O5 B535133 Methotrexate CAS No. 59-05-2

Methotrexate

Cat. No.: B535133
CAS No.: 59-05-2
M. Wt: 454.4 g/mol
InChI Key: FBOZXECLQNJBKD-ZDUSSCGKSA-N
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Description

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 .

Mechanism of Action

Biochemical Analysis

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

This compound 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, this compound disrupts the synthesis of nucleotides, thereby affecting DNA replication and cell division .

Molecular Mechanism

This compound 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 this compound 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 this compound adherence .

Dosage Effects in Animal Models

The effects of this compound vary with different dosages in animal models. High doses of this compound can lead to toxic or adverse effects. The specific threshold effects observed in these studies are beyond the scope of this article .

Metabolic Pathways

This compound 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, this compound disrupts the folate metabolic pathway .

Transport and Distribution

This compound 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 this compound and its effects on its activity or function are crucial. This compound primarily localizes in the cytoplasm where it exerts its inhibitory effects on DHFR .

Preparation Methods

Synthetic Routes and Reaction Conditions: Methotrexate is synthesized through a multi-step process involving the reaction of 4-aminobenzoic acid with 2,4-diamino-6-hydroxypyrimidine to form 4-amino-4-deoxy-N10-methylpteroic acid. This intermediate is then coupled with L-glutamic acid to produce this compound .

Industrial Production Methods: Industrial production of this compound involves large-scale synthesis using similar reaction conditions as the laboratory synthesis but optimized for higher yields and purity. The process includes rigorous purification steps such as crystallization and chromatography to ensure the final product meets pharmaceutical standards .

Comparison with Similar Compounds

Methotrexate is structurally similar to folic acid and aminopterin. it is unique in its N-methylated form, which enhances its potency as an antimetabolite . Similar compounds include:

This compound’s unique structure and mechanism of action make it a valuable therapeutic agent with diverse applications in medicine and research.

Properties

IUPAC Name

(2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid
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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 PubChem
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InChI Key

FBOZXECLQNJBKD-ZDUSSCGKSA-N
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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
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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
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Molecular Formula

C20H22N8O5
Record name METHOTREXATE
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Related CAS

15475-56-6 (hydrochloride salt), 7413-34-5 (di-hydrochloride salt)
Record name Methotrexate [USAN:USP:INN:BAN:JAN]
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DSSTOX Substance ID

DTXSID4020822
Record name Methotrexate
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Molecular Weight

454.4 g/mol
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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.
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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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Vapor Pressure

2.1X10-19 mm Hg at 25 °C /Estimated/
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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.
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Color/Form

Orange-brown, crystalline powder

CAS No.

59-05-2
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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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Retrosynthesis Analysis

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Feasible Synthetic Routes

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