67022-39-3

Usage

Uses

1. Used in Anticancer Applications:
Methotrexate γ-Methyl Ester is used as an antineoplastic agent for the treatment of various types of cancer. It functions by inhibiting the activity of dihydrofolate reductase, a key enzyme involved in the synthesis of DNA and RNA, thereby disrupting the rapid cell division associated with cancerous growth.
2. Used in Antirheumatic Applications:
Methotrexate γ-Methyl Ester is also utilized as an antirheumatic agent, particularly in the management of autoimmune diseases such as rheumatoid arthritis. It exhibits anti-inflammatory and immunosuppressive effects, which help alleviate symptoms and slow the progression of the disease.
3. Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methotrexate γ-Methyl Ester is used as an impurity in the production of Methotrexate (M260675). The presence of this impurity is essential for the development and formulation of the final drug product, as it contributes to the overall efficacy and therapeutic potential of Methotrexate.
4. Used in Research and Development:
Methotrexate γ-Methyl Ester serves as a valuable compound in the field of research and development, particularly in the study of folic acid antagonists and their potential applications in cancer treatment and autoimmune disease management. It provides researchers with insights into the structure-activity relationships and mechanisms of action of related compounds, paving the way for the development of novel therapeutic agents.

Upstream product

• 67-56-1 methanol 
• 59-05-2 N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid 
• 19741-14-1 4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoic acid 
• 79974-15-5 N-<4-<<(benzyloxy)carbonyl>methylamino>benzoyl>-L-glutamic acid γ-methyl ester 
• 2528-30-5 4-<<(benzyloxy)carbonyl>methylamino>benzoic acid 
• 1499-55-4 L-glutamic acid 5-methyl ester 
• 10541-83-0 N-methyl-p-aminobenzoic acid 
• 79640-72-5 L-glutamic acid 1-tert-butyl ester 5-methyl ester 
• 79648-88-7 α-tert-butyl γ-methyl N'-<4--N-methylamino>benzoyl>-L-glutamate 
• 52853-40-4 6-bromomethyl-2,4-diaminopteridine hydrobromide 
• 79974-19-9 N-<4-(methylamino)benzoyl>-L-glutamic acid γ-methyl ester 
• 34378-65-9 dimethyl N-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzoyl)-L-glutamate 
• 66891-86-9 benzyl (4-(chlorocarbonyl)phenyl)(methyl)carbamate 

Downstream Products

• 79640-75-8 N'-<4--N-methylamino>benzoyl>-L-glutamic acid γ-hydrazide 
• 121788-84-9 (S)-2-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-[2,2,2-trifluoro-eth-(E)-ylidene-hydrazinocarbonyl]-butyric acid 
• 121788-83-8 (S)-4-Azidocarbonyl-2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-butyric acid 
• 203723-22-2 methotrexate α,γ-bis(methyl 2-aminotetradecanoate) 

Relevant academic research and scientific papers

The use of Tris-lipidation to modify drug cytotoxicity in multidrug resistant cells expressing P-glycoprotein or MRP1

1. Increasing the lipophilicity is a strategy often used to improve a compound's cellular uptake and retention but this may also convert it into a substrate for an ATP-dependent transporter such as P-glycoprotein or the multidrug resistance-associated pro

Synthesis of methotrexate-antibody conjugates by regiospecific coupling and assessment of drug and antitumor activities

In order to increase the retention of drug activity, regiospecific coupling has been used to synthesize conjugates of methotrexate (MTX, 1) with normal rabbit IgG (NRG) and a mouse anti-human renal cancer monoclonal IgG (Dal K-20). MTX γ-methyl ester (4) was produced either by selective esterification of MTX or by coupling of 4-amino-4-deoxy-N10-methylpteroic acid (2) with suitable glutamic acid derivatives. The MTX γ-methyl ester (4) was then converted to the corresponding hydrazide 6. An amide-linked conjugate was formed when the MTX γ-hydrazide (6) was converted to reactive acylating species 7 by using tert-butyl nitrite or trifluoroacetaldehyde, which were reacted with nucleophilic centers, presumably ε-amino groups, in native IgG. A hydrazone-linked conjugate was formed when MTX γ-hydrazide (6) was reacted directly with IgG that had first been oxidized with periodate to form polyaldehyde IgG. The regiospecifically synthesized conjugates were somewhat more effective inhibitors in vitro of dihydrofolate reductase and of colony formation by human renal cancer (Caki-1) cells than were control nonregiospecific conjugates.

Methotrexate Analogues. 13. Chemical and Pharmacological Studies on Amide, Hydrazide, and Hydroxamic Acid Derivatives of the Glutamate Side Chain

Carbodiimide-mediated condensation of 4-amino-4-deoxy-N10-methylpteroic acid (APA) with several alkyl, aralkyl, and aryl amines, in the presence or absence of N-hydroxysuccinimide, was employed in order to prepare new lipid-soluble bis(amide) d