Category: DMARDs

Folate, folic acid or folinic acid to reduce adverse effects of methotrexate?

What is the difference between folate, folic acid, and folinic acid? And how do each of them contribute or are involved in the methotrexate pathway?

Folate is the naturally occurring salt form of vitamin B9. Folic acid is a synthetic water-soluble acid form of vitamin B9. Folate and folic acid are metabolised by dihydrofolate reductase, the enzyme inhibited by methotrexate, to FH2 and then FH4, which in turn is converted to N5, N10-methylene-FH4.

Folinic acid (also known as leucovorin) is N5-formyl-FH4 and can be converted rapidly to N5, N10-methylene-FH4 without the need for dihydrofolate reductase and so bypasses the inhibition of the pathway by methotrexate.

In the treatment of rheumatoid arthritis with methotrexate, adverse effects include nausea and vomiting, mouth and gastrointestinal ulcers, and hair loss are caused by the reduction in N5, N10-methylene-FH4, which is required for the synthesis of amino acids and nucleic acids necessary for cell proliferation.  Folic acid at high enough doses to overcome the methotrexate inhibition of dihydrofolate reductase or folinic acid is therefore used to reduce the adverse effects of methotrexate.

Why does increasing adenosine levels with methotrexate help rheumatoid arthritis?

Methotrexate can be used to control the autoimmune attack and auto-inflammatory response in rheumatoid arthritis.  It has a number of mechanisms of action, including increasing adenosine levels. How does increasing adenosine levels help to combat autoimmune and auto-inflammatory attack on the joints? 

Let’s first dispel a potential misunderstanding. Adenosine is not the same thing as adenine.  If we confuse adenosine with adenine, then it may appear contradictory that the mechanisms of action of methotrexate include both increasing adenosine levels and reducing pyrimidine levels. There is no contradiction here. Adenine and guanine are purines. Purines and pyrimidines are nitrogenous bases required for the nucleotide building blocks of DNA. Thus depletion of pyrimidines with drugs such as methotrexate and leflunomide or depletion of purines, including adenine, with drugs such as azathioprine and mycophenolate can interfere with DNA synthesis and proliferation of immune system and inflammatory cells.

Adenosine is a purine nucleoside composed of a molecule of adenine attached to a ribose sugar molecule.  It is a ribonucleoside necessary for the synthesis of RNA but has many other cellular functions as well. Adenosine triphosphate (ATP) is, of course, well-known as the cellular energy currency.  Adenosine itself is also a transmitter acting at adenosine receptors. Adenosine signalling suppresses recruitment and functions of inflammatory and immune cells. Thus increasing adenosine levels has an anti-inflammatory and immunosuppressant effect.

 

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