chemistry

Levomefolic acid

Levomefolic acid is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Levomefolic acid rather than just read about it. In short: Levomefolic acid (INN, also known as L-5-MTHF, L-methylfolate and L-5-methyltetrahydrofolate and (6S)-5-methyltetrahydrofolate, and (6S)-5-MTHF) is the primary biologically active form of folate used at the cellular level for DNA reproduction, the cysteine cycle and the regulation of homocysteine. It is also the form found in circulation and transported across membranes into tissues and across the blood–brain barrie…

Key takeaways

Levomefolic acid belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Levomefolic acid to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Levomefolic acid from memory before moving on to harder problems.

Reference excerpt

Levomefolic acid (INN, also known as L-5-MTHF, L-methylfolate and L-5-methyltetrahydrofolate and (6S)-5-methyltetrahydrofolate, and (6S)-5-MTHF) is the primary biologically active form of folate used at the cellular level for DNA reproduction, the cysteine cycle and the regulation of homocysteine. It is also the form found in circulation and transported across membranes into tissues and across the blood–brain barrier. In the cell, L-methylfolate is used in the methylation of homocysteine to form methionine and tetrahydrofolate (THF). THF is the immediate acceptor of one carbon unit for the synthesis of thymidine-DNA, purines (RNA and DNA) and methionine. The un-methylated form, folic acid (vitamin B9), is a synthetic form of folate, and must undergo enzymatic reduction by dihydrofolate reductase (DHFR) to become biologically active. Systematic reviews suggest that adjunctive L-methylfolate modestly improves symptoms in major depressive disorder. It is synthesized in the absorptive cells of the small intestine from polyglutamylated dietary folate. It is a methylated derivative of tetrahydrofolate. Levomefolic acid is generated by methylenetetrahydrofolate reductase (MTHFR) from 5,10-methylenetetrahydrofolate (MTHF) and used to recycle homocysteine back to methionine by methionine synthase (MS). L-methylfolate is water-soluble and primarily excreted via the kidneys. In a study of 21 subjects with coronary artery disease, peak plasma levels were reached in one to three hours following oral or parenteral administration. Peak concentrations were found to be more than seven times higher than folic acid (129 ng/ml vs. 14.1 ng/ml). Patients at risk for vitamin B12 deficiency should consult with their medical provider prior to taking L-Methylfolate. The interrelationship between these two vitamins (L-Methylfolate and B12) is best explained by the methyl trap hypothesis.

Metabolism

Medical uses

Major depressive disorder and other psychiatric conditions Systematic reviews suggest that adjunctive L-methylfolate modestly improves symptoms in major depressive disorder and may benefit other psychiatric conditions with good tolerability. In patients with depression augmenting SSRI/SNRI treatment, L-methylfolate augmentation led to higher medication adherence and lower health care utilization and costs compared to augmentation with second-generation atypical antipsychotics.

Cardiovascular disease and cancer Levomefolic acid (and folic acid in turn) has been proposed for treatment of cardiovascular disease and advanced cancers such as breast and colorectal cancers. It bypasses several metabolic steps in the body and better binds thymidylate synthase with FdUMP, a metabolite of the drug fluorouracil.

Patent issues In March 2012, Merck & Cie of Switzerland, Pamlab LLC (maker of Metanx and Cerefolin, Neevo DHA, and Deplin), and South Alabama Medical Science Foundation (SAMSF) (the plaintiffs) filed a complaint in the United States District Court for the Eastern District of Texas against four defendants: Macoven Pharmaceuticals (owned by Pernix Therapeutics), Gnosis SpA of Italy, Gnosis U.S.A and Gnosis Bioresearch Switzerland. The plaintiffs alleged that the defendants infringed on several of the plaintiffs' patents. The Macoven products named in the suit are: "Vitaciric-B", "ALZ-NAC", "PNV DHA", and l-methylfolate calcium (levomefolate calcium). In September 2012, the same three plaintiffs filed a complaint requesting that the International Trade Commission begin a 19 U.S.C. § 1337 investigation of the same four defendants. The complaint states that Gnosis' "Extrafolic-S" and products which are made from it, infringe upon three of their patents: US 5997915 , US 6673381 , and US 7172778 .

Formulations Levomefolate calcium, a calcium salt of levomefolic acid is sold under the brand name Metafolin and incorporated in Deplin. Levomefolate magnesium is a magnesium salt of levomefolic acid, manufactured as DeltaFolate, a primary ingredient in EnLyte. Levomefolate calcium (a calcium salt of levomefolic acid) is manufactured as Cerebrofolate.

See also 5,10-Methylenetetrahydrofolate S-Adenosylmethionine (SAMe)

References

External links Calcium L5-methyltetrahydrofolate (L-5-MTHF-Ca) Brockton NT (October 2006). "Localized depletion: the key to colorectal cancer risk mediated by MTHFR genotype and folate?". Cancer Causes & Control. 17 (8): 1005–16. doi:10.1007/s10552-006-0051-5. PMID 16933051. S2CID 20394873. Stahl SM (October 2007). "Novel therapeutics for depression: L-methylfolate as a trimonoamine modulator and antidepressant-augmenting agent". CNS Spectrums. 12 (10): 739–44. doi:10.1017/S1092852900015418. PMID 17934378. S2CID 27000937.

Illustrations

Worked examples

Example 1 — a first encounter with Levomefolic acid

Start with the simplest possible case. Write down what Levomefolic acid claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Levomefolic acid before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Levomefolic acid ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Levomefolic acid

In research: Levomefolic acid appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Levomefolic acid in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Levomefolic acid is common in secondary-school and first-year university syllabi. It links to neighbouring topics Coenzymes, Folates, Medical food, so understanding it makes those chapters shorter.
In everyday life: Look for Levomefolic acid outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Levomefolic acid in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Levomefolic acid means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain Levomefolic acid out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Levomefolic acid in simple terms?

Why does Levomefolic acid matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Levomefolic acid?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Levomefolic acid.