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L-Methylfolate

L-Methylfolate structure

CAS No:
31690-09-2
Formula:
C20H25N7O6
Chemical Name:
L-Methylfolate
Synonyms:
L-Glutamic acid,N-[4-[[[(6S)-2-amino-3,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl]methyl]amino]benzoyl]-;Glutamic acid,N-[p-[[(2-amino-5,6,7,8-tetrahydro-4-hydroxy-5-methyl-6-pteridinyl)methyl]amino]benzoyl]-,L-(-)-;L-Glutamic acid,N-[4-[[(2-amino-1,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-,(S)-;L-Glutamic acid,N-[4-[[[(6S)-2-amino-1,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl]methyl]amino]benzoyl]-;N-[4-[[[(6S)-2-Amino-3,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl]methyl]amino]benzoyl]-L-glutamic acid;l-N5-Methyl-L-tetrahydrofolic acid;(6S)-5-Methyltetrahydrofolic acid;5-Methyl-(6S)-tetrahydrofolic acid;Levomefolic acid;LMSR;L-Methylfolate;150950-03-1
Categories:
Active Pharmaceutical Ingredients > Vitamins and Minerals Medicines

Description

Levomefolic acid is a tetrahydrofolic acid.|Levomefolic acid (INN) is the metabolite of folic acid (Vitamin B9) and it is a predominant active form of folate found in foods and in the blood circulation, accounting for 98% of folates in human plasma. It is transported across the membranes including the blood-brain barrier into various tissues where it plays an essential role in the DNA synthesis, cysteine cycle and regulation of homocysteine, where it methylates homocysteine and forms methionine and tetrahydrofolate (THF). Levomefolate is approved as a food additive and is designated a GRAS (generally regarded as safe) compound. It is available commercially as a crystalline form of the calcium salt (Metafolin(R)), which has the stability required for use as a supplement. Supplementation of levomefolic acid is desired over folic acid due to reduced potential for masking vitamin B12 deficiency symptoms.

L-Methylfolate Basic Attributes

Molecular Weight：

459.46

Exact Mass：

459.46

EC Number：

603-809-2

UNII：

8S95DH25XC

DSSTox ID：

DTXSID4048278|DTXSID00185583

Characteristics

PSA：

199

XLogP3：

-0.5

Density：

1.62

Boiling Point：

221

Water Solubility：

Approximately 0.3 mg/ml

Collision Cross Section：

199.8 Å² [M-H]-

Safety Information

GHS Classification：

|Warning|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P302+P352, P321, P333+P313, P363, and P501|Aggregated GHS information provided by 5 companies from 2 notifications to the ECHA C&L Inventory.

Toxicity

Toxicity Summary：

Overdose of levomefolic acid is unlikely to cause clinically significant adverse events.

Protein Binding：

Approximately 56% bound to plasma proteins

Drug Information

Drug Indication：

For the treatment and prevention of folate deficiency and for use as an antidote against folic acid antagonists. Contained in oral contraceptives to reduce the risk of neural tube defects arising from folic acid deficiency for pregnant women who conceived during use or shortly after the discontinuation of the product. Being studied for use as a treatment for cardiovascular diseases and adjunct therapy for patients undergoing antidepressant pharmacotherapy.|Contraception, Inappropriate diet and eating habits|Contraception, Inappropriate diet and eating habits, Treatment of acne vulgaris

Pharmacology：

Levomefolic acid is an active metabolite of folic acid and a methyl group donor in one-carbon metabolism reactions. It regulates important cellular functions such as DNA biosynthesis, gene expression regulation, amino acid synthesis and metabolism, and myelin synthesis and repair. As a only form of folate that can cross the blood-brain barrier, it acts as a cofactor in the production of monoamine neurotransmitters such as dopamine, serotonin and norepinephrine. Levomefolic acid is also involved in red blood cell formation.

Absorption：

Absorbed in the proximal small intestines via the active proton-coupled folate transporter (PCFT) that transports both oxidized and reduced folic acids. Passive diffusion also occurs at the proximal and distal portions of the small intestines. A single oral dose of 906nmol of levomefolic acid in healthy females resulted in the mean peak plasma concentration of 39.4nmol/L.|Mainly eliminated through renal or fecal excretion. Small proportion of excreted levomefolic acid is in unchanged form as over 99% of tissue folate is in polyglutamate form. Some portions of levomefolic acid is secreted into bile.|Circulates in its free form or loosely bound to plasma proteins

Metabolism/Metabolites：

Levomefolic acid is further converted into tetrahydrofolate (THF) via the vitamin B12-dependent enzyme methionine synthase before effective polyglutamylation by folylpolyglutamate synthetase (FPG). Polyglumate forms of folic acids are more effective substrates for associated enzymes in folate-dependent reactions.

Biological Half-Life：

The mean elimination half-life is approximately 3 hours after 5mg of oral L-methylfolate, administered daily for 7 days [775].

Mechanism of Action：

Levomefolic acid plays a critical role in methylating homocysteines into methionine by acting as a methyl donor in a reaction catalyzed by vitamine B12-dependent methionine synthase. Homocysteine must either be further metabolized via transulfuration to become cysteine, taurine, and glutathione via a B6-dependent process, or re-methylated to become methionine again. Methionine formed from remethylation of homocysteine by levomefolic acid forms the downstream metabolite S-adenosylmethionine (SAMe), which is involved in numerous biochemical methyl donation reactions, including reactions forming monoamine neurotransmitters. Studies suggest that high plasma levels of homocysteine is associated with increased incidences of arterial plaque formation.

MeSH Entry Terms：

5-methyltetrahydrofolate

L-Methylfolate Use and Manufacturing

Uses

A natural, active form of folic acid used at the cellular level for DNA reproduction, the cysteine cycle and the regulation of homocysteine among other functions. It is a coenzymated form of folic acid and a more bioavailable alternative in dietary supple

Use Classification：

Human Drugs -> EU pediatric investigation plans

Computed Properties

Molecular Weight:459.5
XLogP3:-0.5
Hydrogen Bond Donor Count:7
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:9
Exact Mass:459.18663154
Monoisotopic Mass:459.18663154
Topological Polar Surface Area:199
Heavy Atom Count:33
Complexity:865
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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