Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H25N7O6 |
Molecular Weight | 459.4558 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1[C@@H](CNC2=CC=C(C=C2)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CNC3=C1C(=O)NC(N)=N3
InChI
InChIKey=ZNOVTXRBGFNYRX-STQMWFEESA-N
InChI=1S/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t12-,13-/m0/s1
For people with MTHFR gene variations, supplementing with the already activated form of folate (5-MTHF/5- METHYLTETRAHYDROFOLATE/LEVOMEFOLIC ACID) is far more effective in providing this form of folate than introducing the pre-converted form to the body through typical folate supplements. L-Methylfolate (5-MTHF) supplements provide the active form of folate naturally present in the body and available for biological action. 5-MTHF—the “active” form of folate that is able to pass the blood brain barrier. However, without a properly functioning methylenetetrahydrofolate reductase, MTHFR this conversion cannot take place and folate is not converted to forms that can cross the blood brain barrier. That is where 5-MTHF supplements come in. Levomefolate calcium is structurally identical to L-5-methyltetrahydrofolate (L-5-methyl-THF), a metabolite of vitamin B9. Mean baseline concentrations of about 15 nmol/L are reached in populations without folate food fortification under normal nutritional conditions. Orally administered levomefolate calcium is absorbed and is incorporated into the body folate pool. Peak plasma concentrations of about 50 nmol/L above baseline are reached within 0.5 – 1.5 hours after single oral administration of 0.451 mg levomefolate calcium. Steady state conditions for total folate in plasma after intake of 0.451 mg levomefolate calcium. In red blood cells, achievement of steady state is delayed due to the long lifespan of red blood cells of about 120 days. Levomefolate calcium is a part of contraceptive tablets: SAFYRA. Safyral is an estrogen/progestin COC (Combined Oral Contraceptive) containing a folate, indicated for use by women to: prevent pregnancy and raise folate levels in women who choose to use an oral contraceptive for contraception. COCs lower the risk of becoming pregnant primarily by suppressing ovulation. Other possible mechanisms may include cervical mucus changes that inhibit sperm penetration and endometrial changes that reduce the likelihood of implantation.
CNS Activity
Approval Year
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | SAFYRAL Approved Use1.1 Oral Contraceptive: Safyral is indicated for use by women to prevent pregnancy. 1.2 Folate Supplementation
Safyral is indicated in women who choose to use an oral contraceptive as their method of contraception, to raise folate levels for the purpose of reducing the risk of a neural tube defect in a pregnancy conceived while taking the product or shortly after discontinuing the product. Launch Date1.29237123E12 |
PubMed
Title | Date | PubMed |
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Serum folate levels after UVA exposure: a two-group parallel randomised controlled trial. | 2001 |
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Determination of folates in foods by high-performance liquid chromatography with fluorescence detection after precolumn conversion to 5-methyltetrahydrofolates. | 2001 Aug 31 |
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Association of methylenetetrahydrofolate reductase polymorphism C677T and dietary folate with the risk of cervical dysplasia. | 2001 Dec |
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Folate protects against oxidative modification of human LDL. | 2001 Dec |
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Assays of methylenetetrahydrofolate reductase and methionine synthase activities by monitoring 5-methyltetrahydrofolate and tetrahydrofolate using high-performance liquid chromatography with fluorescence detection. | 2001 Dec 15 |
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Carrier-mediated transport of folic acid in BeWo cell monolayers as a model of the human trophoblast. | 2001 Nov |
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Plasma folate, vitamin B(12), and total homocysteine and homozygosity for the C677T mutation of the 5,10-methylene tetrahydrofolate reductase gene in patients with Alzheimer's dementia. A case-control study. | 2001 Nov-Dec |
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Treatment of hyperhomocysteinemia in end-stage renal disease. | 2001 Oct |
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High-performance liquid chromatographic measurement of 5,10-methylenetetrahydrofolate in liver. | 2001 Oct 15 |
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Monitoring of methotrexate and reduced folates in the cerebrospinal fluid of cancer patients. | 2002 Dec |
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Preponderance of methylenetetrahydrofolate reductase C677T homozygosity among leukemia patients intolerant to methotrexate. | 2002 Dec |
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Distribution of plasma folate forms in hemodialysis patients receiving high daily doses of L-folinic or folic acid. | 2002 Dec |
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Downregulation of reduced-folate transporter by glucose in cultured RPE cells and in RPE of diabetic mice. | 2002 Feb |
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Folic acid improves endothelial function in coronary artery disease via mechanisms largely independent of homocysteine lowering. | 2002 Jan 1 |
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Rapid method for the determination of total 5-methyltetrahydrofolate in blood by liquid chromatography with fluorescence detection. | 2002 Jan 25 |
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Impaired NO-dependent vasodilation in patients with Type II (non-insulin-dependent) diabetes mellitus is restored by acute administration of folate. | 2002 Jul |
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Nature and nurture in vitamin B12 deficiency. | 2002 Jul |
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5,10-Methylenetetrahydrofolate reductase (MTHFR) assay in the forward direction: residual activity in MTHFR deficiency. | 2002 Jun |
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The C677T mutation in the methylenetetrahydrofolate reductase gene contributes to hyperhomocysteinemia in patients taking anticonvulsants. | 2002 Jun |
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Interaction of 5-methyltetrahydrofolate and tetrahydrobiopterin on endothelial function. | 2002 Jun |
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Vitamin C therapy ameliorates vascular endothelial dysfunction in treated patients with homocystinuria. | 2002 May |
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Role of the C-terminus and the long cytoplasmic loop in reduced folate carrier expression and function. | 2002 May 1 |
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Cytoplasmic serine hydroxymethyltransferase mediates competition between folate-dependent deoxyribonucleotide and S-adenosylmethionine biosyntheses. | 2002 Oct 11 |
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Effect of low doses of 5-methyltetrahydrofolate and folic acid on plasma homocysteine in healthy subjects with or without the 677C-->T polymorphism of methylenetetrahydrofolate reductase. | 2002 Sep |
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Multiple transcription start sites and alternative splicing in the methylenetetrahydrofolate reductase gene result in two enzyme isoforms. | 2002 Sep |
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The enrichment of eggs with folic acid through supplementation of the laying hen diet. | 2002 Sep |
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Intimal redox stress: accelerated atherosclerosis in metabolic syndrome and type 2 diabetes mellitus. Atheroscleropathy. | 2002 Sep 27 |
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Measurement of red blood cell methylfolate. | 2002 Sep 28 |
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Uptake of 5-methyltetrahydrofolate into PC-3 human prostate cancer cells is carrier-mediated. | 2003 Aug |
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Dietary prevention of post-angioplasty restenosis. From illusion and disillusion to pragmatism. | 2003 Dec |
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Cobalamin-dependent methionine synthase: probing the role of the axial base in catalysis of methyl transfer between methyltetrahydrofolate and exogenous cob(I)alamin or cob(I)inamide. | 2003 Dec 16 |
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Determination of 5-methyltetrahydrofolic acid and folic acid in citrus juices using stable isotope dilution-mass spectrometry. | 2003 Feb 26 |
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A comparison of folic acid and 5-methyltetrahydrofolate for prevention of DNA damage and cell death in human lymphocytes in vitro. | 2003 Jan |
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Analysis of the human folate receptor beta gene for an association with neural tube defects. | 2003 Jun |
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A mass spectrometric validated high-performance liquid chromatography procedure for the determination of folates in foods. | 2003 Jun 18 |
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Residues 45 and 404 in the murine reduced folate carrier may interact to alter carrier binding and mobility. | 2003 Jun 27 |
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Hyperhomocystinemia in children with inflammatory bowel disease. | 2003 Nov |
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Regulation of S-adenosylmethionine levels in Saccharomyces cerevisiae. | 2003 Oct 31 |
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The C677 mutation in methylene tetrahydrofolate reductase gene: correlation with uric acid and cardiovascular risk factors in elderly Korean men. | 2004 Apr |
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Normal dopaminergic and serotonergic metabolites in cerebrospinal fluid and blood of restless legs syndrome patients. | 2004 Feb |
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Folate, homocysteine, endothelial function and cardiovascular disease. | 2004 Feb |
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Determination of folate vitamers in human serum by stable-isotope-dilution tandem mass spectrometry and comparison with radioassay and microbiologic assay. | 2004 Feb |
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Red cell N5-methyltetrahydrofolate concentrations and C677T methylenetetrahydrofolate reductase genotype in patients with stroke. | 2004 Jan |
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Thymidylate synthase and methylenetetrahydrofolate reductase gene polymorphisms: relationships with 5-fluorouracil sensitivity. | 2004 Jan 26 |
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Placental folate transport and binding are not impaired in pregnancies complicated by fetal growth restriction. | 2004 Jul |
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Folic acid rescues nitric oxide-induced neural tube closure defects. | 2004 Mar |
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Homocysteine and reactive oxygen species in metabolic syndrome, type 2 diabetes mellitus, and atheroscleropathy: the pleiotropic effects of folate supplementation. | 2004 May 10 |
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The methionine synthase polymorphism D919G alters susceptibility to primary central nervous system lymphoma. | 2004 May 17 |
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Folic acid-mediated inhibition of serum-induced activation of EGFR promoter in colon cancer cells. | 2004 Sep |
|
Betaine rescue of an animal model with methylenetetrahydrofolate reductase deficiency. | 2004 Sep 15 |
Patents
Sample Use Guides
Take one tablet daily by mouth at the same time every day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23332600
neural stem cells (NSCs) were exposed to folic acid or 5-methyltetrahydrofolate (5-MTHF) (0-200 μmol/L) for 24, 48 or 72 h
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Code System | Code | Type | Description | ||
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8S95DH25XC
Created by
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4621
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LEVOMEFOLIC ACID
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135398561
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31690-09-2
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8917
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8S95DH25XC
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C81119
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100000127631
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DB11256
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SUB33688
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1025342
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18608
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DTXSID00185583
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1592257
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C1505
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CONCEPT | Dietary Supplement | ||
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TT-129
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CHEMBL1231574
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ACTIVE MOIETY
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