Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H23N7O6.Mg |
Molecular Weight | 481.7449 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Mg++].CN1[C@@H](CNC2=CC=C(C=C2)C(=O)N[C@@H](CCC([O-])=O)C([O-])=O)CNC3=C1C(=O)N=C(N)N3
InChI
InChIKey=UNKHRTFYDNBUHK-QNTKWALQSA-L
InChI=1S/C20H25N7O6.Mg/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);/q;+2/p-2/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 Date2010 |
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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Methylenetetrahydrofolate reductase 677 C/T genotype and cardiovascular disease mortality in postmenopausal women. | 2001 Apr 1 |
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Binding of radiolabeled folate and 5-methyltetrahydrofolate to cow's milk folate binding protein at pH 7.4 and 5.0. Relationship to concentration and polymerization equilibrium of the purified protein. | 2001 Dec |
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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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Antisense modulation of 5,10-methylenetetrahydrofolate reductase expression produces neural tube defects in mouse embryos. | 2001 Jan-Feb |
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Folate and chemoprevention of colorectal cancer: Is 5-methyl-tetrahydrofolate an active antiproliferative agent in folate-treated colon-cancer cells? | 2001 Jul-Aug |
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Effect of feeding on circulating micronutrient concentrations in the Burmese python (Python molurus). | 2001 Jun |
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A novel neurodevelopmental syndrome responsive to 5-hydroxytryptophan and carbidopa. | 2001 Jun |
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Enzymatic determination of homocysteine in cell extracts. | 2001 Mar |
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Methylenetetrahydrofolate reductase polymorphism and susceptibility to breast cancer. | 2002 |
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Syntheses of labeled vitamers of folic acid to be used as internal standards in stable isotope dilution assays. | 2002 Aug 14 |
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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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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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Vitamin C therapy ameliorates vascular endothelial dysfunction in treated patients with homocystinuria. | 2002 May |
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The enrichment of eggs with folic acid through supplementation of the laying hen diet. | 2002 Sep |
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Uptake of 5-methyltetrahydrofolate into PC-3 human prostate cancer cells is carrier-mediated. | 2003 Aug |
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Tetrahydrofolate and 5-methyltetrahydrofolate are folates with high antioxidant activity. Identification of the antioxidant pharmacophore. | 2003 Dec 18 |
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Transport of 5-formyltetrahydrofolate into primary cultured cerebellar granule cells. | 2003 Feb 7 |
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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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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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Specific and sensitive quantification of folate vitamers in foods by stable isotope dilution assays using high-performance liquid chromatography-tandem mass spectrometry. | 2003 May |
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Characterization of mutations in severe methylenetetrahydrofolate reductase deficiency reveals an FAD-responsive mutation. | 2003 May |
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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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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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Solid-phase extraction-electrospray ionization mass spectrometry for the quantification of folate in human plasma or serum. | 2004 Feb 1 |
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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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Pharmacokinetic study on the utilisation of 5-methyltetrahydrofolate and folic acid in patients with coronary artery disease. | 2004 Mar |
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Folic acid rescues nitric oxide-induced neural tube closure defects. | 2004 Mar |
|
Sodium-dependent methotrexate carrier-1 is expressed in rat kidney: cloning and functional characterization. | 2004 Mar |
|
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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1549106
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100000170337
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1VZZ62R081
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1429498-11-2
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135565020
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1VZZ62R081
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DBSALT001534
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SUB184178
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ACTIVE MOIETY
ACTIVE MOIETY
SUBSTANCE RECORD