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
Molecular Formula | C20H23N7O6 |
Molecular Weight | 457.4399 |
Charge | -2 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | Mg |
Molecular Weight | 24.305 |
Charge | 2 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|---|---|
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 |
---|---|---|
Comparison of dihydrofolate reductase activities for folic acid in pigs and rats using in vivo and in vitro evaluation techniques. | 2001 Apr |
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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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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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Low seminal plasma folate concentrations are associated with low sperm density and count in male smokers and nonsmokers. | 2001 Feb |
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Treatment of hyperhomocysteinemia in hemodialysis patients and renal transplant recipients. | 2001 Feb |
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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 improves endothelial function in coronary artery disease: an effect mediated by reduction of intracellular superoxide? | 2001 Jul |
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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 |
|
Effect of feeding on circulating micronutrient concentrations in the Burmese python (Python molurus). | 2001 Jun |
|
Enzymatic determination of homocysteine in cell extracts. | 2001 Mar |
|
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 |
|
High-performance liquid chromatographic measurement of 5,10-methylenetetrahydrofolate in liver. | 2001 Oct 15 |
|
Folic-acid-mediated inhibition of human colon-cancer cell growth. | 2001 Sep |
|
Psychomotor retardation, spastic paraplegia, cerebellar ataxia and dyskinesia associated with low 5-methyltetrahydrofolate in cerebrospinal fluid: a novel neurometabolic condition responding to folinic acid substitution. | 2002 Dec |
|
Distribution of plasma folate forms in hemodialysis patients receiving high daily doses of L-folinic or folic acid. | 2002 Dec |
|
Folic acid improves endothelial function in coronary artery disease via mechanisms largely independent of homocysteine lowering. | 2002 Jan 1 |
|
Impaired NO-dependent vasodilation in patients with Type II (non-insulin-dependent) diabetes mellitus is restored by acute administration of folate. | 2002 Jul |
|
5,10-Methylenetetrahydrofolate reductase (MTHFR) assay in the forward direction: residual activity in MTHFR deficiency. | 2002 Jun |
|
The C677T mutation in the methylenetetrahydrofolate reductase gene contributes to hyperhomocysteinemia in patients taking anticonvulsants. | 2002 Jun |
|
Interaction of 5-methyltetrahydrofolate and tetrahydrobiopterin on endothelial function. | 2002 Jun |
|
Determination of 5-methyltetrahydrofolate (13C-labeled and unlabeled) in human plasma and urine by combined liquid chromatography mass spectrometry. | 2002 Jun 15 |
|
Red blood cell methylfolate and plasma homocysteine as risk factors for venous thromboembolism: a matched case-control study. | 2002 Mar 2 |
|
Role of the C-terminus and the long cytoplasmic loop in reduced folate carrier expression and function. | 2002 May 1 |
|
Multiple transcription start sites and alternative splicing in the methylenetetrahydrofolate reductase gene result in two enzyme isoforms. | 2002 Sep |
|
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 |
|
Effect of riboflavin status on the homocysteine-lowering effect of folate in relation to the MTHFR (C677T) genotype. | 2003 Feb |
|
Transport of 5-formyltetrahydrofolate into primary cultured rat astrocytes. | 2003 Feb 1 |
|
Antisense modulation of the coding or regulatory sequence of the folate receptor (folate binding protein-1) in mouse embryos leads to neural tube defects. | 2003 Jul |
|
A mass spectrometric validated high-performance liquid chromatography procedure for the determination of folates in foods. | 2003 Jun 18 |
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Methylenetetrahydrofolate reductase polymorphism in advanced colorectal cancer: a novel genomic predictor of clinical response to fluoropyrimidine-based chemotherapy. | 2003 May |
|
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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Model studies on the stability of folic acid and 5-methyltetrahydrofolic acid degradation during thermal treatment in combination with high hydrostatic pressure. | 2003 May 21 |
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Thrombophilia and pregnancy. | 2003 Nov 14 |
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Hyperproliferation of homocysteine-treated colon cancer cells is reversed by folate and 5-methyltetrahydrofolate. | 2004 Apr |
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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 |
|
Quantitative evaluation of the drug-drug interactions between methotrexate and nonsteroidal anti-inflammatory drugs in the renal uptake process based on the contribution of organic anion transporters and reduced folate carrier. | 2004 Apr |
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A review of folate receptor alpha cycling and 5-methyltetrahydrofolate accumulation with an emphasis on cell models in vitro. | 2004 Apr 29 |
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Folate, homocysteine, endothelial function and cardiovascular disease. | 2004 Feb |
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Methylenetetrahydrofolate reductase and transcobalamin genetic polymorphisms in human spontaneous abortion: biological and clinical implications. | 2004 Feb 17 |
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Mutations of the MTHFR gene (428C>T and [458G>T+459C>T]) markedly decrease MTHFR enzyme activity. | 2004 Jun |
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Folic acid rescues nitric oxide-induced neural tube closure defects. | 2004 Mar |
|
Homocysteine and reactive oxygen species in metabolic syndrome, type 2 diabetes mellitus, and atheroscleropathy: the pleiotropic effects of folate supplementation. | 2004 May 10 |
|
The methionine synthase polymorphism D919G alters susceptibility to primary central nervous system lymphoma. | 2004 May 17 |
|
Folic acid-mediated inhibition of serum-induced activation of EGFR promoter in colon cancer cells. | 2004 Sep |
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:07:12 GMT 2023
by
admin
on
Sat Dec 16 09:07:12 GMT 2023
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Record UNII |
1VZZ62R081
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Record Status |
Validated (UNII)
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Record Version |
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-
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100000170337
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SUB184178
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