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 Date1.29237123E12 |
PubMed
Title | Date | PubMed |
---|---|---|
Serum folate levels after UVA exposure: a two-group parallel randomised controlled trial. | 2001 |
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Association of methylenetetrahydrofolate reductase polymorphism C677T and dietary folate with the risk of cervical dysplasia. | 2001 Dec |
|
Folate protects against oxidative modification of human LDL. | 2001 Dec |
|
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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Methylenetetrahydrofolate reductase polymorphism and susceptibility to breast cancer. | 2002 |
|
Syntheses of labeled vitamers of folic acid to be used as internal standards in stable isotope dilution assays. | 2002 Aug 14 |
|
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 |
|
Preponderance of methylenetetrahydrofolate reductase C677T homozygosity among leukemia patients intolerant to methotrexate. | 2002 Dec |
|
Distribution of plasma folate forms in hemodialysis patients receiving high daily doses of L-folinic or folic acid. | 2002 Dec |
|
Downregulation of reduced-folate transporter by glucose in cultured RPE cells and in RPE of diabetic mice. | 2002 Feb |
|
Folic acid improves endothelial function in coronary artery disease via mechanisms largely independent of homocysteine lowering. | 2002 Jan 1 |
|
Rapid method for the determination of total 5-methyltetrahydrofolate in blood by liquid chromatography with fluorescence detection. | 2002 Jan 25 |
|
Impaired NO-dependent vasodilation in patients with Type II (non-insulin-dependent) diabetes mellitus is restored by acute administration of folate. | 2002 Jul |
|
Nature and nurture in vitamin B12 deficiency. | 2002 Jul |
|
Antisense inhibition of methylenetetrahydrofolate reductase reduces survival of methionine-dependent tumour lines. | 2002 Jul 15 |
|
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 |
|
Vitamin C therapy ameliorates vascular endothelial dysfunction in treated patients with homocystinuria. | 2002 May |
|
5-methyltetrahydrofolate restores endothelial function in uraemic patients on convective haemodialysis. | 2002 May |
|
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 |
|
The enrichment of eggs with folic acid through supplementation of the laying hen diet. | 2002 Sep |
|
Intimal redox stress: accelerated atherosclerosis in metabolic syndrome and type 2 diabetes mellitus. Atheroscleropathy. | 2002 Sep 27 |
|
Measurement of red blood cell methylfolate. | 2002 Sep 28 |
|
Uptake of 5-methyltetrahydrofolate into PC-3 human prostate cancer cells is carrier-mediated. | 2003 Aug |
|
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 |
|
Effect of riboflavin status on the homocysteine-lowering effect of folate in relation to the MTHFR (C677T) genotype. | 2003 Feb |
|
Affinity extraction combined with stable isotope dilution LC/MS for the determination of 5-methyltetrahydrofolate in human plasma. | 2003 Feb 1 |
|
Determination of 5-methyltetrahydrofolic acid and folic acid in citrus juices using stable isotope dilution-mass spectrometry. | 2003 Feb 26 |
|
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 |
|
Residues 45 and 404 in the murine reduced folate carrier may interact to alter carrier binding and mobility. | 2003 Jun 27 |
|
Specific and sensitive quantification of folate vitamers in foods by stable isotope dilution assays using high-performance liquid chromatography-tandem mass spectrometry. | 2003 May |
|
Characterization of mutations in severe methylenetetrahydrofolate reductase deficiency reveals an FAD-responsive mutation. | 2003 May |
|
Folate improves endothelial function in patients with coronary heart disease. | 2003 Nov |
|
Age dependence of the influence of methylenetetrahydrofolate reductase genotype on plasma homocysteine level. | 2003 Nov 1 |
|
Characterization of a pseudogene for murine methylenetetrahydrofolate reductase. | 2003 Oct |
|
Cerebrospinal fluid pterins and folates in Aicardi-Goutières syndrome: a new phenotype. | 2003 Sep 9 |
|
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 |
|
Mutations of the MTHFR gene (428C>T and [458G>T+459C>T]) markedly decrease MTHFR enzyme activity. | 2004 Jun |
|
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 |
|
Methionine metabolism in plants: chloroplasts are autonomous for de novo methionine synthesis and can import S-adenosylmethionine from the cytosol. | 2004 May 21 |
|
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 14:36:12 UTC 2023
by
admin
on
Thu Jul 06 14:36:12 UTC 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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100000170337
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SUB184178
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