Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H23N7O6.2Na |
Molecular Weight | 503.4195 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[Na+].CN1[C@@H](CNC2=CC=C(C=C2)C(=O)N[C@@H](CCC([O-])=O)C([O-])=O)CNC3=NC(N)=NC(O)=C13
InChI
InChIKey=KKIWVYLOTHCGRV-NJHZPMQHSA-L
InChI=1S/C20H25N7O6.2Na/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*+1/p-2/t12-,13-;;/m0../s1
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
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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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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Folate protects against oxidative modification of human LDL. | 2001 Dec |
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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 |
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Carrier-mediated transport of folic acid in BeWo cell monolayers as a model of the human trophoblast. | 2001 Nov |
|
Folic-acid-mediated inhibition of human colon-cancer cell growth. | 2001 Sep |
|
Monitoring of methotrexate and reduced folates in the cerebrospinal fluid of cancer patients. | 2002 Dec |
|
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 |
|
5,10-Methylenetetrahydrofolate reductase (MTHFR) assay in the forward direction: residual activity in MTHFR deficiency. | 2002 Jun |
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Interaction of 5-methyltetrahydrofolate and tetrahydrobiopterin on endothelial function. | 2002 Jun |
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Determination of 5-methyltetrahydrofolate (13C-labeled and unlabeled) in human plasma and urine by combined liquid chromatography mass spectrometry. | 2002 Jun 15 |
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Red blood cell methylfolate and plasma homocysteine as risk factors for venous thromboembolism: a matched case-control study. | 2002 Mar 2 |
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Vitamin C therapy ameliorates vascular endothelial dysfunction in treated patients with homocystinuria. | 2002 May |
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Cytoplasmic serine hydroxymethyltransferase mediates competition between folate-dependent deoxyribonucleotide and S-adenosylmethionine biosyntheses. | 2002 Oct 11 |
|
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 |
|
Measurement of red blood cell methylfolate. | 2002 Sep 28 |
|
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 |
|
A method for the analysis of natural and synthetic folate in foods. | 2003 Jan 15 |
|
A mass spectrometric validated high-performance liquid chromatography procedure for the determination of folates in foods. | 2003 Jun 18 |
|
Residues 45 and 404 in the murine reduced folate carrier may interact to alter carrier binding and mobility. | 2003 Jun 27 |
|
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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Folate improves endothelial function in patients with coronary heart disease. | 2003 Nov |
|
Thrombophilia and pregnancy. | 2003 Nov 14 |
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Normal dopaminergic and serotonergic metabolites in cerebrospinal fluid and blood of restless legs syndrome patients. | 2004 Feb |
|
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 |
|
5-Methyltetrahydrofolic acid and folic acid measured in plasma with liquid chromatography tandem mass spectrometry: applications to folate absorption and metabolism. | 2004 Mar 15 |
|
Methionine metabolism in plants: chloroplasts are autonomous for de novo methionine synthesis and can import S-adenosylmethionine from the cytosol. | 2004 May 21 |
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 10:09:11 GMT 2023
by
admin
on
Sat Dec 16 10:09:11 GMT 2023
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Record UNII |
B3KYL5163W
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Record Status |
Validated (UNII)
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Record Version |
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1423663-76-6
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135565435
Created by
admin on Sat Dec 16 10:09:12 GMT 2023 , Edited by admin on Sat Dec 16 10:09:12 GMT 2023
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B3KYL5163W
Created by
admin on Sat Dec 16 10:09:12 GMT 2023 , Edited by admin on Sat Dec 16 10:09:12 GMT 2023
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ACTIVE MOIETY |