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 Date1.29237123E12 |
PubMed
Title | Date | PubMed |
---|---|---|
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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Folate improves endothelial function in coronary artery disease: an effect mediated by reduction of intracellular superoxide? | 2001 Jul |
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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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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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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 |
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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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Nature and nurture in vitamin B12 deficiency. | 2002 Jul |
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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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5-methyltetrahydrofolate restores endothelial function in uraemic patients on convective haemodialysis. | 2002 May |
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Cytoplasmic serine hydroxymethyltransferase mediates competition between folate-dependent deoxyribonucleotide and S-adenosylmethionine biosyntheses. | 2002 Oct 11 |
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The enrichment of eggs with folic acid through supplementation of the laying hen diet. | 2002 Sep |
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Does the interaction between maternal folate intake and the methylenetetrahydrofolate reductase polymorphisms affect the risk of cleft lip with or without cleft palate? | 2003 Apr 1 |
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Dietary prevention of post-angioplasty restenosis. From illusion and disillusion to pragmatism. | 2003 Dec |
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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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A mass spectrometric validated high-performance liquid chromatography procedure for the determination of folates in foods. | 2003 Jun 18 |
|
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 |
|
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 |
|
Folate improves endothelial function in patients with coronary heart disease. | 2003 Nov |
|
Hyperhomocystinemia in children with inflammatory bowel disease. | 2003 Nov |
|
Age dependence of the influence of methylenetetrahydrofolate reductase genotype on plasma homocysteine level. | 2003 Nov 1 |
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Thrombophilia and pregnancy. | 2003 Nov 14 |
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Characterization of a pseudogene for murine methylenetetrahydrofolate reductase. | 2003 Oct |
|
Regulation of S-adenosylmethionine levels in Saccharomyces cerevisiae. | 2003 Oct 31 |
|
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 |
|
Normal dopaminergic and serotonergic metabolites in cerebrospinal fluid and blood of restless legs syndrome patients. | 2004 Feb |
|
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 UTC 2023
by
admin
on
Sat Dec 16 10:09:11 UTC 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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-
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1423663-76-6
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135565435
Created by
admin on Sat Dec 16 10:09:12 UTC 2023 , Edited by admin on Sat Dec 16 10:09:12 UTC 2023
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B3KYL5163W
Created by
admin on Sat Dec 16 10:09:12 UTC 2023 , Edited by admin on Sat Dec 16 10:09:12 UTC 2023
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |