Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H25N7O6 |
Molecular Weight | 459.4558 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1[C@@H](CNC2=CC=C(C=C2)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CNC3=C1C(=O)NC(N)=N3
InChI
InChIKey=ZNOVTXRBGFNYRX-STQMWFEESA-N
InChI=1S/C20H25N7O6/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)/t12-,13-/m0/s1
Molecular Formula | C20H25N7O6 |
Molecular Weight | 459.4558 |
Charge | 0 |
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 |
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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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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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Folate protects against oxidative modification of human LDL. | 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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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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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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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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Nature and nurture in vitamin B12 deficiency. | 2002 Jul |
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The C677T mutation in the methylenetetrahydrofolate reductase gene contributes to hyperhomocysteinemia in patients taking anticonvulsants. | 2002 Jun |
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Cytoplasmic serine hydroxymethyltransferase mediates competition between folate-dependent deoxyribonucleotide and S-adenosylmethionine biosyntheses. | 2002 Oct 11 |
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Measurement of red blood cell methylfolate. | 2002 Sep 28 |
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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 |
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Affinity extraction combined with stable isotope dilution LC/MS for the determination of 5-methyltetrahydrofolate in human plasma. | 2003 Feb 1 |
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Transport of 5-formyltetrahydrofolate into primary cultured rat astrocytes. | 2003 Feb 1 |
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Determination of 5-methyltetrahydrofolic acid and folic acid in citrus juices using stable isotope dilution-mass spectrometry. | 2003 Feb 26 |
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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 |
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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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Methylenetetrahydrofolate reductase polymorphism in advanced colorectal cancer: a novel genomic predictor of clinical response to fluoropyrimidine-based chemotherapy. | 2003 May |
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Folate improves endothelial function in patients with coronary heart disease. | 2003 Nov |
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Cerebrospinal fluid pterins and folates in Aicardi-Goutières syndrome: a new phenotype. | 2003 Sep 9 |
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Hyperproliferation of homocysteine-treated colon cancer cells is reversed by folate and 5-methyltetrahydrofolate. | 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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Thymidylate synthase and methylenetetrahydrofolate reductase gene polymorphisms: relationships with 5-fluorouracil sensitivity. | 2004 Jan 26 |
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Sodium-dependent methotrexate carrier-1 is expressed in rat kidney: cloning and functional characterization. | 2004 Mar |
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Homocysteine and reactive oxygen species in metabolic syndrome, type 2 diabetes mellitus, and atheroscleropathy: the pleiotropic effects of folate supplementation. | 2004 May 10 |
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Methionine metabolism in plants: chloroplasts are autonomous for de novo methionine synthesis and can import S-adenosylmethionine from the cytosol. | 2004 May 21 |
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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
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Edited
Fri Dec 15 16:31:26 GMT 2023
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Record UNII |
8S95DH25XC
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Record Status |
Validated (UNII)
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8S95DH25XC
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LEVOMEFOLIC ACID
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C1505
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CONCEPT | Dietary Supplement | ||
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CHEMBL1231574
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PARENT -> METABOLITE |
Levomefolate calcium is structurally identical to L-5-methyltetrahydrofolate (L-5-methyl-THF), a metabolite of vitamin B9
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ACTIVE MOIETY |