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
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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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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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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Association of methylenetetrahydrofolate reductase polymorphism C677T and dietary folate with the risk of cervical dysplasia. | 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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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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Effect of feeding on circulating micronutrient concentrations in the Burmese python (Python molurus). | 2001 Jun |
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A novel neurodevelopmental syndrome responsive to 5-hydroxytryptophan and carbidopa. | 2001 Jun |
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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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High-performance liquid chromatographic measurement of 5,10-methylenetetrahydrofolate in liver. | 2001 Oct 15 |
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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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Preponderance of methylenetetrahydrofolate reductase C677T homozygosity among leukemia patients intolerant to methotrexate. | 2002 Dec |
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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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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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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 |
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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 |
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Uptake of 5-methyltetrahydrofolate into PC-3 human prostate cancer cells is carrier-mediated. | 2003 Aug |
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Reduced folate transport to the CNS in female Rett patients. | 2003 Aug 26 |
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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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Transport of 5-formyltetrahydrofolate into primary cultured rat astrocytes. | 2003 Feb 1 |
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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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Analysis of the human folate receptor beta gene for an association with neural tube defects. | 2003 Jun |
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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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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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Folate improves endothelial function in patients with coronary heart disease. | 2003 Nov |
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Hyperhomocystinemia in children with inflammatory bowel disease. | 2003 Nov |
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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 |
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Regulation of S-adenosylmethionine levels in Saccharomyces cerevisiae. | 2003 Oct 31 |
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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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The C677 mutation in methylene tetrahydrofolate reductase gene: correlation with uric acid and cardiovascular risk factors in elderly Korean men. | 2004 Apr |
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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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Comparative study on pressure and temperature stability of 5-methyltetrahydrofolic acid in model systems and in food products. | 2004 Feb 11 |
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Pharmacokinetic study on the utilisation of 5-methyltetrahydrofolate and folic acid in patients with coronary artery disease. | 2004 Mar |
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Folic acid rescues nitric oxide-induced neural tube closure defects. | 2004 Mar |
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Sodium-dependent methotrexate carrier-1 is expressed in rat kidney: cloning and functional characterization. | 2004 Mar |
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5-Methyltetrahydrofolic acid and folic acid measured in plasma with liquid chromatography tandem mass spectrometry: applications to folate absorption and metabolism. | 2004 Mar 15 |
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The methionine synthase polymorphism D919G alters susceptibility to primary central nervous system lymphoma. | 2004 May 17 |
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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
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Code System | Code | Type | Description | ||
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8S95DH25XC
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4621
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LEVOMEFOLIC ACID
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135398561
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8S95DH25XC
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C81119
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100000127631
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DB11256
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1592257
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C1505
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CONCEPT | Dietary Supplement | ||
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TT-129
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CHEMBL1231574
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ACTIVE MOIETY
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