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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
Structure of LEVOMEFOLATE MAGNESIUM

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

HIDE SMILES / InChI

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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
SAFYRAL

Approved Use

1.1 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 Date

1.29237123E12
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Serum folate levels after UVA exposure: a two-group parallel randomised controlled trial.
2001
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
Carrier-mediated transport of folic acid in BeWo cell monolayers as a model of the human trophoblast.
2001 Nov
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
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
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 Thu Jul 06 14:36:12 UTC 2023
Edited
by admin
on Thu Jul 06 14:36:12 UTC 2023
Record UNII
1VZZ62R081
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVOMEFOLATE MAGNESIUM
Common Name English
Magnesium levomefolate [WHO-DD]
Common Name English
MAGNESIUM LEVOMEFOLATE
WHO-DD  
Common Name English
L-METHYLFOLATE MAGNESIUM
Common Name English
L-GLUTAMIC ACID, N-(4-((((6S)-2-AMINO-3,4,5,6,7,8-HEXAHYDRO-5-METHYL-4-OXO-6-PTERIDINYL)METHYL)AMINO)BENZOYL)-, MAGNESIUM SALT (1:1)
Systematic Name English
Code System Code Type Description
RXCUI
1549106
Created by admin on Thu Jul 06 14:36:12 UTC 2023 , Edited by admin on Thu Jul 06 14:36:12 UTC 2023
PRIMARY RxNorm
SMS_ID
100000170337
Created by admin on Thu Jul 06 14:36:12 UTC 2023 , Edited by admin on Thu Jul 06 14:36:12 UTC 2023
PRIMARY
DAILYMED
1VZZ62R081
Created by admin on Thu Jul 06 14:36:12 UTC 2023 , Edited by admin on Thu Jul 06 14:36:12 UTC 2023
PRIMARY
CAS
1429498-11-2
Created by admin on Thu Jul 06 14:36:12 UTC 2023 , Edited by admin on Thu Jul 06 14:36:12 UTC 2023
PRIMARY
PUBCHEM
135565020
Created by admin on Thu Jul 06 14:36:12 UTC 2023 , Edited by admin on Thu Jul 06 14:36:12 UTC 2023
PRIMARY
FDA UNII
1VZZ62R081
Created by admin on Thu Jul 06 14:36:12 UTC 2023 , Edited by admin on Thu Jul 06 14:36:12 UTC 2023
PRIMARY
DRUG BANK
DBSALT001534
Created by admin on Thu Jul 06 14:36:12 UTC 2023 , Edited by admin on Thu Jul 06 14:36:12 UTC 2023
PRIMARY
EVMPD
SUB184178
Created by admin on Thu Jul 06 14:36:12 UTC 2023 , Edited by admin on Thu Jul 06 14:36:12 UTC 2023
PRIMARY
Related Record Type Details
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Related Record Type Details
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