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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
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

2010
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Serum folate levels after UVA exposure: a two-group parallel randomised controlled trial.
2001
Methylenetetrahydrofolate reductase 677 C/T genotype and cardiovascular disease mortality in postmenopausal women.
2001 Apr 1
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
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
Antisense modulation of 5,10-methylenetetrahydrofolate reductase expression produces neural tube defects in mouse embryos.
2001 Jan-Feb
Folate and chemoprevention of colorectal cancer: Is 5-methyl-tetrahydrofolate an active antiproliferative agent in folate-treated colon-cancer cells?
2001 Jul-Aug
Effect of feeding on circulating micronutrient concentrations in the Burmese python (Python molurus).
2001 Jun
A novel neurodevelopmental syndrome responsive to 5-hydroxytryptophan and carbidopa.
2001 Jun
Enzymatic determination of homocysteine in cell extracts.
2001 Mar
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
Monitoring of methotrexate and reduced folates in the cerebrospinal fluid of cancer patients.
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
Impaired NO-dependent vasodilation in patients with Type II (non-insulin-dependent) diabetes mellitus is restored by acute administration of folate.
2002 Jul
Vitamin C therapy ameliorates vascular endothelial dysfunction in treated patients with homocystinuria.
2002 May
The enrichment of eggs with folic acid through supplementation of the laying hen diet.
2002 Sep
Uptake of 5-methyltetrahydrofolate into PC-3 human prostate cancer cells is carrier-mediated.
2003 Aug
Tetrahydrofolate and 5-methyltetrahydrofolate are folates with high antioxidant activity. Identification of the antioxidant pharmacophore.
2003 Dec 18
Transport of 5-formyltetrahydrofolate into primary cultured cerebellar granule cells.
2003 Feb 7
A comparison of folic acid and 5-methyltetrahydrofolate for prevention of DNA damage and cell death in human lymphocytes in vitro.
2003 Jan
Analysis of the human folate receptor beta gene for an association with neural tube defects.
2003 Jun
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
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
Determination of folate vitamers in human serum by stable-isotope-dilution tandem mass spectrometry and comparison with radioassay and microbiologic assay.
2004 Feb
Solid-phase extraction-electrospray ionization mass spectrometry for the quantification of folate in human plasma or serum.
2004 Feb 1
Red cell N5-methyltetrahydrofolate concentrations and C677T methylenetetrahydrofolate reductase genotype in patients with stroke.
2004 Jan
Thymidylate synthase and methylenetetrahydrofolate reductase gene polymorphisms: relationships with 5-fluorouracil sensitivity.
2004 Jan 26
Pharmacokinetic study on the utilisation of 5-methyltetrahydrofolate and folic acid in patients with coronary artery disease.
2004 Mar
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
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
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 Sat Dec 16 09:07:13 GMT 2023 , Edited by admin on Sat Dec 16 09:07:13 GMT 2023
PRIMARY RxNorm
SMS_ID
100000170337
Created by admin on Sat Dec 16 09:07:13 GMT 2023 , Edited by admin on Sat Dec 16 09:07:13 GMT 2023
PRIMARY
DAILYMED
1VZZ62R081
Created by admin on Sat Dec 16 09:07:13 GMT 2023 , Edited by admin on Sat Dec 16 09:07:13 GMT 2023
PRIMARY
CAS
1429498-11-2
Created by admin on Sat Dec 16 09:07:13 GMT 2023 , Edited by admin on Sat Dec 16 09:07:13 GMT 2023
PRIMARY
PUBCHEM
135565020
Created by admin on Sat Dec 16 09:07:13 GMT 2023 , Edited by admin on Sat Dec 16 09:07:13 GMT 2023
PRIMARY
FDA UNII
1VZZ62R081
Created by admin on Sat Dec 16 09:07:13 GMT 2023 , Edited by admin on Sat Dec 16 09:07:13 GMT 2023
PRIMARY
DRUG BANK
DBSALT001534
Created by admin on Sat Dec 16 09:07:13 GMT 2023 , Edited by admin on Sat Dec 16 09:07:13 GMT 2023
PRIMARY
EVMPD
SUB184178
Created by admin on Sat Dec 16 09:07:13 GMT 2023 , Edited by admin on Sat Dec 16 09:07:13 GMT 2023
PRIMARY