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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

2010
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Serum folate levels after UVA exposure: a two-group parallel randomised controlled trial.
2001
Marked suppression of the activity of some, but not all, antifolate compounds by augmentation of folate cofactor pools within tumor cells.
2001 Apr 1
Determination of folates in foods by high-performance liquid chromatography with fluorescence detection after precolumn conversion to 5-methyltetrahydrofolates.
2001 Aug 31
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
Influence of a methionine synthase (D919G) polymorphism on plasma homocysteine and folate levels and relation to risk of myocardial infarction.
2001 Feb 15
Effect of food on the oral bioavailability of UFT and leucovorin in cancer patients.
2001 Mar
Treatment of hyperhomocysteinemia in end-stage renal disease.
2001 Oct
High-performance liquid chromatographic measurement of 5,10-methylenetetrahydrofolate in liver.
2001 Oct 15
Folic-acid-mediated inhibition of human colon-cancer cell growth.
2001 Sep
Syntheses of labeled vitamers of folic acid to be used as internal standards in stable isotope dilution assays.
2002 Aug 14
Downregulation of reduced-folate transporter by glucose in cultured RPE cells and in RPE of diabetic mice.
2002 Feb
Rapid method for the determination of total 5-methyltetrahydrofolate in blood by liquid chromatography with fluorescence detection.
2002 Jan 25
Red blood cell methylfolate and plasma homocysteine as risk factors for venous thromboembolism: a matched case-control study.
2002 Mar 2
The enrichment of eggs with folic acid through supplementation of the laying hen diet.
2002 Sep
Measurement of red blood cell methylfolate.
2002 Sep 28
Tetrahydrofolate and 5-methyltetrahydrofolate are folates with high antioxidant activity. Identification of the antioxidant pharmacophore.
2003 Dec 18
A method for the analysis of natural and synthetic folate in foods.
2003 Jan 15
Analysis of the human folate receptor beta gene for an association with neural tube defects.
2003 Jun
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
Characterization of a pseudogene for murine methylenetetrahydrofolate reductase.
2003 Oct
Hyperproliferation of homocysteine-treated colon cancer cells is reversed by folate and 5-methyltetrahydrofolate.
2004 Apr
The C677 mutation in methylene tetrahydrofolate reductase gene: correlation with uric acid and cardiovascular risk factors in elderly Korean men.
2004 Apr
A review of folate receptor alpha cycling and 5-methyltetrahydrofolate accumulation with an emphasis on cell models in vitro.
2004 Apr 29
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
Placental folate transport and binding are not impaired in pregnancies complicated by fetal growth restriction.
2004 Jul
Mutations of the MTHFR gene (428C>T and [458G>T+459C>T]) markedly decrease MTHFR enzyme activity.
2004 Jun
Sodium-dependent methotrexate carrier-1 is expressed in rat kidney: cloning and functional characterization.
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
The methionine synthase polymorphism D919G alters susceptibility to primary central nervous system lymphoma.
2004 May 17
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 Sat Dec 16 09:07:12 GMT 2023
Edited
by admin
on Sat Dec 16 09:07:12 GMT 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 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
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ACTIVE MOIETY