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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H23N7O6.2Na
Molecular Weight 503.4195
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOMEFOLATE SODIUM

SMILES

[Na+].[Na+].CN1[C@@H](CNC2=CC=C(C=C2)C(=O)N[C@@H](CCC([O-])=O)C([O-])=O)CNC3=NC(N)=NC(O)=C13

InChI

InChIKey=KKIWVYLOTHCGRV-NJHZPMQHSA-L
InChI=1S/C20H25N7O6.2Na/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*+1/p-2/t12-,13-;;/m0../s1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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
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
Folate improves endothelial function in coronary artery disease: an effect mediated by reduction of intracellular superoxide?
2001 Jul
Carrier-mediated transport of folic acid in BeWo cell monolayers as a model of the human trophoblast.
2001 Nov
Treatment of hyperhomocysteinemia in end-stage renal disease.
2001 Oct
High-performance liquid chromatographic measurement of 5,10-methylenetetrahydrofolate in liver.
2001 Oct 15
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
Folic acid improves endothelial function in coronary artery disease via mechanisms largely independent of homocysteine lowering.
2002 Jan 1
Nature and nurture in vitamin B12 deficiency.
2002 Jul
Determination of 5-methyltetrahydrofolate (13C-labeled and unlabeled) in human plasma and urine by combined liquid chromatography mass spectrometry.
2002 Jun 15
5-methyltetrahydrofolate restores endothelial function in uraemic patients on convective haemodialysis.
2002 May
Cytoplasmic serine hydroxymethyltransferase mediates competition between folate-dependent deoxyribonucleotide and S-adenosylmethionine biosyntheses.
2002 Oct 11
The enrichment of eggs with folic acid through supplementation of the laying hen diet.
2002 Sep
Does the interaction between maternal folate intake and the methylenetetrahydrofolate reductase polymorphisms affect the risk of cleft lip with or without cleft palate?
2003 Apr 1
Dietary prevention of post-angioplasty restenosis. From illusion and disillusion to pragmatism.
2003 Dec
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
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
Folate improves endothelial function in patients with coronary heart disease.
2003 Nov
Hyperhomocystinemia in children with inflammatory bowel disease.
2003 Nov
Age dependence of the influence of methylenetetrahydrofolate reductase genotype on plasma homocysteine level.
2003 Nov 1
Thrombophilia and pregnancy.
2003 Nov 14
Characterization of a pseudogene for murine methylenetetrahydrofolate reductase.
2003 Oct
Regulation of S-adenosylmethionine levels in Saccharomyces cerevisiae.
2003 Oct 31
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
Normal dopaminergic and serotonergic metabolites in cerebrospinal fluid and blood of restless legs syndrome patients.
2004 Feb
5-Methyltetrahydrofolic acid and folic acid measured in plasma with liquid chromatography tandem mass spectrometry: applications to folate absorption and metabolism.
2004 Mar 15
Methionine metabolism in plants: chloroplasts are autonomous for de novo methionine synthesis and can import S-adenosylmethionine from the cytosol.
2004 May 21
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 10:09:11 UTC 2023
Edited
by admin
on Sat Dec 16 10:09:11 UTC 2023
Record UNII
B3KYL5163W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVOMEFOLATE SODIUM
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)-, SODIUM SALT (1:2)
Systematic Name English
Code System Code Type Description
CAS
1423663-76-6
Created by admin on Sat Dec 16 10:09:12 UTC 2023 , Edited by admin on Sat Dec 16 10:09:12 UTC 2023
PRIMARY
PUBCHEM
135565435
Created by admin on Sat Dec 16 10:09:12 UTC 2023 , Edited by admin on Sat Dec 16 10:09:12 UTC 2023
PRIMARY
FDA UNII
B3KYL5163W
Created by admin on Sat Dec 16 10:09:12 UTC 2023 , Edited by admin on Sat Dec 16 10:09:12 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY