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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H25N7O6
Molecular Weight 459.4566
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOMEFOLIC ACID

SMILES

CN1[C@@]([H])(CNc2ccc(cc2)C(=O)N[C@@]([H])(CCC(=O)O)C(=O)O)CNc3c1c(nc(=N)[nH]3)O

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

HIDE SMILES / InChI

Molecular Formula C20H25N7O6
Molecular Weight 459.4566
Charge 0
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

1292371200000
PubMed

PubMed

TitleDatePubMed
Determination of folates in foods by high-performance liquid chromatography with fluorescence detection after precolumn conversion to 5-methyltetrahydrofolates.
2001 Aug 31
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
Treatment of hyperhomocysteinemia in hemodialysis patients and renal transplant recipients.
2001 Feb
Folate improves endothelial function in coronary artery disease: an effect mediated by reduction of intracellular superoxide?
2001 Jul
Effect of feeding on circulating micronutrient concentrations in the Burmese python (Python molurus).
2001 Jun
High-performance liquid chromatographic measurement of 5,10-methylenetetrahydrofolate in liver.
2001 Oct 15
Methylenetetrahydrofolate reductase polymorphism and susceptibility to breast cancer.
2002
Downregulation of reduced-folate transporter by glucose in cultured RPE cells and in RPE of diabetic mice.
2002 Feb
Interaction of 5-methyltetrahydrofolate and tetrahydrobiopterin on endothelial function.
2002 Jun
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
Measurement of red blood cell methylfolate.
2002 Sep 28
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
Uptake of 5-methyltetrahydrofolate into PC-3 human prostate cancer cells is carrier-mediated.
2003 Aug
Reduced folate transport to the CNS in female Rett patients.
2003 Aug 26
Dietary prevention of post-angioplasty restenosis. From illusion and disillusion to pragmatism.
2003 Dec
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
Tetrahydrofolate and 5-methyltetrahydrofolate are folates with high antioxidant activity. Identification of the antioxidant pharmacophore.
2003 Dec 18
Effect of riboflavin status on the homocysteine-lowering effect of folate in relation to the MTHFR (C677T) genotype.
2003 Feb
Transport of 5-formyltetrahydrofolate into primary cultured rat astrocytes.
2003 Feb 1
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
A mass spectrometric validated high-performance liquid chromatography procedure for the determination of folates in foods.
2003 Jun 18
Residues 45 and 404 in the murine reduced folate carrier may interact to alter carrier binding and mobility.
2003 Jun 27
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
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
Cerebrospinal fluid pterins and folates in Aicardi-Goutières syndrome: a new phenotype.
2003 Sep 9
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
Methylenetetrahydrofolate reductase and transcobalamin genetic polymorphisms in human spontaneous abortion: biological and clinical implications.
2004 Feb 17
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
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
5-Methyltetrahydrofolic acid and folic acid measured in plasma with liquid chromatography tandem mass spectrometry: applications to folate absorption and metabolism.
2004 Mar 15
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 Fri Jun 25 22:41:30 UTC 2021
Edited
by admin
on Fri Jun 25 22:41:30 UTC 2021
Record UNII
8S95DH25XC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVOMEFOLIC ACID
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
N-(4-((((6S)-2-AMINO-5-METHYL-4-OXO-1,4,5,6,7,8-HEXAHYDROPTERIDIN-6- YL)METHYL)AMINO)BENZOYL)-L-GLUTAMIC ACID
Systematic Name English
L-5-MTHF
Common Name English
(6S)-5-METHYLTETRAHYDROFOLATE
WHO-DD  
Common Name English
L-METHYLFOLATE
VANDF  
Common Name English
5- METHYLTETRAHYDROFOLATE
Common Name English
(6S)-5-METHYLTETRAHYDROFOLATE [WHO-DD]
Common Name English
5-METHYL-(6S)-TETRAHYDROFOLIC ACID
Common Name English
LEVOMEFOLATE
VANDF  
Common Name English
LEVOMEFOLIC ACID [INN]
Common Name English
LEVOMEFOLATE [VANDF]
Common Name English
5-MTHF
Common Name English
LEVOMEFOLIC ACID [WHO-DD]
Common Name English
LEVOMEFOLINIC ACID
Common Name English
L-METHYLFOLATE [VANDF]
Common Name English
LMSR
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)-
Common Name English
LEVOMEFOLIC ACID [USAN]
Common Name English
Code System Code Type Description
FDA UNII
8S95DH25XC
Created by admin on Fri Jun 25 22:41:31 UTC 2021 , Edited by admin on Fri Jun 25 22:41:31 UTC 2021
PRIMARY
DRUG CENTRAL
4621
Created by admin on Fri Jun 25 22:41:31 UTC 2021 , Edited by admin on Fri Jun 25 22:41:31 UTC 2021
PRIMARY
WIKIPEDIA
LEVOMEFOLIC ACID
Created by admin on Fri Jun 25 22:41:31 UTC 2021 , Edited by admin on Fri Jun 25 22:41:31 UTC 2021
PRIMARY
PUBCHEM
135398561
Created by admin on Fri Jun 25 22:41:31 UTC 2021 , Edited by admin on Fri Jun 25 22:41:31 UTC 2021
PRIMARY
CAS
31690-09-2
Created by admin on Fri Jun 25 22:41:31 UTC 2021 , Edited by admin on Fri Jun 25 22:41:31 UTC 2021
PRIMARY
INN
8917
Created by admin on Fri Jun 25 22:41:31 UTC 2021 , Edited by admin on Fri Jun 25 22:41:31 UTC 2021
PRIMARY
NCI_THESAURUS
C81119
Created by admin on Fri Jun 25 22:41:31 UTC 2021 , Edited by admin on Fri Jun 25 22:41:31 UTC 2021
PRIMARY
DRUG BANK
DB11256
Created by admin on Fri Jun 25 22:41:31 UTC 2021 , Edited by admin on Fri Jun 25 22:41:31 UTC 2021
PRIMARY
EVMPD
SUB33688
Created by admin on Fri Jun 25 22:41:31 UTC 2021 , Edited by admin on Fri Jun 25 22:41:31 UTC 2021
PRIMARY
RXCUI
1025342
Created by admin on Fri Jun 25 22:41:31 UTC 2021 , Edited by admin on Fri Jun 25 22:41:31 UTC 2021
PRIMARY
EPA CompTox
31690-09-2
Created by admin on Fri Jun 25 22:41:31 UTC 2021 , Edited by admin on Fri Jun 25 22:41:31 UTC 2021
PRIMARY
RXCUI
1592257
Created by admin on Fri Jun 25 22:41:31 UTC 2021 , Edited by admin on Fri Jun 25 22:41:31 UTC 2021
ALTERNATIVE
NCI_THESAURUS
C1505
Created by admin on Fri Jun 25 22:41:31 UTC 2021 , Edited by admin on Fri Jun 25 22:41:31 UTC 2021
CONCEPT Dietary Supplement
ChEMBL
CHEMBL1231574
Created by admin on Fri Jun 25 22:41:31 UTC 2021 , Edited by admin on Fri Jun 25 22:41:31 UTC 2021
PRIMARY
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SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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PARENT -> METABOLITE
Levomefolate calcium is structurally identical to L-5-methyltetrahydrofolate (L-5-methyl-THF), a metabolite of vitamin B9
Related Record Type Details
ACTIVE MOIETY