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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

1.29237123E12
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Methylenetetrahydrofolate reductase 677 C/T genotype and cardiovascular disease mortality in postmenopausal women.
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
Effect of feeding on circulating micronutrient concentrations in the Burmese python (Python molurus).
2001 Jun
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
High-performance liquid chromatographic measurement of 5,10-methylenetetrahydrofolate in liver.
2001 Oct 15
Syntheses of labeled vitamers of folic acid to be used as internal standards in stable isotope dilution assays.
2002 Aug 14
5,10-Methylenetetrahydrofolate reductase (MTHFR) assay in the forward direction: residual activity in MTHFR deficiency.
2002 Jun
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
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
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
A method for the analysis of natural and synthetic folate in foods.
2003 Jan 15
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
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
A review of folate receptor alpha cycling and 5-methyltetrahydrofolate accumulation with an emphasis on cell models in vitro.
2004 Apr 29
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
Thymidylate synthase and methylenetetrahydrofolate reductase gene polymorphisms: relationships with 5-fluorouracil sensitivity.
2004 Jan 26
Placental folate transport and binding are not impaired in pregnancies complicated by fetal growth restriction.
2004 Jul
Pharmacokinetic study on the utilisation of 5-methyltetrahydrofolate and folic acid in patients with coronary artery disease.
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
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
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
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