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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H23N7O6.Ca.5H2O
Molecular Weight 587.594
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOMEFOLATE CALCIUM PENTAHYDRATE

SMILES

O.O.O.O.O.[Ca++].CN1[C@@H](CNC2=CC=C(C=C2)C(=O)N[C@@H](CCC([O-])=O)C([O-])=O)CNC3=C1C(=O)NC(N)=N3

InChI

InChIKey=NVLUUBHWPOLECI-BWDMFOMUSA-L
InChI=1S/C20H25N7O6.Ca.5H2O/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);;5*1H2/q;+2;;;;;/p-2/t12-,13-;;;;;;/m0....../s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Ca
Molecular Weight 40.078
Charge 2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C20H25N7O6
Molecular Weight 459.4558
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

2010
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Methylenetetrahydrofolate reductase 677 C/T genotype and cardiovascular disease mortality in postmenopausal women.
2001 Apr 1
Marked suppression of the activity of some, but not all, antifolate compounds by augmentation of folate cofactor pools within tumor cells.
2001 Apr 1
Influence of a methionine synthase (D919G) polymorphism on plasma homocysteine and folate levels and relation to risk of myocardial infarction.
2001 Feb 15
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
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
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
Rapid method for the determination of total 5-methyltetrahydrofolate in blood by liquid chromatography with fluorescence detection.
2002 Jan 25
Multiple transcription start sites and alternative splicing in the methylenetetrahydrofolate reductase gene result in two enzyme isoforms.
2002 Sep
Intimal redox stress: accelerated atherosclerosis in metabolic syndrome and type 2 diabetes mellitus. Atheroscleropathy.
2002 Sep 27
Measurement of red blood cell methylfolate.
2002 Sep 28
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
Transport of 5-formyltetrahydrofolate into primary cultured cerebellar granule cells.
2003 Feb 7
A method for the analysis of natural and synthetic folate in foods.
2003 Jan 15
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
Methylenetetrahydrofolate reductase polymorphism in advanced colorectal cancer: a novel genomic predictor of clinical response to fluoropyrimidine-based chemotherapy.
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
Characterization of a pseudogene for murine methylenetetrahydrofolate reductase.
2003 Oct
Cerebrospinal fluid pterins and folates in Aicardi-Goutières syndrome: a new phenotype.
2003 Sep 9
Methylenetetrahydrofolate reductase and transcobalamin genetic polymorphisms in human spontaneous abortion: biological and clinical implications.
2004 Feb 17
Folic acid rescues nitric oxide-induced neural tube closure defects.
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
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 Sat Dec 16 11:00:15 GMT 2023
Edited
by admin
on Sat Dec 16 11:00:15 GMT 2023
Record UNII
JEC017DJGT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVOMEFOLATE CALCIUM PENTAHYDRATE
Common Name English
L-GLUTAMIC ACID, N-(4-((((6S)-2-AMINO-1,4,5,6,7,8-HEXAHYDRO-5-METHYL-4-OXO-6-PTERIDINYL)METHYL)AMINO)BENZOYL)-, CALCIUM SALT (1:1), PENTAHYDRATE
Systematic Name English
Code System Code Type Description
FDA UNII
JEC017DJGT
Created by admin on Sat Dec 16 11:00:15 GMT 2023 , Edited by admin on Sat Dec 16 11:00:15 GMT 2023
PRIMARY
CAS
419563-18-1
Created by admin on Sat Dec 16 11:00:15 GMT 2023 , Edited by admin on Sat Dec 16 11:00:15 GMT 2023
PRIMARY
PUBCHEM
135565054
Created by admin on Sat Dec 16 11:00:15 GMT 2023 , Edited by admin on Sat Dec 16 11:00:15 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
Related Record Type Details
ACTIVE MOIETY