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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
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
Syntheses of labeled vitamers of folic acid to be used as internal standards in stable isotope dilution assays.
2002 Aug 14
Preponderance of methylenetetrahydrofolate reductase C677T homozygosity among leukemia patients intolerant to methotrexate.
2002 Dec
Distribution of plasma folate forms in hemodialysis patients receiving high daily doses of L-folinic or folic acid.
2002 Dec
Impaired NO-dependent vasodilation in patients with Type II (non-insulin-dependent) diabetes mellitus is restored by acute administration of folate.
2002 Jul
Nature and nurture in vitamin B12 deficiency.
2002 Jul
Antisense inhibition of methylenetetrahydrofolate reductase reduces survival of methionine-dependent tumour lines.
2002 Jul 15
Cytoplasmic serine hydroxymethyltransferase mediates competition between folate-dependent deoxyribonucleotide and S-adenosylmethionine biosyntheses.
2002 Oct 11
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
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
Determination of 5-methyltetrahydrofolic acid and folic acid in citrus juices using stable isotope dilution-mass spectrometry.
2003 Feb 26
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
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
Residues 45 and 404 in the murine reduced folate carrier may interact to alter carrier binding and mobility.
2003 Jun 27
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
Characterization of mutations in severe methylenetetrahydrofolate reductase deficiency reveals an FAD-responsive mutation.
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
Cerebrospinal fluid pterins and folates in Aicardi-Goutières syndrome: a new phenotype.
2003 Sep 9
The C677 mutation in methylene tetrahydrofolate reductase gene: correlation with uric acid and cardiovascular risk factors in elderly Korean men.
2004 Apr
Quantitative evaluation of the drug-drug interactions between methotrexate and nonsteroidal anti-inflammatory drugs in the renal uptake process based on the contribution of organic anion transporters and reduced folate carrier.
2004 Apr
A review of folate receptor alpha cycling and 5-methyltetrahydrofolate accumulation with an emphasis on cell models in vitro.
2004 Apr 29
Folate, homocysteine, endothelial function and cardiovascular disease.
2004 Feb
Solid-phase extraction-electrospray ionization mass spectrometry for the quantification of folate in human plasma or serum.
2004 Feb 1
Comparative study on pressure and temperature stability of 5-methyltetrahydrofolic acid in model systems and in food products.
2004 Feb 11
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
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
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
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 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