Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H25N7O6 |
Molecular Weight | 459.4558 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
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=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
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.
CNS Activity
Approval Year
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | SAFYRAL Approved Use1.1 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 Date2010 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
57.7 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22909145/ |
0.451 mg single, oral dose: 0.451 mg route of administration: Oral experiment type: SINGLE co-administered: ETHINYL ESTRADIOL |
L-5-METHYLTETRAHYDROFOLATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
370 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22909145/ |
0.451 mg single, oral dose: 0.451 mg route of administration: Oral experiment type: SINGLE co-administered: ETHINYL ESTRADIOL |
L-5-METHYLTETRAHYDROFOLATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22909145/ |
0.451 mg single, oral dose: 0.451 mg route of administration: Oral experiment type: SINGLE co-administered: ETHINYL ESTRADIOL |
L-5-METHYLTETRAHYDROFOLATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
44% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22909145/ |
0.451 mg single, oral dose: 0.451 mg route of administration: Oral experiment type: SINGLE co-administered: ETHINYL ESTRADIOL |
L-5-METHYLTETRAHYDROFOLATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
Low seminal plasma folate concentrations are associated with low sperm density and count in male smokers and nonsmokers. | 2001 Feb |
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Influence of a methionine synthase (D919G) polymorphism on plasma homocysteine and folate levels and relation to risk of myocardial infarction. | 2001 Feb 15 |
|
Effect of food on the oral bioavailability of UFT and leucovorin in cancer patients. | 2001 Mar |
|
Enzymatic determination of homocysteine in cell extracts. | 2001 Mar |
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Carrier-mediated transport of folic acid in BeWo cell monolayers as a model of the human trophoblast. | 2001 Nov |
|
Rapid method for the determination of total 5-methyltetrahydrofolate in blood by liquid chromatography with fluorescence detection. | 2002 Jan 25 |
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Determination of 5-methyltetrahydrofolate (13C-labeled and unlabeled) in human plasma and urine by combined liquid chromatography mass spectrometry. | 2002 Jun 15 |
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5-methyltetrahydrofolate restores endothelial function in uraemic patients on convective haemodialysis. | 2002 May |
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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 |
|
Reduced folate transport to the CNS in female Rett patients. | 2003 Aug 26 |
|
Determination of 5-methyltetrahydrofolic acid and folic acid in citrus juices using stable isotope dilution-mass spectrometry. | 2003 Feb 26 |
|
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 |
|
Analysis of the human folate receptor beta gene for an association with neural tube defects. | 2003 Jun |
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Residues 45 and 404 in the murine reduced folate carrier may interact to alter carrier binding and mobility. | 2003 Jun 27 |
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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 a pseudogene for murine methylenetetrahydrofolate reductase. | 2003 Oct |
|
Regulation of S-adenosylmethionine levels in Saccharomyces cerevisiae. | 2003 Oct 31 |
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Cerebrospinal fluid pterins and folates in Aicardi-Goutières syndrome: a new phenotype. | 2003 Sep 9 |
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Hyperproliferation of homocysteine-treated colon cancer cells is reversed by folate and 5-methyltetrahydrofolate. | 2004 Apr |
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A review of folate receptor alpha cycling and 5-methyltetrahydrofolate accumulation with an emphasis on cell models in vitro. | 2004 Apr 29 |
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Placental folate transport and binding are not impaired in pregnancies complicated by fetal growth restriction. | 2004 Jul |
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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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23332600
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
Edited
Mon Mar 31 18:30:24 GMT 2025
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on
Mon Mar 31 18:30:24 GMT 2025
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Record UNII |
8S95DH25XC
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Record Status |
Validated (UNII)
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Record Version |
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8S95DH25XC
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4621
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LEVOMEFOLIC ACID
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C1505
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TT-129
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CHEMBL1231574
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