Levomefolic acid

Identification

Summary

Levomefolic acid is a folate supplement used to prevent neural tube defects in pregnancy or folate deficiency.

Brand Names
Beyaz 28 Day, EnBrace HR, EnLyte, Safyral 28 Day, Tydemy 28 Day, Yaz Plus
Generic Name
Levomefolic acid
DrugBank Accession Number
DB11256
Background

Levomefolic acid (INN) is the metabolite of folic acid (Vitamin B9) and it is a predominant active form of folate found in foods and in the blood circulation, accounting for 98% of folates in human plasma 8. It is transported across the membranes including the blood-brain barrier into various tissues where it plays an essential role in the DNA synthesis, cysteine cycle and regulation of homocysteine, where it methylates homocysteine and forms methionine and tetrahydrofolate (THF). Levomefolate is approved as a food additive and is designated a GRAS (generally regarded as safe) compound 13. It is available commercially as a crystalline form of the calcium salt (Metafolin(R)), which has the stability required for use as a supplement 8. Supplementation of levomefolic acid is desired over folic acid due to reduced potential for masking vitamin B12 deficiency symptoms.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 459.4558
Monoisotopic: 459.186631567
Chemical Formula
C20H25N7O6
Synonyms
  • (6S)-5-methyltetrahydrofolate
  • (6S)-5-Methyltetrahydrofolic acid
  • (6S)-5-MTHF
  • 5-methyl-(6S)-tetrahydrofolic acid
  • L-5-methyltetrahydrofolate
  • L-5-MTHF
  • L-methylfolate
  • Levomefolate
  • Levomefolic acid
  • LMSR
  • N-[4-[[[(6S)-2-Amino-3,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl]methyl]amino]benzoyl]-L-glutamic acid

Pharmacology

Indication

For the treatment and prevention of folate deficiency and for use as an antidote against folic acid antagonists. Contained in oral contraceptives to reduce the risk of neural tube defects arising from folic acid deficiency for pregnant women who conceived during use or shortly after the discontinuation of the product. Being studied for use as a treatment for cardiovascular diseases 7 and adjunct therapy for patients undergoing antidepressant pharmacotherapy 5,6.

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Associated Therapies
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Pharmacodynamics

Levomefolic acid is an active metabolite of folic acid and a methyl group donor in one-carbon metabolism reactions. It regulates important cellular functions such as DNA biosynthesis, gene expression regulation, amino acid synthesis and metabolism, and myelin synthesis and repair. As a only form of folate that can cross the blood-brain barrier, it acts as a cofactor in the production of monoamine neurotransmitters such as dopamine, serotonin and norepinephrine 6. Levomefolic acid is also involved in red blood cell formation 11.

Mechanism of action

Levomefolic acid plays a critical role in methylating homocysteines into methionine by acting as a methyl donor in a reaction catalyzed by vitamine B12-dependent methionine synthase. Homocysteine must either be further metabolized via transulfuration to become cysteine, taurine, and glutathione via a B6-dependent process, or re-methylated to become methionine again. Methionine formed from remethylation of homocysteine by levomefolic acid forms the downstream metabolite S-adenosylmethionine (SAMe), which is involved in numerous biochemical methyl donation reactions, including reactions forming monoamine neurotransmitters 10. Studies suggest that high plasma levels of homocysteine is associated with increased incidences of arterial plaque formation 9.

Absorption

Absorbed in the proximal small intestines via the active proton-coupled folate transporter (PCFT) that transports both oxidized and reduced folic acids. Passive diffusion also occurs at the proximal and distal portions of the small intestines 9. A single oral dose of 906nmol of levomefolic acid in healthy females resulted in the mean peak plasma concentration of 39.4nmol/L 8.

Volume of distribution

Circulates in its free form or loosely bound to plasma proteins

Protein binding

Approximately 56% bound to plasma proteins

Metabolism

Levomefolic acid is further converted into tetrahydrofolate (THF) via the vitamin B12-dependent enzyme methionine synthase before effective polyglutamylation by folylpolyglutamate synthetase (FPG). Polyglumate forms of folic acids are more effective substrates for associated enzymes in folate-dependent reactions.

Route of elimination

Mainly eliminated through renal or fecal excretion. Small proportion of excreted levomefolic acid is in unchanged form as over 99% of tissue folate is in polyglutamate form. Some portions of levomefolic acid is secreted into bile.

Half-life

The mean elimination half-life is approximately 3 hours after 5mg of oral L-methylfolate, administered daily for 7 days 15.

Clearance

Not Available

Adverse Effects
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Toxicity

Overdose of levomefolic acid is unlikely to cause clinically significant adverse events.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
CapecitabineThe risk or severity of adverse effects can be increased when Levomefolic acid is combined with Capecitabine.
CarbamazepineThe serum concentration of Levomefolic acid can be decreased when it is combined with Carbamazepine.
ColestipolThe serum concentration of Levomefolic acid can be decreased when it is combined with Colestipol.
FlucytosineThe risk or severity of adverse effects can be increased when Levomefolic acid is combined with Flucytosine.
FluorouracilThe risk or severity of adverse effects can be increased when Levomefolic acid is combined with Fluorouracil.
Food Interactions
  • Take with or without food. Recommendations vary from product to product - consult individual product monographs for additional information.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Levomefolate calciumA9R10K3F2F151533-22-1VWBBRFHSPXRJQD-QNTKWALQSA-L
Levomefolate glucosamineQ65PL71Q1A1181972-37-1FZDRYCKUVGVDSO-KWWXADPNSA-N
Levomefolate magnesium1VZZ62R0811429498-11-2UNKHRTFYDNBUHK-QNTKWALQSA-L
Product Images
International/Other Brands
Metafolin
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
L-Methylfolate CalciumTablet15 mg/1OralSeton Pharmaceuticals2010-06-302012-03-17US flag
L-Methylfolate CalciumTablet, coated15 mg/1Oralbryant ranch prepack2015-01-08Not applicableUS flag
L-Methylfolate CalciumTablet, coated7.5 mg/1OralVirtus Pharmaceuticals2012-03-152015-02-15US flag
L-Methylfolate CalciumTablet7.5 mg/1OralWestminster Pharmaceuticals, LLC2021-04-092024-05-01US flag
L-Methylfolate CalciumTablet, coated7.5 mg/1OralVirtus Pharmaceuticals2015-02-09Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
BeyazLevomefolate calcium (0.451 mg/1) + Levomefolate calcium (0.451 mg/1) + Drospirenone (3 mg/1) + Ethinylestradiol (0.02 mg/1)Kit; Tablet, film coatedOralBayer HealthCare Pharmaceuticals Inc.2010-10-07Not applicableUS flag
BeyazLevomefolate calcium (0.451 mg/1) + Levomefolate calcium (0.451 mg/1) + Drospirenone (3 mg/1) + Ethinylestradiol (0.02 mg/1)Kit; Tablet, film coatedOralBayer HealthCare Pharmaceuticals Inc.2010-10-07Not applicableUS flag
Drospirenone, Ethinyl Estradiol and Levomefolate Calcium and Levomefolate CalciumLevomefolate calcium (0.451 mg/1) + Levomefolate calcium (0.451 mg/1) + Drospirenone (3 mg/1) + Ethinylestradiol (0.02 mg/1)Kit; Tablet, film coatedOralLupin Pharmaceuticals, Inc.2018-08-22Not applicableUS flag
Drospirenone, Ethinyl Estradiol and Levomefolate Calcium and Levomefolate CalciumLevomefolate calcium (0.451 mg/1) + Levomefolate calcium (0.451 mg/1) + Drospirenone (3 mg/1) + Ethinylestradiol (0.02 mg/1)Kit; Tablet, film coatedOralLupin Pharmaceuticals, Inc.2018-08-22Not applicableUS flag
Drospirenone/ethinyl estradiol/levomefolate calcium and levomefolate calciumLevomefolate calcium (0.451 mg/1) + Levomefolate calcium (0.451 mg/1) + Drospirenone (3 mg/1) + Ethinylestradiol (0.03 mg/1)Kit; Tablet, film coatedOralSandoz Inc2015-08-01Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Biopar delta-FORTELevomefolate magnesium (7 mg/1) + Cobalamin (50 ug/1) + Cobamamide (50 ug/1) + Dihydrofolic Acid (1 mg/1) + Gastric intrinsic factor (50 mg/1) + Levoleucovorin (2.5 mg/1)CapsuleOralJaymac Pharma2023-06-01Not applicableUS flag
BumP DHALevomefolate magnesium (1 mg/1) + Cobamamide (500 mg/1) + Flavin adenine dinucleotide (1 mg/1) + Flavin mononucleotide (2 mg/1) + Iron (15 mg/1) + Leucovorin (1 mg/1) + Magnesium oxide (125 mg/1) + NADH (25 ug/1) + Omega-3 fatty acids (300 mg/1) + Potassium Iodide (250 ug/1) + Pyridoxal phosphate (5 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Zinc glycinate (15 1/1)CapsuleOralCenturion Labs2017-03-242017-04-17US flag
ChromagenLevomefolic acid (750 ug/1) + Ascorbic acid (60 mg/1) + Cyanocobalamin (10 ug/1) + Ferrous asparto glycinate (25 mg/1) + Ferrous fumarate (50 mg/1) + Folic acid (250 ug/1) + Gastric intrinsic factor (100 mg/1) + Zinc (12 mg/1)CapsuleOralAvion Pharmaceuticals, Llc2017-01-10Not applicableUS flag
Davimet with FluorideLevomefolate calcium (1000 ug/1) + Ascorbic acid (24 mg/1) + Cholecalciferol (10 ug/1) + DL-alpha tocopheryl acetate (6.75 mg/1) + Mecobalamin (4.5 ug/1) + Niacin (13.5 mg/1) + Pyridoxine hydrochloride (1.05 mg/1) + Riboflavin (1.2 mg/1) + Sodium ascorbate (36 mg/1) + Sodium fluoride (0.75 mg/1) + Thiamine mononitrate (1.05 mg/1) + Vitamin A (750 ug/1)Tablet, chewableOralPureTek Corporation2024-02-28Not applicableUS flag
Davimet-MLevomefolate calcium (1000 ug/1) + Ascorbic acid (24 mg/1) + Cholecalciferol (10 ug/1) + DL-alpha tocopheryl acetate (10 mg/1) + Mecobalamin (4.5 ug/1) + Niacin (13.5 mg/1) + Pyridoxine hydrochloride (1.05 mg/1) + Riboflavin (1.2 mg/1) + Sodium ascorbate (36 mg/1) + Thiamine mononitrate (1.05 mg/1) + Vitamin A (750 ug/1)Tablet, chewableOralPureTek Corporation2023-11-30Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pteridines and derivatives
Sub Class
Pterins and derivatives
Direct Parent
Tetrahydrofolic acids
Alternative Parents
Glutamic acid and derivatives / N-acyl-alpha amino acids / Hippuric acids / Aminobenzamides / Aniline and substituted anilines / Phenylalkylamines / Benzoyl derivatives / Dialkylarylamines / Aminopyrimidines and derivatives / Secondary alkylarylamines
show 13 more
Substituents
Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aminobenzamide / Aminobenzoic acid or derivatives / Aminopyrimidine / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Azacycle
show 35 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tetrahydrofolic acid (CHEBI:15641)
Affected organisms
Not Available

Chemical Identifiers

UNII
8S95DH25XC
CAS number
31690-09-2
InChI Key
ZNOVTXRBGFNYRX-STQMWFEESA-N
InChI
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
IUPAC Name
(2S)-2-{[4-({[(6S)-2-amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
SMILES
CN1[C@@H](CNC2=CC=C(C=C2)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CNC2=C1C(=O)N=C(N)N2

References

General References
  1. Fruzzetti F: Beyaz(R): an oral contraceptive fortified with folate. Womens Health (Lond). 2012 Jan;8(1):13-9. doi: 10.2217/whe.11.68. [Article]
  2. Bart S Sr, Marr J, Diefenbach K, Trummer D, Sampson-Landers C: Folate status and homocysteine levels during a 24-week oral administration of a folate-containing oral contraceptive: a randomized, double-blind, active-controlled, parallel-group, US-based multicenter study. Contraception. 2012 Jan;85(1):42-50. doi: 10.1016/j.contraception.2011.05.013. Epub 2011 Jul 13. [Article]
  3. Rapkin RB, Creinin MD: The combined oral contraceptive pill containing drospirenone and ethinyl estradiol plus levomefolate calcium. Expert Opin Pharmacother. 2011 Oct;12(15):2403-10. doi: 10.1517/14656566.2011.610791. Epub 2011 Aug 31. [Article]
  4. Wilson SM, Bivins BN, Russell KA, Bailey LB: Oral contraceptive use: impact on folate, vitamin B(6), and vitamin B(1)(2) status. Nutr Rev. 2011 Oct;69(10):572-83. doi: 10.1111/j.1753-4887.2011.00419.x. [Article]
  5. Ginsberg LD, Oubre AY, Daoud YA: L-methylfolate Plus SSRI or SNRI from Treatment Initiation Compared to SSRI or SNRI Monotherapy in a Major Depressive Episode. Innov Clin Neurosci. 2011 Jan;8(1):19-28. [Article]
  6. Shelton RC, Sloan Manning J, Barrentine LW, Tipa EV: Assessing Effects of l-Methylfolate in Depression Management: Results of a Real-World Patient Experience Trial. Prim Care Companion CNS Disord. 2013;15(4). pii: PCC.13m01520. doi: 10.4088/PCC.13m01520. Epub 2013 Aug 29. [Article]
  7. Willems FF, Boers GH, Blom HJ, Aengevaeren WR, Verheugt FW: Pharmacokinetic study on the utilisation of 5-methyltetrahydrofolate and folic acid in patients with coronary artery disease. Br J Pharmacol. 2004 Mar;141(5):825-30. Epub 2004 Feb 9. [Article]
  8. Pietrzik K, Bailey L, Shane B: Folic acid and L-5-methyltetrahydrofolate: comparison of clinical pharmacokinetics and pharmacodynamics. Clin Pharmacokinet. 2010 Aug;49(8):535-48. doi: 10.2165/11532990-000000000-00000. [Article]
  9. Miraglia N, Agostinetto M, Bianchi D, Valoti E: Enhanced oral bioavailability of a novel folate salt: comparison with folic acid and a calcium folate salt in a pharmacokinetic study in rats. Minerva Ginecol. 2016 Apr;68(2):99-105. [Article]
  10. Miller AL: The methylation, neurotransmitter, and antioxidant connections between folate and depression. Altern Med Rev. 2008 Sep;13(3):216-26. [Article]
  11. Lamers Y, Prinz-Langenohl R, Bramswig S, Pietrzik K: Red blood cell folate concentrations increase more after supplementation with [6S]-5-methyltetrahydrofolate than with folic acid in women of childbearing age. Am J Clin Nutr. 2006 Jul;84(1):156-61. [Article]
  12. Dailymed [Link]
  13. FDA Center for Drug Evaluation and Research: Summary Review [Link]
  14. Cayman Chemicals Safety Data Sheet [Link]
  15. Dailymed L-Methyl-MC-NAC Tablets [Link]
KEGG Compound
C00440
PubChem Compound
444412
PubChem Substance
347827954
ChemSpider
392351
BindingDB
50391007
RxNav
1025342
ChEBI
136009
ChEMBL
CHEMBL1231574
ZINC
ZINC000002005305
PharmGKB
PA166129561
PDBe Ligand
THH
Drugs.com
Drugs.com Drug Page
Wikipedia
Levomefolic_acid
PDB Entries
1b02 / 1q8j / 1tls / 1tsn / 1u1j / 1wsv / 1xpg / 1xr2 / 1zp4 / 2e7f
show 27 more
MSDS
Download (51 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentPolycystic Ovarian Syndrome (PCOS)1
4Not Yet RecruitingOtherGeneralized Anxiety Disorder1
4RecruitingTreatmentAcute Diarrhea1
4RecruitingTreatmentIron Deficiency Anemia of Pregnancy / Iron Storage Disease1
4TerminatedTreatmentAnemia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Kit; tablet, film coatedOral
CapsuleOral15 mg/1
Capsule, delayed release pelletsOral
Solution / dropsOral
TabletOral
TabletOral15 mg/1
TabletOral7.5 mg/1
Tablet, coatedOral15 mg/1
Tablet, coatedOral7.5 mg/1
Tablet, coatedOral
CapsuleOral
Capsule, liquid filled; kit; tabletOral
Capsule, liquid filled; kit; tablet, film coatedOral
Suspension / dropsOral
KitOral
Tablet, film coatedOral
Capsule, gelatin coatedOral
LiquidOral
Capsule, liquid filledOral
Tablet, chewableOral
Capsule; kit; tablet, coatedOral
PowderOral; Topical
PowderOral
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7163931No2007-01-162021-12-20US flag
US6958326No2005-10-252021-12-20US flag
US5798338No1998-08-252015-07-10US flag
US6441168No2002-08-272022-07-30US flag
US8617597No2013-12-312030-02-08US flag
US11617751No2010-07-172030-07-17US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
boiling point (°C)221MSDS
water solubilityApproximately 0.3 mg/mlCayman Chemical Safety Data Sheet
Predicted Properties
PropertyValueSource
Water Solubility0.332 mg/mLALOGPS
logP-0.58ALOGPS
logP-3Chemaxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.23Chemaxon
pKa (Strongest Basic)5.32Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count7Chemaxon
Polar Surface Area198.48 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity126.68 m3·mol-1Chemaxon
Polarizability46.56 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0209000000-bc39a561e34ef2dd829c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0002900000-9f11e687468c9cb33847
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0209100000-57a17001eef7ce551306
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ue9-1904300000-971d324927f268b4a519
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0913000000-2ac627a3103a392beb1c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uxu-3837900000-71bc9ab44596b01eeedd
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-243.4135067
predicted
DarkChem Lite v0.1.0
[M-H]-243.3961067
predicted
DarkChem Lite v0.1.0
[M-H]-193.82654
predicted
DeepCCS 1.0 (2019)
[M+H]+243.5589067
predicted
DarkChem Lite v0.1.0
[M+H]+243.3271067
predicted
DarkChem Lite v0.1.0
[M+H]+196.2221
predicted
DeepCCS 1.0 (2019)
[M+Na]+242.9517067
predicted
DarkChem Lite v0.1.0
[M+Na]+242.7082067
predicted
DarkChem Lite v0.1.0
[M+Na]+202.13463
predicted
DeepCCS 1.0 (2019)

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Cofactor
General Function
Zinc ion binding
Specific Function
Catalyzes the transfer of a methyl group from methyl-cobalamin to homocysteine, yielding enzyme-bound cob(I)alamin and methionine. Subsequently, remethylates the cofactor using methyltetrahydrofola...
Gene Name
MTR
Uniprot ID
Q99707
Uniprot Name
Methionine synthase
Molecular Weight
140525.91 Da
References
  1. Pietrzik K, Bailey L, Shane B: Folic acid and L-5-methyltetrahydrofolate: comparison of clinical pharmacokinetics and pharmacodynamics. Clin Pharmacokinet. 2010 Aug;49(8):535-48. doi: 10.2165/11532990-000000000-00000. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Methotrexate transporter activity
Specific Function
Has been shown to act both as an intestinal proton-coupled high-affinity folate transporter and as an intestinal heme transporter which mediates heme uptake from the gut lumen into duodenal epithel...
Gene Name
SLC46A1
Uniprot ID
Q96NT5
Uniprot Name
Proton-coupled folate transporter
Molecular Weight
49770.04 Da
References
  1. Zhao R, Aluri S, Goldman ID: The proton-coupled folate transporter (PCFT-SLC46A1) and the syndrome of systemic and cerebral folate deficiency of infancy: Hereditary folate malabsorption. Mol Aspects Med. 2017 Feb;53:57-72. doi: 10.1016/j.mam.2016.09.002. Epub 2016 Sep 21. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Reduced folate carrier activity
Specific Function
Transporter for the intake of folate. Uptake of folate in human placental choriocarcinoma cells occurs by a novel mechanism called potocytosis which functionally couples three components, namely th...
Gene Name
SLC19A1
Uniprot ID
P41440
Uniprot Name
Folate transporter 1
Molecular Weight
64867.62 Da
References
  1. Hou Z, Matherly LH: Biology of the major facilitative folate transporters SLC19A1 and SLC46A1. Curr Top Membr. 2014;73:175-204. doi: 10.1016/B978-0-12-800223-0.00004-9. [Article]

Drug created at December 03, 2015 16:51 / Updated at February 22, 2024 01:23