5-methyltetrahydrofolic acid

Identification

Name
5-methyltetrahydrofolic acid
Accession Number
DB04789
Description

5-methyltetrahydrofolic acid is a methylated derivate of tetrahydrofolate. It is generated by methylenetetrahydrofolate reductase from 5,10-methylenetetrahydrofolate and used to recycle homocysteine back to methionine by 5-methyltetrahydrofolate-homocysteine methyltransferases (also called methionine synthases).

Type
Small Molecule
Groups
Investigational, Nutraceutical
Structure
Thumb
Weight
Average: 459.463
Monoisotopic: 459.186631553
Chemical Formula
C20H25N7O6
Synonyms
  • 5-Methyl-5,6,7,8-tetrahydrofolic acid
  • 5-Methyl-5,6,7,8-tetrahydropteroyl-L-glutamic acid
  • 5-Methyltetrahydropteroyl monoglutamate
  • 5-Methyltetrahydropteroylglutamic acid
  • N-Methyltetrahydrofolate
  • N-Methyltetrahydrofolic acid
  • N5-Methyltetrahydrofolate
  • N5-Methyltetrahydrofolic acid
  • N5-Methyltetrahydropteroylglutamate

Pharmacology

Indication
Not Available
Associated Therapies
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAminomethyltransferase, mitochondrialNot AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half-life
Not Available
Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity
Not Available
Affected organisms
Not Available
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 5-methyltetrahydrofolic acid is combined with Capecitabine.
CarbamazepineThe serum concentration of Carbamazepine can be decreased when it is combined with 5-methyltetrahydrofolic acid.
ColestipolThe serum concentration of 5-methyltetrahydrofolic acid can be decreased when it is combined with Colestipol.
FlucytosineThe risk or severity of adverse effects can be increased when 5-methyltetrahydrofolic acid is combined with Flucytosine.
FluorouracilThe risk or severity of adverse effects can be increased when 5-methyltetrahydrofolic acid is combined with Fluorouracil.
FosphenytoinThe serum concentration of Fosphenytoin can be decreased when it is combined with 5-methyltetrahydrofolic acid.
GlucarpidaseThe serum concentration of the active metabolites of 5-methyltetrahydrofolic acid can be reduced when 5-methyltetrahydrofolic acid is used in combination with Glucarpidase resulting in a loss in efficacy.
PhenobarbitalThe serum concentration of Phenobarbital can be decreased when it is combined with 5-methyltetrahydrofolic acid.
PhenytoinThe serum concentration of Phenytoin can be decreased when it is combined with 5-methyltetrahydrofolic acid.
PrimidoneThe serum concentration of Primidone can be decreased when it is combined with 5-methyltetrahydrofolic acid.
Additional Data Available
  • Extended Description
    Extended Description
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    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity
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    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level
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    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action
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Food Interactions
Not Available

Products

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International/Other Brands
Prefolic A
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Prenate Elite5-methyltetrahydrofolic acid (600 ug/1) + Ascorbic acid (75 mg/1) + Beta carotene (2600 [iU]/1) + Biotin (330 ug/1) + Cholecalciferol (600 [iU]/1) + Cupric oxide (1.5 mg/1) + Cyanocobalamin (13 ug/1) + DL-alpha tocopheryl acetate (40 [iU]/1) + Ferrous asparto glycinate (20 mg/1) + Folic acid (400 ug/1) + Calcium formate (155 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (21 mg/1) + Potassium Iodide (150 ug/1) + Pyridoxine hydrochloride (21 mg/1) + Riboflavin (3.5 mg/1) + Thiamine mononitrate (3 mg/1) + Zinc oxide (15 mg/1)Tablet, coatedOralAvion Pharmaceuticals, Llc2014-06-05Not applicableUS flag
Prenate Essential5-methyltetrahydrofolic acid (600 ug/1) + Ascorbic acid (90 mg/1) + Biotin (280 ug/1) + Cholecalciferol (220 [iU]/1) + Cyanocobalamin (13 ug/1) + DL-alpha tocopheryl acetate (10 [iU]/1) + Doconexent (300 mg/1) + Ferrous asparto glycinate (18 mg/1) + Folic acid (400 ug/1) + Calcium formate (155 mg/1) + Icosapent (40 mg/1) + Magnesium oxide (50 mg/1) + Potassium Iodide (150 ug/1) + Pyridoxine hydrochloride (26 mg/1)Capsule, gelatin coatedOralAvion Pharmaceuticals, Llc2014-07-18Not applicableUS flag
Sodium Polysulthionate, 5-mthf5-methyltetrahydrofolic acid (.5 mg/1) + Octasulfur (388 mg/1) + Sodium sulfate decahydrate (8 mg/1) + Sodium thiosulfate pentahydrate (1.8 mg/1)CapsuleOralSolubiomix2016-01-092016-01-12US flag
Xizflus5-methyltetrahydrofolic acid (.5 mg/1) + Octasulfur (388 mg/1) + Sodium sulfate decahydrate (8 mg/1) + Sodium thiosulfate pentahydrate (1.8 mg/1)CapsuleOralBasiem2016-01-092016-01-12US flag
Xizflus5-methyltetrahydrofolic acid (.125 g/100g) + Octasulfur (97 g/100g) + Sodium sulfate decahydrate (2 g/100g) + Sodium thiosulfate pentahydrate (.45 g/100g)PowderOral; TopicalBasiem2015-07-142016-01-12US 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
Not Available

Chemical Identifiers

UNII
TYK22LML8F
CAS number
134-35-0
InChI Key
ZNOVTXRBGFNYRX-ABLWVSNPSA-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-{[(2-amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
SMILES
CN1C(CNC2=CC=C(C=C2)C(=O)N[[email protected]@H](CCC(O)=O)C(O)=O)CNC2=C1C(=O)N=C(N)N2

References

General References
Not Available
PubChem Compound
9825434
PubChem Substance
46505172
ChemSpider
8001181
RxNav
1313966
ChEMBL
CHEMBL1221561
Wikipedia
5-Methyltetrahydrofolate

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, coatedOral
Tablet, chewableOral
Capsule, gelatin coatedOral
KitOral
CapsuleOral
PowderOral; Topical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
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
Polarizability46.19 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.5477
Blood Brain Barrier-0.9162
Caco-2 permeable-0.8516
P-glycoprotein substrateSubstrate0.8413
P-glycoprotein inhibitor INon-inhibitor0.9223
P-glycoprotein inhibitor IINon-inhibitor0.9933
Renal organic cation transporterNon-inhibitor0.8623
CYP450 2C9 substrateNon-substrate0.7153
CYP450 2D6 substrateNon-substrate0.8217
CYP450 3A4 substrateNon-substrate0.5221
CYP450 1A2 substrateNon-inhibitor0.8546
CYP450 2C9 inhibitorNon-inhibitor0.8537
CYP450 2D6 inhibitorNon-inhibitor0.9295
CYP450 2C19 inhibitorNon-inhibitor0.8801
CYP450 3A4 inhibitorNon-inhibitor0.9463
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9338
Ames testNon AMES toxic0.7803
CarcinogenicityNon-carcinogens0.9459
BiodegradationNot ready biodegradable0.8995
Rat acute toxicity2.6188 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9337
hERG inhibition (predictor II)Inhibitor0.5
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transaminase activity
Specific Function
The glycine cleavage system catalyzes the degradation of glycine.
Gene Name
AMT
Uniprot ID
P48728
Uniprot Name
Aminomethyltransferase, mitochondrial
Molecular Weight
43945.65 Da

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Kusuhara H, Han YH, Shimoda M, Kokue E, Suzuki H, Sugiyama Y: Reduced folate derivatives are endogenous substrates for cMOAT in rats. Am J Physiol. 1998 Oct;275(4 Pt 1):G789-96. [PubMed:9756510]

Drug created on September 11, 2007 11:49 / Updated on June 12, 2020 10:52

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