Identification
- Generic Name
- 5-methyltetrahydrofolic acid
- DrugBank Accession Number
- DB04789
- Background
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
Structure for 5-methyltetrahydrofolic acid (DB04789)
- 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
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UAminomethyltransferase, mitochondrial Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
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.
Drug Interaction Integrate drug-drug
interactions in your softwareCapecitabine The risk or severity of adverse effects can be increased when 5-methyltetrahydrofolic acid is combined with Capecitabine. Carbamazepine The serum concentration of 5-methyltetrahydrofolic acid can be decreased when it is combined with Carbamazepine. Colestipol The serum concentration of 5-methyltetrahydrofolic acid can be decreased when it is combined with Colestipol. Cycloguanil The therapeutic efficacy of Cycloguanil can be decreased when used in combination with 5-methyltetrahydrofolic acid. Dapsone The therapeutic efficacy of Dapsone can be decreased when used in combination with 5-methyltetrahydrofolic acid. Flucytosine The risk or severity of adverse effects can be increased when 5-methyltetrahydrofolic acid is combined with Flucytosine. Fluorouracil The risk or severity of adverse effects can be increased when 5-methyltetrahydrofolic acid is combined with Fluorouracil. Fosphenytoin The serum concentration of Fosphenytoin can be decreased when it is combined with 5-methyltetrahydrofolic acid. Glucarpidase The 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. Methotrexate The therapeutic efficacy of Methotrexate can be decreased when used in combination with 5-methyltetrahydrofolic acid. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Prefolic A
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Prenate Elite 5-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, coated Oral Avion Pharmaceuticals, Llc 2014-06-05 Not applicable US 
Prenate Essential 5-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 coated Oral Avion Pharmaceuticals, Llc 2014-07-18 Not applicable US Sodium Polysulthionate, 5-mthf 5-methyltetrahydrofolic acid (.5 mg/1) + Octasulfur (388 mg/1) + Sodium sulfate decahydrate (8 mg/1) + Sodium thiosulfate pentahydrate (1.8 mg/1) Capsule Oral Solubiomix 2016-01-09 2016-01-12 US Xizflus 5-methyltetrahydrofolic acid (.5 mg/1) + Octasulfur (388 mg/1) + Sodium sulfate decahydrate (8 mg/1) + Sodium thiosulfate pentahydrate (1.8 mg/1) Capsule Oral Basiem 2016-01-09 2016-01-12 US Xizflus 5-methyltetrahydrofolic acid (.125 g/100g) + Octasulfur (97 g/100g) + Sodium sulfate decahydrate (2 g/100g) + Sodium thiosulfate pentahydrate (.45 g/100g) Powder Oral; Topical Basiem 2015-07-14 2016-01-12 US
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
- Affected organisms
- 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[C@@H](CCC(O)=O)C(O)=O)CNC2=C1C(=O)N=C(N)N2
References
- General References
- Not Available
- External Links
- PubChem Compound
- 9825434
- PubChem Substance
- 46505172
- ChemSpider
- 8001181
- 1313966
- ChEMBL
- CHEMBL1221561
- Wikipedia
- 5-Methyltetrahydrofolate
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, coated Oral Injection, powder, for solution Intramuscular; Intravenous Tablet Oral Tablet, chewable Oral Capsule, gelatin coated Oral Kit Oral Capsule Oral Powder Oral; Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.332 mg/mL ALOGPS logP -0.58 ALOGPS logP -3 Chemaxon logS -3.1 ALOGPS pKa (Strongest Acidic) 3.23 Chemaxon pKa (Strongest Basic) 5.32 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 12 Chemaxon Hydrogen Donor Count 7 Chemaxon Polar Surface Area 198.48 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 126.68 m3·mol-1 Chemaxon Polarizability 46.19 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.5477 Blood Brain Barrier - 0.9162 Caco-2 permeable - 0.8516 P-glycoprotein substrate Substrate 0.8413 P-glycoprotein inhibitor I Non-inhibitor 0.9223 P-glycoprotein inhibitor II Non-inhibitor 0.9933 Renal organic cation transporter Non-inhibitor 0.8623 CYP450 2C9 substrate Non-substrate 0.7153 CYP450 2D6 substrate Non-substrate 0.8217 CYP450 3A4 substrate Non-substrate 0.5221 CYP450 1A2 substrate Non-inhibitor 0.8546 CYP450 2C9 inhibitor Non-inhibitor 0.8537 CYP450 2D6 inhibitor Non-inhibitor 0.9295 CYP450 2C19 inhibitor Non-inhibitor 0.8801 CYP450 3A4 inhibitor Non-inhibitor 0.9463 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9338 Ames test Non AMES toxic 0.7803 Carcinogenicity Non-carcinogens 0.9459 Biodegradation Not ready biodegradable 0.8995 Rat acute toxicity 2.6188 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9337 hERG inhibition (predictor II) Inhibitor 0.5
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- 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. [Article]
Drug created at September 11, 2007 17:49 / Updated at September 28, 2021 21:54