5-methyltetrahydrofolic acid (2024)

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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 hom*ocysteine back to methionine by 5-methyltetrahydrofolate-hom*ocysteine methyltransferases (also called methionine synthases).

Type

Small Molecule

Groups

Investigational, Nutraceutical

Structure

3D

MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

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

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Pharmacology

Indication

Not Available

Reduce drug development failure rates

See Also

L-Methylfolate (5-MTHF): Your Must-Read Beginner’s Guide | Diet vs Disease5-MTHF: de beste keuze voor een foliumzuur-supplementSafety evaluation of calcium L-methylfolateL-Methylfolate, Methylfolate, 5-MTHF, L-5-MTHF. Why many variations?

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Associated Therapies

• Nutritional supplementation

Contraindications & Blackbox Warnings

Avoid life-threatening adverse drug events with our Clinical APILearn more

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

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Capecitabine	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.

Food Interactions

Not Available

Products

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See Also

The pharmaco*kinetic advantage of 5-methyltetrahydrofolate for minimization of the risk for birth defects

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
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
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
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
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

Categories

Drug Categories

• Coenzymes
• Enzymes and Coenzymes
• Folic Acid and Derivatives
• Heterocyclic Compounds, Fused-Ring
• Pteridines
• Pterins
• Vitamin B Complex
• Vitamins

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

RxNav

1313966

ChEMBL

CHEMBL1221561

Wikipedia

5-Methyltetrahydrofolate

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-03di-0209000000-bc39a561e34ef2dd829c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0002900000-9f11e687468c9cb33847
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-03di-0209100000-57a17001eef7ce551306
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0ue9-1904300000-971d324927f268b4a519
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-001i-0913000000-2ac627a3103a392beb1c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0uxu-3837900000-71bc9ab44596b01eeedd
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	195.27055	predicted	DeepCCS 1.0 (2019)
[M+H]+	197.66612	predicted	DeepCCS 1.0 (2019)
[M+Na]+	203.57866	predicted	DeepCCS 1.0 (2019)

Drug created at September 11, 2007 17:49 / Updated at September 28, 2021 21:54