5-METHYLTETRAHYDROFOLIC ACID

First approved in 2012

Details

Stereochemistry	EPIMERIC
Molecular Formula	C20H25N7O6
Molecular Weight	459.4558
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 5-METHYLTETRAHYDROFOLIC ACID

Structure Search

SMILES

CN1C(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-ABLWVSNPSA-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

HIDE SMILES / InChI

Molecular Formula	C20H25N7O6
Molecular Weight	459.4558
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	1 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26898294

Methylenetetrahydrofolate reductase (MTHFR) is an enzyme required for the formation of 5-methyltetrahydrofolate (5-MTHF), a form of folate able to cross the blood-brain barrier and which is necessary as a substrate for the remethylation of homocysteine to methionine by methionine synthase. Patients with severe MTHFR deficiency cannot make 5-MTHF and have extremely low levels in the CSF. Only treatment with oral 5-MTHF given as calcium mefolinate resulted in an increase in CSF 5-MTHF.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Methionine synthase 4 Target ID: Q99707 Gene ID: 4548.0 Gene Symbol: MTR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26898294	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Methylenetetrahydrofolate reductase deficiency 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26898294	Primary		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
5-methyltetrahydrofolate, the active form of folic acid, restores endothelial function in familial hypercholesterolemia.	1998 Jan 27	9462523
Treatment with Mefolinate (5-Methyltetrahydrofolate), but Not Folic Acid or Folinic Acid, Leads to Measurable 5-Methyltetrahydrofolate in Cerebrospinal Fluid in Methylenetetrahydrofolate Reductase Deficiency.	2016	26898294

Sample Use Guides

In Vivo Use Guide

calcium mefolinate at doses of 15–60 mg/kg/day

Route of Administration: Oral

In Vitro Use Guide

To study the actions of 5-methyltetrahydrofolate (5-MTHF) as an antioxidant, the effects of 5-MTHF (10, 100, and 1000 μmol/L) on superoxide generation by purified recombinant eNOS and xanthine oxidase/hypoxanthine were investigated. 5-MTHF dose-dependently reduced superoxide production by both xanthine oxidase and eNOS.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:17:18 GMT 2023` Edited by `admin` on `Fri Dec 15 15:17:18 GMT 2023`
Record UNII	TYK22LML8F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

5-METHYLTETRAHYDROFOLIC ACID

Common Name

English

MEFOLIC ACID

Common Name

English

5-METHYLTETRAHYDROFOLATE

Common Name

English

5-METHYLTETRAHYDROFOLIC ACID [DSC]

Common Name

English

METHYL FOLATE

Common Name

English

N5-METHYLTETRAHYDROFOLIC ACID

Common Name

English

L-GLUTAMIC ACID, N-(4-(((2-AMINO-1,4,5,6,7,8-HEXAHYDRO-5-METHYL-4-OXO-6-PTERIDINYL)METHYL)AMINO)BENZOYL)-

Common Name

English

5-Methyltetrahydrofolate [WHO-DD]

Common Name

English

N5-METHYLTETRAHYDROFOLATE

Common Name

English

N5-METHYLTETRAHYDROPTEROYLGLUTAMATE

Common Name

English

PREFOLIC A

Common Name

English

Classification Tree Code System Code

LOINC

47547-5