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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H25N7O6.2C6H13NO5
Molecular Weight 817.798
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOMEFOLATE GLUCOSAMINE

SMILES

N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO.N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO.CN1[C@@H](CNC2=CC=C(C=C2)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CNC3=C1C(=O)NC(N)=N3

InChI

InChIKey=FZDRYCKUVGVDSO-KWWXADPNSA-N
InChI=1S/C20H25N7O6.2C6H13NO5/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;2*7-3(1-8)5(11)6(12)4(10)2-9/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31);2*1,3-6,9-12H,2,7H2/t12-,13-;2*3-,4+,5+,6+/m000/s1

HIDE SMILES / InChI

Molecular Formula C6H13NO5
Molecular Weight 179.1711
Charge 0
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C20H25N7O6
Molecular Weight 459.4558
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Levomefolate glucosamine is prodrug of Levomefolic acid. 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. 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. It is available commercially as a crystalline form of the calcium salt (Metafolin(R)), which has the stability required for use as a supplement. Supplementation of levomefolic acid is desired over folic acid due to reduced potential for masking vitamin B12 deficiency symptoms.

Approval Year

Substance Class Chemical
Record UNII
Q65PL71Q1A
Record Status Validated (UNII)
Record Version