Folate sodiumProduct ingredient for Folic acid

Name
Folate sodium
Drug Entry
Folic acid

Folic acid, also known as folate or Vitamin B9, is a member of the B vitamin family and an essential cofactor for enzymes involved in DNA and RNA synthesis. More specifically, folic acid is required by the body for the synthesis of purines, pyrimidines, and methionine before incorporation into DNA or protein. Folic acid is particularly important during phases of rapid cell division, such as infancy, pregnancy, and erythropoiesis, and plays a protective factor in the development of cancer. As humans are unable to synthesize folic acid endogenously, diet and supplementation is necessary to prevent deficiencies. For example, folic acid is present in green vegetables, beans, avocado, and some fruits.9

In order to function within the body, folic acid must first be reduced by the enzyme dihydrofolate reductase (DHFR) into the cofactors dihydrofolate (DHF) and tetrahydrofolate (THF). This important pathway, which is required for de novo synthesis of nucleic acids and amino acids, is disrupted by anti-metabolite therapies such as Methotrexate as they function as DHFR inhibitors to prevent DNA synthesis in rapidly dividing cells, and therefore prevent the formation of DHF and THF. When used in high doses such as for cancer therapy, or in low doses such as for Rheumatoid Arthritis or psoriasis, Methotrexate impedes the body's ability to create folic acid. This results in a deficiency of coenzymes and a resultant buildup of toxic substances that are responsible for numerous adverse side effects. As a result, supplementation with 1-5mg of folic acid is recommended to prevent deficiency and a number of side effects associated with MTX therapy including mouth ulcers and gastrointestinal irritation. Leucovorin (also known as folinic acid) supplementation is typically used for high-dose MTX regimens for the treatment of cancer. Levoleucovorin and leucovorin are analogs of tetrahydrofolate (THF) and are able to bypass DHFR reduction to act as a cellular replacement for the co-factor THF.

There are also several antiepileptic drugs (AEDs) that are associated with reduced serum and red blood cell folate, including Carbamazepine (CBZ), Phenytoin (PHT), or barbiturates.7 Folic acid is therefore often provided as supplementation to individuals using these medications, particularly to women of child-bearing age.

Inadequate folate levels can result in a number of health concerns including cardiovascular disease, megaloblastic anemias, cognitive deficiencies, and neural tube defects (NTDs). Folic acid is typically supplemented during pregnancy to prevent the development of NTDs and in individuals with alcoholism to prevent the development of neurological disorders, for example.

Accession Number
DBSALT001918
Structure
Thumb
Synonyms
Folic acid sodium salt / Folic acid, monosodium salt / Sodium folate / Sodium pteroylglutamate
UNII
9P9W8GGU78
CAS Number
6484-89-5
Weight
Average: 485.368
Monoisotopic: 485.10356986
Chemical Formula
C19H17N7Na2O6
InChI Key
SWIRFWUEJODNRG-CURYUGHLSA-L
InChI
InChI=1S/C19H19N7O6.2Na/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28;;/h1-4,8,12,21H,5-7H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30);;/q;2*+1/p-2/t12-;;/m1../s1
IUPAC Name
disodium (4R)-4-carboxy-4-[(4-{[(2-imino-4-oxido-1,2-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]butanoate
SMILES
[Na+].[Na+].[H][C@](CCC([O-])=O)(NC(=O)C1=CC=C(NCC2=NC3=C(NC(=N)N=C3[O-])N=C2)C=C1)C(O)=O
ChemSpider
21512
Predicted Properties
PropertyValueSource
Water Solubility0.161 mg/mLALOGPS
logP0.88ALOGPS
logP-0.5ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)3.37ChemAxon
pKa (Strongest Basic)2.09ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area215.64 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity143.41 m3·mol-1ChemAxon
Polarizability42.68 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon