Folate synthesis

Folic acid

Clinical data
Pronunciation	foe' lik
AHFS/Drugs.com	Monograph
MedlinePlus	a682591
Pregnancy category	US: A (No risk in human studies)
Routes of administration	By mouth, IM, IV, sub-Q
ATC code	B03BB01 (WHO)
Legal status
Legal status	US: OTC
Pharmacokinetic data
Bioavailability	50–100%
Metabolism	Liver
Excretion	Urine
Identifiers
IUPAC name (2S)-2-[[4-[(2-Amino-4-oxo-1H-pteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid
Synonyms	N-(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid, pteroyl-L-glutamic acid, vitamin B9, vitamin Bc, vitamin M, folacin, pteroyl-L-glutamate
CAS Number	59-30-3
PubChem CID	6037
IUPHAR/BPS	4563
DrugBank	DB00158 Y
ChemSpider	5815
UNII	935E97BOY8
KEGG	C00504
ChEBI	CHEBI:27470
ChEMBL	CHEMBL1622
ECHA InfoCard	100.000.381
Chemical and physical data
Formula	C19H19N7O6
Molar mass	441.40 g·mol−1
3D model (Jmol)	Interactive image
Melting point	250 °C (482 °F) (decomposition)
Solubility in water	1.6 mg/L (25 °C) mg/mL (20 °C)
SMILES O=C(N[C@H](C(O)=O)CCC(O)=O)C1=CC=C(NCC2=NC(C(NC(N)=N3)=O)=C3N=C2)C=C1
InChI InChI=1S/C19H19N7O6/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)/t12-/m0/s1 Key:OVBPIULPVIDEAO-LBPRGKRZSA-N

Folic acid, another form of which is known as folate, is one of the B vitamins. It is used as a supplement by women to prevent neural tube defects (NTDs) developing during pregnancy. It is also used to treat anemia caused by folic acid deficiency. More than 50 countries require fortification of certain foods with folic acid as a measure to decrease the rate of NTDs in the population. The recommended daily intake level of folate is 400 micrograms from foods or dietary supplements. Long term supplementation is also associated with small reductions in the risk of stroke and cardiovascular disease. It may be taken by mouth or by injection.

There are no common side effects. It is not known whether high doses over a long period of time are of concern. There are concerns that large amounts of folic acid might hide vitamin B12 deficiency. Folate is essential for the body to make DNA, RNA, and metabolise amino acids which are required for cell division. As humans cannot make folic acid, it is required from the diet, making it an essential vitamin.

Not enough folate can lead to folate deficiency. This may result in a type of anemia in which low numbers of large red blood cells occur. Symptoms may include feeling tired, heart palpitations, shortness of breath, open sores on the tongue, and changes in the color of the skin or hair. Low levels in early pregnancy are believed to be the cause more than half of cases of neural tube defects in babies. Deficiency in children may develop within a month of poor dietary intake. In adults normal total body folate is between 10,000–30,000 micrograms (µg) with blood levels of greater than 7 nmol/L (3 ng/mL).