Drug Information

General Information
Drug ID
DR00134
Drug Name
Folic acid
Synonyms
(2S)-2-[[4-[(2-amino-4-oxo-1H-pteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid; Acfol (Spain); Acide folique [INN-French]; Acidefolique; Acido folico; Acido folico [INN-Spanish]; Acidum folicum; Acidum folicum [INN-Latin]; Acifolic; Antianemia factor; Apo-Folic; BIF0608; Cytofol; Dosfolat B activ; F0043; FOL; Facid; Factor U; Folacid; Folacin; Folaemin; Folaemin [Netherlands]; Folan; Folasic (Australia); Folate; Folbal; Folcidin; Folcidin (VAN); Folcysteine; Foldine; Foldine [France]; Folettes; Foliamin; Folic; Folic acid (JP15/USP/INN); Folic acid (TN); Folic acid [BAN:INN:JAN]; Folic acid [INN:BAN:JAN]; Folic acid dihydrate; Folicet; Folicet (TN); Folico; Folico (Italy); Folina; Folina (Italy); Folipac; Folsaeure; Folsan; Folsaure; Folsav; Folvite; Folvron; Glutamic acid, N-(p-(((2-amino-4-hydroxypyrimido(4,5-b)pyrazin-6-yl)methyl)amino)benzoyl)-, L; Incafolic; Kyselina listova; Kyselina listova [Czech]; LiverLactobacillus casei factor; Millafol; Mission prenatal; Mittafol; N-(4-(((2-Amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl)amino)benzo-yl)-L-glutamic acid; N-(4-((2-Amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-glutamic acid; N-(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid; N-(p-(((2-Amino-4-hydroxy-6-pteridinyl)methyl)amino)benzoyl)-L-glutamic acid; Nifolin; Nifolin [Denmark]; Novofolacid; Novofolacid [Canada]; PGA (VAN); PteGlu; Pteroyl-L-glutamic acid; Pteroyl-L-monoglutamic acid; Pteroylglutamic acid; Pteroylmonoglutamate; Pteroylmonoglutamic acid; Serum Folate Level; Usaf cb-13; Vitamin B11; Vitamin B9; Vitamin Bc; Vitamin Be; Vitamin M
Drug Type
Small molecular drug
Indication Vitamin deficiency [ICD11:5B55-5B7Z] Approved [1]
Therapeutic Class
Vitamins
Structure
3D MOL 2D MOL
Formula
C19H19N7O6
Canonical SMILES
C1=CC(=CC=C1C(=O)NC(CCC(=O)O)C(=O)O)NCC2=CN=C3C(=N2)C(=O)NC(=N3)N
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
InChIKey
OVBPIULPVIDEAO-LBPRGKRZSA-N
CAS Number
CAS 59-30-3
Pharmaceutical Properties Molecular Weight 441.4 Topological Polar Surface Area 209
Heavy Atom Count 32 Rotatable Bond Count 9
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 10
XLogP
-1.1
PubChem CID
135398658
PubChem SID
10318222 ,10321330 ,11112150 ,11335669 ,11360908 ,11364275 ,11366837 ,11369399 ,11371658 ,11375360 ,11377561 ,11461880 ,11485093 ,11489275 ,11490565 ,11493565 ,11495195 ,11537760 ,14857129 ,14930521 ,16028504 ,16077361 ,22389272 ,24845192 ,24894950 ,24894973 ,24894977 ,24894979 ,26612259 ,26680757 ,26704619 ,3787 ,584223 ,7847138 ,7887399 ,7887539 ,7979297 ,8144505 ,8149795 ,8153763 ,829573 ,831381 ,831592 ,831633 ,831664 ,834516 ,835597 ,835744 ,837196 ,841329
ChEBI ID
ChEBI:27470
TTD Drug ID
D0Z0DW
DT(s) Transporting This Drug BCRP Transporter Info Breast cancer resistance protein Substrate [2]
FLOT1 Transporter Info Folate transporter 1 Substrate [3]
MFT Transporter Info Mitochondrial folate transporter/carrier Substrate [4]
MRP1 Transporter Info Multidrug resistance-associated protein 1 Substrate [5]
MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [6]
MRP3 Transporter Info Multidrug resistance-associated protein 3 Substrate [7]
MRP4 Transporter Info Multidrug resistance-associated protein 4 Substrate [8]
MRP5 Transporter Info Multidrug resistance-associated protein 5 Substrate [9]
P-GP Transporter Info P-glycoprotein 1 Substrate [10]
PCFT Transporter Info Proton-coupled folate transporter Substrate [11]
SNAT3 Transporter Info Sodium-coupled neutral amino acid transporter 3 Substrate [12]
Drug-Transporter Activity Data
Drug-Transporter Activity Data MRP3 Transporter Info Km =1960 microM Human embryonic kidney cells (HEK293)-MRP3 [7]
MRP4 Transporter Info Km =170 microM Spodoptera frugiperda (Sf9) cells-MRP4 [8]
MRP5 Transporter Info Km =1000 microM Human embryonic kidney cells (HEK293)-MRP5 [9]
References
1 Folic acid was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 The effect of low pH on breast cancer resistance protein (ABCG2)-mediated transport of methotrexate, 7-hydroxymethotrexate, methotrexate diglutamate, folic acid, mitoxantrone, topotecan, and resveratrol in in vitro drug transport models. Mol Pharmacol. 2007 Jan;71(1):240-9.
3 Biology of the major facilitative folate transporters SLC19A1 and SLC46A1. Curr Top Membr. 2014;73:175-204.
4 Polymorphism of SLC25A32, the folate transporter gene, is associated with plasma folate levels and bone fractures in Japanese postmenopausal women. Geriatr Gerontol Int. 2014 Oct;14(4):942-6.
5 Folate concentration dependent transport activity of the Multidrug Resistance Protein 1 (ABCC1). Biochem Pharmacol. 2004 Apr 15;67(8):1541-8.
6 Mammalian multidrug-resistance proteins (MRPs). Essays Biochem. 2011 Sep 7;50(1):179-207.
7 Transport of methotrexate (MTX) and folates by multidrug resistance protein (MRP) 3 and MRP1: effect of polyglutamylation on MTX transport. Cancer Res. 2001 Oct 1;61(19):7225-32.
8 Analysis of methotrexate and folate transport by multidrug resistance protein 4 (ABCC4): MRP4 is a component of the methotrexate efflux system. Cancer Res. 2002 Jun 1;62(11):3144-50.
9 The human multidrug resistance protein MRP5 transports folates and can mediate cellular resistance against antifolates. Cancer Res. 2005 May 15;65(10):4425-30.
10 Folate transporter expression decreases in the human placenta throughout pregnancy and in pre-eclampsia. Pregnancy Hypertens. 2012 Apr;2(2):123-31.
11 Characterization of uptake of folates by rat and human blood-brain barrier endothelial cells. Biofactors. 2010 May-Jun;36(3):201-9.
12 Purification of recombinant human N-acetyltransferase type 1 (NAT1) expressed in E. coli and characterization of its potential role in folate metabolism. Biochem Pharmacol. 1995 Jun 16;49(12):1759-67.

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