folinic acid   

GtoPdb Ligand ID: 4816

Synonyms: 5-formyltetrahydrofolic acid | leucovorin | Wellcovorin®
folinic acid is an approved drug (FDA (1952))
Compound class: Synthetic organic
Comment: Folinic acid is the biologically active form of folic acid (also known as the (-)-l-isomer, citrovorum factor or (-)-folinic acid). The approved drug is called leucovorin.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 13
Hydrogen bond donors 7
Rotatable bonds 11
Topological polar surface area 219.84
Molecular weight 473.17
XLogP -1.66
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES O=CN1C(CNc2ccc(cc2)C(=O)NC(C(=O)O)CCC(=O)O)CNc2c1c(=O)nc([nH]2)N
Isomeric SMILES O=CN1C(CNc2ccc(cc2)C(=O)N[C@H](C(=O)O)CCC(=O)O)CNc2c1c(=O)nc([nH]2)N
InChI InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32)/t12?,13-/m0/s1
InChI Key VVIAGPKUTFNRDU-ABLWVSNPSA-N
No information available.
Summary of Clinical Use
Used to treat the folic acid-reducing effects of high doses of drugs such as methotrexate, pyrimethamine and trimethoprim, and to treat megaloblastic anemias caused by folic acid deficiency. Leucovorin has also been used to enhance the activity of fluorouracil in the treatment of advanced colorectal cancer.
Mechanism Of Action and Pharmacodynamic Effects
Folate derivatives, especially the fully reduced form, tetrahydrofolate, are substrates/cofactors in a number of single-carbon-transfer reactions required for the synthesis of purines and thymidine as well as in the remethylation cycle of homocysteine to methionine. Folate derivatives are therefore essential for the synthesis of DNA and RNA and are required by all living cells. See the DrugBank link on the Summary tab of this ligand page for further details.