Folinic acid

Not to be confused with folic acid.

Folinic acid
Skeletal formula of folinic acid
Ball-and-stick model of the folinic acid molecule
Clinical data
PronunciationLeucovorin /ˌljuːkoʊˈvɔːrɪn/
Trade namesMany
Other namescitrovorum factor, 5-formyltetrahydrofolate
AHFS/Drugs.comMonograph
MedlinePlusa608038
License data
Pregnancy
category
  • AU: A
Routes of
administration		Intravenous, IM, by mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityDose dependent
Protein binding~15%
Elimination half-life6.2 hours
ExcretionKidney
Identifiers
  • (2S)-2-{[4-[(2-amino-5-formyl-4-oxo-5,6,7,8-
    tetrahydro-1H-pteridin-6-yl)methylamino]
    benzoyl]amino}pentanedioic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.328 Edit this at Wikidata
Chemical and physical data
FormulaC20H23N7O7
Molar mass473.446 g·mol−1
3D model (JSmol)
Melting point245 °C (473 °F) decomp
Solubility in water~0.3[1] mg/mL (20 °C)
  • O=C(O)[C@@H](NC(=O)c1ccc(cc1)NCC3N(/C2=C(/N/C(=N\C2=O)N)NC3)C=O)CCC(=O)O
  • 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 checkY
  • Key:VVIAGPKUTFNRDU-ABLWVSNPSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Folinic acid, also known as leucovorin, is a medication used to decrease the toxic effects of methotrexate and pyrimethamine.[2][3] It is also used in combination with 5-fluorouracil to treat colorectal cancer and pancreatic cancer, may be used to treat folate deficiency that results in anemia, and methanol poisoning.[3][4] It is taken by mouth, injection into a muscle, or injection into a vein.[3]

Side effects may include trouble sleeping, allergic reactions, or fever.[2][3] Use in pregnancy or breastfeeding is generally regarded as safe.[2] When used for anemia it is recommended that pernicious anemia as a cause be ruled out first.[3] Folinic acid is a form of folic acid that does not require activation by dihydrofolate reductase to be useful to the body.[3]

Folinic acid was first made in 1945.[5] It is on the World Health Organization's List of Essential Medicines.[6]

  1. ^ "Safety Data Sheet Folinic Acid (calcium salt)" (PDF). Retrieved 25 January 2018.
  2. ^ a b c British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 576–577. ISBN 9780857111562.
  3. ^ a b c d e f "Leucovorin Calcium". The American Society of Health-System Pharmacists. Archived from the original on 10 May 2017. Retrieved 8 December 2016.
  4. ^ Munjal YP, Sharm SK (2012). API Textbook of Medicine, Ninth Edition, Two Volume Set. JP Medical Ltd. p. 1945. ISBN 9789350250747. Archived from the original on 10 May 2017.
  5. ^ Sneader W (2005). Drug Discovery: A History. John Wiley & Sons. p. 235. ISBN 9780471899792. Archived from the original on 10 May 2017.
  6. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.