Folinic acid

Folinic acid
Clinical data
Pronunciation	Leucovorin /ˌljuːkoʊˈvɔːrɪn/
Trade names	Many
Other names	citrovorum factor, 5-formyltetrahydrofolate
AHFS/Drugs.com	Monograph
MedlinePlus	a608038
License data	US DailyMed: Leucovorin calcium;
Pregnancy; category	AU: A;
Routes of; administration	Intravenous, IM, by mouth
ATC code	V03AF03 (WHO) ;
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Bioavailability	Dose dependent
Protein binding	~15%
Elimination half-life	6.2 hours
Excretion	Kidney
Identifiers
	IUPAC name (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	1492-18-8 ;
PubChem CID	6006;
IUPHAR/BPS	4816;
DrugBank	DB00650 ;
ChemSpider	5784 ;
UNII	RPR1R4C0P4;
ChEMBL	ChEMBL1679 ;
CompTox Dashboard (EPA)	DTXSID0048216 ;
ECHA InfoCard	100.000.328
Chemical and physical data
Formula	C20H23N7O7
Molar mass	473.446 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	245 °C (473 °F) decomp
Solubility in water	~0.3 mg/mL (20 °C)
	SMILES 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 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 ; Key:VVIAGPKUTFNRDU-ABLWVSNPSA-N ;
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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]

^ "Safety Data Sheet Folinic Acid (calcium salt)" (PDF). Retrieved 25 January 2018.
^ ^a ^b ^c British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 576–577. ISBN 9780857111562.
^ ^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.
^ 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.
^ Sneader W (2005). Drug Discovery: A History. John Wiley & Sons. p. 235. ISBN 9780471899792. Archived from the original on 10 May 2017.
^ 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.

[1] "Safety Data Sheet Folinic Acid (calcium salt)" (PDF). Retrieved 25 January 2018.

[BNF69-2] British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 576–577. ISBN 9780857111562.

[AHFS2016-3] ^ ^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.

[WHO21st-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.

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