Leflunomide

Leflunomide
Clinical data
Trade names	Arava, Lefumide, Arabloc, others
AHFS/Drugs.com	Monograph
MedlinePlus	a600032
License data	EU EMA: by INN; US DailyMed: Leflunomide;
Pregnancy; category	AU: X (High risk); ;
Routes of; administration	By mouth
ATC code	L04AK01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); CA: ℞-only; UK: POM (Prescription only); US: WARNINGRx-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	80%
Protein binding	>99%
Metabolism	GI mucosa and liver
Metabolites	Teriflunomide
Elimination half-life	14–18 days
Excretion	Faeces (48%), urine (43%)
Identifiers
	IUPAC name 5-methyl-N-[4-(trifluoromethyl) phenyl]-isoxazole-4-carboxamide;
CAS Number	75706-12-6 ;
PubChem CID	3899;
IUPHAR/BPS	6825;
DrugBank	DB01097 ;
ChemSpider	3762 ;
UNII	G162GK9U4W;
KEGG	D00749 ;
ChEBI	CHEBI:6402 ;
ChEMBL	ChEMBL960 ;
CompTox Dashboard (EPA)	DTXSID9023201 ;
ECHA InfoCard	100.123.883
Chemical and physical data
Formula	C12H9F3N2O2
Molar mass	270.211 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(Nc1ccc(cc1)C(F)(F)F)c2c(onc2)C;
	InChI InChI=1S/C12H9F3N2O2/c1-7-10(6-16-19-7)11(18)17-9-4-2-8(3-5-9)12(13,14)15/h2-6H,1H3,(H,17,18) ; Key:VHOGYURTWQBHIL-UHFFFAOYSA-N ;
	(verify)

Leflunomide, sold under the brand name Arava among others, is an immunosuppressive disease-modifying antirheumatic drug (DMARD),^[8] used in active moderate-to-severe rheumatoid arthritis and psoriatic arthritis. It is a pyrimidine synthesis inhibitor that works by inhibiting dihydroorotate dehydrogenase.^[9]

Bottle of Leflunomide (Arava) and tablet

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
^ Cite error: The named reference TGA was invoked but never defined (see the help page).
^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
^ Cite error: The named reference Arava SmPC was invoked but never defined (see the help page).
^ Cite error: The named reference Arava FDA label was invoked but never defined (see the help page).
^ "Arava EPAR". European Medicines Agency. 25 August 2023. Retrieved 26 August 2023.
^ ^a ^b ^c ^d ^e "Arava (leflunomide) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Retrieved 11 March 2014.
^ Dougados M, Emery P, Lemmel EM, Zerbini CA, Brin S, van Riel P (January 2005). "When a DMARD fails, should patients switch to sulfasalazine or add sulfasalazine to continuing leflunomide?". Annals of the Rheumatic Diseases. 64 (1): 44–51. doi:10.1136/ard.2003.016709. PMC 1755199. PMID 15271770.
^ Pinto P, Dougados M (2006). "Leflunomide in clinical practice" (PDF). Acta Reumatologica Portuguesa. 31 (3): 215–24. PMID 17094333.

[FDA-AllBoxedWarnings-1] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.

[TGA-2] Cite error: The named reference TGA was invoked but never defined (see the help page).

[3] Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.

[Arava_SmPC-4] Cite error: The named reference Arava SmPC was invoked but never defined (see the help page).

[Arava_FDA_label-5] Cite error: The named reference Arava FDA label was invoked but never defined (see the help page).

[Arava_EPAR-6] "Arava EPAR". European Medicines Agency. 25 August 2023. Retrieved 26 August 2023.

[MSR-7] "Arava (leflunomide) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Retrieved 11 March 2014.

[pmid15271770-8] Dougados M, Emery P, Lemmel EM, Zerbini CA, Brin S, van Riel P (January 2005). "When a DMARD fails, should patients switch to sulfasalazine or add sulfasalazine to continuing leflunomide?". Annals of the Rheumatic Diseases. 64 (1): 44–51. doi:10.1136/ard.2003.016709. PMC 1755199. PMID 15271770.

[pmid17094333-9] Pinto P, Dougados M (2006). "Leflunomide in clinical practice" (PDF). Acta Reumatologica Portuguesa. 31 (3): 215–24. PMID 17094333.

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