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Leflunomide (original brand name Arava ) is an immunosuppressive disease-modifying antirheumatic drug ( DMARD ),
Bottle of Leflunomide (Arava) and tablet
1 Medical use
2 Side effects
3 Mechanism of action
5 Leflunomide metabolism and similarity to teriflunomide
7 External links
Rheumatoid arthritis and psoriatic arthritis are the only indications that have received regulatory approval.
Polyoma BK virus nephropathy
Systemic lupus erythematosus
Granulomatosis with polyangiitis
Prevention of organ transplant rejection
The dose-limiting side effects are liver damage, lung disease and immunosuppression. anaphylaxis, angiooedema, anaemia, agranulocytosis, eosinophilia, leucopenia, pancytopenia, vasculitis, toxic epidermal necrolysis, Stevens-Johnson syndrome, cutaneous lupus erythematosus, severe infection, interstitial lung disease, cirrhosis and liver failure.
Though not reported elsewhere, 80 cases of interstitial pneumonitis involving leflunomide have been reported in Japan between 2003 and 2006. One such case resulting in a death was reported in a 2006 article from Japan and the authors suggest a “an inter-racial difference” for the interstitial pneumonitis.
Pregnancy, women of childbearing potential (unless contraception used)
Liver disease, hepatitis B / C seropositive
Active serious infections
Other immunomodulatory treatments should be avoided due to the potential for additive immunosuppressant effects, or in the case of immunostimulants like echinacea or astragalus, reduced therapeutic effects.
The concomitant use of methotrexate, in particular, may lead to severe or even fatal liver-damage or hepatotoxicity. Seventy-five percent of all cases of severe liver damage reported until early 2001 were seen under combined drug therapy leflunomide plus methotrexate.
Mechanism of action
Leflunomide is an immunomodulatory drug that achieves its effects by inhibiting the mitochondrial enzyme dihydroorotate dehydrogenase (DHODH), which plays a key role in the de novo synthesis of uridine monophosphate (rUMP), which is required for the synthesis of DNA and RNA. Hence, leflunomide inhibits the reproduction of rapidly dividing cells, especially lymphocytes.
The inhibition of human DHODH by teriflunomide, the active metabolite of leflunomide, occurs at levels (approximately 600 nM) that are achieved during treatment of rheumatoid arthritis (RA).
It has an oral bioavailability of 80%, protein binding of >99%, metabolism sites of the GI mucosa and liver, volume of distribution (V d ) of 0.13 L/kg, elimination half-life of 14–18 days and excretion routes of faeces (48%) and urine (43%).
Leflunomide metabolism and similarity to teriflunomide
Teriflunomide is the main active in vivo metabolite of leflunomide. Upon administration of leflunomide, 70% of the drug administered converts into teriflunomide. The only difference between the molecules is the opening of the isoxazole ring. Upon oral administration of leflunomide in vivo, the isoxazole ring of leflunomide is opened and teriflunomide is formed.
Teriflunomide is the active metabolite of leflunomide, responsible for its therapeutic actions. It results from the reaction of isoxazole ring opening, which occurs in vivo. Teriflunomide then can interconvert between the E and Z enolic forms (and the corresponding keto-amide), with the Z -enol being the most stable and therefore most predominant form.
“Regardless of the substance administered (leflunomide or teriflunomide), it is the same molecule (teriflunomide)—the one exerting the pharmacological, immunological or metabolic action in view of restoring, correcting or modifying physiological functions, and does not present, in clinical use, a new chemical entity to patients.”
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