Efinaconazole

Efinaconazole
Clinical data
Trade names	Jublia, Clenafin
License data	US FDA: Efinaconazole;
Routes of; administration	Topical (solution)
ATC code	D01AC19 (WHO) ;
Legal status
Legal status	CA: ℞-only ; US: ℞-only ;
Identifiers
	IUPAC name (2R,3R)-2-(2,4-Difluorophenyl)-3-(4-methylene-1-piperidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol;
CAS Number	164650-44-6;
PubChem CID	489181;
ChemSpider	428538;
KEGG	D10021;
ChEBI	CHEBI:82718 ;
CompTox Dashboard (EPA)	DTXSID40167787 ;
ECHA InfoCard	100.245.862
Chemical and physical data
Formula	C18H22F2N4O
Molar mass	348.39 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@H]([C@](CN1C=NC=N1)(C2=C(C=C(C=C2)F)F)O)N3CCC(=C)CC3;
	InChI InChI=1S/C18H22F2N4O/c1-13-5-7-23(8-6-13)14(2)18(25,10-24-12-21-11-22-24)16-4-3-15(19)9-17(16)20/h3-4,9,11-12,14,25H,1,5-8,10H2,2H3/t14-,18-/m1/s1; Key:NFEZZTICAUWDHU-RDTXWAMCSA-N;

Efinaconazole, sold under the brand names Jublia and Clenafin, is a triazole antifungal. It is approved for use in the United States, Canada, and Japan as a 10% topical solution for the treatment of onychomycosis (fungal infection of the nail).[1][2] Efinaconazole acts as a 14α-demethylase inhibitor.[3][4]

Medical uses

In two clinical trials 17.8% and 15.2% of patients using efinaconazole were cured, compared to 3.3% and 5.5% of patients using a placebo.[4]

Efinaconazole is not especially effective, but it is currently the best topical treatment available, with cure rates two or three times better than the next best topical treatment, ciclopirox. It is considered a reasonable option for patients with mild cases, or patients who can not take oral treatment.[5]

History

In 2014, the U.S. Food and Drug Administration (FDA) approved the New Drug Application (NDA).[6] According to Valeant Pharmaceuticals International Inc CEO J. Michael Pearson they acquired Jublia through their purchase of Dow Pharmaceutical Sciences in 2008.[6]

Society and culture

Cost

In 2015 the cost of treatment with efinaconazole in the United States was said to be $2317 per nail.[7]

References

Patel T, Dhillon S (Nov 2013). "Efinaconazole: first global approval". Drugs. 73 (17): 1977–1983. doi:10.1007/s40265-013-0152-x. PMID 24249649.
Tschen EH, Bucko AD, Oizumi N, Kawabata H, Olin JT, Pillai R (Feb 2013). "Efinaconazole solution in the treatment of toenail onychomycosis: a phase 2, multicenter, randomized, double-blind study". J Drugs Dermatol. 12 (2): 186–192. PMID 23377392.
Tatsumi Y, Nagashima M, Shibanushi T, et al. (May 2013). "Mechanism of action of efinaconazole, a novel triazole antifungal agent". Antimicrob Agents Chemother. 57 (5): 2405–2509. doi:10.1128/aac.02063-12. PMC 3632939.
"Drugs at FDA: JUBLIA" (PDF). Retrieved 26 June 2014.
"A Closer Look At A New Topical Option For Onychomycosis". Retrieved 21 May 2015.
"Valeant Pharmaceuticals Announces FDA Approval Of Jublia® for the Treatment of Onychomycosis". Valeant Pharmaceuticals. Laval, Quebec. 9 June 2014. Archived from the original on 8 November 2015. Retrieved 1 November 2015.
Mikailov A, Cohen J, Joyce C, Mostaghimi A (2015). "Cost-effectiveness of Confirmatory Testing Before Treatment of Onychomycosis". JAMA Dermatology: 1–6. doi:10.1001/jamadermatol.2015.4190. PMID 26716567.

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[1] Patel T, Dhillon S (Nov 2013). "Efinaconazole: first global approval". Drugs. 73 (17): 1977–1983. doi:10.1007/s40265-013-0152-x. PMID 24249649.

[2] Tschen EH, Bucko AD, Oizumi N, Kawabata H, Olin JT, Pillai R (Feb 2013). "Efinaconazole solution in the treatment of toenail onychomycosis: a phase 2, multicenter, randomized, double-blind study". J Drugs Dermatol. 12 (2): 186–192. PMID 23377392.

[3] Tatsumi Y, Nagashima M, Shibanushi T, et al. (May 2013). "Mechanism of action of efinaconazole, a novel triazole antifungal agent". Antimicrob Agents Chemother. 57 (5): 2405–2509. doi:10.1128/aac.02063-12. PMC 3632939.

[drugsatfda-4] "Drugs at FDA: JUBLIA" (PDF). Retrieved 26 June 2014.

[podiatrytoday-5] "A Closer Look At A New Topical Option For Onychomycosis". Retrieved 21 May 2015.

[valeant-6] "Valeant Pharmaceuticals Announces FDA Approval Of Jublia® for the Treatment of Onychomycosis". Valeant Pharmaceuticals. Laval, Quebec. 9 June 2014. Archived from the original on 8 November 2015. Retrieved 1 November 2015.

[Mikailov-7] Mikailov A, Cohen J, Joyce C, Mostaghimi A (2015). "Cost-effectiveness of Confirmatory Testing Before Treatment of Onychomycosis". JAMA Dermatology: 1–6. doi:10.1001/jamadermatol.2015.4190. PMID 26716567.