Fosravuconazole

Fosravuconazole
Clinical data
Trade names	Nailin
Other names	BMS-379224; BFE-1224; E-1224
ATC code	D01BA03 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name [(2R,3R)-3-[4-(4-Cyanophenyl)-1,3-thiazol-2-yl]-2-(2,4-difluorophenyl)-1-(1,2,4-triazol-1-yl)butan-2-yl]oxymethyl dihydrogen phosphate;
CAS Number	351227-64-0;
PubChem CID	9807507;
UNII	L4Q6O5430L;
KEGG	D10762;
CompTox Dashboard (EPA)	DTXSID70188627 ;
Chemical and physical data
Formula	C23H20F2N5O5PS
Molar mass	547.47 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@@H](c1nc(-c2ccc(C#N)cc2)cs1)[C@@](Cn1cncn1)(OCOP(=O)(O)O)c1ccc(F)cc1F;
	InChI InChI=1S/C23H20F2N5O5PS/c1-15(22-29-21(10-37-22)17-4-2-16(9-26)3-5-17)23(11-30-13-27-12-28-30,34-14-35-36(31,32)33)19-7-6-18(24)8-20(19)25/h2-8,10,12-13,15H,11,14H2,1H3,(H2,31,32,33)/t15-,23+/m0/s1; Key:SYTNEMZCCLUTNX-NPMXOYFQSA-N;

Fosravuconazole (trade name Nailin) is a triazole antifungal agent.^[1]^[2] In Japan, it is approved for the treatment of onychomycosis, a fungal infection of the nail.^[3] It is a prodrug that is converted into ravuconazole.^[1]

Drugs for Neglected Diseases Initiative (DNDi) and the Japanese pharmaceutical company Eisai found that fosravuconazole works as a treatment for mycetoma, a serious condition.^[1]^[4]^[5] The Phase II clinical trial found that oral fosravuconazole was safe, patient-friendly, and effective in treating eumycetoma.^[6]^[7] Eumycetoma mainly affects young adults in poorer, rural areas; the standard treatment is itraconazole, which is much more expensive at about US$2,000 for a year than fosravuconazole and unaffordable, and not available in all endemic countries.^[7]

References

^ ^a ^b ^c Yamaguchi H (2016). "Potential of Ravuconazole and its Prodrugs as the New OralTherapeutics for Onychomycosis". Medical Mycology Journal. 57 (4): E93–E110. doi:10.3314/mmj.16-00006. PMID 27904057.
^ "Fosravuconazole - Seren Pharmaceuticals". Adis Insight. Springer Nature Switzerland AG.
^ "Oral Antifungal Agent Nailin Capsules 100 mg Approved in Japan" (Press release). Eisai. January 19, 2018.
^ "Fosravuconazole". Drugs for Neglected Diseases Initiative. 23 November 2023 [Project started in 2015; updated in 2023 with results of the Phase II clinical trial].
^ "Drugs for Neglected Diseases initiative and Eisai Co., Ltd. to Test Drug Candidate for Eumycetoma" (Press release). Eisai Co., Ltd. 10 September 2015.
^ "World's first clinical trial for devastating fungal disease mycetoma shows efficacy of new, promising treatment" (Press release). Drugs for Neglected Diseases initiative (DNDi). 23 November 2023.
^ ^a ^b Johnson, Sarah (23 November 2023). "Cheap over-the-counter nail drug found to work on crippling flesh-eating disease". The Guardian. The head of mycetoma at the DNDi labelled the discovery 'momentous', and said 'We were all very excited, it's going to be a gamechanger'.

[Yamaguchi-1] Yamaguchi H (2016). "Potential of Ravuconazole and its Prodrugs as the New OralTherapeutics for Onychomycosis". Medical Mycology Journal. 57 (4): E93–E110. doi:10.3314/mmj.16-00006. PMID 27904057.

[2] "Fosravuconazole - Seren Pharmaceuticals". Adis Insight. Springer Nature Switzerland AG.

[3] "Oral Antifungal Agent Nailin Capsules 100 mg Approved in Japan" (Press release). Eisai. January 19, 2018.

[4] "Fosravuconazole". Drugs for Neglected Diseases Initiative. 23 November 2023 [Project started in 2015; updated in 2023 with results of the Phase II clinical trial].

[5] "Drugs for Neglected Diseases initiative and Eisai Co., Ltd. to Test Drug Candidate for Eumycetoma" (Press release). Eisai Co., Ltd. 10 September 2015.

[6] "World's first clinical trial for devastating fungal disease mycetoma shows efficacy of new, promising treatment" (Press release). Drugs for Neglected Diseases initiative (DNDi). 23 November 2023.

[johnson-7] Johnson, Sarah (23 November 2023). "Cheap over-the-counter nail drug found to work on crippling flesh-eating disease". The Guardian. The head of mycetoma at the DNDi labelled the discovery 'momentous', and said 'We were all very excited, it's going to be a gamechanger'.

[1]

[2]

[3]

[4]

[5]

[6]

[7]