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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 -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
3D model (JSmol)	Interactive image
SMILES C(c1nc(-c2ccc(C#N)cc2)cs1)(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. In Japan, it is approved for the treatment of onychomycosis, a fungal infection of the nail. It is a prodrug that is converted into ravuconazole.

Drugs for Neglected Diseases Initiative (DNDi) and the Japanese pharmaceutical company Eisai found that fosravuconazole works as a treatment for mycetoma, a serious condition. The Phase II clinical trial found that oral fosravuconazole was safe, patient-friendly, and effective in treating eumycetoma. 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.

References

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 .
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.
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'.

• Triazole antifungals
• Fluoroarenes
• Thiazoles
• Phosphinates
• Nitriles
• Prodrugs
• Japanese inventions