170864-29-6 Usage
Description
Ravuconazole is a second-generation triazole antifungal agent, developed to address the limitations, drug resistance, and drug interactions associated with earlier triazoles. It is structurally related to fluconazole and voriconazole but has a longer half-life, similar to isavuconazole. Ravuconazole was discovered by Eisai Co. Ltd. in Japan, developed by Bristol-Myers Squibb, and is now held again by Eisai. It is an off-white solid and functions as an ergosterol biosynthesis inhibitor, making it effective against various fungal infections.
Uses
Used in Pharmaceutical Industry:
Ravuconazole is used as an antifungal agent for the treatment of fungal infections. It works by inhibiting ergosterol biosynthesis, which is essential for the growth and survival of fungi. This makes it a valuable tool in combating fungal infections and overcoming drug resistance associated with earlier antifungal medications.
Used in Antifungal Applications:
Ravuconazole is employed as an antifungal agent, particularly effective against a wide range of fungal pathogens. Its long half-life allows for less frequent dosing, improving patient compliance and convenience. It is used to treat various fungal infections, including onychomycosis, aspergillosis, and candidiasis, among others.
Used in Drug Resistance Management:
Ravuconazole is used to address the issue of drug resistance in antifungal treatments. Its development was aimed at overcoming limitations and resistance associated with earlier triazoles, making it a crucial component in the management of drug-resistant fungal infections.
Used in Drug Interaction Mitigation:
Ravuconazole is utilized to minimize drug interactions that may occur with earlier triazoles. Its improved pharmacokinetic profile and reduced potential for drug interactions make it a safer and more effective option for patients requiring antifungal therapy.
Antimicrobial activity
The primary mode of action of ravuconazole is by inhibition of cytochrome P450 14a-demethylase, an enzyme in the sterol biosynthesis pathway. It is most potent against Candida spp. but has a broader spectrum of activity than fluconazole and itraconazole. It also has activity against Cryptococcus neoformans, Aspergillus fumigatus, dermatophytes, and dematiaceous fungi with limited activity against Sporothrix schenckii, Pseudallescheria boydii, Scedosporium apiospermum, Fusarium spp., and Zygomycetes. It is currently undergoing phase II clinical trials.
Biological Activity
In animal models, the oral bioavailability of ravuconazole ranged from 48% to 74%. The presence of food enhanced absorption, with a 2- to 4-fold increase in bioavailability when administered with a high-fat meal. Ravuconazole had a long serum elimination half-life ranging from 3.9 to 202 hours. Protein binding was high at 95.8% to 98%.
Mechanism of action
As with the other azoles, ravuconazole inhibits the P450-dependent enzyme lanosterol 14-a demethylase, resulting in depletion of ergosterol and the accumulation of 14-a demethylated precursors. This interferes with the function of ergosterol in fungal membranes and breaks down the integrity of the membranes.
Toxicology
For doses o2.5 mg/kg/day in human volunteers, there has been
minimal hepatotoxicity and nephrotoxicity. Headache and abdominal
pain were most frequently reported, followed by diarrhea, pruritus, and
rash. No side-effects have been
noted in rats and dogs treated with ravuconazole for a week.
There are still ongoing clinical trials assessing the tolerability of this
drug in both the oral and parenteral formulations.
Drug interactions
Ravuconazole may have a lower potential for drug interactions as it is a
less-potent inhibitor of CYP3A4 than voriconazole; however, no
information is available about interaction with other liver cytochrome
enzymes such as CYP2C9 or 2C19. One
clinical trial of ravuconazole in subjects with oral candidiasis and HIV
found that rifampicin reduced ravuconazole levels by over 50%.
Check Digit Verification of cas no
The CAS Registry Mumber 170864-29-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,0,8,6 and 4 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 170864-29:
(8*1)+(7*7)+(6*0)+(5*8)+(4*6)+(3*4)+(2*2)+(1*9)=146
146 % 10 = 6
So 170864-29-6 is a valid CAS Registry Number.
170864-29-6Relevant articles and documents
Azole antifungal agents, processes for the preparation thereof, and intermediates
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Page 75, (2010/01/31)
A compound represented by the general formula: wherein R1 and R2 denote a halogen atom or hydrogen atoms; R3 means a hydrogen atoms or lower alkyl group; r and m stand for 0 or 1; A is N or CH; W denotes an aromatic ring or a condensed ring thereof; X means another aromatic rings, an alkanediyl group, an alkenediyl group, or an alkynediyl group; Y stand for -S-, etc.; Z denotes a hydrogen atom, etc., or a salt thereof, and intermediates thereof or a salt thereof as well as processes for the preparation thereof, and pharmacetical composition suitable for use as an antifungal agent.