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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H20F2N5O5PS
Molecular Weight 547.471
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FOSRAVUCONAZOLE

SMILES

C[C@@H](C1=NC(=CS1)C2=CC=C(C=C2)C#N)[C@@](CN3C=NC=N3)(OCOP(O)(O)=O)C4=CC=C(F)C=C4F

InChI

InChIKey=SYTNEMZCCLUTNX-NPMXOYFQSA-N
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

HIDE SMILES / InChI

Molecular Formula C23H20F2N5O5PS
Molecular Weight 547.471
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Ravuconazole is a triazole with antifungal properties that inhibits cytochrome P450 sterol 14a-demethylase, an enzyme involved in sterol synthesis, resulting in lysis of the fungal cell wall and fungal cell death. It was investigated for the treatment of aspergillosis, candidiasis, and onychomycosis, but these studies were discontinued. Ravuconazole is now in phase II clinical trials to investigate efficacy in preventing fungal infections in patients undergoing chemotherapy and stem cell transplantation.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown
Preventing
Unknown
Curative
Unknown

Drug as perpetrator​

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
In an asceding oral dose study, single doses of ravuconazole (from 50 to 800 mg once daily)
Route of Administration: Oral
In Vitro Use Guide
Ravuconazole showed very potent in vitro anti-T. cruzi activity with minimal inhibitory concentrations (MIC) of 300 and 1 nM against the extracellular epimastigote and intracellular amastigote forms, respectively.
Substance Class Chemical
Record UNII
L4Q6O5430L
Record Status Validated (UNII)
Record Version