U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C23H20F2N5O5PS.C6H14N2O2
Molecular Weight 693.659
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FOSRAVUCONAZOLE L-LYSINE

SMILES

NCCCC[C@H](N)C(O)=O.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=GTJFQIOLLGYOSL-SWQYEYERSA-N
InChI=1S/C23H20F2N5O5PS.C6H14N2O2/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;7-4-2-1-3-5(8)6(9)10/h2-8,10,12-13,15H,11,14H2,1H3,(H2,31,32,33);5H,1-4,7-8H2,(H,9,10)/t15-,23+;5-/m00/s1

HIDE SMILES / InChI

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

Cmax

ValueDoseCo-administeredAnalytePopulation
1052 ng/mL
400 mg single, oral
RAVUCONAZOLE plasma
Homo sapiens
9133 ng/mL
400 mg 1 times / day multiple, oral
RAVUCONAZOLE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
13872 ng × h/mL
400 mg single, oral
RAVUCONAZOLE plasma
Homo sapiens
153561 ng × h/mL
400 mg 1 times / day multiple, oral
RAVUCONAZOLE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
192 h
400 mg 1 times / day multiple, oral
RAVUCONAZOLE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
200 mg single, topical
RAVUCONAZOLE plasma
Homo sapiens

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.