Details of the Drug

General Information of Drug (ID: DMSV12M)

Drug Name
Isavuconazole
Synonyms
Isavuconazole; 241479-67-4; isavuconazol; BAL 4815; BAL-4815; UNII-60UTO373KE; Isavuconazole [INN]; 60UTO373KE; Isavuconazole(BAL-4815; RO-0094815); RO 0094815; CHEBI:85979; Isavuconazole (INN); RO-0094815; 4-[2-[(1R,2R)-2-(2,5-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-thiazolyl]benzonitrile; 1286730-05-9; 4-[2-[(2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl]benzonitrile
Indication
Disease Entry ICD 11 Status REF
Candidemia 1F23.3Y Phase 3 [1]
Invasive aspergillosis 1F20.0 Phase 3 [1]
Invasive candidiasis 1F23 Phase 3 [1]
Affected Organisms
Aspergillis, Candida and other fungi
ATC Code
J02AC05: Isavuconazole
J02AC: Triazole and tetrazole derivatives
J02A: ANTIMYCOTICS FOR SYSTEMIC USE
J02: ANTIMYCOTICS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
J02AC05: Isavuconazole
J02AC: Triazole and tetrazole derivatives
J02A: ANTIMYCOTICS FOR SYSTEMIC USE
J02: ANTIMYCOTICS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 437.5
Logarithm of the Partition Coefficient (xlogp) 3.5
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 8
ADMET Property
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 7499 mcg/L [2]
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 2C3 h [2]
Clearance
The clearance of drug is 2.5 +/- 1.6 L/h [3]
Elimination
Following oral administration, 46.1% of total radiolabelled isavuconzaole was detected in the feces, and about 45.5% was recovered in urine []
Half-life
The concentration or amount of drug in body reduced by one-half in 130 hours [2]
Metabolism
The drug is metabolized via the esterase-mediated hydrolysis []
Vd
The volume of distribution (Vd) of drug is 450 L []
Chemical Identifiers
Formula
C22H17F2N5OS
IUPAC Name
4-[2-[(2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl]benzonitrile
Canonical SMILES
C[C@@H](C1=NC(=CS1)C2=CC=C(C=C2)C#N)[C@](CN3C=NC=N3)(C4=C(C=CC(=C4)F)F)O
InChI
InChI=1S/C22H17F2N5OS/c1-14(21-28-20(10-31-21)16-4-2-15(9-25)3-5-16)22(30,11-29-13-26-12-27-29)18-8-17(23)6-7-19(18)24/h2-8,10,12-14,30H,11H2,1H3/t14-,22+/m0/s1
InChIKey
DDFOUSQFMYRUQK-RCDICMHDSA-N
Cross-matching ID
PubChem CID
6918485
ChEBI ID
CHEMBL85979
CAS Number
241479-67-4
UNII
60UTO373KE
DrugBank ID
DB11633
TTD ID
D07VHS
INTEDE ID
DR0883
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Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 ClinicalTrials.gov (NCT00634049) Isavuconazole in the Treatment of Renally Impaired Aspergillosis and Rare Fungi. U.S. National Institutes of Health.
2 EMA Label: Cresemba, Isavuconazole - European Medicines Agency - Europa EU
3 Kovanda LL, Desai AV, Lu Q, Townsend RW, Akhtar S, Bonate P, Hope WW: Isavuconazole Population Pharmacokinetic Analysis Using Nonparametric Estimation in Patients with Invasive Fungal Disease (Results from the VITAL Study). Antimicrob Agents Chemother. 2016 Jul 22;60(8):4568-76. doi: 10.1128/AAC.00514-16. Print 2016 Aug.
4 Pharmacokinetic evaluation of CYP3A4-mediated drug-drug interactions of isavuconazole with rifampin, ketoconazole, midazolam, and ethinyl estradiol/norethindrone in healthy adults. Clin Pharmacol Drug Dev. 2017 Jan;6(1):44-53.