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Details

Stereochemistry EPIMERIC
Molecular Formula C35H35F2N8O5S.HO4S
Molecular Weight 814.835
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISAVUCONAZONIUM SULFATE

SMILES

OS([O-])(=O)=O.CNCC(=O)OCC1=CC=CN=C1N(C)C(=O)OC(C)[N+]2=CN(C[C@@](O)([C@@H](C)C3=NC(=CS3)C4=CC=C(C=C4)C#N)C5=CC(F)=CC=C5F)N=C2

InChI

InChIKey=LWXUIUUOMSMZKJ-KLFWAVJMSA-M
InChI=1S/C35H35F2N8O5S.H2O4S/c1-22(33-42-30(18-51-33)25-9-7-24(15-38)8-10-25)35(48,28-14-27(36)11-12-29(28)37)19-45-21-44(20-41-45)23(2)50-34(47)43(4)32-26(6-5-13-40-32)17-49-31(46)16-39-3;1-5(2,3)4/h5-14,18,20-23,39,48H,16-17,19H2,1-4H3;(H2,1,2,3,4)/q+1;/p-1/t22-,23?,35+;/m0./s1

HIDE SMILES / InChI

Molecular Formula HO4S
Molecular Weight 97.071
Charge -1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C35H35F2N8O5S
Molecular Weight 717.765
Charge 1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 2 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Isavuconazole is an active form of isavuconazonium, a prodrug which is marketed under the name Cresemba. Isavuconazole inhibits lanosterol 14-alpha demethylase (or CYP51A1) and leads to the accumulation of ergosterol toxic precursors in the fungal cytoplasm. Isavuconazole is indicated for the treatment of invasive aspergillosis and invasive mucormycosis.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CRESEMBA
Curative
CRESEMBA

Cmax

ValueDoseCo-administeredAnalytePopulation
7499 ng/mL
200 mg 1 times / day steady-state, oral
ISAVUCONAZOLE plasma
Homo sapiens
20028 ng/mL
600 mg 1 times / day steady-state, oral
ISAVUCONAZOLE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
121402 ng × h/mL
200 mg 1 times / day steady-state, oral
ISAVUCONAZOLE plasma
Homo sapiens
352805 ng × h/mL
600 mg 1 times / day steady-state, oral
ISAVUCONAZOLE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
130 h
200 mg 1 times / day steady-state, oral
ISAVUCONAZOLE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
200 mg 1 times / day steady-state, oral
ISAVUCONAZOLE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Loading Dose: 372 mg isavuconazonium sulfate (equivalent to 200 mg of isavuconazole) every 8 hours for 6 doses (48 hours) via oral (2 capsules) or intravenous administration (1 reconstituted vial) Maintenance Dose: 372 mg isavuconazonium sulfate (equivalent to 200 mg of isavuconazole) once daily via oral (2 capsules) or intravenous administration (1 reconstituted vial) starting 12 to 24 hours after the last loading dose.
Route of Administration: Other
In Vitro Use Guide
Isavuconazole exhibited MIC50 values of 1–4 ug/ mL and MIC90 values of 4–16 ug/mL, against Mucorales isolates. MIC90 against Aspergillus fumigatus was 0.5–2 ug/ml, MIC90 against Aspergillus terreus was 0.5–4 ug/ml, MIC90 against Aspergillus flavus was 1–16 ug/ml, MIC90 against Aspergillus niger was 2–4 ug/ml.
Substance Class Chemical
Record UNII
31Q44514JV
Record Status Validated (UNII)
Record Version