Isavuconazonium

Isavuconazonium
Clinical data
Trade namesCresemba
AHFS/Drugs.comMonograph
License data
Pregnancy
category
Routes of
administration		By mouth, intravenous
ATC code
  • None
Legal status
Legal status
Identifiers
IUPAC name
  • 1-[(2R,3R)-3-[4-(4-cyanophenyl)-1,3-thiazol-2-yl]-2-(2,5-difluorophenyl)-2-hydroxybutyl]-4-[1-({methyl[3-({[2-(methylamino)acetyl]oxy}methyl)pyridin-2-yl]carbamoyl}oxy)ethyl]-1H-1,2,4-triazol-4-ium
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC35H35F2N8O5S
Molar mass717.77 g·mol−1
3D model (JSmol)
SMILES
  • [H]C(C)(OC(=O)N(C)C1=C(COC(=O)CNC)C=CC=N1)[N+]1=CN(C[C@](O)(C2=C(F)C=CC(F)=C2)[C@@]([H])(C)C2=NC(=CS2)C2=CC=C(C=C2)C#N)N=C1

  • sulfate: OS([O-])(=O)=O.[H]C(C)(OC(=O)N(C)C1=C(COC(=O)CNC)C=CC=N1)[N+]1=CN(C[C@](O)(C2=C(F)C=CC(F)=C2)[C@@]([H])(C)C2=NC(=CS2)C2=CC=C(C=C2)C#N)N=C1
InChI
  • InChI=1S/C35H35F2N8O5S/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/h5-14,18,20-23,39,48H,16-17,19H2,1-4H3/q+1/t22-,23?,35+/m0/s1
  • Key:RSWOJTICKMKTER-QXLBVTBOSA-N

  • sulfate: 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
  • Key:LWXUIUUOMSMZKJ-KLFWAVJMSA-M
 NY (what is this?)  (verify)
Isavuconazole
Clinical data
Other namesBAL8557
Pregnancy
category
Routes of
administration		By mouth, intravenous
ATC code
Identifiers
IUPAC name
  • 4-{2-[(1R,2R)-(2,5-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-1,3-thiazol-4-yl}benzonitrile
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H17F2N5OS
Molar mass437.47 g·mol−1
3D model (JSmol)
Melting point122[11] °C (252 °F)
Solubility in water14.2 ± 0.5 × 10−6 mol/L (pH 7.4)[11]
SMILES
  • C[C@@H](c1nc(-c2ccc(C#N)cc2)cs1)[C@](O)(Cn1cncn1)c1cc(F)ccc1F
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 N
  • Key:DDFOUSQFMYRUQK-RCDICMHDSA-N N
 NY (what is this?)  (verify)

Isavuconazonium, sold under the brand name Cresemba, is a systemic antifungal medication of the triazole class which is used to treat invasive aspergillosis and mucormycosis.[9][7][8][12] It is used as the sulfate.[9] It is taken by mouth or given via injection into a vein.[9]

The most common side effects include abnormal liver enzyme tests, nausea, vomiting, difficulty breathing, abdominal pain, diarrhea, injection site reactions, headache, low blood potassium, and skin rash.[10]

Isavuconazonium is a prodrug of isavuconazole.[13]

  1. ^ a b "Isavuconazonium (Cresemba) Use During Pregnancy". Drugs.com. 31 January 2020. Archived from the original on 2 December 2020. Retrieved 26 August 2020.
  2. ^ "Cresemba isavuconazole (as isavuconazonium sulfate) 200 mg powder for injection vial". Therapeutic Goods Administration (TGA). ARTG ID 305480. Archived from the original on 19 June 2022. Retrieved 5 September 2021.
  3. ^ "Cresemba isavuconazole (as isavuconazonium sulfate) 100 mg capsule blister pack". Therapeutic Goods Administration (TGA). ARTG ID 305452. Archived from the original on 5 September 2021. Retrieved 5 September 2021.
  4. ^ "AusPAR: Isavuconazole (as sulphate)". Therapeutic Goods Administration (TGA). 22 January 2020. Archived from the original on 5 September 2021. Retrieved 5 September 2021.
  5. ^ "Regulatory Decision Summary for Cresemba". Drug and Health Product Register. 23 October 2014. Archived from the original on 7 June 2022. Retrieved 7 June 2022.
  6. ^ "Drug and medical device highlights 2018: Helping you maintain and improve your health". Health Canada. 14 October 2020. Archived from the original on 17 April 2024. Retrieved 17 April 2024.
  7. ^ a b "Cresemba 100 mg hard capsules - Summary of Product Characteristics (SmPC)". (emc). 28 June 2021. Archived from the original on 5 September 2021. Retrieved 5 September 2021.
  8. ^ a b "Cresemba 200mg Powder for concentrate for solution for infusion - Summary of Product Characteristics (SmPC)". (emc). 28 June 2021. Archived from the original on 18 June 2017. Retrieved 5 September 2021.
  9. ^ a b c d "Cresemba- isavuconazonium sulfate capsule; Cresemba- isavuconazonium sulfate injection, powder, lyophilized, for solution". DailyMed. 2 December 2019. Archived from the original on 30 March 2021. Retrieved 26 August 2020.
  10. ^ a b Cite error: The named reference Cresemba EPAR was invoked but never defined (see the help page).
  11. ^ a b Cite error: The named reference Voronin_2021 was invoked but never defined (see the help page).
  12. ^ Donnelley MA, Zhu ES, Thompson GR (2 June 2016). "Isavuconazole in the treatment of invasive aspergillosis and mucormycosis infections". Infection and Drug Resistance. 9: 79–86. doi:10.2147/IDR.S81416. PMC 4898026. PMID 27330318.
  13. ^ Wilkes GM, Barton-Burke M (2019). 2020-2021 Oncology Nursing Drug Handbook. Jones & Bartlett Learning. pp. 1874–1876. ISBN 978-1-284-17132-7.
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