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    Chemistry

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    Also known as: 946075-13-4, Cresemba, Isavuconazonium (sulfate), Bal-8557-002, Isavuconazonium sulfate [usan], Chebi:85977
    Molecular Formula
    C35H36F2N8O9S2
    Molecular Weight
    814.8  g/mol
    InChI Key
    LWXUIUUOMSMZKJ-KLFWAVJMSA-M
    FDA UNII
    31Q44514JV
    Isavuconazonium Sulfate
    Isavuconazonium Sulfate is the sulfate ester form of isavuconazonium, a prodrug of the triazole antifungal agent isavuconazole, with broad-spectrum antifungal activity. Upon administration, isavuconazonium sulfate is hydrolyzed by plasma esterases to yield the active moiety isavuconazole. Isavuconazole binds to and inhibits the fungal cytochrome P450 family enzyme lanosterol 14-alpha-demethylase (CYP51), which catalyzes the demethylation of lanosterol to yield ergosterol, an important component of the fungal cell membrane. Inhibition of CYP51 leads to a decrease in fungal ergosterol production and disrupts synthesis of the fungal cell membrane, which decreases membrane integrity, increases cell membrane permeability and promotes the loss of essential intracellular elements. This results in fungal cell lysis and death.
    1 2D Structure

    Isavuconazonium Sulfate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [2-[1-[1-[(2R,3R)-3-[4-(4-cyanophenyl)-1,3-thiazol-2-yl]-2-(2,5-difluorophenyl)-2-hydroxybutyl]-1,2,4-triazol-4-ium-4-yl]ethoxycarbonyl-methylamino]pyridin-3-yl]methyl 2-(methylamino)acetate;hydrogen sulfate
    2.1.2 InChI
    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
    2.1.3 InChI Key
    LWXUIUUOMSMZKJ-KLFWAVJMSA-M
    2.1.4 Canonical SMILES
    CC(C1=NC(=CS1)C2=CC=C(C=C2)C#N)C(CN3C=[N+](C=N3)C(C)OC(=O)N(C)C4=C(C=CC=N4)COC(=O)CNC)(C5=C(C=CC(=C5)F)F)O.OS(=O)(=O)[O-]
    2.1.5 Isomeric SMILES
    C[C@@H](C1=NC(=CS1)C2=CC=C(C=C2)C#N)[C@](CN3C=[N+](C=N3)C(C)OC(=O)N(C)C4=C(C=CC=N4)COC(=O)CNC)(C5=C(C=CC(=C5)F)F)O.OS(=O)(=O)[O-]
    2.2 Other Identifiers
    2.2.1 UNII
    31Q44514JV
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1-((2r,3r)-3-(4-(4-cyanophenyl)-1,3-thiazol-2-yl)-2-(2,5-difluorophenyl)-2-hydroxybutyl)-4-((1rs)-1-((methyl(3-((((methylamino)acetyl)oxy)methyl)pyridin-2-yl)carbamoyl)oxy)ethyl)-1h-1,2,4-triazol-4-ium Monosulfate

    2. 4-(2-((2r,3r)-3-(2,5-difluorophenyl)-3-hydroxy-4-(1h-1,2,4-triazol-1-yl)butan-2-yl)-1,3-thiazol-4-yl)benzonitrile

    3. Ak-1820

    4. Ak1820

    5. Bal 4815

    6. Bal 8557

    7. Bal-4815

    8. Bal-8557

    9. Bal-8557-002

    10. Bal4815

    11. Bal8557

    12. Bal8557-002

    13. Cresemba

    14. Isavuconazole

    2.3.2 Depositor-Supplied Synonyms

    1. 946075-13-4

    2. Cresemba

    3. Isavuconazonium (sulfate)

    4. Bal-8557-002

    5. Isavuconazonium Sulfate [usan]

    6. Chebi:85977

    7. Ak1820

    8. 31q44514jv

    9. Ak-1820

    10. Bal8557-002

    11. [2-[1-[1-[(2r,3r)-3-[4-(4-cyanophenyl)-1,3-thiazol-2-yl]-2-(2,5-difluorophenyl)-2-hydroxybutyl]-1,2,4-triazol-4-ium-4-yl]ethoxycarbonyl-methylamino]pyridin-3-yl]methyl 2-(methylamino)acetate;hydrogen Sulfate

    12. 1-((2r,3r)-3-(4-(4-cyanophenyl)-1,3-thiazol-2-yl)-2-(2,5-difluorophenyl)-2-hydroxybutyl)-4-((1rs)-1-((methyl(3-((((methylamino)acetyl)oxy)methyl)pyridin-2-yl)carbamoyl)oxy)ethyl)-1h-1,2,4-triazol-4-ium Monosulfate

    13. Glycine, N-methyl-, (2-(((1-(1-((2r,3r)-3-(4-(4-cyanophenyl)-2-thiazolyl)-2-(2,5-difluorophenyl)-2-hydroxybutyl)-4h-1,2,4-triazolium-4-yl)ethoxy)carbonyl)methylamino)-3-pyridinyl)methyl Ester, Sulfate (1:1)

    14. Isavuconazonium Sulfate (usan)

    15. 1-((2r,3r)-3-(4-(4-cyanophenyl)thiazol-2-yl)-2-(2,5-difluorophenyl)-2-hydroxybutyl)-4-(1-((methyl(3-(((methylglycyl)oxy)methyl)pyridin-2-yl)carbamoyl)oxy)ethyl)-1h-1,2,4-triazol-4-ium Hydrogen Sulfate

    16. Unii-31q44514jv

    17. Chembl3137333

    18. Dtxsid901026216

    19. Ex-a1786

    20. Isavuconazonium Sulfate [jan]

    21. Akos030527357

    22. Isavuconazonium Sulfate [who-dd]

    23. Ac-31126

    24. As-35043

    25. Hy-100373

    26. Cs-0018702

    27. Isavuconazonium Sulfate [orange Book]

    28. D10643

    29. A900138

    30. Q27158829

    31. (2-{[(1-{1-[(2r,3r)-3-[4-(4-cyanophenyl)-1,3-thiazol-2-yl]-2-(2,5-difluorophenyl)-2-hydroxybutyl]-1h-1,2,4-triazol-4-ium-4-yl}ethoxy)carbonyl](methyl)amino}pyridin-3-yl)methyl N-methylglycinate Hydrogen Sulfate

    2.4 Create Date
    2013-12-16
    3 Chemical and Physical Properties
    Molecular Weight 814.8 g/mol
    Molecular Formula C35H36F2N8O9S2
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count17
    Rotatable Bond Count15
    Exact Mass814.20147343 g/mol
    Monoisotopic Mass814.20147343 g/mol
    Topological Polar Surface Area273 Ų
    Heavy Atom Count56
    Formal Charge0
    Complexity1290
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Indication

    Treatment of invasive aspergillosis, Treatment of mucormycosis

    Treatment of Candida infections

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antifungal Agents

    Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Azoles [CS]; Cytochrome P450 3A4 Inhibitors [MoA]; Organic Cation Transporter 2 Inhibitors [MoA]; P-Glycoprotein Inhibitors [MoA]; Azole Antifungal [EPC]

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    Virupaksha Organics

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    (2R,3S)-2-(2,5-difluorophenyl)-3-methyl-2-[(1H-1,2...

    CAS Number : 241479-73-2

    End Use API : Isavuconazonium Sulfate

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    (2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-...

    CAS Number : 368421-58-3

    End Use API : Isavuconazonium Sulfate

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    (2R,3R)-3-(2,5-Difluorophenyl)-3-hydroxy-2-Methyl-...

    CAS Number : 368421-58-3

    End Use API : Isavuconazonium Sulfate

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    4-(2-Bromoacetyl)benzonitrile

    CAS Number : 20099-89-2

    End Use API : Isavuconazonium Sulfate

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    RO-0098557

    CAS Number : 338990-31-1

    End Use API : Isavuconazonium Sulfate

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    Porton Pharma Solutions

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    (2R,3R)-3-(2,5-Difluorophenyl)-3-hydroxy- 2-Methyl...

    CAS Number : 368421-58-3

    End Use API : Isavuconazonium Sulfate

    About The Company : Porton Pharma Solutions Ltd. was founded in 2005, & the company's stock was successfully listed in Shenzhen Stock Exchange in 2014. Our R&D, manufacturing & ope...

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    Porton Pharma Solutions

    China
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    Virtual BoothPorton Pharma Solutions: Value creation via innovation & discovery through technical platforms.

    (2-(((1-chloroethoxy)carbonyl)(met hyl)amino)pyrid...

    CAS Number : 338990-31-1

    End Use API : Isavuconazonium Sulfate

    About The Company : Porton Pharma Solutions Ltd. was founded in 2005, & the company's stock was successfully listed in Shenzhen Stock Exchange in 2014. Our R&D, manufacturing & ope...

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    Porton Pharma Solutions

    China
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    Virtual BoothPorton Pharma Solutions: Value creation via innovation & discovery through technical platforms.

    4-(2-Bromoacetyl)benzonitrile

    CAS Number : 20099-89-2

    End Use API : Isavuconazonium Sulfate

    About The Company : Porton Pharma Solutions Ltd. was founded in 2005, & the company's stock was successfully listed in Shenzhen Stock Exchange in 2014. Our R&D, manufacturing & ope...

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    Porton Pharma Solutions

    China
    2024 ACI Convention
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    • EDQM
    • WHO-GMP

    Virtual BoothPorton Pharma Solutions: Value creation via innovation & discovery through technical platforms.

    (2R,3S)-2-(2,5-difluorophenyl)-3-methyl-2- [(1H-1,...

    CAS Number : 241479-73-2

    End Use API : Isavuconazonium Sulfate

    About The Company : Porton Pharma Solutions Ltd. was founded in 2005, & the company's stock was successfully listed in Shenzhen Stock Exchange in 2014. Our R&D, manufacturing & ope...

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    Porton Pharma Solutions

    China
    2024 ACI Convention
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    • EDQM
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    Virtual BoothPorton Pharma Solutions: Value creation via innovation & discovery through technical platforms.

    (2-(methylamino)pyridin-3- yl)methyl 2-(tertbutoxy...

    CAS Number : 1180002-01-0

    End Use API : Isavuconazonium Sulfate

    About The Company : Porton Pharma Solutions Ltd. was founded in 2005, & the company's stock was successfully listed in Shenzhen Stock Exchange in 2014. Our R&D, manufacturing & ope...

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    DOSAGE - CAPSULE;ORAL - 186MG

    USFDA APPLICATION NUMBER - 207500

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    DOSAGE - CAPSULE;ORAL - 74.5MG

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