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    CAS 229614-56-6

    BUILDING BLOCK

    PharmaCompass
    Xls

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    2D Structure
    Also known as: 330600-85-6, Bcx-1812, 229614-55-5, Rapiacta, Rwj-270201, Rapivab
    Molecular Formula
    C15H28N4O4
    Molecular Weight
    328.41  g/mol
    InChI Key
    XRQDFNLINLXZLB-CKIKVBCHSA-N
    FDA UNII
    9ZS94HQO3B
    Peramivir is an antiviral agent developed by Biocryst Pharmaceuticals to treat influenza A/B. The development of peramivir has been supported by the US Department of Health and Human Services as part of the government's effort to prepare for a flu pandemic. Being an influenza virus neuraminidase inhibitor, peramivir works by preventing new viruses from emerging from infected cells. Due to the poor oral bioavailability, the oral formulation of the drug was previously abandoned by Johnson and Johnson Company. The injectable intravenous formulation of peramivir was approved by the FDA in September 2017 for the treatment of acute uncomplicated influenza to pediatric patients 2 years and older who have been symptomatic for no more than two days.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1S,2S,3S,4R)-3-[(1S)-1-acetamido-2-ethylbutyl]-4-(diaminomethylideneamino)-2-hydroxycyclopentane-1-carboxylic acid
    2.1.2 InChI
    InChI=1S/C15H28N4O4/c1-4-8(5-2)12(18-7(3)20)11-10(19-15(16)17)6-9(13(11)21)14(22)23/h8-13,21H,4-6H2,1-3H3,(H,18,20)(H,22,23)(H4,16,17,19)/t9-,10+,11+,12-,13+/m0/s1
    2.1.3 InChI Key
    XRQDFNLINLXZLB-CKIKVBCHSA-N
    2.1.4 Canonical SMILES
    CCC(CC)C(C1C(CC(C1O)C(=O)O)N=C(N)N)NC(=O)C
    2.1.5 Isomeric SMILES
    CCC(CC)[C@@H]([C@H]1[C@@H](C[C@@H]([C@H]1O)C(=O)O)N=C(N)N)NC(=O)C
    2.2 Other Identifiers
    2.2.1 UNII
    9ZS94HQO3B
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (1s,2s,3r,4r)-3-((1s)-1-acetamido-2-ethylbutyl)-4-((amino(imino)methyl)amino)-2-hydroxycyclopentanecarboxylic Acid Trihydrate

    2. 3-(1'-acetylamino-2'-ethyl)butyl-4-((aminoimino)methyl)amino-2-hydroxycyclopentane-1-carboxylic Acid

    3. Bcx 1812

    4. Bcx-1812

    5. Bcx1812

    6. Peramivir Trihydrate

    7. Rapivab

    8. Rwj 270201

    9. Rwj-270201

    10. Rwj270201

    2.3.2 Depositor-Supplied Synonyms

    1. 330600-85-6

    2. Bcx-1812

    3. 229614-55-5

    4. Rapiacta

    5. Rwj-270201

    6. Rapivab

    7. Peramivir Anhydrous

    8. Chebi:85202

    9. Bcx1812

    10. Bcx 1812

    11. Peramivir, (+/-)-

    12. Rwj270201

    13. (1s,2s,3s,4r)-3-[(1s)-1-acetamido-2-ethylbutyl]-4-(diaminomethylideneamino)-2-hydroxycyclopentane-1-carboxylic Acid

    14. 229614-56-6

    15. Rwj 270201

    16. 9zs94hqo3b

    17. Idl9q29886

    18. (1s,2s,3r,4r)-3-((s)-1-acetamido-2-ethylbutyl)-4-guanidino-2-hydroxycyclopentanecarboxylic Acid

    19. 330600-85-6 (free)

    20. (1s,2s,3r,4r)-4-carbamimidamido-3-[(1s)-1-acetamido-2-ethylbutyl]-2-hydroxycyclopentane-1-carboxylic Acid

    21. 3-(1-acetylamino-2-ethyl-butyl)-4-guanidino-2-hydroxy-cyclopentanecarboxylic Acid

    22. 3-(1'-acetylamino-2'-ethyl)butyl-4-((aminoimino)methyl)amino-2-hydroxycyclopentane-1-carboxylic Acid

    23. Bcz

    24. Cyclopentanecarboxylic Acid, 3-[(1s)-1-(acetylamino)-2-ethylbutyl]-4-[(aminoiminomethyl)amino]-2-hydroxy-, (1s,2s,3r,4r)-

    25. (+/-)-peramivir

    26. Peramivir [usan:inn]

    27. Unii-9zs94hqo3b

    28. Peramiflu

    29. Unii-idl9q29886

    30. S-021812

    31. Cyclopentanecarboxylic Acid, 3-((1s)-1-(acetylamino)-2-ethylbutyl)-4-((aminoiminomethyl)amino)-2-hydroxy-, (1s,2s,3r,4r)-

    32. Peramivir [inn]

    33. Peramivir [mi]

    34. Schembl744373

    35. Bdbm5024

    36. Chembl139367

    37. Schembl12795462

    38. Dtxsid10904727

    39. Bcpp000117

    40. (1s,2r,3r,4r)-3-(1-acetamido-2-ethyl-butyl)-4-(diaminomethylideneamino)-2-hydroxy-cyclopentane-1-carboxylic Acid

    41. Zinc3981610

    42. Bdbm50181441

    43. Hy-17015a

    44. Mfcd09837902

    45. Akos016007760

    46. Akos037652424

    47. Peramivir (+/-)-form [mi]

    48. Cs-0638

    49. Db06614

    50. Dt-0029

    51. Ncgc00346433-06

    52. Ncgc00346433-07

    53. (1s,2s,3r,4r)-3-((1s)-1-acetylamino-2-ethylbutyl))-4-((aminoiminomethyl)amino)-2-hydroxycyclopentane

    54. (1s,2s,3r,4r)-3-((s)-1-acetamido-2-ethylbutyl)-4-guanidino-2-hydroxycyclopentane-1-carboxylic Acid

    55. Ac-22715

    56. Cyclopentanecarboxylic Acid, 3-((1r)-1-(acetylamino)-2-ethylbutyl)-4-((aminoiminomethyl)amino)-2-hydroxy-, (1r,2r,3s,4s)-rel-

    57. P2892

    58. W19713

    59. Ab01566838_01

    60. 600p856

    61. A896277

    62. Q412734

    63. (-)-(1s,2s,3r,4r)-3-[(1s)-1-(acetylamino)-2-ethylbutyl]-4-{[amino(imino)methyl]amino}-2-hydroxycyclopentanecarboxylic Acid

    64. (1s,2s,3r,4r)-3-((1s)-1-acetylamino-2-ethylbutyl)-4-((aminoiminomethyl)amino)-2-hydroxycyclopentanecarboxylic Acid

    65. (1s,2s,3r,4r)-3-[(1s)-1-(acetylamino)-2-ethylbutyl]-4-[(aminoiminomethyl)amino]-2-hydroxycyclopentanecarboxylic Acid Trihydrate

    66. (1s,2s,3r,4r)-3-[(1s)-1-(acetylamino)-2-ethylbutyl]-4-carbamimidamido-2-hydroxycyclopentanecarboxylic Acid

    67. (1s,2s,3r,4r)-3-[(1s)-1-acetamido-2-ethyl-butyl]-4-guanidino-2-hydroxy-cyclopentanecarboxylic Acid

    68. (1s,2s,3r,4r)-3-[(1s)-1-acetamido-2-ethylbutyl]-4-carbamimidamido-2-hydroxycyclopentane-1-carboxylic Acid

    69. (1s,2s,3s,4r)-4-[(diaminomethylidene)amino]-3-[(1s)-1-acetamido-2-ethylbutyl]-2-hydroxycyclopentane-1-carboxylic Acid

    70. Cyclopentanecarboxylic Acid, 3-((1s)-1-(acetylamino)-2-ethylbutyl)-4-((aminoiminomethyl)amino)-2-hydroxy-, (1r,2r,3s,4s)-rel-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 328.41 g/mol
    Molecular Formula C15H28N4O4
    XLogP30
    Hydrogen Bond Donor Count5
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count7
    Exact Mass328.21105539 g/mol
    Monoisotopic Mass328.21105539 g/mol
    Topological Polar Surface Area151 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity460
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 1  
    Drug NameRAPIVAB
    Active IngredientPERAMIVIR
    CompanyBIOCRYST (Application Number: N206426. Patents: 6503745, 6562861, 8778997)

    4.2 Drug Indication

    Indicated for the treatment of acute uncomplicated influenza in patients 18 years and older who have been symptomatic for no more than two days.

    FDA Label

    Alpivab is indicated for the treatment of uncomplicated influenza in adults and children from the age of 2 years.

    Treatment of influenza

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antiviral Agents

    Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)

    Enzyme Inhibitors

    Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

    5.2 ATC Code

    J05AH03

    J - Antiinfectives for systemic use

    J05 - Antivirals for systemic use

    J05A - Direct acting antivirals

    J05AH - Neuraminidase inhibitors

    J05AH03 - Peramivir

    5.3 Mechanism of Action

    Peramivir is an inhibitor of influenza neuraminidase, preventing new virus particles from leaving infected cells.