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Chemistry

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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

CAS 229614-56-6

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 Formula	C₁₅H₂₈N₄O₄
Molecular Weight	328.41 g/mol
XLogP3	0
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	7
Exact Mass	328.21105539 g/mol
Monoisotopic Mass	328.21105539 g/mol
Topological Polar Surface Area	151 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	460
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 1
Drug Name	RAPIVAB
Active Ingredient	PERAMIVIR
Company	BIOCRYST (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.

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