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2D Structure
Also known as: 204255-11-8, Tamiflu, Oseltamivir (phosphate), Oseltamir phosphate, Agucort, Ro 64-0796/002
Molecular Formula
C16H31N2O8P
Molecular Weight
410.40  g/mol
InChI Key
PGZUMBJQJWIWGJ-ONAKXNSWSA-N
FDA UNII
4A3O49NGEZ

An acetamido cyclohexene that is a structural homolog of SIALIC ACID and inhibits NEURAMINIDASE.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
ethyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylate;phosphoric acid
2.1.2 InChI
InChI=1S/C16H28N2O4.H3O4P/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19;1-5(2,3)4/h9,12-15H,5-8,17H2,1-4H3,(H,18,19);(H3,1,2,3,4)/t13-,14+,15+;/m0./s1
2.1.3 InChI Key
PGZUMBJQJWIWGJ-ONAKXNSWSA-N
2.1.4 Canonical SMILES
CCC(CC)OC1C=C(CC(C1NC(=O)C)N)C(=O)OCC.OP(=O)(O)O
2.1.5 Isomeric SMILES
CCC(CC)O[C@@H]1C=C(C[C@@H]([C@H]1NC(=O)C)N)C(=O)OCC.OP(=O)(O)O
2.2 Other Identifiers
2.2.1 UNII
4A3O49NGEZ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Gs 4071

2. Gs 4104

3. Gs-4071

4. Gs-4104

5. Gs4071

6. Gs4104

7. Oseltamivir

8. Tamiflu

2.3.2 Depositor-Supplied Synonyms

1. 204255-11-8

2. Tamiflu

3. Oseltamivir (phosphate)

4. Oseltamir Phosphate

5. Agucort

6. Ro 64-0796/002

7. Aseltamivir Phosphate

8. Gs 4104

9. Oseltamivir (as Phosphate)

10. 4a3o49ngez

11. Ethyl (3r,4r,5s)-4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate Phosphate

12. Chebi:7799

13. Ethyl (3r,4r,5s)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate Phosphate (1:1)

14. (3r,4r,5s)-ethyl 4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate Phosphate

15. (3r-(3alpha,4beta,5alpha))-ethyl 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate Phosphate (1:1)

16. Ro-64-0796-002

17. Ro-64-0796/002

18. 1-cyclohexene-1-carboxylic Acid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, Ethyl Ester, (3r,4r,5s)-, Phosphate (1:1)

19. Phosphoric Acid Ethyl (3r,4r,5s)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

20. Oseltamivir Phosphate [usan]

21. Unii-4a3o49ngez

22. Sr-05000001499

23. Mfcd08059548

24. Ebilfumin (tn)

25. Oseltamivir Phosphate [usan:usp]

26. Ethyl (3r,4r,5s)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylate;phosphoric Acid

27. Tamiflu (tn)

28. Oseltamiviri Phosphas

29. Gs 4104 Phosphate

30. Schembl8730

31. (3r-(3alpha,4beta,5alpha)-ethyl 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate Phosphate (1:1)

32. Mls006011559

33. Amy583

34. Chembl1200340

35. Dtxsid0044230

36. Oseltamivir Phosphate (jan/usp)

37. Bcpp000138

38. Oseltamivir Phosphate [mi]

39. Oseltamivir Phosphate [jan]

40. Act03369

41. Oseltamivir Phosphate [vandf]

42. S2597

43. Oseltamivir Phosphate [mart.]

44. Akos015896056

45. Oseltamivir Phosphate [usp-rs]

46. Oseltamivir Phosphate [who-dd]

47. Oseltamivir Phosphate [who-ip]

48. Bcp9001033

49. Ccg-230250

50. Cs-0871

51. Ks-1184

52. Nsc 758897

53. Oseltamivir Phosphate, >=98% (hplc)

54. 1-cyclohexene-1-carboxylic Acid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, Ethyl Ester, (3r-(3alpha,4beta,5alpha)-, Phosphate (1:1)

55. Ac-25911

56. Bo164181

57. Ethyl (3r,4r,5s)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate, Phosphate (1:1)

58. Hy-17016

59. Smr004703323

60. Oseltamivir Phosphate [orange Book]

61. Oseltamivir Phosphate [ep Monograph]

62. Oseltamivir Phosphate [usp Impurity]

63. Oseltamivir Phosphate [usp Monograph]

64. Oseltamiviri Phosphas [who-ip Latin]

65. Gs-4104/002

66. C08093

67. D00900

68. 255o118

69. Sr-05000001960

70. J-013302

71. J-523838

72. Sr-05000001499-2

73. Sr-05000001960-1

74. Q27107588

75. Z1550675456

76. Benzofuran-3-yl-(3-boc-amino-azetidin-1-yl)-aceticacid

77. Oseltamivir Phosphate, United States Pharmacopeia (usp) Reference Standard

78. Oseltamivir Phosphate (impurity B Free), European Pharmacopoeia (ep) Reference Standard

79. Oseltamivir Phosphate, Pharmaceutical Secondary Standard; Certified Reference Material

80. (3r,4r,5s)-4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic Acid Ethyl Ester Phosphate

81. (3r,4r,5s)-4-acetylamino-5-amino-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic Acid Ethyl Ester Phosphate

82. (3r,4r,5s)-4-acetylamino-5-amino-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic Acid Ethyl Ester Phosphoric Acid Salt

83. (3r,5s)-ethyl 4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate Phosphate;osteltamivir Phosphate

84. (3r-(3.alpha.,4.beta.,5.alpha.))-ethyl 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate Phosphate (1:1)

85. Ethyl (3r,4r,5s)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate; Phosphoric Acid

86. Ethyl-(3r,4r,5s)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate Phosphate

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 410.40 g/mol
Molecular Formula C16H31N2O8P
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count9
Rotatable Bond Count8
Exact Mass410.18180295 g/mol
Monoisotopic Mass410.18180295 g/mol
Topological Polar Surface Area168 Ų
Heavy Atom Count27
Formal Charge0
Complexity468
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameOseltamivir phosphate
PubMed HealthOseltamivir (By mouth)
Drug ClassesAntiviral
Drug LabelTAMIFLU (oseltamivir phosphate) is available as capsules containing 30 mg, 45 mg, or 75 mg oseltamivir for oral use, in the form of oseltamivir phosphate, and as a powder for oral suspension, which when constituted with water as directed contains 6 m...
Active IngredientOseltamivir phosphate
Dosage FormCapsule
Routeoral
Strength30mg
Market StatusTentative Approval
CompanyNatco Pharma

2 of 4  
Drug NameTamiflu
Drug LabelTAMIFLU (oseltamivir phosphate) is available as capsules containing 30 mg, 45 mg, or 75 mg oseltamivir for oral use, in the form of oseltamivir phosphate, and as a powder for oral suspension, which when constituted with water as directed contains 6 m...
Active IngredientOseltamivir phosphate
Dosage FormCapsule; For suspension
RouteOral
Strengtheq 75mg base; eq 6mg base/ml; eq 30mg base; eq 45mg base
Market StatusPrescription
CompanyRoche

3 of 4  
Drug NameOseltamivir phosphate
PubMed HealthOseltamivir (By mouth)
Drug ClassesAntiviral
Drug LabelTAMIFLU (oseltamivir phosphate) is available as capsules containing 30 mg, 45 mg, or 75 mg oseltamivir for oral use, in the form of oseltamivir phosphate, and as a powder for oral suspension, which when constituted with water as directed contains 6 m...
Active IngredientOseltamivir phosphate
Dosage FormCapsule
Routeoral
Strength30mg
Market StatusTentative Approval
CompanyNatco Pharma

4 of 4  
Drug NameTamiflu
Drug LabelTAMIFLU (oseltamivir phosphate) is available as capsules containing 30 mg, 45 mg, or 75 mg oseltamivir for oral use, in the form of oseltamivir phosphate, and as a powder for oral suspension, which when constituted with water as directed contains 6 m...
Active IngredientOseltamivir phosphate
Dosage FormCapsule; For suspension
RouteOral
Strengtheq 75mg base; eq 6mg base/ml; eq 30mg base; eq 45mg base
Market StatusPrescription
CompanyRoche

4.2 Drug Indication

* Treatment of influenza:

Tamiflu is indicated in adults and children including full term neonates who present with symptoms typical of influenza, when influenza virus is circulating in the community. Efficacy has been demonstrated when treatment is initiated within two days of first onset of symptoms. Prevention of influenza

- Post-exposure prevention in individuals one year of age or older following contact with a clinically diagnosed influenza case when influenza virus is circulating in the community.

- The appropriate use of Tamiflu for prevention of influenza should be determined on a case-by-case basis by the circumstances and the population requiring protection. In exceptional situations (e. g. in case of a mismatch between the circulating and vaccine virus strains, and a pandemic situation) seasonal prevention could be considered in individuals one year of age or older.

- Tamiflu is indicated for post-exposure prevention of influenza in infants less than 1 year of age during a pandemic-influenza outbreak.

Tamiflu is not a substitute for influenza vaccination.

The use of antivirals for the treatment and prevention of influenza should be determined on the basis of official recommendations. Decisions regarding the use of oseltamivir for treatment and prophylaxis should take into consideration what is known about the characteristics of the circulating influenza viruses, available information on influenza drug susceptibility patterns for each season and the impact of the disease in different geographical areas and patient populations.


Treatment and prevention of influenza


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

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.)


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.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Neuraminidase Inhibitors [MoA]; Neuraminidase Inhibitor [EPC]
5.3 ATC Code

J05AH02