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Laninamivir

Laninamivir

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Also known as: 203120-17-6, R-125489, (2r,3r,4s)-3-acetamido-4-(diaminomethylideneamino)-2-[(1r,2r)-2,3-dihydroxy-1-methoxypropyl]-3,4-dihydro-2h-pyran-6-carboxylic acid, B408iw3gl5, Laninamivir (inn), D-glycero-d-galacto-non-2-enonic acid, 5-(acetylamino)-4-[(aminoiminomethyl)amino]-2,6-anhydro-3,4,5-trideoxy-7-o-methyl-

Molecular Formula

C₁₃H₂₂N₄O₇

Molecular Weight

346.34 g/mol

InChI Key

QNRRHYPPQFELSF-CNYIRLTGSA-N

FDA UNII

B408IW3GL5

Laninamivir has been used in trials studying the treatment of Influenza.

1 2D Structure

Laninamivir

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3R,4S)-3-acetamido-4-(diaminomethylideneamino)-2-[(1R,2R)-2,3-dihydroxy-1-methoxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid

2.1.2 InChI

InChI=1S/C13H22N4O7/c1-5(19)16-9-6(17-13(14)15)3-8(12(21)22)24-11(9)10(23-2)7(20)4-18/h3,6-7,9-11,18,20H,4H2,1-2H3,(H,16,19)(H,21,22)(H4,14,15,17)/t6-,7+,9+,10+,11+/m0/s1

2.1.3 InChI Key

QNRRHYPPQFELSF-CNYIRLTGSA-N

2.1.4 Canonical SMILES

CC(=O)NC1C(C=C(OC1C(C(CO)O)OC)C(=O)O)N=C(N)N

2.1.5 Isomeric SMILES

CC(=O)N[C@@H]1[C@H](C=C(O[C@H]1[C@@H]([C@@H](CO)O)OC)C(=O)O)N=C(N)N

2.2 Other Identifiers

2.2.1 UNII

B408IW3GL5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5-(acetylamino)-4-((aminoiminomethyl)amino)-2,6-anhydro-3,4,5-trideoxy-7-o-methyl-d-glycero-d-galacto-non-2-enonic Acid

2. Laninamivir Octanoate

3. Laninamivir Octanoate Hydrate

4. Laninamivir Octanoate Monohydrate

5. Laninamivir Trifluoroacetate

6. R 125489

7. R-125489

8. R125489

2.3.2 Depositor-Supplied Synonyms

1. 203120-17-6

2. R-125489

3. (2r,3r,4s)-3-acetamido-4-(diaminomethylideneamino)-2-[(1r,2r)-2,3-dihydroxy-1-methoxypropyl]-3,4-dihydro-2h-pyran-6-carboxylic Acid

4. B408iw3gl5

5. Laninamivir (inn)

6. D-glycero-d-galacto-non-2-enonic Acid, 5-(acetylamino)-4-[(aminoiminomethyl)amino]-2,6-anhydro-3,4,5-trideoxy-7-o-methyl-

7. Laninamivir [inn]

8. (2r,3r,4s)-3-acetamido-2-((1r,2r)-2,3-dihydroxy-1-methoxypropyl)-4-guanidino-3,4-dihydro-2h-pyran-6-carboxylic Acid

9. (4s,5r,6r)-5-acetamido-4-carbamimidamido-6-((1r,2r)-3-hydroxy-2-methoxypropyl)-5,6-dihydro-4h-pyran-2-carboxylic Acid

10. 5-(acetylamino)-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-7-o-methyl-d-glycero-d-galacto-non-2-enonic Acid

11. Laninamivir [inn:jan]

12. Laninamivir (cs-8958)

13. Unii-b408iw3gl5

14. Lani

15. Laninamivir [mi]

16. Laninamivir [mart.]

17. Laninamivir [who-dd]

18. Chembl466246

19. Schembl12284832

20. Dtxsid60942457

21. Chebi:177801

22. Bcpp000190

23. Glxc-15033

24. Bcp27633

25. Ex-a4019

26. Zinc3985629

27. Bdbm50009296

28. Akos015850995

29. Akos032947260

30. Bcp9000836

31. Db12791

32. (2r,3r,4s)-3-acetamido-2-[(1r,2r)-2,3-dihydroxy-1-methoxy-propyl]-4-guanidino-3,4-dihydro-2h-pyran-6-carboxylic Acid

33. (4s,5r,6r)-5-acetamido-4-guanidino-6-((1r,2r)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4h-pyran-2-carboxylic Acid

34. Ac-36457

35. Hy-14818

36. Cs-0003575

37. C21557

38. D09410

39. 120l176

40. A814430

41. Q6487096

42. R 125489r 125489

43. (4s,5r,6r)-5-acetamido-4-guanidino-6- ((1r,2r)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4h-pyran-2-carboxylic Acid

44. 5-(acetylamino)-4-[(aminoiminomethyl)amino]-2,6-anhydro-3,4,5-trideoxy-7-o-methyl-d-glycero-d-galacto-non-2-enonic Acid

45. 5-acetylamino-4-(diaminomethyl-amino)-6-(2,3-dihydroxy-1-methoxy-propyl)-5,6-dihydro-4h-pyran-2-carboxylic Acid

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₂₂N₄O₇
Molecular Weight	346.34 g/mol
XLogP3	-3.2
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	7
Exact Mass	346.14884905 g/mol
Monoisotopic Mass	346.14884905 g/mol
Topological Polar Surface Area	190 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	532
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 Pharmacology and Biochemistry

4.1 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.)

4.2 ATC Code

J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AH - Neuraminidase inhibitors

J05AH04 - Laninamivir