Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H36N4O8 |
| Molecular Weight | 472.5325 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]1(OC(=C[C@H](NC(N)=N)[C@H]1NC(C)=O)C(O)=O)[C@H](OC)[C@H](O)COC(=O)CCCCCCC
InChI
InChIKey=UKTIJASCFRNWCB-RMIBSVFLSA-N
InChI=1S/C21H36N4O8/c1-4-5-6-7-8-9-16(28)32-11-14(27)18(31-3)19-17(24-12(2)26)13(25-21(22)23)10-15(33-19)20(29)30/h10,13-14,17-19,27H,4-9,11H2,1-3H3,(H,24,26)(H,29,30)(H4,22,23,25)/t13-,14+,17+,18+,19+/m0/s1
| Molecular Formula | C21H36N4O8 |
| Molecular Weight | 472.5325 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21973296 | http://www.daiichisankyo.com/media_investors/media_relations/press_releases/detail/006052.html
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21973296 | http://www.daiichisankyo.com/media_investors/media_relations/press_releases/detail/006052.html
Laninamivir (R-125489), a new neuraminidase (NA) inhibitor, was discovered, and in this study, its NA inhibitory activities against various influenza viruses including oseltamivir-resistant viruses are reported. Laninamivir octanoate, has been approved for use in Japanese clinics for the treatment and prevention of influenza in both adults and children. The inhaled laninamivir octanoate is converted into its active form, laninamivir, in the lungs where a high concentration persists for a long period of time.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL6135 |
39.2 nM [IC50] | ||
Target ID: CHEMBL2051 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | INAVIR Approved UseInavir® Dry Powder Inhaler 20mg (generic name: Laninamivir Octanoate Hydrate) is approved in Japan for the treatment and prevention of influenza in both adults and children. Launch Date2010 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Synthesis and anti-influenza virus activity of 7-O-alkylated derivatives related to zanamivir. | 2002 Aug 5 |
|
| Synthesis and anti-influenza virus activity of 4-guanidino-7-substituted Neu5Ac2en derivatives. | 2002 Aug 5 |
|
| CS-8958, a prodrug of the new neuraminidase inhibitor R-125489, shows long-acting anti-influenza virus activity. | 2009 Jan |
|
| Comprehensive assessment of 2009 pandemic influenza A (H1N1) virus drug susceptibility in vitro. | 2010 |
|
| Laninamivir and its prodrug, CS-8958: long-acting neuraminidase inhibitors for the treatment of influenza. | 2010 |
|
| Antiviral strategies for pandemic and seasonal influenza. | 2010 Aug |
|
| Pharmacokinetics and disposition of CS-8958, a long-acting prodrug of the novel neuraminidase inhibitor laninamivir in rats. | 2010 Mar |
|
| Clinical pharmacokinetics of laninamivir, a novel long-acting neuraminidase inhibitor, after single and multiple inhaled doses of its prodrug, CS-8958, in healthy male volunteers. | 2010 Nov |
|
| Neuraminidase inhibitor susceptibility testing in human influenza viruses: a laboratory surveillance perspective. | 2010 Oct |
Patents
Sample Use Guides
1. For treatment of the influenza virus
Adults: A single inhaled dose of 40 mg of laninamivir octanoate
Children: If less than 10 years old, a single inhaled dose of 20 mg of laninamivir octanoate
If 10 years old or older, a single inhaled dose of 40 mg.
2. For prevention of the influenza virus
Adults and children over 10 years of age: Daily single inhaled dosage of 20 mg of laninamivir octanoate for two days
Route of Administration:
Respiratory
| Substance Class |
Chemical
Created
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E026V904RL
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Validated (UNII)
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METABOLITE ACTIVE -> PRODRUG |
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ACTIVE MOIETY |
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