LANINAMIVIR OCTANOATE

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

Structure Search

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18955520
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
Neuraminidase 21 Target ID: CHEMBL6135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18955520	Inhibitor 8297		39.2 nM [IC50]
Neuraminidase 21 Target ID: CHEMBL2051 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18955520	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Influenza virus infections 33 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21973296	Curative		Approved 8429	INAVIR Approved Use Inavir® 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 Date 2010

PubMed

Title	Date	PubMed
Synthesis and anti-influenza virus activity of 7-O-alkylated derivatives related to zanamivir.	2002 Aug 5	12113810
Synthesis and anti-influenza virus activity of 4-guanidino-7-substituted Neu5Ac2en derivatives.	2002 Aug 5	12113809
Synthesis and anti-influenza evaluation of polyvalent sialidase inhibitors bearing 4-guanidino-Neu5Ac2en derivatives.	2003 Dec	14646315
CS-8958, a prodrug of the new neuraminidase inhibitor R-125489, shows long-acting anti-influenza virus activity.	2009 Jan	18955520
CS-8958, a prodrug of the novel neuraminidase inhibitor R-125489, demonstrates a favorable long-retention profile in the mouse respiratory tract.	2009 Nov	19687241
Comprehensive assessment of 2009 pandemic influenza A (H1N1) virus drug susceptibility in vitro.	2010	21149922
Laninamivir and its prodrug, CS-8958: long-acting neuraminidase inhibitors for the treatment of influenza.	2010	21107016
Antiviral strategies for pandemic and seasonal influenza.	2010 Aug	21994706
Pharmacokinetics and disposition of CS-8958, a long-acting prodrug of the novel neuraminidase inhibitor laninamivir in rats.	2010 Mar	20146556
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	20145259
Neuraminidase inhibitor susceptibility testing in human influenza viruses: a laboratory surveillance perspective.	2010 Oct	21994620
[In vitro and in vivo effects of a long-acting anti-influenza agent CS-8958 (laninamivir octanoate, Inavir) against pandemic (H1N1) 2009 influenza viruses].	2010 Oct	21268406
[Present and future in development of new anti-influenza drugs].	2010 Sep	20845748

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

Laninamivir (R-125489) neuraminidase inhibitory activity depends on virus strain. IC50 values lie in low nanomolar range.

Name

Type

Language

LANINAMIVIR OCTANOATE

Common Name

English

LANINAMIVIR OCTANOIC ACID ESTER [MI]

Common Name

English

(2R,3R,4S)-3-ACETAMIDO-4-GUANIDINO-2-((1R,2R)-2-HYDROXY-1-METHOXY-3-(OCTANOYLOXY)PROPYL)-3,4-DIHYDRO-2H-PYRAN-6-CARBOXYLIC ACID

Systematic Name

English

Laninamivir octanoate [WHO-DD]

Common Name

English

LANINAMIVIR OCTANOATE, (+)-

Common Name

English

R-118958

Code

English

Code System Code Type Description

CAS

203120-46-1