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

CCCCCCCC(=O)OC[C@@H](O)[C@@H](OC)[C@@H]1OC(=C[C@H](NC(N)=N)[C@H]1NC(C)=O)C(O)=O

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

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

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 ocatanoate is a prodrug of 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 8504		39.2 nM [IC50]
Neuraminidase 21 Target ID: CHEMBL2051 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18955520	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Influenza virus infections 34 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21973296	Curative		Approved 8583	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

C_max

Value	Dose	Analyte	Population
0.162 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22526307/	40 mg single, respiratory dose: 40 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
40.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	40 mg single, respiratory dose: 40 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
55.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	80 mg single, respiratory dose: 80 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
77.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	160 mg single, respiratory dose: 160 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
134.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	240 mg single, respiratory dose: 240 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
193.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	320 mg single, respiratory dose: 320 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
54.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	320 mg single, respiratory dose: 320 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
40 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	240 mg single, respiratory dose: 240 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
26.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	160 mg single, respiratory dose: 160 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
14.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	80 mg single, respiratory dose: 80 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
10.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	40 mg single, respiratory dose: 40 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
0.705 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22526307/	40 mg single, respiratory dose: 40 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
193.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	40 mg single, respiratory dose: 40 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
325.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	80 mg single, respiratory dose: 80 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
485.2 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	160 mg single, respiratory dose: 160 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1102 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	240 mg single, respiratory dose: 240 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1504 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	320 mg single, respiratory dose: 320 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
5059 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	320 mg single, respiratory dose: 320 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3164 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	240 mg single, respiratory dose: 240 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1629 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	160 mg single, respiratory dose: 160 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
810.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	80 mg single, respiratory dose: 80 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
371.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	40 mg single, respiratory dose: 40 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
2.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22526307/	40 mg single, respiratory dose: 40 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.84 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	40 mg single, respiratory dose: 40 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.11 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	80 mg single, respiratory dose: 80 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.01 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	160 mg single, respiratory dose: 160 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
34.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	240 mg single, respiratory dose: 240 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
55.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	320 mg single, respiratory dose: 320 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
165.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	320 mg single, respiratory dose: 320 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
144.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	240 mg single, respiratory dose: 240 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
115.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	160 mg single, respiratory dose: 160 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
95 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	80 mg single, respiratory dose: 80 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
58.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	40 mg single, respiratory dose: 40 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Analyte	Population
99.9% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22526307/	40 mg single, respiratory dose: 40 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
99.9% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	40 mg single, respiratory dose: 40 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
99.9% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	80 mg single, respiratory dose: 80 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
99.9% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	160 mg single, respiratory dose: 160 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
99.9% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	240 mg single, respiratory dose: 240 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
99.9% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	320 mg single, respiratory dose: 320 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR OCTANOATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
99.9% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	320 mg single, respiratory dose: 320 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
99.9% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	240 mg single, respiratory dose: 240 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
99.9% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	160 mg single, respiratory dose: 160 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
99.9% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	80 mg single, respiratory dose: 80 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
99.9% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29061751/	40 mg single, respiratory dose: 40 mg route of administration: Respiratory experiment type: SINGLE co-administered:	LANINAMIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
120 mg single, respiratory Highest studied dose Dose: 120 mg Route: respiratory Route: single Dose: 120 mg Sources: https://pubmed.ncbi.nlm.nih.gov/20145259/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20145259/	Sources: https://pubmed.ncbi.nlm.nih.gov/20145259/
40 mg 2 times / day multiple, respiratory Studied dose Dose: 40 mg, 2 times / day Route: respiratory Route: multiple Dose: 40 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20145259/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20145259/	Sources: https://pubmed.ncbi.nlm.nih.gov/20145259/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087 inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C19 2057		CYP1A2 832

Drug as perpetrator

Target	Modality	Activity	Metabolite
CYP1A2 2333	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2010/P201000050/430574000_22200AMX00925_A100_1.pdf Page: 31.0	no [IC50 >30 uM]	LANINAMIVIR 3
CYP2C19 2141	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2010/P201000050/430574000_22200AMX00925_A100_1.pdf Page: 31.0	no [IC50 >30 uM]	LANINAMIVIR 3
CYP2C9 2497	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2010/P201000050/430574000_22200AMX00925_A100_1.pdf Page: 31.0	no [IC50 >30 uM]	LANINAMIVIR 3
CYP2D6 2546	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2010/P201000050/430574000_22200AMX00925_A100_1.pdf Page: 31.0	no [IC50 >30 uM]	LANINAMIVIR 3
CYP3A4 2633	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2010/P201000050/430574000_22200AMX00925_A100_1.pdf	no [IC50 >30 uM]	LANINAMIVIR 3
CYP1A2 2333	inducer 1966 Sources: https://www.pmda.go.jp/drugs/2010/P201000050/430574000_22200AMX00925_I100_1.pdf Page: 39.0	no	LANINAMIVIR 3
CYP3A4 2633	inducer 1966 Sources: https://www.pmda.go.jp/drugs/2010/P201000050/430574000_22200AMX00925_I100_1.pdf Page: 39.0	no	LANINAMIVIR 3

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.pmda.go.jp/drugs/2010/P201000050/430574000_22200AMX00925_A100_1.pdf Page: 24.0		LANINAMIVIR 3

PubMed

Title	Date	PubMed
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.	2010-11	20145259
Neuraminidase inhibitor susceptibility testing in human influenza viruses: a laboratory surveillance perspective.	2010-10	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].	2010-10	21268406
[Present and future in development of new anti-influenza drugs].	2010-09	20845748
Antiviral strategies for pandemic and seasonal influenza.	2010-08	21994706
Pharmacokinetics and disposition of CS-8958, a long-acting prodrug of the novel neuraminidase inhibitor laninamivir in rats.	2010-03	20146556
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
CS-8958, a prodrug of the novel neuraminidase inhibitor R-125489, demonstrates a favorable long-retention profile in the mouse respiratory tract.	2009-11	19687241
CS-8958, a prodrug of the new neuraminidase inhibitor R-125489, shows long-acting anti-influenza virus activity.	2009-01	18955520
Synthesis and anti-influenza evaluation of polyvalent sialidase inhibitors bearing 4-guanidino-Neu5Ac2en derivatives.	2003-12	14646315
Synthesis and anti-influenza virus activity of 7-O-alkylated derivatives related to zanamivir.	2002-08-05	12113810
Synthesis and anti-influenza virus activity of 4-guanidino-7-substituted Neu5Ac2en derivatives.	2002-08-05	12113809

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 octanoateIf 10 years old or older, a single inhaled dose of 40 mg.2. For prevention of the influenza virusAdults 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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:33:21 GMT 2025` Edited by `admin` on `Mon Mar 31 21:33:21 GMT 2025`
Record UNII	E026V904RL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LANINAMIVIR OCTANOATE

Common Name

English

R-118958

Preferred 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

CS-8958

Common Name

English

Code System Code Type Description

CAS

203120-46-1