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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H36N4O8.H2O
Molecular Weight 490.5478
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LANINAMIVIR OCTANOATE MONOHYDRATE

SMILES

O.[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=IBFFAVWCRFPPNZ-QZAMVOJNSA-N
InChI=1S/C21H36N4O8.H2O/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);1H2/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
Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 39.2 nM [IC50]
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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

1.28735995E12
PubMed

PubMed

TitleDatePubMed
Synthesis and anti-influenza evaluation of polyvalent sialidase inhibitors bearing 4-guanidino-Neu5Ac2en derivatives.
2003 Dec
CS-8958, a prodrug of the new neuraminidase inhibitor R-125489, shows long-acting anti-influenza virus activity.
2009 Jan
Laninamivir and its prodrug, CS-8958: long-acting neuraminidase inhibitors for the treatment of influenza.
2010
[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
Patents

Patents

20100035947
3
20100113373
3

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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 07:38:48 UTC 2023
Edited
by admin
on Sat Dec 16 07:38:48 UTC 2023
Record UNII
MCG28BI87W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LANINAMIVIR OCTANOATE MONOHYDRATE
WHO-DD  
Common Name English
INAVIR
Brand Name English
LANINAMIVIR OCTANOATE HYDRATE
JAN  
Common Name English
Laninamivir octanoate monohydrate [WHO-DD]
Common Name English
LANINAMIVIR OCTANOATE HYDRATE [JAN]
Common Name English
LANINAMIVIR OCTANOIC ACID ESTER HYDRATE [MI]
Common Name English
LANINAMIVIR OCTANOATE HYDRATE, (+)-
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 MONOHYDRATE
Systematic Name English
Code System Code Type Description
DRUG CENTRAL
4822
Created by admin on Sat Dec 16 07:38:48 UTC 2023 , Edited by admin on Sat Dec 16 07:38:48 UTC 2023
PRIMARY
EVMPD
SUB181431
Created by admin on Sat Dec 16 07:38:48 UTC 2023 , Edited by admin on Sat Dec 16 07:38:48 UTC 2023
PRIMARY
FDA UNII
MCG28BI87W
Created by admin on Sat Dec 16 07:38:48 UTC 2023 , Edited by admin on Sat Dec 16 07:38:48 UTC 2023
PRIMARY
CAS
371755-92-9
Created by admin on Sat Dec 16 07:38:48 UTC 2023 , Edited by admin on Sat Dec 16 07:38:48 UTC 2023
NON-SPECIFIC STOICHIOMETRY
MERCK INDEX
m6676
Created by admin on Sat Dec 16 07:38:48 UTC 2023 , Edited by admin on Sat Dec 16 07:38:48 UTC 2023
PRIMARY
PUBCHEM
46919879
Created by admin on Sat Dec 16 07:38:48 UTC 2023 , Edited by admin on Sat Dec 16 07:38:48 UTC 2023
PRIMARY
CAS
1233643-88-3
Created by admin on Sat Dec 16 07:38:48 UTC 2023 , Edited by admin on Sat Dec 16 07:38:48 UTC 2023
PRIMARY
SMS_ID
100000167046
Created by admin on Sat Dec 16 07:38:48 UTC 2023 , Edited by admin on Sat Dec 16 07:38:48 UTC 2023
PRIMARY
EPA CompTox
DTXSID70153991
Created by admin on Sat Dec 16 07:38:48 UTC 2023 , Edited by admin on Sat Dec 16 07:38:48 UTC 2023
PRIMARY
Related Record Type Details
Structure of LANINAMIVIR OCTANOATE
PARENT -> SALT/SOLVATE
Structure of LANINAMIVIR OCTANOATE
ANHYDROUS->SOLVATE
Related Record Type Details
Structure of LANINAMIVIR
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