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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H36N4O8
Molecular Weight 472.5334
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LANINAMIVIR OCTANOATE

SMILES

CCCCCCCC(=O)OC[C@]([H])([C@]([H])([C@@]1([H])[C@@]([H])([C@]([H])(C=C(C(=O)O)O1)NC(=N)N)N=C(C)O)OC)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 472.5334
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
39.2 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
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
Neuraminidase inhibitor susceptibility testing in human influenza viruses: a laboratory surveillance perspective.
2010 Oct
[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
[Present and future in development of new anti-influenza drugs].
2010 Sep
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
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 Jun 26 02:23:46 UTC 2021
Edited
by admin
on Sat Jun 26 02:23:46 UTC 2021
Record UNII
E026V904RL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LANINAMIVIR OCTANOATE
WHO-DD  
Common Name English
LANINAMIVIR OCTANOATE [WHO-DD]
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, (+)-
Common Name English
R-118958
Code English
Code System Code Type Description
CAS
203120-46-1
Created by admin on Sat Jun 26 02:23:46 UTC 2021 , Edited by admin on Sat Jun 26 02:23:46 UTC 2021
PRIMARY
FDA UNII
E026V904RL
Created by admin on Sat Jun 26 02:23:46 UTC 2021 , Edited by admin on Sat Jun 26 02:23:46 UTC 2021
PRIMARY
DRUG BANK
DB11888
Created by admin on Sat Jun 26 02:23:46 UTC 2021 , Edited by admin on Sat Jun 26 02:23:46 UTC 2021
PRIMARY
MERCK INDEX
M6676
Created by admin on Sat Jun 26 02:23:46 UTC 2021 , Edited by admin on Sat Jun 26 02:23:46 UTC 2021
PRIMARY Merck Index
EVMPD
SUB34944
Created by admin on Sat Jun 26 02:23:46 UTC 2021 , Edited by admin on Sat Jun 26 02:23:46 UTC 2021
PRIMARY
PUBCHEM
9847629
Created by admin on Sat Jun 26 02:23:46 UTC 2021 , Edited by admin on Sat Jun 26 02:23:46 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG