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Details

Stereochemistry ABSOLUTE
Molecular Formula C13H22N4O7
Molecular Weight 346.3369
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LANINAMIVIR

SMILES

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

InChI

InChIKey=QNRRHYPPQFELSF-CNYIRLTGSA-N
InChI=1S/C13H22N4O7/c1-5(19)16-9-6(17-13(14)15)3-8(12(21)22)24-11(9)10(23-2)7(20)4-18/h3,6-7,9-11,18,20H,4H2,1-2H3,(H,16,19)(H,21,22)(H4,14,15,17)/t6-,7+,9+,10+,11+/m0/s1

HIDE SMILES / InChI

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
39.2000000000000028 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

1287360000000
PubMed

PubMed

TitleDatePubMed
Synthesis and anti-influenza virus activity of 7-O-alkylated derivatives related to zanamivir.
2002 Aug 5
CS-8958, a prodrug of the novel neuraminidase inhibitor R-125489, demonstrates a favorable long-retention profile in the mouse respiratory tract.
2009 Nov
Antiviral strategies for pandemic and seasonal influenza.
2010 Aug
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
[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

Sample Use Guides

1. For treatment of the influenza virus
Route of Administration: Respiratory
Laninamivir (R-125489) neuraminidase inhibitory activity depends on virus strain. IC50 values lie in low nanomolar range.
Name Type Language
LANINAMIVIR
INN   MART.   MI   WHO-DD  
INN  
Official Name English
LANINAMIVIR [INN]
Common Name English
(4S,5R,6R)-5-ACETAMIDO-4-CARBAMIMIDAMIDO-6-((1R,2R)-3-HYDROXY-2-METHOXYPROPYL)-5,6-DIHYDRO-4H-PYRAN-2-CARBOXYLIC ACID
Common Name English
LANINAMIVIR [MI]
Common Name English
R-125489
Common Name English
LANINAMIVIR [WHO-DD]
Common Name English
LANINAMIVIR [MART.]
Common Name English
Code System Code Type Description
DRUG BANK
DB12791
Created by admin on Sat Jun 26 04:52:29 UTC 2021 , Edited by admin on Sat Jun 26 04:52:29 UTC 2021
PRIMARY
INN
9047
Created by admin on Sat Jun 26 04:52:29 UTC 2021 , Edited by admin on Sat Jun 26 04:52:29 UTC 2021
PRIMARY
NCI_THESAURUS
C174629
Created by admin on Sat Jun 26 04:52:29 UTC 2021 , Edited by admin on Sat Jun 26 04:52:29 UTC 2021
PRIMARY
WIKIPEDIA
Laninamivir
Created by admin on Sat Jun 26 04:52:29 UTC 2021 , Edited by admin on Sat Jun 26 04:52:29 UTC 2021
PRIMARY
PUBCHEM
502272
Created by admin on Sat Jun 26 04:52:29 UTC 2021 , Edited by admin on Sat Jun 26 04:52:29 UTC 2021
PRIMARY
CAS
203120-17-6
Created by admin on Sat Jun 26 04:52:29 UTC 2021 , Edited by admin on Sat Jun 26 04:52:29 UTC 2021
PRIMARY
MERCK INDEX
M6676
Created by admin on Sat Jun 26 04:52:29 UTC 2021 , Edited by admin on Sat Jun 26 04:52:29 UTC 2021
PRIMARY Merck Index
FDA UNII
B408IW3GL5
Created by admin on Sat Jun 26 04:52:29 UTC 2021 , Edited by admin on Sat Jun 26 04:52:29 UTC 2021
PRIMARY
EVMPD
SUB89575
Created by admin on Sat Jun 26 04:52:29 UTC 2021 , Edited by admin on Sat Jun 26 04:52:29 UTC 2021
PRIMARY