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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

Molecular Formula C13H22N4O7
Molecular Weight 346.3369
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
Synthesis and anti-influenza virus activity of 7-O-alkylated derivatives related to zanamivir.
2002 Aug 5
Synthesis and anti-influenza virus activity of 4-guanidino-7-substituted Neu5Ac2en derivatives.
2002 Aug 5
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
CS-8958, a prodrug of the novel neuraminidase inhibitor R-125489, demonstrates a favorable long-retention profile in the mouse respiratory tract.
2009 Nov
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
Pharmacokinetics and disposition of CS-8958, a long-acting prodrug of the novel neuraminidase inhibitor laninamivir in rats.
2010 Mar
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
[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 04:52:29 UTC 2021
Edited
by admin
on Sat Jun 26 04:52:29 UTC 2021
Record UNII
B408IW3GL5
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
ACTIVE MOIETY