LANINAMIVIR

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H22N4O7
Molecular Weight	346.3364
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

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	346.3364
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 (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 8297		39.2 nM [IC50]
Neuraminidase 21 Target ID: CHEMBL2051 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18955520	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Influenza virus infections 33 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21973296	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 2010

PubMed

Title	Date	PubMed
Synthesis and anti-influenza virus activity of 4-guanidino-7-substituted Neu5Ac2en derivatives.	2002 Aug 5	12113809
CS-8958, a prodrug of the novel neuraminidase inhibitor R-125489, demonstrates a favorable long-retention profile in the mouse respiratory tract.	2009 Nov	19687241
Antiviral strategies for pandemic and seasonal influenza.	2010 Aug	21994706

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 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 17:53:30 GMT 2023` Edited by `admin` on `Sat Dec 16 17:53:30 GMT 2023`
Record UNII	B408IW3GL5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LANINAMIVIR

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

Code

English

Laninamivir [WHO-DD]

Common Name

English

LANINAMIVIR [MART.]

Common Name

English

Code System Code Type Description

DRUG BANK

DB12791