Laninamivir

Laninamivir
Clinical data
Routes of; administration	Inhalation
ATC code	J05AH04 (WHO) ;
Identifiers
	IUPAC name (4S,5R,6R)-5-acetamido-4-carbamimidamido-6-[(1R,2R)-3-hydroxy-2-methoxypropyl]-5,6-dihydro-4H-pyran-2-carboxylic acid;
CAS Number	203120-17-6 ;
PubChem CID	502272;
ChemSpider	439182 ;
UNII	B408IW3GL5;
ChEMBL	ChEMBL466246 ;
CompTox Dashboard (EPA)	DTXSID60942457 ;
Chemical and physical data
Formula	C13H22N4O7
Molar mass	346.340 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O)C=1O[C@@H]([C@H](OC)[C@H](O)CO)[C@H](NC(=O)C)[C@@H](/N=C(\N)N)C=1;
	InChI 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 ; Key:QNRRHYPPQFELSF-CNYIRLTGSA-N ;
	(what is this?) (verify)

Laninamivir (CS-8958) is a neuraminidase inhibitor that is a drug used for the treatment and prophylaxis of Influenzavirus A and Influenzavirus B.^[1] It is currently in Phase III clinical trials.^[2] It is a long-acting neuraminidase inhibitor administered by nasal inhalation.^[3]

Laninamivir was approved for influenza treatment in Japan in 2010 and for prophylaxis in 2013. It is currently marketed under the name Inavir by Daiichi Sankyo. Biota Pharmaceuticals ^[4] and Daiichi Sankyo co-own Laninamivir. On 1 April 2011, BARDA awarded up to an estimated U$231m to Biota Pharmaceuticals (Formerly Biota Holdings Ltd) wholly owned subsidiary, Biota Scientific Management Pty Ltd, for the advanced development of Laninamivir in the US.^[5] It is under clinical evaluations in other countries.^[3]^[6]

References

^ Yamashita M, Tomozawa T, Kakuta M, Tokumitsu A, Nasu H, Kubo S (January 2009). "CS-8958, a prodrug of the new neuraminidase inhibitor R-125489, shows long-acting anti-influenza virus activity". Antimicrobial Agents and Chemotherapy. 53 (1): 186–192. doi:10.1128/AAC.00333-08. PMC 2612152. PMID 18955520.
^ Hayden F (January 2009). "Developing new antiviral agents for influenza treatment: what does the future hold?". Clinical Infectious Diseases. 48. 48 Suppl 1 (S1): S3-13. doi:10.1086/591851. PMID 19067613.
^ ^a ^b Samson M, Pizzorno A, Abed Y, Boivin G (May 2013). "Influenza virus resistance to neuraminidase inhibitors". Antiviral Research. 98 (2): 174–185. doi:10.1016/j.antiviral.2013.03.014. PMID 23523943.
^ "Aviragen Therapeutics - Home". Archived from the original on 2016-04-17. Retrieved 2013-04-12.
^ "Biota Pharmaceuticals - Home". Archived from the original on 2016-03-05. Retrieved 2013-04-12.
^ Ishjida T (2020). "Treatment Guidelines for Influenza Virus Infection: What Does the Recent Guideline State?". In Fujita J (ed.). Influenza: Advances in Diagnosis and Management. Respiratory Disease Series: Diagnostic Tools and Disease Managements. Singapore: Springer. pp. 129–136 (132). doi:10.1007/978-981-15-9109-9_13. ISBN 978-981-15-9109-9. S2CID 228892521.

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[pmid18955520-1] Yamashita M, Tomozawa T, Kakuta M, Tokumitsu A, Nasu H, Kubo S (January 2009). "CS-8958, a prodrug of the new neuraminidase inhibitor R-125489, shows long-acting anti-influenza virus activity". Antimicrobial Agents and Chemotherapy. 53 (1): 186–192. doi:10.1128/AAC.00333-08. PMC 2612152. PMID 18955520.

[pmid19067613-2] Hayden F (January 2009). "Developing new antiviral agents for influenza treatment: what does the future hold?". Clinical Infectious Diseases. 48. 48 Suppl 1 (S1): S3-13. doi:10.1086/591851. PMID 19067613.

[samson_review-3] Samson M, Pizzorno A, Abed Y, Boivin G (May 2013). "Influenza virus resistance to neuraminidase inhibitors". Antiviral Research. 98 (2): 174–185. doi:10.1016/j.antiviral.2013.03.014. PMID 23523943.

[4] "Aviragen Therapeutics - Home". Archived from the original on 2016-04-17. Retrieved 2013-04-12.

[5] "Biota Pharmaceuticals - Home". Archived from the original on 2016-03-05. Retrieved 2013-04-12.

[6] Ishjida T (2020). "Treatment Guidelines for Influenza Virus Infection: What Does the Recent Guideline State?". In Fujita J (ed.). Influenza: Advances in Diagnosis and Management. Respiratory Disease Series: Diagnostic Tools and Disease Managements. Singapore: Springer. pp. 129–136 (132). doi:10.1007/978-981-15-9109-9_13. ISBN 978-981-15-9109-9. S2CID 228892521.

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