Laninamivir

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 462088695

| IUPAC_name = (4S,5R,6R)-5-acetamido-4-carbamimidamido-6-[(1R,2R)-3-hydroxy-2-methoxypropyl]-5,6-dihydro-4H-pyran-2-carboxylic acid

| image = Laninamivir.svg

| width = 200px

| tradename =

| routes_of_administration = Inhalation

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 203120-17-6

| ATC_prefix = J05

| ATC_suffix = AH04

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 466246

| PubChem = 502272

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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 439182

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = B408IW3GL5

| C=13 | H=22 | N=4 | O=7

| 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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

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File:Inavir.jpg

Laninamivir (CS-8958) is a neuraminidase inhibitor that is a drug used for the treatment and prophylaxis of Influenzavirus A and Influenzavirus B.{{cite journal | vauthors = Yamashita M, Tomozawa T, Kakuta M, Tokumitsu A, Nasu H, Kubo S | title = CS-8958, a prodrug of the new neuraminidase inhibitor R-125489, shows long-acting anti-influenza virus activity | journal = Antimicrobial Agents and Chemotherapy | volume = 53 | issue = 1 | pages = 186–192 | date = January 2009 | pmid = 18955520 | pmc = 2612152 | doi = 10.1128/AAC.00333-08 }} It is currently in Phase III clinical trials.{{cite journal | vauthors = Hayden F | title = Developing new antiviral agents for influenza treatment: what does the future hold? | journal = Clinical Infectious Diseases | volume = 48 Suppl 1 | issue = S1 | pages = S3-13 | date = January 2009 | pmid = 19067613 | doi = 10.1086/591851 | series = 48 | doi-access = free }} It is a long-acting neuraminidase inhibitor administered by inhalation.{{cite journal | vauthors = Samson M, Pizzorno A, Abed Y, Boivin G | title = Influenza virus resistance to neuraminidase inhibitors | journal = Antiviral Research | volume = 98 | issue = 2 | pages = 174–185 | date = May 2013 | pmid = 23523943 | doi = 10.1016/j.antiviral.2013.03.014 }}

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 {{Cite web |url=http://www.biotapharma.com/ |title=Aviragen Therapeutics - Home |access-date=2013-04-12 |archive-date=2016-04-17 |archive-url=https://web.archive.org/web/20160417124102/http://www.biotapharma.com/ |url-status=dead }} 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.{{Cite web |url=http://www.biotapharma.com/?page=1021001&subpage=1021019 |title=Biota Pharmaceuticals - Home |access-date=2013-04-12 |archive-date=2016-03-05 |archive-url=https://web.archive.org/web/20160305125510/http://biotapharma.com/?page=1021001&subpage=1021019 |url-status=dead }} It is under clinical evaluations in other countries.{{cite book | vauthors = Ishjida T | chapter = Treatment Guidelines for Influenza Virus Infection: What Does the Recent Guideline State? | veditors = Fujita J | title = Influenza: Advances in Diagnosis and Management | series = Respiratory Disease Series: Diagnostic Tools and Disease Managements. | publisher = Springer | location = Singapore | doi = 10.1007/978-981-15-9109-9_13 | isbn = 978-981-15-9109-9 | chapter-url = https://books.google.com/books?id=J0UIEAAAQBAJ&dq=Laninamivir+clinical+evaluations+in+other+countries&pg=PA132 | date = 2020 | pages = 129–136 (132) | s2cid = 228892521 }}