Laninamivir free base
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MedKoo CAT#: 598292

CAS#: 203120-17-6 (free base)

Description: Laninamivir, also known as CS-8958, is a neuraminidase inhibitor that is a drug used for the treatment and prophylaxis of Influenzavirus A and Influenzavirus B. It is a long-acting neuraminidase inhibitor administered by nasal inhalation. Laninamivir was approved for influenza treatment in Japan in 2010 and for prophylaxis in 2013


Chemical Structure

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Laninamivir free base
CAS# 203120-17-6 (free base)

Theoretical Analysis

MedKoo Cat#: 598292
Name: Laninamivir free base
CAS#: 203120-17-6 (free base)
Chemical Formula: C13H22N4O7
Exact Mass: 346.1488
Molecular Weight: 346.34
Elemental Analysis: C, 45.08; H, 6.40; N, 16.18; O, 32.34

Price and Availability

Size Price Availability Quantity
10.0mg USD 150.0 Same day
25.0mg USD 250.0 Same day
50.0mg USD 450.0 Same day
100.0mg USD 650.0 Same day
200.0mg USD 950.0 Same day
500.0mg USD 1950.0 Same day
1.0g USD 2950.0 Same day
2.0g USD 5250.0 Same day
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Related CAS #: 203120-17-6 (free base)   203120-18-7 (TFA)   203120-46-1 (octanoate)   1233643-88-3 (octanoate hydrate)    

Synonym: Laninamivir; R-125489; R 125489; R125489; CS8958; CS-8958; CS 8958;

IUPAC/Chemical Name: (4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid

InChi Key: QNRRHYPPQFELSF-GAOFYXTMSA-N

InChi Code: 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+/m1/s1

SMILES Code: O=C(C1=C[C@@H](NC(N)=N)[C@H](NC(C)=O)[C@@H]([C@@H](OC)[C@@H](O)CO)O1)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

Biological target: Laninamivir (R 125489) is a potent influenza neuraminidase (NA) inhibitor with IC50s of 0.90 nM, 1.83 nM and 3.12 nM for avian H12N5 NA (N5), pH1N1 N1 NA (p09N1) and A/RI/5+/1957 H2N2 N2 (p57N2), respectively.
In vitro activity: In this study, the viral fitness of an NAI‐resistant influenza A/Brisbane/10/2007‐like (H3N2) strain containing a large NA deletion and a P194L HA substitution that emerged under in vitro laninamivir pressure was evaluated. This variant corresponds to the 9th passage in which the growth medium contained 2 μM of laninamivir.9 In addition to the P194L mutation, the HA protein of this variant contained an S138A substitution, which is unlikely to be linked to the NAI pressure as it was also detected in the virus that was subjected to 9 passages without drug.9 When blast analyses using GenBank database sequences were performed, the 194L HA genotype was detected in numerous American, Asian, and Australian A(H3N2) viruses that have circulated since 2007 whereas no large NA deletion equivalent to that of LRVp9 could be detected. Residue 194 of influenza A(H3N2) HA is located at the globular head of the molecule and is part of the RBS. Therefore, changes at this position could naturally occur during influenza evolution contrasting to the internal region of NA protein which contains the highly conserved active site whose deletion seems to be strictly linked to the NAI pressure. Reference: Influenza Other Respir Viruses. 2016 Mar; 10(2): 122–126. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4746560/
In vivo activity: In this study, the tissue distribution profiles after a single intranasal administration of CS-8958 (0.5 μmol/kg of body weight) to mice were investigated, focusing especially on the retention of CS-8958 in the respiratory tract by comparing it with R-125489 and a marketed drug, zanamivir. After administration of [14C]CS-8958, radioactivity was retained in the respiratory tract over long periods. At 24 h postdose, the radioactivity concentrations after administration of [14C]CS-8958 were approximately 10-fold higher in both the trachea and the lung than those of [14C]R-125489 and [14C]zanamivir. The [14C]CS-8958-derived radioactivity present in these two tissues consisted both of unchanged CS-8958 and of R-125489 at 1 h postdose, while only R-125489, and no other metabolites, was detected at 24 h postdose. After administration of unlabeled CS-8958, CS-8958 was rapidly eliminated from the lungs, whereas the lung R-125489 concentration reached a maximum at 3 h postdose and gradually declined, with an elimination half-life of 41.4 h. The conversion of CS-8958 to R-125489 was observed in mouse trachea and lung S9 fractions and was inhibited by esterase inhibitors, such as diisopropylfluorophosphate and bis-p-nitrophenylphosphate. These results demonstrated that CS-8958 administered intranasally to mice was efficiently converted to R-125489 by a hydrolase(s) such as carboxylesterase, and then R-125489 was slowly eliminated from the respiratory tract. These data support the finding that CS-8958 has potential as a long-acting neuraminidase inhibitor, leading to significant efficacy as an anti-influenza drug by a single treatment. Reference: Antimicrob Agents Chemother. 2009 Nov; 53(11): 4845–4851. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2772300/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
H2O 5.0 14.44

Preparing Stock Solutions

The following data is based on the product molecular weight 346.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Jeong JH, Choi WS, Antigua KJC, Choi YK, Govorkova EA, Webby RJ, Baek YH, Song MS. In Vitro Profiling of LaninamivirResistant Substitutions in N3 to N9 Avian Influenza Virus Neuraminidase Subtypes and Their Association with In Vivo Susceptibility. J Virol. 2020 Dec 9;95(1):e01679-20. doi: 10.1128/JVI.01679-20. Erratum in: J Virol. 2021 Feb 24;95(6): PMID: 33055248; PMCID: PMC7737746. 2. Ann J, Abed Y, Beaulieu E, Bouhy X, Joly MH, Dubé K, Carbonneau J, Hamelin ME, Mallett C, Boivin G. Impact of a large deletion in the neuraminidase protein identified in a laninamivir-selected influenza A/Brisbane/10/2007 (H3N2) variant on viral fitness in vitro and in ferrets. Influenza Other Respir Viruses. 2016 Mar;10(2):122-6. doi: 10.1111/irv.12356. Epub 2016 Jan 29. PMID: 26526406; PMCID: PMC4746560. 3. Koyama K, Takahashi M, Oitate M, Nakai N, Takakusa H, Miura S, Okazaki O. CS-8958, a prodrug of the novel neuraminidase inhibitor R-125489, demonstrates a favorable long-retention profile in the mouse respiratory tract. Antimicrob Agents Chemother. 2009 Nov;53(11):4845-51. doi: 10.1128/AAC.00731-09. Epub 2009 Aug 17. PMID: 19687241; PMCID: PMC2772300. 4. Kubo S, Tomozawa T, Kakuta M, Tokumitsu A, Yamashita M. Laninamivir prodrug CS-8958, a long-acting neuraminidase inhibitor, shows superior anti-influenza virus activity after a single administration. Antimicrob Agents Chemother. 2010 Mar;54(3):1256-64. doi: 10.1128/AAC.01311-09. Epub 2010 Jan 4. PMID: 20047917; PMCID: PMC2825999.
In vitro protocol: 1. Jeong JH, Choi WS, Antigua KJC, Choi YK, Govorkova EA, Webby RJ, Baek YH, Song MS. In Vitro Profiling of LaninamivirResistant Substitutions in N3 to N9 Avian Influenza Virus Neuraminidase Subtypes and Their Association with In Vivo Susceptibility. J Virol. 2020 Dec 9;95(1):e01679-20. doi: 10.1128/JVI.01679-20. Erratum in: J Virol. 2021 Feb 24;95(6): PMID: 33055248; PMCID: PMC7737746. 2. Ann J, Abed Y, Beaulieu E, Bouhy X, Joly MH, Dubé K, Carbonneau J, Hamelin ME, Mallett C, Boivin G. Impact of a large deletion in the neuraminidase protein identified in a laninamivir-selected influenza A/Brisbane/10/2007 (H3N2) variant on viral fitness in vitro and in ferrets. Influenza Other Respir Viruses. 2016 Mar;10(2):122-6. doi: 10.1111/irv.12356. Epub 2016 Jan 29. PMID: 26526406; PMCID: PMC4746560.
In vivo protocol: 1. Koyama K, Takahashi M, Oitate M, Nakai N, Takakusa H, Miura S, Okazaki O. CS-8958, a prodrug of the novel neuraminidase inhibitor R-125489, demonstrates a favorable long-retention profile in the mouse respiratory tract. Antimicrob Agents Chemother. 2009 Nov;53(11):4845-51. doi: 10.1128/AAC.00731-09. Epub 2009 Aug 17. PMID: 19687241; PMCID: PMC2772300. 2. Kubo S, Tomozawa T, Kakuta M, Tokumitsu A, Yamashita M. Laninamivir prodrug CS-8958, a long-acting neuraminidase inhibitor, shows superior anti-influenza virus activity after a single administration. Antimicrob Agents Chemother. 2010 Mar;54(3):1256-64. doi: 10.1128/AAC.01311-09. Epub 2010 Jan 4. PMID: 20047917; PMCID: PMC2825999.

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This message contains search results from the National Center for Biotechnology Information (NCBI) at the U.S. National Library of Medicine (NLM). Do not reply directly to this message

Sent On: Tue Sep 29 14:02:14 2020

Search: Laninamivir [title]

20 selected items

PubMed Results
Items 1-20 of 20 (Display the 20 citations in PubMed)

1: Adams SE, Lugovtsev VY, Kan A, Bovin NV, Donnelly RP, Ilyushina NA. Laninamivir-Interferon Lambda 1 Combination Treatment Promotes Resistance by Influenza A Virus More Rapidly than Laninamivir Alone. Antimicrob Agents Chemother. 2020 Jun 23;64(7):e00301-20. doi: 10.1128/AAC.00301-20. PMID: 32393488; PMCID: PMC7318019.

2: Ogawa T, Tanaka K, Ohgino K, Omori N, Betsuyaku T, Sayama K. Drug-induced pneumonitis following the administration of laninamivir octanoate: The first two reported cases. J Infect Chemother. 2019 Dec;25(12):1043-1046. doi: 10.1016/j.jiac.2019.05.008. Epub 2019 Jun 6. PMID: 31178281.

3: Kawaguchi T, Arinaga-Hino T, Shimizu M, Tanikawa K, Tokushige T, Hirai S, Nagamatsu H, Tateishi H, Takata A, Ide T, Torimura T. Immune-mediated Drug- induced Liver Injury Caused by Laninamivir Octanoate Hydrate. Intern Med. 2019 Sep 1;58(17):2501-2505. doi: 10.2169/internalmedicine.2740-19. Epub 2019 May 22. PMID: 31118398; PMCID: PMC6761336.

4: Tomozawa T, Hoshino K, Yamashita M, Kubo S. Efficacy of laninamivir octanoate in mice with advanced inflammation stage caused by infection of highly lethal influenza virus. J Infect Chemother. 2019 Aug;25(8):584-588. doi: 10.1016/j.jiac.2019.02.023. Epub 2019 Mar 29. PMID: 30935767.

5: Lloren KKS, Kwon JJ, Choi WS, Jeong JH, Ahn SJ, Choi YK, Baek YH, Song MS. In Vitro and In Vivo Characterization of Novel Neuraminidase Substitutions in Influenza A(H1N1)pdm09 Virus Identified Using Laninamivir- Mediated In Vitro Selection. J Virol. 2019 Mar 5;93(6):e01825-18. doi: 10.1128/JVI.01825-18. PMID: 30602610; PMCID: PMC6401420.

6: Ikematsu H, Kawai N, Iwaki N, Kashiwagi S, Ishikawa Y, Yamaguchi H, Shiosakai K. Duration of fever and other symptoms after the inhalation of laninamivir octanoate hydrate in the 2016/17 Japanese influenza season; comparison with the 2011/12 to 2015/16 seasons. J Infect Chemother. 2018 Sep;24(9):718-724. doi: 10.1016/j.jiac.2018.04.013. Epub 2018 Jun 1. PMID: 29861186.

7: Ishiguro N, Koseki N, Kaiho M, Ariga T, Kikuta H, Oba K, Togashi T, Morita K, Inagawa A, Okamura A, Yamazaki S, Shida S, Konno M, Kawamura N, Ishizaka A, Takada K, Tsubakihara K, Nagano N, Shibata M, Furuyama H, Matsuzono Y, Koike A, Murashita M, Hatae Y, Arioka H, Yamanaka T, Watanabe T, Tabata Y, Kumita Y, Hazama K, Akutsu Y, Aoyagi H, Tobise C, Azuma K, Yasoshima K, Sawada Y, Uetsuji K, Tsuchida A, Tsuchiyama A, Yasuda K, Odagawa Y, Yoshioka M. Clinical effectiveness of four neuraminidase inhibitors (oseltamivir, zanamivir, laninamivir, and peramivir) for children with influenza A and B in the 2014-2015 to 2016-2017 influenza seasons in Japan. J Infect Chemother. 2018 Jun;24(6):449-457. doi: 10.1016/j.jiac.2018.01.013. Epub 2018 Feb 24. PMID: 29487035.

8: Murasaka T, Ikemura K, Enokiya T, Muraki Y, Ikemura M, Terada K, Iwamoto T, Okuda M. Impact of the number of repeated inhalations and patient characteristics on the residual amount of inhaled laninamivir octanoate hydrate dry powder in pediatric patients with influenza. J Pharm Health Care Sci. 2017 Nov 8;3:26. doi: 10.1186/s40780-017-0094-7. PMID: 29152321; PMCID: PMC5678805.

9: Toyama K, Furuie H, Ishizuka H. Intrapulmonary Pharmacokinetics of Laninamivir, a Neuraminidase Inhibitor, after a Single Nebulized Administration of Laninamivir Octanoate in Healthy Japanese Subjects. Antimicrob Agents Chemother. 2017 Dec 21;62(1):e01722-17. doi: 10.1128/AAC.01722-17. PMID: 29061751; PMCID: PMC5740362.

10: Higashiguchi M, Matsumoto T, Fujii T. A meta-analysis of laninamivir octanoate for treatment and prophylaxis of influenza. Antivir Ther. 2018;23(2):157-165. doi: 10.3851/IMP3189. PMID: 28869418.

11: Ikematsu H, Kawai N, Iwaki N, Kashiwagi S. Duration of fever and other symptoms after the inhalation of laninamivir octanoate hydrate; comparison of the 2011/12 to 2015/16 Japanese influenza seasons. J Infect Chemother. 2017 Sep;23(9):627-633. doi: 10.1016/j.jiac.2017.06.008. Epub 2017 Jul 11. PMID: 28709902.

12: Nakano T, Ishiwada N, Sumitani T, Uemori M, Isobe K; Laninamivir Prophylaxis Study Group. Inhaled Laninamivir Octanoate as Prophylaxis for Influenza in Children. Pediatrics. 2016 Dec;138(6):e20160109. doi: 10.1542/peds.2016-0109. Epub 2016 Nov 2. PMID: 27940664.

13: Yoshino Y, Seo K, Koga I, Kitazawa T, Ota Y. Clinical efficacy of laninamivir and peramivir in patients with seasonal influenza: a randomized clinical trial. Infect Dis (Lond). 2017 May;49(5):417-419. doi: 10.1080/23744235.2016.1242773. Epub 2016 Oct 21. PMID: 27766921.

14: Ikematsu H, Kawai N, Iwaki N, Kashiwagi S. Duration of fever and other symptoms after the inhalation of laninamivir octanoate hydrate for influenza treatment; comparison among the four Japanese influenza seasons from 2011-2012 to 2014-2015. J Infect Chemother. 2016 Sep;22(9):605-10. doi: 10.1016/j.jiac.2016.06.003. Epub 2016 Aug 1. PMID: 27493024.

15: Kashiwagi S, Watanabe A, Ikematsu H, Uemori M, Awamura S; Laninamivir Prophylaxis Study Group. Long-acting Neuraminidase Inhibitor Laninamivir Octanoate as Post-exposure Prophylaxis for Influenza. Clin Infect Dis. 2016 Aug 1;63(3):330-7. doi: 10.1093/cid/ciw255. Epub 2016 Apr 26. PMID: 27118785; PMCID: PMC4946013.

16: Kondo H, Shobugawa Y, Hibino A, Yagami R, Dapat C, Okazaki M, Otsuka T, Fujii K, Hassan MR, Saito R. Influenza Virus Shedding in Laninamivir-Treated Children upon Returning to School. Tohoku J Exp Med. 2016 Feb;238(2):113-21. doi: 10.1620/tjem.238.113. PMID: 26806610.

17: Ann J, Abed Y, Beaulieu E, Bouhy X, Joly MH, Dubé K, Carbonneau J, Hamelin ME, Mallett C, Boivin G. Impact of a large deletion in the neuraminidase protein identified in a laninamivir-selected influenza A/Brisbane/10/2007 (H3N2) variant on viral fitness in vitro and in ferrets. Influenza Other Respir Viruses. 2016 Mar;10(2):122-6. doi: 10.1111/irv.12356. Epub 2016 Jan 29. PMID: 26526406; PMCID: PMC4746560.

18: Ikematsu H, Kawai N, Iwaki N, Kashiwagi S. Clinical outcome of laninamivir octanoate hydrate for influenza in the 2013-2014 Japanese season. J Infect Chemother. 2015 Nov;21(11):802-7. doi: 10.1016/j.jiac.2015.08.013. Epub 2015 Sep 26. PMID: 26410550.

19: Azuma T, Ishiuchi H, Inoyama T, Teranishi Y, Yamaoka M, Sato T, Yamashita N, Tanaka H, Mino Y. Detection of peramivir and laninamivir, new anti-influenza drugs, in sewage effluent and river waters in Japan. PLoS One. 2015 Jun 25;10(6):e0131412. doi: 10.1371/journal.pone.0131412. PMID: 26110817; PMCID: PMC4482326.

20: Panozzo J, Oh DY, Margo K, Morton DA, Piedrafita D, Mosse J, Hurt AC. Evaluation of a dry powder delivery system for laninamivir in a ferret model of influenza infection. Antiviral Res. 2015 Aug;120:66-71. doi: 10.1016/j.antiviral.2015.05.007. Epub 2015 May 26. PMID: 26022199.