Laninamivir Octanoate | CAS# 203120-46-1 | Neuraminidase Inhibitor

MedKoo Cat#: 565049 | Name: Laninamivir Octanoate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Laninamivir Octanoate, also known as CS-8958, is a long acting neuraminidase inhibitor which shows superior anti-influenza virus activity. Laninamivir octanoate and artificial surfactant combination therapy significantly increases survival of mice infected with lethal influenza H1N1 Virus. A single intranasal administration of CS-8958 showed a superior reduction of virus load in lungs in mouse infection model.

Chemical Structure

Laninamivir Octanoate

CAS#203120-46-1 (octanoate)

Theoretical Analysis

MedKoo Cat#: 565049

Name: Laninamivir Octanoate

CAS#: 203120-46-1 (octanoate)

Chemical Formula: C21H36N4O8

Exact Mass: 472.2533

Molecular Weight: 472.54

Elemental Analysis: C, 53.38; H, 7.68; N, 11.86; O, 27.09

Price and Availability

Size	Price	Availability
5mg	USD 200.00	Ready to ship
10mg	USD 350.00	Ready to ship
25mg	USD 650.00	Ready to ship
50mg	USD 1,050.00	Ready to ship
100mg	USD 1,650.00	Ready to ship

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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 Octanoate; CS-8958; CS 8958; CS8958; R-125489; R 125489; R125489;

IUPAC/Chemical Name

(4S,5R,6R)-5-Acetamido-4-guanidino-6-[(1R,2R)- 2-hydroxy-1-methoxy-3-(octanoyloxy)propyl]-5,6-dihydro-4H-pyran-2-carboxylic Acid

InChi Key

UKTIJASCFRNWCB-RMIBSVFLSA-N

InChi Code

InChI=1S/C21H36N4O8/c1-4-5-6-7-8-9-16(28)32-11-14(27)18(31-3)19-17(24-12(2)26)13(25-21(22)23)10-15(33-19)20(29)30/h10,13-14,17-19,27H,4-9,11H2,1-3H3,(H,24,26)(H,29,30)(H4,22,23,25)/t13-,14+,17+,18+,19+/m0/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)COC(CCCCCCC)=O)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

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot# T22D09P20

QC Data

View QC data: current batch, Lot#T22D09P20

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Laninamivir octanoate (CS-8958), a prodrug of Laninamivir, is a long-acting neuraminidase (NA) inhibitor with anti-influenza virus activity. Laninamivir octanoate shows anti-influenza activity against Oseltamivir-resistant viruses, and also against the pandemic influenza viruses.

In vitro activity:

Furthermore, this study has found that the laninamivir octanoate prodrug has a unique binding mode in p09N1 that is different from that of group 2 p57N2, but with some similarities to NA-oseltamivir binding, which provides additional insight into group specific differences of oseltamivir binding and resistance. Reference: PLoS Pathog. 2011 Oct;7(10):e1002249. https://pubmed.ncbi.nlm.nih.gov/22028647/

In vivo activity:

LAN (laninamivir octanoate) and OSE (oseltamivir phosphate) are approved to treat influenza in human adults by a single inhalation at 40 mg as a hydrate form, and by twice daily for 5 days at 98.5 mg as a phosphate form, respectively. Given that human body weight is 60 kg, the doses were calculated to be 0.69 mg/kg for LAN and 1.64 mg/kg for OSE. Virus titers in the BALF of all mice administered with either compound were significantly decreased compared to that of the control mice, as analyzed by two-way ANOVA including all time points (Fig. 2). Single administration of LAN at 0.1 × HD showed a comparable reduction of virus titers to that of repeated administration of OSE at 2.4 and 24 × HD. Moreover, LAN at 1 × HD showed significant reduction of virus titers compared to that of repeated administration of OSE at 24 × HD (Fig. 2). Reference: J Infect Chemother. 2019 Aug;25(8):584-588. https://pubmed.ncbi.nlm.nih.gov/30935767/

	Solvent	mg/mL	mM
Solubility
	DMSO	97.5	206.33
	Ethanol	5.0	10.58

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 472.54 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.

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. Vavricka CJ, Li Q, Wu Y, Qi J, Wang M, Liu Y, Gao F, Liu J, Feng E, He J, Wang J, Liu H, Jiang H, Gao GF. Structural and functional analysis of laninamivir and its octanoate prodrug reveals group specific mechanisms for influenza NA inhibition. PLoS Pathog. 2011 Oct;7(10):e1002249. doi: 10.1371/journal.ppat.1002249. Epub 2011 Oct 20. PMID: 22028647; PMCID: PMC3197600. 2. Yamashita M, Tomozawa T, Kakuta M, Tokumitsu A, Nasu H, Kubo S. CS-8958, a prodrug of the new neuraminidase inhibitor R-125489, shows long-acting anti-influenza virus activity. Antimicrob Agents Chemother. 2009 Jan;53(1):186-92. doi: 10.1128/AAC.00333-08. Epub 2008 Oct 27. PMID: 18955520; PMCID: PMC2612152. 3. 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. 4. Fukushi M, Yamashita M, Miyoshi-Akiyama T, Kubo S, Yamamoto K, Kudo K. Laninamivir octanoate and artificial surfactant combination therapy significantly increases survival of mice infected with lethal influenza H1N1 Virus. PLoS One. 2012;7(8):e42419. doi: 10.1371/journal.pone.0042419. Epub 2012 Aug 1. PMID: 22879974; PMCID: PMC3409853.

In vitro protocol:

In vivo protocol:

1. 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. 2. Fukushi M, Yamashita M, Miyoshi-Akiyama T, Kubo S, Yamamoto K, Kudo K. Laninamivir octanoate and artificial surfactant combination therapy significantly increases survival of mice infected with lethal influenza H1N1 Virus. PLoS One. 2012;7(8):e42419. doi: 10.1371/journal.pone.0042419. Epub 2012 Aug 1. PMID: 22879974; PMCID: PMC3409853.

1: 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. 2: 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. 3: 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. 4: 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. 5: 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. 6: 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. 7: 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. 8: 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. 9: 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. 10: 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. 11: 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. 12: 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. 13: Koyama K, Ogura Y, Nakai D, Watanabe M, Munemasa T, Oofune Y, Kubota K, Shinagawa A, Izumi T. Identification of bioactivating enzymes involved in the hydrolysis of laninamivir octanoate, a long-acting neuraminidase inhibitor, in human pulmonary tissue. Drug Metab Dispos. 2014 Jun;42(6):1031-8. doi: 10.1124/dmd.114.057620. Epub 2014 Mar 28. PMID: 24682756. 14: Ikematsu H, Kawai N, Iwaki N, Kashiwagi S. The duration of fever and other symptoms after the initiation of laninamivir octanoate hydrate in the Japanese 2011-2012 influenza season. J Infect Chemother. 2014 Feb;20(2):81-5. doi: 10.1016/j.jiac.2013.07.013. Epub 2013 Dec 11. PMID: 24486167. 15: Kakuta M, Kubo S, Tanaka M, Tobiume S, Tomozawa T, Yamashita M. Efficacy of a single intravenous administration of laninamivir (an active metabolite of laninamivir octanoate) in an influenza virus infection mouse model. Antiviral Res. 2013 Oct;100(1):190-5. doi: 10.1016/j.antiviral.2013.08.004. Epub 2013 Aug 15. PMID: 23954190. 16: Koseki N, Kaiho M, Kikuta H, Oba K, Togashi T, Ariga T, Ishiguro N. Comparison of the clinical effectiveness of zanamivir and laninamivir octanoate for children with influenza A(H3N2) and B in the 2011-2012 season. Influenza Other Respir Viruses. 2014 Mar;8(2):151-8. doi: 10.1111/irv.12147. Epub 2013 Aug 19. PMID: 23953886; PMCID: PMC4186462. 17: Kashiwagi S, Watanabe A, Ikematsu H, Awamura S, Okamoto T, Uemori M, Ishida K. Laninamivir octanoate for post-exposure prophylaxis of influenza in household contacts: a randomized double blind placebo controlled trial. J Infect Chemother. 2013 Aug;19(4):740-9. doi: 10.1007/s10156-013-0622-9. Epub 2013 Jun 4. PMID: 23732307; PMCID: PMC3738841. 18: Yoshihara K, Ishizuka H, Kubo Y. Population pharmacokinetics of laninamivir and its prodrug laninamivir octanoate in healthy subjects and in adult and pediatric patients with influenza virus infection. Drug Metab Pharmacokinet. 2013;28(5):416-26. doi: 10.2133/dmpk.dmpk-12-rg-115. Epub 2013 Apr 9. PMID: 23574886. 19: Nakano T, Okumura A, Tanabe T, Niwa S, Fukushima M, Yonemochi R, Eda H, Tsutsumi H. Safety evaluation of laninamivir octanoate hydrate through analysis of adverse events reported during early post-marketing phase vigilance. Scand J Infect Dis. 2013 Jun;45(6):469-77. doi: 10.3109/00365548.2012.763104. Epub 2013 Feb 4. PMID: 23373850. 20: Koyama K, Nakai D, Takahashi M, Nakai N, Kobayashi N, Imai T, Izumi T. Pharmacokinetic mechanism involved in the prolonged high retention of laninamivir in mouse respiratory tissues after intranasal administration of its prodrug laninamivir octanoate. Drug Metab Dispos. 2013 Jan;41(1):180-7. doi: 10.1124/dmd.112.048280. Epub 2012 Oct 22. PMID: 23091189. 21: Kashiwagi S, Yoshida S, Yamaguchi H, Mitsui N, Tanigawa M, Shiosakai K, Yamanouchi N, Shiozawa T, Yamaguchi F. Clinical efficacy of long-acting neuraminidase inhibitor laninamivir octanoate hydrate in postmarketing surveillance. J Infect Chemother. 2013 Apr;19(2):223-32. doi: 10.1007/s10156-012-0481-9. Epub 2012 Oct 20. PMID: 23085742. 22: Fukushi M, Yamashita M, Miyoshi-Akiyama T, Kubo S, Yamamoto K, Kudo K. Laninamivir octanoate and artificial surfactant combination therapy significantly increases survival of mice infected with lethal influenza H1N1 Virus. PLoS One. 2012;7(8):e42419. doi: 10.1371/journal.pone.0042419. Epub 2012 Aug 1. PMID: 22879974; PMCID: PMC3409853. 23: Kashiwagi S, Yoshida S, Yamaguchi H, Niwa S, Mitsui N, Tanigawa M, Shiosakai K, Yamanouchi N, Shiozawa T, Yamaguchi F. Safety of the long-acting neuraminidase inhibitor laninamivir octanoate hydrate in post-marketing surveillance. Int J Antimicrob Agents. 2012 Nov;40(5):381-8. doi: 10.1016/j.ijantimicag.2012.06.017. Epub 2012 Aug 4. PMID: 22871369. 24: Katsumi Y, Otabe O, Matsui F, Kidowaki S, Mibayashi A, Tsuma Y, Ito H. Effect of a single inhalation of laninamivir octanoate in children with influenza. Pediatrics. 2012 Jun;129(6):e1431-6. doi: 10.1542/peds.2011-2054. Epub 2012 May 21. PMID: 22614774. 25: Ishizuka H, Toyama K, Yoshiba S, Okabe H, Furuie H. Intrapulmonary distribution and pharmacokinetics of laninamivir, a neuraminidase inhibitor, after a single inhaled administration of its prodrug, laninamivir octanoate, in healthy volunteers. Antimicrob Agents Chemother. 2012 Jul;56(7):3873-8. doi: 10.1128/AAC.06456-11. Epub 2012 Apr 23. PMID: 22526307; PMCID: PMC3393442. 26: Ikematsu H, Kawai N. Laninamivir octanoate: a new long-acting neuraminidase inhibitor for the treatment of influenza. Expert Rev Anti Infect Ther. 2011 Oct;9(10):851-7. doi: 10.1586/eri.11.112. PMID: 21973296. 27: Kubo S, Kakuta M, Yamashita M. [In vitro and in vivo effects of a long- acting anti-influenza agent CS-8958 (laninamivir octanoate, Inavir) against pandemic (H1N1) 2009 influenza viruses]. Jpn J Antibiot. 2010 Oct;63(5):337-46. Japanese. PMID: 21268406. 28: Watanabe A, Chang SC, Kim MJ, Chu DW, Ohashi Y; MARVEL Study Group. Long- acting neuraminidase inhibitor laninamivir octanoate versus oseltamivir for treatment of influenza: A double-blind, randomized, noninferiority clinical trial. Clin Infect Dis. 2010 Nov 15;51(10):1167-75. doi: 10.1086/656802. Epub 2010 Oct 11. PMID: 20936975. 29: Sugaya N, Ohashi Y. Long-acting neuraminidase inhibitor laninamivir octanoate (CS-8958) versus oseltamivir as treatment for children with influenza virus infection. Antimicrob Agents Chemother. 2010 Jun;54(6):2575-82. doi: 10.1128/AAC.01755-09. Epub 2010 Apr 5. PMID: 20368393; PMCID: PMC2876358.