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

MedKoo CAT#: 565049

CAS#: 203120-46-1

Description: Laninamivir Octanoate is a long acting neuraminidase inhibitor which shows superior anti-influenza virus activity.


Price and Availability

Size
Price

1mg
USD 855
Size
Price

2mg
USD 1540
Size
Price

5mg
USD 3250

Laninamivir Octanoate, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data, and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 565049
Name: Laninamivir Octanoate
CAS#: 203120-46-1
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


Related CAS #: 1233643-88-3 (Monohydrate)  

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

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


Technical Data

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).

Harmonized System Code:
2934.99.90.01


References

1: 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. PubMed PMID: 29861186.

2: 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. eCollection 2017. PubMed PMID: 29152321; PubMed Central PMCID: PMC5678805.

3: 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). pii: e01722-17. doi: 10.1128/AAC.01722-17. Print 2018 Jan. PubMed PMID: 29061751; PubMed Central PMCID: PMC5740362.

4: 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. PubMed PMID: 28869418.

5: 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. PubMed PMID: 28709902.

6: 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). pii: e20160109. Epub 2016 Nov 2. PubMed PMID: 27940664.

7: 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. PubMed PMID: 27493024.

8: 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. PubMed PMID: 27118785; PubMed Central PMCID: PMC4946013.

9: 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. PubMed PMID: 26410550.

10: 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. PubMed PMID: 24682756.

11: 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. PubMed PMID: 24486167.

12: 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. PubMed PMID: 23954190.

13: 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. PubMed PMID: 23953886; PubMed Central PMCID: PMC4186462.

14: 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. PubMed PMID: 23732307; PubMed Central PMCID: PMC3738841.

15: 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. Epub 2013 Apr 9. PubMed PMID: 23574886.

16: 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. PubMed PMID: 23373850.

17: 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. PubMed PMID: 23091189.

18: 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. PubMed PMID: 23085742.

19: 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. PubMed PMID: 22879974; PubMed Central PMCID: PMC3409853.

20: 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. Review. PubMed PMID: 22871369.