Laninamivir Octanoate Monohydrate

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

MedKoo CAT#: 328707

CAS#: 1233643-88-3 (Monohydrate)

Description: Laninamivir Octanoate Monohydrate, also known as Inavir and CS-8958, is a neuraminidase inhibitor that exhibits clinical efficacy for both treatment and prophylaxis of influenza virus infection, resulting from hydrolytic bioactivation into its pharmacologically active metabolite laninamivir in the pulmonary tissue.


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Laninamivir Octanoate Monohydrate (Inavir, CS-8958) is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 328707
Name: Laninamivir Octanoate Monohydrate
CAS#: 1233643-88-3 (Monohydrate)
Chemical Formula: C21H38N4O9
Exact Mass:
Molecular Weight: 490.554
Elemental Analysis: C, 51.42; H, 7.81; N, 11.42; O, 29.35


Related CAS #: 1233643-88-3 (Monohydrate)   203120-46-1(free)  

Synonym: Laninamivir Octanoate Monohydrate; CS-8958; CS 8958; CS8958; Inavir

IUPAC/Chemical Name: (2R,3R,4S)-3-acetamido-4-guanidino-2-((1R,2R)-2-hydroxy-1-methoxy-3-(octanoyloxy)propyl)-3,4-dihydro-2H-pyran-6-carboxylic acid hydrate

InChi Key: IBFFAVWCRFPPNZ-QZAMVOJNSA-N

InChi Code: InChI=1S/C21H36N4O8.H2O/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);1H2/t13-,14+,17+,18+,19+;/m0./s1

SMILES Code: CCCCCCCC(OC[C@@H](O)[C@@H](OC)[C@H]1[C@H](NC(C)=O)[C@@H](NC(N)=N)C=C(C(O)=O)O1)=O.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:
>2 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:
293490


Additional Information

Related CAS#

203120-46-1(Laninamivir Octanoate )
1233643-88-3(Laninamivir Octanoate Monohydrate)


References

1: 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.

2: 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.

3: 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.

4: 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.

5: 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.

6: 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.

7: 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.

8: 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.

9: 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.

10: 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. Review. PubMed PMID: 21973296.