Laninamivir trifluoroacetate

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

MedKoo CAT#: 598293

CAS#: 203120-18-7

Description: Laninamivir trifluoroacetate is an antiviral agent.


Price and Availability

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Laninamivir trifluoroacetate is not in stock, 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#: 598293
Name: Laninamivir trifluoroacetate
CAS#: 203120-18-7
Chemical Formula: C15H23F3N4O9
Exact Mass:
Molecular Weight: 460.36
Elemental Analysis: Chemical Formula: Exact Mass: Molecular Weight: Elemental Analysis: C, 39.14; H, 5.04; F, 12.38; N, 12.17; O, 31.28


Related CAS #: 203120-17-6 (free)  

Synonym: Laninamivir trifluoroacetate;

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

InChi Key: DAGFMLSFZMOWFA-WWIZLJSCSA-N

InChi Code: InChI=1S/C13H22N4O7.C2HF3O2/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;3-2(4,5)1(6)7/h3,6-7,9-11,18,20H,4H2,1-2H3,(H,16,19)(H,21,22)(H4,14,15,17);(H,6,7)/t6-,7+,9+,10+,11+;/m0./s1

SMILES Code: CO[C@@H]([C@@H]1OC(C(O)=O)=C[C@@H]([C@H]1NC(C)=O)NC(N)=N)[C@@H](CO)O.OC(C(F)(F)F)=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:
2934.99.03.00


References

1: Minakami H, Kubo T, Nakai A, Saito S, Unno N. Pregnancy outcomes of women exposed to laninamivir during pregnancy. Pharmacoepidemiol Drug Saf. 2014 Oct;23(10):1084-7. doi: 10.1002/pds.3684. Epub 2014 Jul 29. PubMed PMID: 25074683; PubMed Central PMCID: PMC4265256.

2: Samson M, Abed Y, Desrochers FM, Hamilton S, Luttick A, Tucker SP, Pryor MJ, Boivin G. Characterization of drug-resistant influenza virus A(H1N1) and A(H3N2) variants selected in vitro with laninamivir. Antimicrob Agents Chemother. 2014 Sep;58(9):5220-8. doi: 10.1128/AAC.03313-14. Epub 2014 Jun 23. PubMed PMID: 24957832; PubMed Central PMCID: PMC4135884.

3: McKimm-Breschkin JL, Barrett S. Neuraminidase mutations conferring resistance to laninamivir lead to faster drug binding and dissociation. Antiviral Res. 2015 Feb;114:62-6. doi: 10.1016/j.antiviral.2014.12.004. Epub 2014 Dec 9. PubMed PMID: 25499124.

4: 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.

5: 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.

6: 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.

7: 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. PubMed PMID: 26022199.

8: Watanabe A. A randomized double-blind controlled study of laninamivir compared with oseltamivir for the treatment of influenza in patients with chronic respiratory diseases. J Infect Chemother. 2013 Feb;19(1):89-97. doi: 10.1007/s10156-012-0460-1. Epub 2012 Aug 21. PubMed PMID: 22907567.

9: Leang SK, Kwok S, Sullivan SG, Maurer-Stroh S, Kelso A, Barr IG, Hurt AC. Peramivir and laninamivir susceptibility of circulating influenza A and B viruses. Influenza Other Respir Viruses. 2014 Mar;8(2):135-9. PubMed PMID: 24734292; PubMed Central PMCID: PMC4186459.

10: 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.

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

12: 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.

13: Ikematsu H, Kawai N, Iwaki N, Kashiwagi S. Continued effectiveness of laninamivir octanate hydrate for influenza treatment in Japan: comparison between the 2011-2012 and 2012-2013 influenza seasons. J Infect Chemother. 2014 Dec;20(12):799-803. PubMed PMID: 25444677.

14: 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.

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. PubMed PMID: 23954190.

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: Tian J, Zhong J, Li Y, Ma D. Organocatalytic and scalable synthesis of the anti-influenza drugs zanamivir, laninamivir, and CS-8958. Angew Chem Int Ed Engl. 2014 Dec 8;53(50):13885-8. doi: 10.1002/anie.201408138. Epub 2014 Oct 14. PubMed PMID: 25314609.

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: 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.

20: 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. eCollection 2015. PubMed PMID: 26110817; PubMed Central PMCID: PMC4482326.