Laninamivir

• CAT Number: R013334
• CAS Number: 203120-17-6
• Molecular Formula: C13H22N4O7
• Molecular Weight: 346.34
• Purity: ≥95%
• Storage: Store at RT
• IUPAC Name: (2R,3R,4S)-3-acetamido-4-(diaminomethylideneamino)-2-[(1R,2R)-2,3-dihydroxy-1-methoxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• InChI: 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+/m0/s1
• InChIKey: QNRRHYPPQFELSF-CNYIRLTGSA-N
• SMILES: CC(=O)NC1C(C=C(OC1C(C(CO)O)OC)C(=O)O)N=C(N)N

Laninamivir (CAS 203120-17-6) is a new potent neuraminidase (NA) inhibitor used for the treatment and prophylaxis of Influenzavirus A and Influenzavirus B, shows long-acting anti-influenza virus activity.

Overview of Clinical Research

Laninamivir was approved for influenza treatment in Japan in 2010 and for prophylaxis in 2013. 

Reference

1. Int J Antimicrob Agents. 2012 Nov;40(5):381-8. doi: 10.1016/j.ijantimicag.2012.06.017. Epub 2012 Aug 4.
Safety of the long-acting neuraminidase inhibitor laninamivir octanoate hydrate in post-marketing surveillance.
Kashiwagi S(1), Yoshida S, Yamaguchi H, Niwa S, Mitsui N, Tanigawa M, Shiosakai K, Yamanouchi N, Shiozawa T, Yamaguchi F.
Author information:
(1)Kashiwagi Clinic, Hakata Station Area Business Center 1F, 3-25-21, Hakataekimae, Hakata-ku, Fukuoka City 812-0011, Japan.
Laninamivir octanoate hydrate (laninamivir) is a long-acting neuraminidase inhibitor (NAI) that completes treatment with only a single inhalation. It was launched in Japan in October 2010 as an anti-influenza agent. A post-marketing surveillance study was conducted in the 2010/2011 influenza season to assess the safety of this drug in clinical settings. Adverse drug reactions (ADRs) were observed in 50 patients (59 events) out of 3542 patients subjected to safety evaluation (incidence 1.41%). Commonly reported ADRs were psychiatric disorders (abnormal behaviour, etc.), gastrointestinal disorders (diarrhoea, nausea, etc.) and nervous system disorders (dizziness, etc.), with incidences of 0.48% (n=17), 0.45% (n=16) and 0.17% (n=6), respectively. No serious ADRs occurred. ADRs usually emerged on the day on which laninamivir was inhaled (52.5%) and ADRs emerged within 3 days after inhalation in >90% of adversely affected patients. ADRs resolved or improved within 3 days in >85% of patients. The incidence of adverse events involving abnormal behaviour was 3.1% (30/959) among patients <10 years of age, 0.7% (8/1088) among patients aged 10-19 years, 0.1% (2/1431) among adult patients aged 20-64 years and 0.0% (0/64) among patients aged ≥65 years. It was confirmed that laninamivir is unlikely to cause delayed ADRs or a prolonged duration of ADRs despite this drug being a long-acting NAI. Furthermore, the incidence of ADRs was not found to have increased compared with that observed during clinical trials, and the types of ADR observed during this study were similar to those previously observed. Thus, laninamivir octanoate hydrate was confirmed to have no noticeable problem with safety.
2. Expert Rev Anti Infect Ther. 2011 Oct;9(10):851-7. doi: 10.1586/eri.11.112.
Laninamivir octanoate: a new long-acting neuraminidase inhibitor for the treatment of influenza.
Ikematsu H(1), Kawai N.
Author information:
(1)Department of Clinical Trials, Center for Advanced Medical Innovation, Kyushu University, 3-1-1 Maidashi Higashi-ku, Fukuoka, Japan.
Oseltamivir and zanamivir are well-established and well-researched drugs for the treatment of influenza in Japan and the rest of the world. A new neuraminidase inhibitor, laninamivir octanoate, has been approved for use in Japanese clinics. Laninamivir octanoate is an inhaled drug with unique characteristics. The inhaled laninamivir octanoate is converted into its active form, laninamivir, in the lungs where a high concentration persists for a long period of time. The concentration of laninamivir exceeds the level necessary for influenza virus replication inhibition for at least 5 days, thus influenza can be treated with a single administration. The drug is delivered using one device requiring four inhalations for children and two devices requiring eight inhalations for adults. Clinical trials have shown comparable efficacy for laninamivir octanoate and oseltamivir. Laninamivir octanoate also displayed a sufficient antiviral effect to treat infection with H275Y-mutated oseltamivir-resistant virus. Laninamivir octanoate has displayed clinical efficacy comparable to that of oseltamivir and zanamivir against the H1N1 pandemic influenza strain from 2009, seasonal H3N2 influenza and influenza B viruses. The prophylactic efficacy of laninamivir octanoate has been shown in animal models. The effectiveness of laninamivir against the highly pathogenic avian influenza virus H5N1 has also been shown in vitro and in animal models. A major clinical benefit of this drug is that the single administration is very convenient for both the patient and doctor, which leads to improved compliance. Furthermore, this drug shows promise for the treatment of influenza in future pandemics.
3. Antivir Chem Chemother. 2010;21(2):71-84. doi: 10.3851/IMP1688.
Laninamivir and its prodrug, CS-8958: long-acting neuraminidase inhibitors for the treatment of influenza.
Yamashita M(1).
Author information:
(1)Biological Research Laboratories, Daiichi Sankyo Co., Ltd, Tokyo, Japan.
Oseltamivir and zanamivir are currently licensed worldwide for influenza treatment and chemoprophylaxis. Both drugs require twice-daily administration for 5 days for treatment. A new influenza drug, laninamivir (code name R-125489), and its prodrug form, CS-8958 (laninamivir octanoate or laninamivir prodrug), which are long-acting neuraminidase inhibitors, are introduced in this review. Laninamivir potently inhibited the neuraminidase activities of various influenza A and B viruses, including subtypes N1-N9, pandemic (2009) H1N1 virus, highly pathogenic avian influenza (HPAI) H5N1 viruses and oseltamivir-resistant viruses. Because of the long retention of laninamivir in mouse lungs after an intranasal administration of CS-8958, therapeutic administration of a single dose of CS-8958 showed superior efficacy to repeated administrations of zanamivir or oseltamivir in animal infection models for influenza A and B viruses. These include pandemic (2009) H1N1 virus and HPAI H5N1 virus. Prophylactic single administration of CS-8958, as early as 7 days prior to infection, also showed superior efficacy. Finally, the potential of a single inhalation of CS-8958 for influenza patients was demonstrated by clinical studies, and CS-8958 has been approved and is commercially available as Inavir(®) (Daiichi Sankyo Co., Ltd, Tokyo) in Japan.