Zanamivir

  • CAT Number: A000209
  • CAS Number: 139110-80-8
  • Molecular Formula: C₁₂H₂₀N₄O₇
  • Molecular Weight: 332.31
  • Purity: ≥95%
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Zanamivir is a neuraminidase inhibitor used in the treatment and prophylaxis of influenza caused by influenza A and B viruses. It was developed by the Australian biotech firm Biota Holdings. It was licensed to Glaxo in 1990 and approved in the US in 1999, only for use as a treatment for influenza. In 2006, it was approved for prevention of influenza A and B. Zanamivir was the first neuraminidase inhibitor commercially developed. Zanamivir works by binding to the active site of the neuraminidase protein, rendering the influenza virus unable to escape its host cell and infect others.[14] It is also an inhibitor of influenza virus replication in vitro and in vivo.

Catalog Number A000209
CAS Number 139110-80-8
Molecular Formula

C₁₂H₂₀N₄O₇

Purity 95%
Target neuraminidase
Solubility >16.6mg/mL in DMSO
Storage -20°C
InChI InChI=1S/C12H20N4O7/c1-4(18)15-8-5(16-12(13)14)2-7(11(21)22)23-10(8)9(20)6(19)3-17/h2,5-6,8-10,17,19-20H,3H2,1H3,(H,15,18)(H,21,22)(H4,13,14,16)/t5-,6+,8+,9+,10+/m0/s1
InChIKey ARAIBEBZBOPLMB-UFGQHTETSA-N
SMILES CC(=O)NC1C(C=C(OC1C(C(CO)O)O)C(=O)O)N=C(N)N
Reference

1: Pires de Mello CP, Drusano GL, Adams JR, Shudt M, Kulawy R, Brown AN. Oseltamivir-zanamivir combination therapy suppresses drug-resistant H1N1 influenza A viruses in the hollow fiber infection model (HFIM) system. Eur J Pharm Sci. 2017 Oct 25;111:443-449. doi: 10.1016/j.ejps.2017.10.027. [Epub ahead of print] PubMed PMID: 29079337.<br />
2: Bradley JS, Blumer JL, Romero JR, Michaels MG, Munoz FM, Kimberlin DW, Pahud B, DeBiasi RL, Yamamoto G, Roberts G, Hossain M, Shortino D, Yates PJ, Adams B, Peppercorn A. Intravenous Zanamivir in Hospitalized Patients With Influenza. Pediatrics. 2017 Nov;140(5). pii: e20162727. doi: 10.1542/peds.2016-2727. PubMed PMID: 29051331.<br />
3: Abed Y, Boivin G. A Review of Clinical Influenza A and B Infections With Reduced Susceptibility to Both Oseltamivir and Zanamivir. Open Forum Infect Dis. 2017 May 18;4(3):ofx105. doi: 10.1093/ofid/ofx105. eCollection 2017 Summer. Review. PubMed PMID: 28852674; PubMed Central PMCID: PMC5569976.<br />
4: Oh DY, Panozzo J, Vitesnik S, Farrukee R, Piedrafita D, Mosse J, Hurt AC. Selection of multi-drug resistant influenza A and B viruses under zanamivir pressure and their replication fitness in ferrets. Antivir Ther. 2017 Feb 14. doi: 10.3851/IMP3135. [Epub ahead of print] PubMed PMID: 28195559.<br />
5: Dholakia D, Goyal S, Jamal S, Singh A, Das A, Grover A. Molecular modeling and lead design of substituted zanamivir derivatives as potent anti-influenza drugs. BMC Bioinformatics. 2016 Dec 22;17(Suppl 19):512. doi: 10.1186/s12859-016-1374-1. PubMed PMID: 28155702; PubMed Central PMCID: PMC5259988.<br />
6: Trebbien R, Pedersen SS, Vorborg K, Franck KT, Fischer TK. Development of oseltamivir and zanamivir resistance in influenza A(H1N1)pdm09 virus, Denmark, 2014. Euro Surveill. 2017 Jan 19;22(3). pii: 30445. doi: 10.2807/1560-7917.ES.2017.22.3.30445. PubMed PMID: 28128091; PubMed Central PMCID: PMC5322288.<br />
7: Marty FM, Vidal-Puigserver J, Clark C, Gupta SK, Merino E, Garot D, Chapman MJ, Jacobs F, Rodriguez-Noriega E, Husa P, Shortino D, Watson HA, Yates PJ, Peppercorn AF. Intravenous zanamivir or oral oseltamivir for hospitalised patients with influenza: an international, randomised, double-blind, double-dummy, phase 3 trial. Lancet Respir Med. 2017 Feb;5(2):135-146. doi: 10.1016/S2213-2600(16)30435-0. Epub 2017 Jan 14. PubMed PMID: 28094141.<br />
8: Mancano MA. ISMP Adverse Drug Reactions: Sildenafil-Induced Erythema Multiforme Acute Liver Injury Due to Febuxostat Intravenous Acetaminophen-Induced Acute Hepatotoxicity Acute Transient Myopia Induced by Zanamivir Lidocaine-Induced Hoigne Syndrome. Hosp Pharm. 2016 Dec;51(11):884-887. doi: 10.1310/hpj5111-884. PubMed PMID: 28057946; PubMed Central PMCID: PMC5199219.<br />
9: Wu Y, Gao F, Qi J, Bi Y, Fu L, Mohan S, Chen Y, Li X, Pinto BM, Vavricka CJ, Tien P, Gao GF. Resistance to Mutant Group 2 Influenza Virus Neuraminidases of an Oseltamivir-Zanamivir Hybrid Inhibitor. J Virol. 2016 Nov 14;90(23):10693-10700. Print 2016 Dec 1. PubMed PMID: 27654293; PubMed Central PMCID: PMC5110174.<br />
10: Abed Y, Carbonneau J, L/&#39;Huillier AG, Kaiser L, Boivin G. Droplet digital PCR to investigate quasi-species at codons 119 and 275 of the A(H1N1)pdm09 neuraminidase during zanamivir and oseltamivir therapies. J Med Virol. 2017 Apr;89(4):737-741. doi: 10.1002/jmv.24680. Epub 2016 Sep 14. PubMed PMID: 27602879.

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