Zanamivir

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.

Product information

CAS Number: 139110-80-8

Molecular Weight: 332.31

Formula: C12H20N4O7

Synonym:

GR-121167X

GG-167

Relenza

GR121167X

GR 121167X

GG167

GG 167

Zanamivir

trade name Relenza

Chemical Name: (2R,3R,4S)-3-acetamido-4-(diaminomethylideneamino)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid

Smiles: CC(=O)N[C@H]1[C@@H](OC(=C[C@@H]1N=C(N)N)C(O)=O)[C@H](O)[C@H](O)CO

InChiKey: ARAIBEBZBOPLMB-UFGQHTETSA-N

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

Technical Data

Appearance: Solid Power.

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO, not in water

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined.

HS Tariff Code: 382200

How to use

In Vitro:

Zanamivir interacts with a group of amino acids in the active site of neuraminidase, which are conserved in all influenza A and B strains. Zanamivir blocks the action of neuraminidase, which prevents the cleavage of sialic acid on the cell receptors, thus preventing release and spread of the newly formed virions.

In Vivo:

Zanamivir has a poor bioavailability in oral administration, with only 4–17% of the agent. Oral delivery of zanamivir has been a problem due to its strong hydrophilic nature that limits its transport across the intestinal epithelium. Permeation enhancers such as sodium cholate, hydroxypropyl β-cyclodextrin could be used with zanamivir to enhance the intestinal permeability.

References:

1. Jackson RJ, Cooper KL, Tappenden P, Rees A, Simpson EL, Read RC, Nicholson KG. Oseltamivir, zanamivir and amantadine in the prevention of influenza: a systematic review. J Infect. 2011 Jan;62(1):14-25. doi: 10.1016/j.jinf.2010.10.003. Epub 2010 Oct 13. Review. PubMed PMID: 20950645.
2. Magano J. Synthetic approaches to the neuraminidase inhibitors zanamivir (Relenza) and oseltamivir phosphate (Tamiflu) for the treatment of influenza. Chem Rev. 2009 Sep;109(9):4398-438. doi: 10.1021/cr800449m. Review. PubMed PMID: 19537777.
3. Kashiwagi S. [Zanamivir, oseltamivir]. Nihon Rinsho. 2004 Dec;62 Suppl 12:445-7. Review. Japanese. PubMed PMID: 15658359.

Products are for research use only. Not for human use.