Zanamivir


Catalog No. size PriceQuantity
M7182-2 2mg solid $77
M7182-10 10mg solid $328

Description

Cas:139110-80-8

Product Information:

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.

 

Chemical Formula: C12H20N4O7

 

Exact Mass: 332.1332

 

Molecular Weight: 332.313

 

Elemental Analysis: C, 43.37; H, 6.07; N, 16.86; O, 33.70

 

Synonym:

 

GR-121167X

GR121167X

GR 121167X

GG167

GG-167

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

 

InChi Key:

ARAIBEBZBOPLMB-UFGQHTETSA-N

 

InChi Code: 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

 

Smiles Code:

O=C(C1=C[C@H](/N=C(N)\N)[C@@H](NC(C)=O)[C@H]([C@H](O)[C@H](O)CO)O1)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, not in water

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).

HS Tariff Code: 2934.99.9001

 

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. Heneghan CJ, Onakpoya I, Thompson M, Spencer EA, Jones M, Jefferson T. Zanamivir for influenza in adults and children: systematic review of clinical study reports and summary of regulatory comments. BMJ. 2014 Apr 9;348:g2547. doi: 10.1136/bmj.g2547. Review. PubMed PMID: 24811412; PubMed Central PMCID: PMC3981976.

 

  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.

 

  1. 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.

 

  1. Tappenden P, Jackson R, Cooper K, Rees A, Simpson E, Read R, Nicholson K. Amantadine, oseltamivir and zanamivir for the prophylaxis of influenza (including a review of existing guidance no. 67): a systematic review and economic evaluation. Health Technol Assess. 2009 Feb;13(11):iii, ix-xii, 1-246. doi: 10.3310/hta13110. Review. PubMed PMID: 19215705.

 

  1. 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.

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