Zanamivir
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MedKoo CAT#: 318993

CAS#: 139110-80-8 (free base)

Description: 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 Structure

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Zanamivir
CAS# 139110-80-8 (free base)

Theoretical Analysis

MedKoo Cat#: 318993
Name: Zanamivir
CAS#: 139110-80-8 (free base)
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

Price and Availability

Size Price Availability Quantity
5.0mg USD 190.0 2 Weeks
10.0mg USD 320.0 2 Weeks
25.0mg USD 560.0 2 Weeks
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Related CAS #: 139110-80-8 (free base)   551942-41-7 (hydrate)  

Synonym: GR-121167X; GR121167X; GR 121167X; GG167; GG-167; GG 167; Zanamivir; trade name Relenza.

IUPAC/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

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

Certificate of Analysis:

Safety Data Sheet (SDS):

Preparing Stock Solutions

The following data is based on the product molecular weight 332.313 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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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.

2: 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.

3: 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.

4: 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.

5: Kashiwagi S. [Zanamivir, oseltamivir]. Nihon Rinsho. 2004 Dec;62 Suppl 12:445-7. Review. Japanese. PubMed PMID: 15658359.

6: de Jong JC, Beyer WE, Rimmelzwaan GF, Fouchier RA, Osterhaus AD. [Neuraminidase inhibitors oseltamivir and zanamivir: new means of defence against influenza]. Ned Tijdschr Geneeskd. 2004 Jan 10;148(2):73-9. Review. Dutch. Erratum in: Ned Tijdschr Geneeskd. 2004 Feb 14;148(7):348. PubMed PMID: 14753128.

7: Cheer SM, Wagstaff AJ. Spotlight on zanamivir in influenza. Am J Respir Med. 2002;1(2):147-52. Review. PubMed PMID: 14720068.

8: Fleming DM. Zanamivir in the treatment of influenza. Expert Opin Pharmacother. 2003 May;4(5):799-805. Review. PubMed PMID: 12740002.

9: Höffken G, Gillissen A. Efficacy and safety of zanamivir in patients with influenza--impact of age, severity of infections and specific risk factors. Med Microbiol Immunol. 2002 Dec;191(3-4):169-73. Epub 2002 Sep 11. Review. PubMed PMID: 12458354.

10: Burls A, Clark W, Stewart T, Preston C, Bryan S, Jefferson T, Fry-Smith A. Zanamivir for the treatment of influenza in adults: a systematic review and economic evaluation. Health Technol Assess. 2002;6(9):1-87. Review. PubMed PMID: 12065066.

11: Cheer SM, Wagstaff AJ. Zanamivir: an update of its use in influenza. Drugs. 2002;62(1):71-106. Review. PubMed PMID: 11790157.

12: Elliott M. Zanamivir: from drug design to the clinic. Philos Trans R Soc Lond B Biol Sci. 2001 Dec 29;356(1416):1885-93. Review. PubMed PMID: 11779388; PubMed Central PMCID: PMC1088565.

13: Gravenstein S, Johnston SL, Loeschel E, Webster A. Zanamivir: a review of clinical safety in individuals at high risk of developing influenza-related complications. Drug Saf. 2001;24(15):1113-25. Review. PubMed PMID: 11772145.

14: Abad-Santos F, Gallego Sandín S, Novalbos Reina J, Martínez Sancho E, Gálvez Múgica MA. [Efficacy of inhaled zanamivir in the treatment and prevention of influenza]. An Med Interna. 2001 Feb;18(2):93-9. Review. Spanish. PubMed PMID: 11322008.

15: Dreitlein WB, Maratos J, Brocavich J. Zanamivir and oseltamivir: two new options for the treatment and prevention of influenza. Clin Ther. 2001 Mar;23(3):327-55. Review. PubMed PMID: 11318072.

16: Why not [symbol: see text]zanamivir? Drug Ther Bull. 2001 Feb;39(2):9-10. Review. PubMed PMID: 11235064.

17: Penn CR, Osterhaus A. Zanamivir: a rational approach to influenza B. Scand J Infect Dis. 2001;33(1):33-40. Review. PubMed PMID: 11234975.

18: McNicholl IR, McNicholl JJ. Neuraminidase inhibitors: zanamivir and oseltamivir. Ann Pharmacother. 2001 Jan;35(1):57-70. Review. PubMed PMID: 11197587.

19: Caballero E, Prieto C, Ruiz M, Azanza JR. [Zanamivir: new therapeutic option for influenza]. Rev Med Univ Navarra. 2000 Jan-Mar;44(1):56-61. Review. Spanish. PubMed PMID: 11002900.

20: Chapple KJ, Hendrick AE, McCarthy MW. Zanamivir in the treatment and prevention of influenza. Ann Pharmacother. 2000 Jun;34(6):798-801. Review. PubMed PMID: 10860141.