Zanamivir

Names

[ Name ]:
Zanamivir

[Synonym ]:
5-(Acetylamino)-4-[(aminoiminomethyl)amino]-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic Acid
5-(acetylamino)-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid
4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid 4-Guanidino-Neu5Ac2en
(6R)-5-Acetamido-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-L-threo-hex-2-enonic acid
5-(acetylamino)-4-{[amino(imino)methyl]amino}-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid
GANA
D-glycero-D-galacto-Non-2-enonic acid, 5-(acetylamino)-4-[(aminoiminomethyl)amino]-2,6-anhydro-3,4,5-trideoxy-
GG 167
Zanamir
Zanamivir
Relenza
Zanamavir
Zanamivir Hydrate
5-Acetamido-4-guanidino-2,3,4,5-tetradeoxy-D-glycero-D-galacto-non-2-enopyranosonic Acid
5-Acetamido-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid
Unii-L6o3xi777i

Biological Activity

[Description]:

Zanamivir is an influenza viral neuraminidase inhibitor with IC50 values of 0.95 nM and 2.7 nM for influenza A and B, respectively.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Influenza Virus

Research Areas >> Infection

[Target]

IC50: 0.95 nM (Influenza A); 2.7 nM (Influenza B)[1]

[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[2].

[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[3].

[Animal admin]

Rats: Formulations PO-SC (Zanamivir with SC for p.o.) and PO-C (Zanamivir control solution for p.o.) are administered orally at a Zanamivir dose of 10 mg/kg, and IV-R (reference Zanamivir saline solution for i.v.) is administered i.v. at a dose of 1 mg/kg to rats under conscious condition. Blood samples are collected prior to and at 0.5, 1, 2, 3, 4, 6, 8, and 24 hr after administration. At each sampling point, three rats from each group are sacrificed after blood collection to extract the lungs. The lungs are cleansed with saline after extraction of lungs from the rats through a chest incision. The lungs are then transferred into E-tube and stored in the freezer (-80°C) until analysis. Plasma samples are harvested by centrifugation at 1,500 × g for 10 min and stored at -20°C until analysis. The analysis of Zanamivir in both plasma and lungs is performed using before-mentioned LC-MS/MS method[3].

[References]

[1]. Gubareva LV, et al. Comparison of the activities of zanamivir, oseltamivir, and RWJ-270201 against clinical isolates ofinfluenza virus and neuraminidase inhibitor-resistant variants. Antimicrob Agents Chemother. 2001 Dec;45(12):3403-8.

[2]. McKimm-Breschkin JL, et al. Management of influenza virus infections with neuraminidase inhibitors: detection, incidence, and implications of drug resistance. Treat Respir Med. 2005;4(2):107-16.

[3]. Shanmugam S, et al. Zanamivir oral delivery: enhanced plasma and lung bioavailability in rats. Biomol Ther (Seoul). 2013 Mar;21(2):161-9.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Melting Point ]:
256ºC (dec.)

[ Molecular Formula ]:
C₁₂H₂₀N₄O₇

[ Molecular Weight ]:
332.310

[ Exact Mass ]:
332.133209

[ PSA ]:
198.22000

[ LogP ]:
-4.13

[ Index of Refraction ]:
1.679

[ Storage condition ]:
2~8℃

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22-36/37/38

[ Safety Phrases ]:
26

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
RA9451000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Cochrane researchers continue to face challenges over access to data on flu drugs.

BMJ 346 , f3190, (2013)

Structure-based design and synthesis of C-1- and C-4-modified analogs of zanamivir as neuraminidase inhibitors.

J. Med. Chem. 56(3) , 671-84, (2013)

In order to exploit the 430-cavity in the active sites of neuraminidases, 22 zanamivir analogs with C-1 and C-4 modification were synthesized, and their inhibitory activities against both group-1 (H5N...

Mechanism-based covalent neuraminidase inhibitors with broad-spectrum influenza antiviral activity.

Science 340(6128) , 71-5, (2013)

Influenza antiviral agents play important roles in modulating disease severity and in controlling pandemics while vaccines are prepared, but the development of resistance to agents like the commonly u...

Related Compounds

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