ZANAMIVIR HYDRATE

  Zanamivir was discovered in 1989 by scientists led by Mark von Itzstein, at the Victorian College of Pharmacy, Monash University, in collaboration with the CSIRO and scientists at Glaxo, UK. Zanamivir was the first of the neuraminidase inhibitors. The discovery was funded initially by the Australian biotechnology company Biota and was part of Biota's ongoing program to develop antiviral agents through rational drug design. Its strategy relied on the availability of the structure of influenza neuraminidase, by X-ray crystallography. It was also known, as far back as 1974, that 2-deoxy-2,3-didehydro-N-acetylneuraminic acid (DANA), a sialic acid analogue, was an inhibitor of neuraminidase. Sialic acid (N-acetyl neuraminic acid, NANA), the substrate of neuraminidase, is itself a mild inhibitor of the enzyme, but the dehydrated derivative DANA, a transition-state analogue, is a better inhibitor.

The IUPAC name of Zanamivir is (2R,3R,4S)-3-acetamido-4-(diaminomethylideneamino)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid. With the CAS registry number 139110-80-8, it is also named as 4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid. The product's categories are Anti-viral Compounds; Anti-virals; Intermediates & Fine Chemicals; Pharmaceuticals. It is colorless crystalline solid which is the first neuraminidase inhibitor commercially developed. It is currently marketed by GlaxoSmithKline under the trade name Relenza.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -3.63; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): -6.12; (4)ACD/LogD (pH 7.4): -6.13; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 11; (10)#H bond donors: 9; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 102.37 Å²; (13)Index of Refraction: 1.678; (14)Molar Refractivity: 71.55 cm³; (15)Molar Volume: 189.6 cm³; (16)Polarizability: 28.36×10^-24 cm³; (17)Rotatable Bond Count: 6; (18)Tautomer Count: 4; (19)Exact Mass: 332.133199; (20)MonoIsotopic Mass: 332.133199; (21)Topological Polar Surface Area: 201; (22)Heavy Atom Count: 23; (23)Complexity: 518; (24)Defined Atom StereoCenter Count: 5.

Preparation of Zanamivir: It can be obtained by the following method:

Uses of Zanamivir: It is a neuraminidase inhibitor used in the treatment and prophylaxis of Influenzavirus A and Influenzavirus B.

People can use the following data to convert to the molecule structure. 
1. SMILES:O=C(O)C=1O[C@@H]([C@H](O)[C@H](O)CO)[C@H](NC(=O)C)[C@@H](/N=C(\N)N)C=1
2. InChI:InChI=1/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