(1S,2S,3R,4R)-4-carbamimidamido-3-[(1S)-1-acetamido-2-ethylbutyl]-2-hydroxycyclopentane-1-carboxylic acid

• ChemBase ID: 73173
• Molecular Formular: C15H28N4O4
• Molecular Mass: 328.40722
• Monoisotopic Mass: 328.2110554
• SMILES: [C@@H]([C@H]1[C@@H](C[C@@H]([C@H]1O)C(=O)O)NC(=N)N)(C(CC)CC)NC(=O)C
• Canonical SMILES: CCC([C@@H]([C@H]1[C@H](NC(=N)N)C[C@@H]([C@H]1O)C(=O)O)NC(=O)C)CC
• InChI: InChI=1S/C15H28N4O4/c1-4-8(5-2)12(18-7(3)20)11-10(19-15(16)17)6-9(13(11)21)14(22)23/h8-13,21H,4-6H2,1-3H3,(H,18,20)(H,22,23)(H4,16,17,19)/t9-,10+,11+,12-,13+/m0/s1
• InChIKey: XRQDFNLINLXZLB-CKIKVBCHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4R)-4-carbamimidamido-3-[(1S)-1-acetamido-2-ethylbutyl]-2-hydroxycyclopentane-1-carboxylic acid
• IUPAC Traditional name: (1S,2S,3R,4R)-4-carbamimidamido-3-[(1S)-1-acetamido-2-ethylbutyl]-2-hydroxycyclopentane-1-carboxylic acid
• Synonyms: Peramivir

Database IDs

• CAS Number: 229614-55-5
• PubChem SID: 162038093
• PubChem CID: 154234

CALCULATED PROPERTIES

• Acid pKa: 4.183867
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -2.1383579
• LogD (pH = 7.4): -2.121641
• Log P: -2.1214879
• Molar Refractivity: 94.4604 cm^3
• Polarizability: 33.063732 Å^3
• Polar Surface Area: 148.53 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1822

Research Area: Infection
Biological Activity:
Peramivir is a transition-state analogue and a potent, specific influenza viral neuraminidase inhibitor with an IC50 of median 0.09 nM. [1] The IC50 for peramivir is markedly lower than that for either zanamivir or oseltamivir. Peramivir increases survival in preclinical influenza models, including mouse and ferret models of highly pathogenic avian influenza H5N1. One day of treatment with peramivir is active, and multiple days of treatment rescues most or all mice with H5N1. Similar data have been obtained in ongoing murine experiments with seasonal influenza A (H1N1)/H274Y. After parenteral administration, peramivir reaches very high plasma concentrations. Peramivir is not metabolized, and is cleared by the means of renal filtration. It has a long half-life, especially in comparison with other neuraminidase inhibitors. Due to the failure of the metabolism of the antivirus compound peramivir, as well as its wide distribution and the excretion in the unchanged form in urine, dosing regimens can be adapted easily for patients with renal impairment and for pediatric populations. [2] Peramivir is originally developed by BioCryst Pharmaceuticals. And peramivir is designed to aim to an antiviral agent. Peramivir has been performed phase III clinical trials for the treatment of influenza.

REFERENCES

• http://en.wikipedia.org/wiki/Peramivir