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

• ChemBase ID: 73182
• Molecular Formular: C15H34N4O7
• Molecular Mass: 382.45306
• Monoisotopic Mass: 382.24274945
• SMILES: C(=N)(N)N[C@H]1[C@@H]([C@@H]([C@H](C1)C(=O)O)O)[C@H](C(CC)CC)NC(=O)C.O.O.O
• 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.O.O.O
• InChI: InChI=1S/C15H28N4O4.3H2O/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);3*1H2/t9-,10+,11+,12-,13+;;;/m0.../s1
• InChIKey: RFUCJKFZFXNIGB-ZBBHRWOZSA-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 trihydrate
• IUPAC Traditional name: (1S,2S,3R,4R)-4-carbamimidamido-3-[(1S)-1-acetamido-2-ethylbutyl]-2-hydroxycyclopentane-1-carboxylic acid trihydrate
• Synonyms: Peramivir Trihydrate

Database IDs

• CAS Number: 1041434-82-5
• PubChem SID: 162038102
• PubChem CID: 11954371

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: Trihydrate

DETAILS

Selleck Chemicals - S2716

Research Area: Neurological Disease
Biological Activity:
Peramivir Trihydrate is a trihydrate of the anti-infection agent Peramivir Trihydrate which 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 Trihydrate is markedly lower than that for either zanamivir or oseltamivir. Peramivir Trihydrate increases survival in preclinical influenza models, including mouse and ferret models of highly pathogenic avian influenza H5N1. One day of treatment with Peramivir Trihydrate 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 Trihydrate reaches very high plasma concentrations. Peramivir Trihydrate 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 Trihydrate, 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 Trihydrate is originally developed by BioCryst Pharmaceuticals. And Peramivir Trihydrate is designed to aim to an antiviral agent. Peramivir Trihydrate has been performed phase III clinical trials for the treatment of influenza.

REFERENCES

• Memoli MJ et al. Clin Infect Dis. 2010 May 1;50(9):1252-5.