| Synonyms |
(3R,4R,5S)-4-(Acetylamino)-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic Acid Ethyl Ester Phosphate; Oseltamir Phosphate; Ro 64-0796/002; Tamiflu |
| IUPAC Name |
ethyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylate;phosphoric acid |
| Molecular Weight |
410.40 |
| Molecular Formula |
C16H31N2O8P |
| Canonical SMILES |
CCC(CC)OC1C=C(CC(C1NC(=O)C)N)C(=O)OCC.OP(=O)(O)O |
| InChI |
InChI=1S/C16H28N2O4.H3O4P/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19;1-5(2,3)4/h9,12-15H,5-8,17H2,1-4H3,(H,18,19);(H3,1,2,3,4)/t13-,14+,15+;/m0./s1 |
| InChIKey |
PGZUMBJQJWIWGJ-ONAKXNSWSA-N |
| Boiling Point |
473.3°C at 760 mmHg |
| Melting Point |
190-196°C |
| Flash Point |
240°C |
| Purity |
>98% |
| Density |
1.08g/cm3 |
| Solubility |
Soluble in Methanol (Slightly), Water (Slightly) |
| Appearance |
White to Off-white Solid |
| Application |
Antiviral Agents |
| Storage |
-20°C |
| Complexity |
468 |
| Exact Mass |
410.18180295 |
| In Vitro |
Oseltamivir phosphate (OP) is a prodrug that is readily absorbed from the gastrointestinal tract after oral administration and is extensively converted predominantly by hepatic esterases to Oseltamivir carboxylate (OC). Oseltamivir phosphate is a widely used anti-influenza sialidase inhibitor. The Metabolic activity of CMA07 and CMT-U27 cell lines is significantly decreased with 305 μM Oseltamivir phosphate treatment (p=0.005 and p<0.0001 respectively) using One Way ANOVA testes. In contrast, no statistically significant alterations are observed with 0.305 μM (p=0.9781), 3.05 μM (p=0.7436) and 30.5 μM (p=0.9623) of Oseltamivir phosphate treatments when compare with control cells. Finally, to assess the effect of Oseltamivir phosphate on CMA07 and CMT-U27 programmed cell death, and given that 305 μM Oseltamivir phosphate treatment impaired cell Metabolic activity, a programmed cell death measurement is performed with the TUNEL assay. Twenty-four hour Oseltamivir phosphate treatment, specifically at 305 μM, significantly increases CMA07 (p=0.001) and CMT-U27 (p=0.0002) DNA fragmentation, suggesting promotion of programmed cell death, when compare with lower Oseltamivir concentrations, or with PBS. |
| In Vivo |
Oseltamivir phosphate-treated mice present significantly more inflammatory infiltrate in primary tumors (p=0.01). Ki-67 antigen and Caspase-3 protein are used to assess CMT-U27 xenograft tumor cell proliferation and Apoptosis respectively. Virtually no differences are found in Ki-67 and Caspase 3 (p=0.2) expression between Oseltamivir-treated and non-treated mice |
| PSA |
178.22000 |
| Target |
Influenza A and B |
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