CAS 204255-11-8|Oseltamivir phosphate
Introduction：Basic information about CAS 204255-11-8|Oseltamivir phosphate, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Oseltamivir phosphate | ||
|---|---|---|---|
| CAS Number | 204255-11-8 | Molecular Weight | 410.400 |
| Density | 1.08g/cm3 | Boiling Point | 473.3ºC at 760 mmHg |
| Molecular Formula | C16H31N2O8P | Melting Point | 196-198°C |
| MSDS | / | Flash Point | 240ºC |
Names
| Name | oseltamivir phosphate |
|---|---|
| Synonym | More Synonyms |
Oseltamivir phosphate BiologicalActivity
| Description | Oseltamivir phosphate (GS 4104) is a neuraminidase inhibitor recommended for the treatment and prophylaxis of influenza A and B. |
|---|---|
| Related Catalog | Signaling Pathways >>Anti-infection >>Influenza VirusResearch Areas >>Infection |
| Target | Influenza A and B[1] |
| 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)[1]. 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[2]. |
| 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[2]. |
| Cell Assay | CMA07 and CMT-U27 cells are cultured in 24-well plates in triplicate for each condition: 0.305 μM, 3.05 μM, 30.5 μM and 305 μM Oseltamivir phosphate and PBS is used as control. Cells are counted every day for 7 days in a Neubauer’s chamber in a 1:2 dilution of cells in 0.4% trypan blue and cell count is done using the volume conversion factor for 1 mm3, which is 1×104. This assay is repeated 3 times and growth curves are traced[2]. |
| Animal Admin | Mice[2] Female NIH(S)II-nu/nu nude mice, aged 4-6 weeks, are orthotopically inoculated with 1×106 viable CMT-U27 canine breast cancer cells in the mammary fat pad using a 25 gauge needle. A total of 8 mice are inoculated. When nodules reached a volume of approximately 500 mm3, mice (n=8) are randomized and divided into control group (n=4) and treatment group (n=4).The animals receive intraperitoneally (IP) dailly either 100 μL of PBS (control group) or 100mg/Kg of Oseltamivir phosphate, diluted in PBS (treatment group) until time of death. Tumor size is measured using calipers, and tumor volume (mm3) is estimated by width×length×height. |
| References | [1]. Huang H, et al. Transplacental transfer of Oseltamivir phosphate and its metabolite Oseltamivir carboxylate using the ex vivo human placenta perfusion model in Chinese Hans population. J Matern Fetal Neonatal Med. 2016 Aug 8:1-5. [2]. de Oliveira JT, et al. Anti-influenza neuraminidase inhibitor Oseltamivir phosphate induces canine mammary cancer cell aggressiveness. PLoS One. 2015 Apr 7;10(4):e0121590. [3]. Li P, et al. A Simple and Robust Approach for Evaluation of Antivirals Using a Recombinant Influenza Virus Expressing Gaussia Luciferase. Viruses. 2018 Jun 13;10(6). pii: E325. |
Chemical & Physical Properties
| Density | 1.08g/cm3 |
|---|---|
| Boiling Point | 473.3ºC at 760 mmHg |
| Melting Point | 196-198°C |
| Molecular Formula | C16H31N2O8P |
| Molecular Weight | 410.400 |
| Flash Point | 240ºC |
| Exact Mass | 410.181793 |
| PSA | 178.22000 |
| LogP | 1.44800 |
| InChIKey | PGZUMBJQJWIWGJ-ONAKXNSWSA-N |
| SMILES | CCOC(=O)C1=CC(OC(CC)CC)C(NC(C)=O)C(N)C1.O=P(O)(O)O |
| Storage condition | -20°C Freezer |
Safety Information
| Hazard Codes | Xn |
|---|---|
| RIDADR | NONH for all modes of transport |
| HS Code | 2942000000 |
Customs
| HS Code | 2924299090 |
|---|---|
| Summary | 2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0% |
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| Hepatic, intestinal, renal, and plasma hydrolysis of prodrugs in human, cynomolgus monkey, dog, and rat: implications for in vitro-in vivo extrapolation of clearance of prodrugs. Drug Metab. Dispos. 42(9) , 1522-31, (2014) Hydrolysis plays an important role in metabolic activation of prodrugs. In the current study, species and in vitro system differences in hepatic and extrahepatic hydrolysis were investigated for 11 pr... |
Synonyms
| Ro-64-0796/002 |
| Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(3-pentanyloxy)-1-cyclohexene-1-carboxylate phosphate (1:1) |
| Oseltamivir phosphate |
| Tamiflu |
| Oselt |
| MFCD08059548 |
| Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate phosphate (1:1) |
| GS-4104/002 |
| Osteltamivir phosphate |
| ethyl (3R,4R,5S)-4-(acetylamino)-5-amino-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate phosphate |
| ethyl (3R,4R,5S)-4-(acetylamino)-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate phosphate (1:1) |
| Phosphorosäure-ethyl-(3R,4R,5S)-4-(acetylamino)-5-amino-3-(1-ethylpropoxy)cyclohex-1-en-1-carboxylat(1:1) |
| Ro 64-0796/002 |
| NTERMEDIATES OF OSELTAMIVIR |
| 1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R,4R,5S)-, phosphate (1:1) |
| acide phosphorique - (3R,4R,5S)-4-(acétylamino)-5-amino-3-(1-éthylpropoxy)cyclohex-1-ène-1-carboxylate d'éthyle (1:1) |
| OseltaMivir Acid-D3 Phosphate |
| Oseltamivir phosphat |
| Oseltamir phosphate |
| Oseltamivir (phosphate) |
