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Oseltamivir phosphate

Names

[ CAS No. ]:
204255-11-8

[ Name ]:
Oseltamivir phosphate

[Synonym ]:
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)

Biological Activity

[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 Virus
Research 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.


[Related Small Molecules]

Baloxavir | Pimodivir | KIN1148 | Zanamivir | Arbidol HCl | Nucleozin | Theaflavin | Desaminotyrosine | Peramivir Trihydrate | RIG-1 modulator 1 | Rimantadine Hydrochloride | Sodium copper chlorophyllin | SP187 | Dehydroandrographolide | M2 ion channel blocker

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

[ Storage condition ]:
-20°C Freezer

MSDS

Safety Information

[ Hazard Codes ]:
Xn

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2942000000

Synthetic Route

Precursor & DownStream

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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Related Compounds