Oseltamivir phosphateCAS# 204255-11-8 |
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Quality Control & MSDS
3D structure
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| Cas No. | 204255-11-8 | SDF | Download SDF |
| PubChem ID | 78000 | Appearance | Powder |
| Formula | C16H31N2O8P | M.Wt | 410.4 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | GS 4104 | ||
| Solubility | H2O : 100 mg/mL (243.66 mM; Need ultrasonic) DMSO : 100 mg/mL (243.66 mM; Need ultrasonic) | ||
| Chemical Name | ethyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylate;phosphoric acid | ||
| SMILES | CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1.O[P](O)(O)=O | ||
| Standard InChIKey | PGZUMBJQJWIWGJ-ONAKXNSWSA-N | ||
| Standard 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 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Oseltamivir phosphate is a neuraminidase inhibitor recommended for the treatment and prophylaxis of influenza A and B.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]. References: | |||||
Oseltamivir phosphate Dilution Calculator
Oseltamivir phosphate Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.4366 mL | 12.1832 mL | 24.3665 mL | 48.7329 mL | 60.9162 mL |
| 5 mM | 0.4873 mL | 2.4366 mL | 4.8733 mL | 9.7466 mL | 12.1832 mL |
| 10 mM | 0.2437 mL | 1.2183 mL | 2.4366 mL | 4.8733 mL | 6.0916 mL |
| 50 mM | 0.0487 mL | 0.2437 mL | 0.4873 mL | 0.9747 mL | 1.2183 mL |
| 100 mM | 0.0244 mL | 0.1218 mL | 0.2437 mL | 0.4873 mL | 0.6092 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Oseltamivir phosphate (GS-4104) is a competitive neuraminidase inhibitor, which is an antiviral drug.
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Transplacental transfer of oseltamivir phosphate and its metabolite oseltamivir carboxylate using the ex vivo human placenta perfusion model in Chinese Hans population.[Pubmed:27426925]
J Matern Fetal Neonatal Med. 2017 Jun;30(11):1288-1292.
OBJECTIVE: The objective of the study was to determine transplacental of Oseltamivir phosphate (OP) and its active metabolite oseltamivir carboxylate (OC) using the ex vivo human placental perfusion model in Chinese Hans population. STUDY DESIGN: Perfusion studies were performed on 20 placentas from healthy term pregnancies. Concentrations typical for 75 mg, twice-daily oral dose were tested (OP 65.2 ng/ml and OC 348 ng/ml), along with the positive control antipyrine 0.1 mg/ml. Each perfusion experiment was conducted for 180 min while samples were taken from both maternal and fetal compartments. Concentrations of OP and its metabolite OC were determined by ultrafast-performance liquid chromatography/tandem mass spectrometry. Integrity and viability of the placenta were determined by measuring fetal volume loss, pH, pO2, DeltahCG, glucose consumption and lactate production during the perfusion experiments. RESULTS: Following 3 h of perfusion, the fetal transfer rates of OP and its metabolite OC were 12.39%+/-3.26%, 10.17%+/-2.03%, respectively. The clearance indexes of OP and OC were 0.36 +/- 0.11 and 0.29 +/- 0.06, respectively. CONCLUSION: These data suggest that OP and its metabolite OC pass through the healthy term placenta at a small amount according to the ex vivo human placental perfusion model, fetal exposure must be considered when treating pregnant women with OP.
Therapeutic designed poly (lactic-co-glycolic acid) cylindrical oseltamivir phosphate-loaded implants impede tumor neovascularization, growth and metastasis in mouse model of human pancreatic carcinoma.[Pubmed:26309402]
Drug Des Devel Ther. 2015 Aug 10;9:4573-86.
Poly (lactic-co-glycolic acid) (PLGA) copolymers have been extensively used in cancer research. PLGA can be chemically engineered for conjugation or encapsulation of drugs in a particle formulation. We reported that Oseltamivir phosphate (OP) treatment of human pancreatic tumor-bearing mice disrupted the tumor vasculature with daily injections. Here, the controlled release of OP from a biodegradable PLGA cylinder (PLGA-OP) implanted at tumor site was investigated for its role in limiting tumor neovascularization, growth, and metastasis. PLGA-OP cylinders over 30 days in vitro indicated 20%-25% release profiles within 48 hours followed by a continuous metronomic low dose release of 30%-50% OP for an additional 16 days. All OP was released by day 30. Surgically implanted PLGA-OP containing 20 mg OP and blank PLGA cylinders at the tumor site of heterotopic xenografts of human pancreatic PANC1 tumors in RAGxCgamma double mutant mice impeded tumor neovascularization, growth rate, and spread to the liver and lungs compared with the untreated cohort. Xenograft tumors from PLGA and PLGA-OP-treated cohorts expressed significant higher levels of human E-cadherin with concomitant reduced N-cadherin and host CD31(+) endothelial cells compared with the untreated cohort. These results clearly indicate that OP delivered from PLGA cylinders surgically implanted at the site of the solid tumor show promise as an effective treatment therapy for cancer.
Selectivity Improvement for Spectrofluorimetric Determination of Oseltamivir Phosphate in Human Plasma and in the Presence of Its Degradation Product.[Pubmed:28293815]
J Fluoresc. 2017 Jul;27(4):1323-1330.
A simple and sensitive spectrofluorimetric method has been developed and validated for determination of Oseltamivir phosphate (OSP). The proposed method is based on condensation reaction of the primary amino group of OSP with ninhydrin and phenylacetaldehyde in buffered medium (pH 6.5). The formed yellow fluorescent product exhibits excitation and emission maxima at 390 and 460 nm, respectively. The selectivity improvement of our proposed method is based on the water insolubility of the oseltamivir carboxylic acid (OSC) the active metabolite of OSP, which contains the same primary amino group as OSP but cannot, condensed with ninhydrin and phenylacetaldehyde reagents. The different experimental parameters affecting the formation and stability of the reaction product were carefully studied and optimized. The fluorescence intensity concentration plot is rectilinear in the range of 2-15 mug ml(-1) with detection and quantitation limits of 0.32 and 0.98 mug ml(-1), respectively. The proposed method was successfully applied for determination of OSP in commercial capsules, suspension and spiked human plasma with good percentage recovery. In addition, the developed procedure was extended to study the stability of OSP under different stress conditions; including acid and alkali hydrolysis, oxidation, photolysis, and thermal degradation. Furthermore, the kinetic of alkaline and acidic degradation of the cited drug were investigated. The apparent first order degradation rate constants were 0.258 and 0.318 K h(-1) with half times of 2.68 and 2.17 h, for acidic and alkaline degradation, respectively.
Anti-influenza neuraminidase inhibitor oseltamivir phosphate induces canine mammary cancer cell aggressiveness.[Pubmed:25850034]
PLoS One. 2015 Apr 7;10(4):e0121590.
Oseltamivir phosphate is a widely used anti-influenza sialidase inhibitor. Sialylation, governed by sialyltransferases and sialidases, is strongly implicated in the oncogenesis and progression of breast cancer. In this study we evaluated the biological behavior of canine mammary tumor cells upon Oseltamivir phosphate treatment (a sialidase inhibitor) in vitro and in vivo. Our in vitro results showed that Oseltamivir phosphate impairs sialidase activity leading to increased sialylation in CMA07 and CMT-U27 canine mammary cancer cells. Surprisingly, Oseltamivir phosphate stimulated, CMT-U27 cell migration and invasion capacity in vitro, in a dose-dependent manner. CMT-U27 tumors xenograft of Oseltamivir phosphate-treated nude mice showed increased sialylation, namely alpha2,6 terminal structures and SLe(x) expression. Remarkably, a trend towards increased lung metastases was observed in Oseltamivir phosphate-treated nude mice. Taken together, our findings revealed that oseltamivir impairs canine mammary cancer cell sialidase activity, altering the sialylation pattern of canine mammary tumors, and leading, surprisingly, to in vitro and in vivo increased mammary tumor aggressiveness.
