Oseltamivir phosphate

Oseltamivir phosphate is an antiviral medication used to treat influenza A and influenza B (flu), and to prevent flu after exposure. The medication is taken orally. The Infectious Disease Society of America, the United States' Centers for Disease Control and Prevention (CDC), and the United Kingdom's National Institute for Health and Care Excellence recommend the use of oseltamavir for people who have complications or are at high risk for complications who present within 48 hours of first symptoms of infection. They recommend its use to prevent infection in at-risk people but not the general population. The CDC recommends that clinicians use their discretion to treat those at lower risk who present within 48 hours of first symptoms of infection.

Product information

CAS Number: 204255-11-8

Molecular Weight: 410.40

Formula: C16H31N2O8P

Synonym:

Oseltamivir

GS-4071

GS-4104

Tamiflu

Chemical Name: ethyl(3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylate;phosphoric acid

Smiles: CC(=O)N[C@@H]1[C@@H](N)CC(=C[C@H]1OC(CC)CC)C(=O)OCC.OP(O)(O)=O

InChiKey: PGZUMBJQJWIWGJ-ONAKXNSWSA-N

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

Technical Data

Appearance: Solid Power.

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO, not in water

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined.

HS Tariff Code: 382200

How to use

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.

References:

1. Esposito S, Principi N. Oseltamivir for influenza infection in children: risks and benefits. Expert Rev Respir Med. 2016;10(1):79-87. doi: 10.1586/17476348.2016.1126182. Epub 2015 Dec 19. Review. PubMed PMID: 26616633.
2. Beigi RH, Pillai VC, Venkataramanan R, Caritis SN. Oseltamivir for the treatment of H1N1 influenza during pregnancy. Clin Pharmacol Ther. 2015 Oct;98(4):403-5. doi: 10.1002/cpt.179. Epub 2015 Jul 22. Review. PubMed PMID: 26108913.
3. McQuade B, Blair M. Influenza treatment with oseltamivir outside of labeled recommendations. Am J Health Syst Pharm. 2015 Jan 15;72(2):112-6. doi: 10.2146/ajhp140390. Review. PubMed PMID: 25550133.

Products are for research use only. Not for human use.