Oseltamivir phosphate
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MedKoo CAT#: 318391

CAS#: 204255-11-8 (phosphate)

Description: Oseltamivir 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.


Chemical Structure

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Oseltamivir phosphate
CAS# 204255-11-8 (phosphate)

Theoretical Analysis

MedKoo Cat#: 318391
Name: Oseltamivir phosphate
CAS#: 204255-11-8 (phosphate)
Chemical Formula: C16H31N2O8P
Exact Mass: 312.405
Molecular Weight: 410.4
Elemental Analysis: C, 46.83; H, 7.61; N, 6.83; O, 31.19; P, 7.55

Price and Availability

Size Price Availability Quantity
1.0g USD 150.0 Ready to ship
5.0g USD 450.0 Ready to ship
10.0g USD 750.0 2 Weeks
100.0g USD 2950.0 2 Weeks
200.0g USD 3950.0 2 Weeks
1.0kg USD 6950.0 2 Weeks
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Related CAS #: 204255-11-8 (phosphate); 196618-13-0 (free base)   204255-09-4 (HCl)    

Synonym: Oseltamivir, GS-4071, GS-4104, Tamiflu

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

InChi Key: PGZUMBJQJWIWGJ-ONAKXNSWSA-N

InChi Code: 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

SMILES Code: O=C(C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1)OCC.O=P(O)(O)O

Appearance: Solid powder

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

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:

Certificate of Analysis:

Safety Data Sheet (SDS):

Biological target: Oseltamivir phosphate (GS 4104) is a neuraminidase inhibitor recommended for the treatment and prophylaxis of influenza A and B.
In vitro activity: The annexin V/PI assay indicated that the number of cells exhibiting both early apoptosis (annexin V+/PI−) and late apoptosis (annexin V+/PI+) in the oseltamivir-treatment group was higher than that of the non-treatment H1/09- or H1/07-infected THP-1 cells at 24 h POI (Fig. 1). There was no difference in the MOCK group cells (data not shown) or in the HN3- or HN1374-infected THP-1 cells for either the oseltamivir treatment group or the non-treatment group (p > 0.05). The TUNEL assay indicated that apoptotic cells were more frequently observed in H1/09- or H1/07-infected A549 cells treated with oseltamivir (Fig. 1E) than in untreated cells (Fig. 2D). The number of apoptotic cells significantly increased with infection progression (p < 0.05, Fig. 2F). Reference: Biochem Biophys Res Commun. 2013 Feb 22;431(4):788-95. https://pubmed.ncbi.nlm.nih.gov/23333739/
In vivo activity: Representative examples of AF induction and stable sinus rhythm under the influence of oseltamivir are displayed in Fig. 3. Treatment with acetylcholine and isoproterenol increased the inducibility of AF. Under baseline conditions, 4 of 12 hearts (33%, 11 episodes, Fig. 4) were inducible. Infusion of acetylcholine and isoproterenol led to AF in 8 of 12 hearts (67%, 69 episodes). Additional treatment with oseltamivir in the presence of continuous infusion of acetylcholine and isoproterenol reduced the occurrence of AF. 3 of 12 hearts (25%, 8 episodes) remained inducible. Reference: Naunyn Schmiedebergs Arch Pharmacol. 2017 Nov;390(11):1155-1161. https://pubmed.ncbi.nlm.nih.gov/28780600/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 10.0 24.4
H2O 30.0 73.1

Preparing Stock Solutions

The following data is based on the product molecular weight 410.4 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Muraki K, Hatano N, Suzuki H, Muraki Y, Iwajima Y, Maeda Y, Ono H. Oseltamivir blocks human neuronal nicotinic acetylcholine receptor-mediated currents. Basic Clin Pharmacol Toxicol. 2015 Feb;116(2):87-95. doi: 10.1111/bcpt.12290. Epub 2014 Jul 31. PMID: 24965031. 2. Gao R, Du N, Liu D, Li Z, Zhu Y, Shu Y. Oseltamivir inhibits both viral entry and release but enhances apoptosis of cells infected with influenza A H1N1. Biochem Biophys Res Commun. 2013 Feb 22;431(4):788-95. doi: 10.1016/j.bbrc.2013.01.019. Epub 2013 Jan 17. PMID: 23333739. 3. Calderón Guzmán D, Osnaya Brizuela N, Ortiz Herrera M, Juárez Olguín H, Veloz Corona Q, Sanchez Reyes L, Valenzuela Peraza A, Barragán Mejía G. Oseltamivir induces favorable response on oxidative damage in the brain of rats treated with Bezafibrate. Int J Neurosci. 2020 Oct 7:1-8. doi: 10.1080/00207454.2020.1828882. Epub ahead of print. PMID: 32976735. 4. Frommeyer G, Mittelstedt A, Wolfes J, Ellermann C, Kochhäuser S, Leitz P, Dechering DG, Eckardt L. The anti-influenza drug oseltamivir reduces atrial fibrillation in an experimental whole-heart model. Naunyn Schmiedebergs Arch Pharmacol. 2017 Nov;390(11):1155-1161. doi: 10.1007/s00210-017-1415-y. Epub 2017 Aug 6. PMID: 28780600.
In vitro protocol: 1. Muraki K, Hatano N, Suzuki H, Muraki Y, Iwajima Y, Maeda Y, Ono H. Oseltamivir blocks human neuronal nicotinic acetylcholine receptor-mediated currents. Basic Clin Pharmacol Toxicol. 2015 Feb;116(2):87-95. doi: 10.1111/bcpt.12290. Epub 2014 Jul 31. PMID: 24965031. 2. Gao R, Du N, Liu D, Li Z, Zhu Y, Shu Y. Oseltamivir inhibits both viral entry and release but enhances apoptosis of cells infected with influenza A H1N1. Biochem Biophys Res Commun. 2013 Feb 22;431(4):788-95. doi: 10.1016/j.bbrc.2013.01.019. Epub 2013 Jan 17. PMID: 23333739.
In vivo protocol: 1. Calderón Guzmán D, Osnaya Brizuela N, Ortiz Herrera M, Juárez Olguín H, Veloz Corona Q, Sanchez Reyes L, Valenzuela Peraza A, Barragán Mejía G. Oseltamivir induces favorable response on oxidative damage in the brain of rats treated with Bezafibrate. Int J Neurosci. 2020 Oct 7:1-8. doi: 10.1080/00207454.2020.1828882. Epub ahead of print. PMID: 32976735. 2. Frommeyer G, Mittelstedt A, Wolfes J, Ellermann C, Kochhäuser S, Leitz P, Dechering DG, Eckardt L. The anti-influenza drug oseltamivir reduces atrial fibrillation in an experimental whole-heart model. Naunyn Schmiedebergs Arch Pharmacol. 2017 Nov;390(11):1155-1161. doi: 10.1007/s00210-017-1415-y. Epub 2017 Aug 6. PMID: 28780600.

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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: Dobson J, Whitley RJ, Pocock S, Monto AS. Oseltamivir treatment for influenza in adults: a meta-analysis of randomised controlled trials. Lancet. 2015 May 2;385(9979):1729-37. doi: 10.1016/S0140-6736(14)62449-1. Epub 2015 Jan 30. Review. Erratum in: Lancet. 2015 May 2;385(9979):1728. Lancet. 2015 May 2;385(9979):1728. PubMed PMID: 25640810.

4: Wagner J, Abdel-Rahman SM. Oseltamivir-warfarin interaction in hypoplastic left heart syndrome: case report and review. Pediatrics. 2015 May;135(5):e1333-6. doi: 10.1542/peds.2014-2578. Review. PubMed PMID: 25917992.

5: 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.

6: In brief: concerns about oseltamivir (Tamiflu). Med Lett Drugs Ther. 2015 Jan 19;57(1460):14. Epub 2015 Jan 19. Review. PubMed PMID: 25536909.

7: Beigi RH, Venkataramanan R, Caritis SN. Oseltamivir for influenza in pregnancy. Semin Perinatol. 2014 Dec;38(8):503-7. doi: 10.1053/j.semperi.2014.08.015. Epub 2014 Oct 1. Review. PubMed PMID: 25281358.

8: Wollenhaupt M, Chandrasekaran A, Tomianovic D. The safety of oseltamivir in pregnancy: an updated review of post-marketing data. Pharmacoepidemiol Drug Saf. 2014 Oct;23(10):1035-42. doi: 10.1002/pds.3673. Epub 2014 Jul 4. Review. PubMed PMID: 24995623.

9: Flannery AH, Thompson Bastin ML. Oseltamivir Dosing in Critically Ill Patients With Severe Influenza. Ann Pharmacother. 2014 May 9;48(8):1011-1018. [Epub ahead of print] Review. PubMed PMID: 24816209.

10: Jefferson T, Jones M, Doshi P, Spencer EA, Onakpoya I, Heneghan CJ. Oseltamivir for influenza in adults and children: systematic review of clinical study reports and summary of regulatory comments. BMJ. 2014 Apr 9;348:g2545. doi: 10.1136/bmj.g2545. Review. PubMed PMID: 24811411; PubMed Central PMCID: PMC3981975.

11: Freemantle N, Shallcross LJ, Kyte D, Rader T, Calvert MJ. Oseltamivir: the real world data. BMJ. 2014 Apr 9;348:g2371. doi: 10.1136/bmj.g2371. Review. PubMed PMID: 24811409.

12: Zhao P, Yang HZ, Lv HY, Wei ZM. Efficacy of Lianhuaqingwen capsule compared with oseltamivir for influenza A virus infection: a meta-analysis of randomized, controlled trials. Altern Ther Health Med. 2014 Mar-Apr;20(2):25-30. Review. PubMed PMID: 24657957.

13: Kosasih H, Bratasena A, Pangesti K, Laras K, Samaan G. Managing seasonal influenza: oseltamivir treatment policy in indonesia? Acta Med Indones. 2014 Jan;46(1):58-65. Review. PubMed PMID: 24760811.

14: Mortada M, Neuenschwander P, Tekko SS. Influenza and oseltamivir phosphate (Tamiflu) in infants: what you need to know. Pediatr Nurs. 2014 Jan-Feb;40(1):16-20. Review. PubMed PMID: 24757915.

15: Ebell MH, Call M, Shinholser J. Effectiveness of oseltamivir in adults: a meta-analysis of published and unpublished clinical trials. Fam Pract. 2013 Apr;30(2):125-33. doi: 10.1093/fampra/cms059. Epub 2012 Sep 20. Review. PubMed PMID: 22997224.

16: Tashani M, Rashid H, Ridda I, Heron L, Memish ZA, Haworth E, Booy R. Oseltamivir for control of influenza at mass gatherings. Infect Disord Drug Targets. 2013 Feb;13(1):46-52. Review. PubMed PMID: 23675926.

17: Standing JF, Tsolia M, Lutsar I. Pharmacokinetics and pharmacodynamics of oseltamivir in neonates, infants and children. Infect Disord Drug Targets. 2013 Feb;13(1):6-14. Review. PubMed PMID: 23675922.

18: Yin JK, Heron L, Salkeld G, Rashid H, Booy R. Oseltamivir use in adolescents and adults: clinical and economic considerations. Infect Disord Drug Targets. 2013 Feb;13(1):53-8. Review. PubMed PMID: 23675927.

19: Dixit R, Khandaker G, Ilgoutz S, Rashid H, Booy R. Emergence of oseltamivir resistance: control and management of influenza before, during and after the pandemic. Infect Disord Drug Targets. 2013 Feb;13(1):34-45. Review. PubMed PMID: 23675925.

20: Karadag-Oncel E, Ceyhan M. Oseltamivir in neonates, infants and young children: a focus on clinical pharmacology. Infect Disord Drug Targets. 2013 Feb;13(1):15-24. Review. PubMed PMID: 23675923.