Oseltamivir Free Base | CAS# 196618-13-0 (free base) | Antiviral drug

Oseltamivir Free Base
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 413986

CAS#: 196618-13-0 (free base)

Description: Oseltamivir Free Base is an acetamido cyclohexene that is a structural homolog of SIALIC ACID and inhibits NEURAMINIDASE. It is used in Influenza treatment

Chemical Structure

Oseltamivir Free Base

CAS# 196618-13-0 (free base)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 413986
Name: Oseltamivir Free Base
CAS#: 196618-13-0 (free base)
Chemical Formula: C16H28N2O4
Exact Mass: 312.20
Molecular Weight: 312.410
Elemental Analysis: C, 61.51; H, 9.03; N, 8.97; O, 20.48

Price and Availability

Size	Price	Availability
100mg	USD 250	2 Weeks
250mg	USD 485	2 Weeks
500mg	USD 750	2 Weeks
1g	USD 1250	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Oseltamivir Free Base; GS4104; GS-4104; GS 4104

IUPAC/Chemical Name: 1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R,4R,5S)-

InChi Key: VSZGPKBBMSAYNT-RRFJBIMHSA-N

InChi Code: InChI=1S/C16H28N2O4/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19/h9,12-15H,5-8,17H2,1-4H3,(H,18,19)/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

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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

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Product Data:

Product Data

Instruction:

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Biological target:	Oseltamivir Free Base is an acetamido cyclohexene that is a structural homolog of SIALIC ACID and inhibits NEURAMINIDASE.
In vitro activity:	Human lumbar IVD (n = 8) tissues were isolated for annulus fibrosus (AF) and nucleus pulposus (NP) primary cell cultures, and human tibial and femoral cartilage tissues (n = 8) were isolated for primary chondrocyte cultures. In the oseltamivir-treated groups, cell proliferation decreased in both AF/NP cell and chondrocyte cultures obtained from IVD cartilage tissues. After Western blotting analysis, changes were observed in the protein expressions of HIF-1α, IL-1β, NF-κB, and the NLRP3 inflammasome in both AF/NP cells and chondrocytes. The results were statistically significant (p < 0.05). Reference: Eur Rev Med Pharmacol Sci. 2022 Jul;26(13):4816-4827. https://pubmed.ncbi.nlm.nih.gov/35856374/
In vivo activity:	Immunocompetent mice received intranasal instillation influenza A or PBS followed by orotracheal inoculation with Aspergillus fumigatus 4 days later. Oseltamivir treatment or placebo was started at day 0, day 2, or day 4. Early oseltamivir treatment prevented severe influenza pneumonia and mitigated the development of IPA and associated mortality. A time-dependent treatment effect was consistently observed with imaging, molecular, and pathological analyses. Reference: Virulence. 2021 Dec;12(1):2493-2508. https://pubmed.ncbi.nlm.nih.gov/34546839/

Preparing Stock Solutions

The following data is based on the product molecular weight 312.41 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.

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. Yilmaz I, Akalan H, Oznam K, Karaarslan N, Yasar Sirin D, Ozbek H. Does oseltamivir protect human chondrocyte and nucleus pulposus cells from degeneration by inhibiting senescence and proinflammation mediated by the NLRP3 inflammasome and NF-κB? Eur Rev Med Pharmacol Sci. 2022 Jul;26(13):4816-4827. doi: 10.26355/eurrev_202207_29207. PMID: 35856374. 2. de Oliveira JT, Santos AL, Gomes C, Barros R, Ribeiro C, Mendes N, de Matos AJ, Vasconcelos MH, Oliveira MJ, Reis CA, Gärtner F. Anti-influenza neuraminidase inhibitor oseltamivir phosphate induces canine mammary cancer cell aggressiveness. PLoS One. 2015 Apr 7;10(4):e0121590. doi: 10.1371/journal.pone.0121590. PMID: 25850034; PMCID: PMC4388625. 3. Seldeslachts L, Vanderbeke L, Fremau A, Reséndiz-Sharpe A, Jacobs C, Laeveren B, Ostyn T, Naesens L, Brock M, Van De Veerdonk FL, Humblet-Baron S, Verbeken E, Lagrou K, Wauters J, Vande Velde G. Early oseltamivir reduces risk for influenza-associated aspergillosis in a double-hit murine model. Virulence. 2021 Dec;12(1):2493-2508. doi: 10.1080/21505594.2021.1974327. PMID: 34546839; PMCID: PMC8923074. 4. Takahashi E, Sawabuchi T, Kimoto T, Sakai S, Kido H. Lactobacillus delbrueckii ssp. bulgaricus OLL1073R-1 feeding enhances humoral immune responses, which are suppressed by the antiviral neuraminidase inhibitor oseltamivir in influenza A virus-infected mice. J Dairy Sci. 2019 Nov;102(11):9559-9569. doi: 10.3168/jds.2019-16268. Epub 2019 Sep 5. PMID: 31495632.
In vitro protocol:	1. Yilmaz I, Akalan H, Oznam K, Karaarslan N, Yasar Sirin D, Ozbek H. Does oseltamivir protect human chondrocyte and nucleus pulposus cells from degeneration by inhibiting senescence and proinflammation mediated by the NLRP3 inflammasome and NF-κB? Eur Rev Med Pharmacol Sci. 2022 Jul;26(13):4816-4827. doi: 10.26355/eurrev_202207_29207. PMID: 35856374. 2. de Oliveira JT, Santos AL, Gomes C, Barros R, Ribeiro C, Mendes N, de Matos AJ, Vasconcelos MH, Oliveira MJ, Reis CA, Gärtner F. Anti-influenza neuraminidase inhibitor oseltamivir phosphate induces canine mammary cancer cell aggressiveness. PLoS One. 2015 Apr 7;10(4):e0121590. doi: 10.1371/journal.pone.0121590. PMID: 25850034; PMCID: PMC4388625.
In vivo protocol:	1. Seldeslachts L, Vanderbeke L, Fremau A, Reséndiz-Sharpe A, Jacobs C, Laeveren B, Ostyn T, Naesens L, Brock M, Van De Veerdonk FL, Humblet-Baron S, Verbeken E, Lagrou K, Wauters J, Vande Velde G. Early oseltamivir reduces risk for influenza-associated aspergillosis in a double-hit murine model. Virulence. 2021 Dec;12(1):2493-2508. doi: 10.1080/21505594.2021.1974327. PMID: 34546839; PMCID: PMC8923074. 2. Takahashi E, Sawabuchi T, Kimoto T, Sakai S, Kido H. Lactobacillus delbrueckii ssp. bulgaricus OLL1073R-1 feeding enhances humoral immune responses, which are suppressed by the antiviral neuraminidase inhibitor oseltamivir in influenza A virus-infected mice. J Dairy Sci. 2019 Nov;102(11):9559-9569. doi: 10.3168/jds.2019-16268. Epub 2019 Sep 5. PMID: 31495632.

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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. PMID: 26616633.

2: Tagarro A, Cruz-Cañete M, Otheo E, Launes C, Couceiro JA, Pérez C, Alfayate S; en nombre del Grupo de trabajo de Infecciones Respiratorias de la Sociedad Española de Infectología Pediátrica (SEIP); Miembros del Grupo de Trabajo de Infecciones Respiratorias de la SEIP que han participado en la revisión del manuscrito. Oseltamivir para el tratamiento de la gripe en niños y adolescentes [Oseltamivir for the treatment of influenza in children and adolescents]. An Pediatr (Barc). 2019 May;90(5):317.e1-317.e8. Spanish. doi: 10.1016/j.anpedi.2019.01.009. Epub 2019 Feb 21. PMID: 30797703.

3: Doshi P, Heneghan C, Jefferson T. Oseltamivir for influenza. Lancet. 2016 Jan 9;387(10014):124. doi: 10.1016/S0140-6736(15)01282-9. Epub 2016 Jan 8. PMID: 26841993.

4: Butler CC, van der Velden AW, Bongard E, Saville BR, Holmes J, Coenen S, Cook J, Francis NA, Lewis RJ, Godycki-Cwirko M, Llor C, Chlabicz S, Lionis C, Seifert B, Sundvall PD, Colliers A, Aabenhus R, Bjerrum L, Jonassen Harbin N, Lindbæk M, Glinz D, Bucher HC, Kovács B, Radzeviciene Jurgute R, Touboul Lundgren P, Little P, Murphy AW, De Sutter A, Openshaw P, de Jong MD, Connor JT, Matheeussen V, Ieven M, Goossens H, Verheij TJ. Oseltamivir plus usual care versus usual care for influenza-like illness in primary care: an open-label, pragmatic, randomised controlled trial. Lancet. 2020 Jan 4;395(10217):42-52. doi: 10.1016/S0140-6736(19)32982-4. Epub 2019 Dec 12. PMID: 31839279.

5: Ono H. [Hypothermic Action of Oseltamivir Not Dependent on Its Anti-influenza Virus Action]. Yakugaku Zasshi. 2019;139(5):767-781. Japanese. doi: 10.1248/yakushi.18-00191. PMID: 31061347.

6: Lee J, Park JH, Jwa H, Kim YH. Comparison of Efficacy of Intravenous Peramivir and Oral Oseltamivir for the Treatment of Influenza: Systematic Review and Meta-Analysis. Yonsei Med J. 2017 Jul;58(4):778-785. doi: 10.3349/ymj.2017.58.4.778. PMID: 28540991; PMCID: PMC5447109.

7: Yun YL, Gao SH, Wen Y, Wang ZP, Miao HJ, Chen WS. Bioequivalence of two oseltamivir formulations in healthy Chinese volunteers. Int J Clin Pharmacol Ther. 2017 Sep;55(9):761-768. doi: 10.5414/CP202926. PMID: 28737128.

8: Wang Y, Fan G, Salam A, Horby P, Hayden FG, Chen C, Pan J, Zheng J, Lu B, Guo L, Wang C, Cao B. Comparative Effectiveness of Combined Favipiravir and Oseltamivir Therapy Versus Oseltamivir Monotherapy in Critically Ill Patients With Influenza Virus Infection. J Infect Dis. 2020 Apr 27;221(10):1688-1698. doi: 10.1093/infdis/jiz656. PMID: 31822885.

9: Malosh RE, Martin ET, Heikkinen T, Brooks WA, Whitley RJ, Monto AS. Efficacy and Safety of Oseltamivir in Children: Systematic Review and Individual Patient Data Meta-analysis of Randomized Controlled Trials. Clin Infect Dis. 2018 May 2;66(10):1492-1500. doi: 10.1093/cid/cix1040. PMID: 29186364.

10: Rech MA. Oseltamivir for All: Should It Become an Over-the-Counter Medication for Influenza Treatment? Pharmacotherapy. 2020 Mar;40(3):182-185. doi: 10.1002/phar.2370. Epub 2020 Feb 12. PMID: 32048321.

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