Oseltamivir carboxylate

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

MedKoo CAT#: 527792

CAS#: 187227-45-8 (free)

Description: Oseltamivir carboxylate is an active metabolite of oseltamivir phosphate (Tamiflu).


Chemical Structure

img
Oseltamivir carboxylate
CAS# 187227-45-8 (free)

Theoretical Analysis

MedKoo Cat#: 527792
Name: Oseltamivir carboxylate
CAS#: 187227-45-8 (free)
Chemical Formula: C14H24N2O4
Exact Mass: 284.1736
Molecular Weight: 284.356
Elemental Analysis: C, 59.14; H, 8.51; N, 9.85; O, 22.51

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Related CAS #: 1415963-60-8 (HCl)   187227-45-8 (free)    

Synonym: Oseltamivir carboxylate

IUPAC/Chemical Name: (3R,4R,5S)-4-Acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylic acid

InChi Key: NENPYTRHICXVCS-YNEHKIRRSA-N

InChi Code: InChI=1S/C14H24N2O4/c1-4-10(5-2)20-12-7-9(14(18)19)6-11(15)13(12)16-8(3)17/h7,10-13H,4-6,15H2,1-3H3,(H,16,17)(H,18,19)/t11-,12+,13+/m0/s1

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

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

Preparing Stock Solutions

The following data is based on the product molecular weight 284.356 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

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Ju H, Zhang J, Sun Z, Huang Z, Qi W, Huang B, Zhan P, Liu X. Discovery of C-1 modified oseltamivir derivatives as potent influenza neuraminidase inhibitors. Eur J Med Chem. 2018 Feb 25;146:220-231. doi: 10.1016/j.ejmech.2018.01.050. Epub 2018 Feb 4. PubMed PMID: 29407952.

2: Wang Y, Hu Y, Xu S, Zhang Y, Musharrafieh R, Hau RK, Ma C, Wang J. In Vitro Pharmacokinetic Optimizations of AM2-S31N Channel Blockers Led to the Discovery of Slow-Binding Inhibitors with Potent Antiviral Activity against Drug-Resistant Influenza A Viruses. J Med Chem. 2018 Feb 8;61(3):1074-1085. doi: 10.1021/acs.jmedchem.7b01536. Epub 2018 Jan 17. PubMed PMID: 29341607.

3: Fukushima A, Fukui A, Takemura Y, Maeda Y, Ono H. The anti-influenza drug oseltamivir evokes hypothermia in mice through dopamine D(2) receptor activation via central actions. J Pharmacol Sci. 2018 Jan;136(1):39-41. doi: 10.1016/j.jphs.2017.12.005. Epub 2017 Dec 15. PubMed PMID: 29292053.

4: Shin JS, Ku KB, Jang Y, Yoon YS, Shin D, Kwon OS, Go YY, Kim SS, Bae MA, Kim M. Comparison of anti-influenza virus activity and pharmacokinetics of oseltamivir free base and oseltamivir phosphate. J Microbiol. 2017 Dec;55(12):979-983. doi: 10.1007/s12275-017-7371-x. Epub 2017 Dec 7. PubMed PMID: 29214495.

5: Quosdorf S, Schuetz A, Kolodziej H. Different Inhibitory Potencies of Oseltamivir Carboxylate, Zanamivir, and Several Tannins on Bacterial and Viral Neuraminidases as Assessed in a Cell-Free Fluorescence-Based Enzyme Inhibition Assay. Molecules. 2017 Nov 17;22(11). pii: E1989. doi: 10.3390/molecules22111989. PubMed PMID: 29149072.

6: Wang K, Yang F, Wang L, Liu K, Sun L, Lin B, Hu Y, Wang B, Cheng M, Tian Y. Synthesis and biological evaluation of NH(2)-acyl oseltamivir analogues as potent neuraminidase inhibitors. Eur J Med Chem. 2017 Dec 1;141:648-656. doi: 10.1016/j.ejmech.2017.10.004. Epub 2017 Oct 5. PubMed PMID: 29107426.

7: Choi WS, Jeong JH, Kwon JJ, Ahn SJ, Lloren KKS, Kwon HI, Chae HB, Hwang J, Kim MH, Kim CJ, Webby RJ, Govorkova EA, Choi YK, Baek YH, Song MS. Screening for Neuraminidase Inhibitor Resistance Markers among Avian Influenza Viruses of the N4, N5, N6, and N8 Neuraminidase Subtypes. J Virol. 2017 Dec 14;92(1). pii: e01580-17. doi: 10.1128/JVI.01580-17. Print 2018 Jan 1. PubMed PMID: 29046464; PubMed Central PMCID: PMC5730757.

8: Hu Y, Zhang J, Musharrafieh RG, Ma C, Hau R, Wang J. Discovery of dapivirine, a nonnucleoside HIV-1 reverse transcriptase inhibitor, as a broad-spectrum antiviral against both influenza A and B viruses. Antiviral Res. 2017 Sep;145:103-113. doi: 10.1016/j.antiviral.2017.07.016. Epub 2017 Aug 2. PubMed PMID: 28778830; PubMed Central PMCID: PMC5599177.

9: Cha YJ, Ghim JL. Role of the ABCB1 Drug Transporter Polymorphisms in the Pharmacokinetics of Oseltamivir in Humans: a Preliminary Report. J Korean Med Sci. 2017 Sep;32(9):1542-1547. doi: 10.3346/jkms.2017.32.9.1542. PubMed PMID: 28776352; PubMed Central PMCID: PMC5546976.

10: Hsueh CH, Hsu V, Zhao P, Zhang L, Giacomini KM, Huang SM. PBPK Modeling of the Effect of Reduced Kidney Function on the Pharmacokinetics of Drugs Excreted Renally by Organic Anion Transporters. Clin Pharmacol Ther. 2018 Mar;103(3):485-492. doi: 10.1002/cpt.750. Epub 2017 Jul 24. PubMed PMID: 28738449.

11: 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. PubMed PMID: 28737128.

12: Li R, Yang C, Du Q, Zhao X, Jiang H, Hu W, Yang Z. Pinanamine Is a Promising Lead Compound against Influenza A Virus: Evidence from in Vitro and in Vivo Efficacy Compared to Amantadine. Biol Pharm Bull. 2017;40(7):954-959. doi: 10.1248/bpb.b16-00774. PubMed PMID: 28674259.

13: Sadasivan S, Sharp B, Schultz-Cherry S, Smeyne RJ. Synergistic effects of influenza and 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) can be eliminated by the use of influenza therapeutics: experimental evidence for the multi-hit hypothesis. NPJ Parkinsons Dis. 2017 May 23;3:18. doi: 10.1038/s41531-017-0019-z. eCollection 2017. PubMed PMID: 28649618; PubMed Central PMCID: PMC5460228.

14: Deng R, Lee AP, Maia M, Lim JJ, Burgess T, Horn P, Derby MA, Newton E, Tavel JA, Hanley WD. Pharmacokinetics of MHAA4549A, an Anti-Influenza A Monoclonal Antibody, in Healthy Subjects Challenged with Influenza A Virus in a Phase IIa Randomized Trial. Clin Pharmacokinet. 2018 Mar;57(3):367-377. doi: 10.1007/s40262-017-0564-y. PubMed PMID: 28639229.

15: Bhatia S, Lauster D, Bardua M, Ludwig K, Angioletti-Uberti S, Popp N, Hoffmann U, Paulus F, Budt M, Stadtmüller M, Wolff T, Hamann A, Böttcher C, Herrmann A, Haag R. Linear polysialoside outperforms dendritic analogs for inhibition of influenza virus infection in vitro and in vivo. Biomaterials. 2017 Sep;138:22-34. doi: 10.1016/j.biomaterials.2017.05.028. Epub 2017 May 20. PubMed PMID: 28550754.

16: Oh J, Lee S, Lee H, Cho JY, Yoon SH, Jang IJ, Yu KS, Lim KS. The novel carboxylesterase 1 variant c.662A>G may decrease the bioactivation of oseltamivir in humans. PLoS One. 2017 Apr 24;12(4):e0176320. doi: 10.1371/journal.pone.0176320. eCollection 2017. PubMed PMID: 28437488; PubMed Central PMCID: PMC5402961.

17: Li Z, Meng Y, Xu S, Shen W, Meng Z, Wang Z, Ding G, Huang W, Xiao W, Xu J. Discovery of acylguanidine oseltamivir carboxylate derivatives as potent neuraminidase inhibitors. Bioorg Med Chem. 2017 May 15;25(10):2772-2781. doi: 10.1016/j.bmc.2017.03.052. Epub 2017 Mar 27. PubMed PMID: 28385598.

18: Jang K, Kim MK, Oh J, Lee S, Cho JY, Yu KS, Choi TK, Lee SH, Lim KS. Effects of dexamethasone coadministered with oseltamivir on the pharmacokinetics of oseltamivir in healthy volunteers. Drug Des Devel Ther. 2017 Mar 9;11:705-711. doi: 10.2147/DDDT.S124307. eCollection 2017. PubMed PMID: 28331290; PubMed Central PMCID: PMC5352149.

19: Kamal MA, Smith PF, Chaiyakunapruk N, Wu DBC, Pratoomsoot C, Lee KKC, Chong HY, Nelson RE, Nieforth K, Dall G, Toovey S, Kong DCM, Kamauu A, Kirkpatrick CM, Rayner CR. Interdisciplinary pharmacometrics linking oseltamivir pharmacology, influenza epidemiology and health economics to inform antiviral use in pandemics. Br J Clin Pharmacol. 2017 Jul;83(7):1580-1594. doi: 10.1111/bcp.13229. Epub 2017 Feb 20. PubMed PMID: 28176362; PubMed Central PMCID: PMC5465331.

20: Azuma T, Ishida M, Hisamatsu K, Yunoki A, Otomo K, Kunitou M, Shimizu M, Hosomaru K, Mikata S, Mino Y. Fate of new three anti-influenza drugs and one prodrug in the water environment. Chemosphere. 2017 Feb;169:550-557. doi: 10.1016/j.chemosphere.2016.11.102. Epub 2016 Nov 26. PubMed PMID: 27898328.