A-315675

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

MedKoo CAT#: 571115

CAS#: 335679-69-1

Description: A-315675 is a potent anti-infuenza agent. It is a neuramidase inhibitor that responds to typically resistant strains.


Price and Availability

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A-315675 is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 571115
Name: A-315675
CAS#: 335679-69-1
Chemical Formula: C17H30N2O4
Exact Mass: 326.2206
Molecular Weight: 326.44
Elemental Analysis: C, 62.55; H, 9.26; N, 8.58; O, 19.60


Synonym: A-315675; A315675; A 315675

IUPAC/Chemical Name: D-Proline, 5-((1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl)-4-(1Z)-1-propenyl-, (4S,5R)-

InChi Key: UUVKABIGWGMYCE-FLMGFEAJSA-N

InChi Code: InChI=1S/C17H30N2O4/c1-6-8-12-10-13(16(21)22)19-14(12)15(18-11(3)20)17(4,23-5)9-7-2/h6,8,12-15,19H,7,9-10H2,1-5H3,(H,18,20)(H,21,22)/b8-6-/t12-,13-,14-,15-,17+/m1/s1

SMILES Code: O=C(O)[C@@H]1N[C@@H]([C@@H](NC(C)=O)[C@@](C)(OC)CCC)[C@H](/C=C\C)C1


Technical Data

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).

Harmonized System Code:
293490


References

1: Garner P, Weerasinghe L, Youngs WJ, Wright B, Wilson D, Jacobs D. [C+NC+CC] coupling-enabled synthesis of influenza neuramidase inhibitor A-315675. Org Lett. 2012 Mar 2;14(5):1326-9. doi: 10.1021/ol3002128. Epub 2012 Feb 17. PubMed PMID: 22339284.

2: DeGoey DA, Chen HJ, Flosi WJ, Grampovnik DJ, Yeung CM, Klein LL, Kempf DJ. Enantioselective synthesis of antiinfluenza compound A-315675. J Org Chem. 2002 Aug 9;67(16):5445-53. PubMed PMID: 12153241.

3: Hanessian S, Bayrakdarian M, Luo X. Total synthesis of A-315675: a potent inhibitor of influenza neuraminidase. J Am Chem Soc. 2002 May 1;124(17):4716-21. Erratum in: J Am Chem Soc. 2003 Apr 23;125(16):4958. PubMed PMID: 11971721.

4: Sleeman K, Mishin VP, Guo Z, Garten RJ, Balish A, Fry AM, Villanueva J, Stevens J, Gubareva LV. Antiviral susceptibility of variant influenza A(H3N2)v viruses isolated in the United States from 2011 to 2013. Antimicrob Agents Chemother. 2014;58(4):2045-51. doi: 10.1128/AAC.02556-13. Epub 2014 Jan 21. PubMed PMID: 24449767; PubMed Central PMCID: PMC4023734.

5: Pizzorno A, Bouhy X, Abed Y, Boivin G. Generation and characterization of recombinant pandemic influenza A(H1N1) viruses resistant to neuraminidase inhibitors. J Infect Dis. 2011 Jan 1;203(1):25-31. doi: 10.1093/infdis/jiq010. PubMed PMID: 21148493; PubMed Central PMCID: PMC3086433.

6: Gubareva LV, Trujillo AA, Okomo-Adhiambo M, Mishin VP, Deyde VM, Sleeman K, Nguyen HT, Sheu TG, Garten RJ, Shaw MW, Fry AM, Klimov AI. Comprehensive assessment of 2009 pandemic influenza A (H1N1) virus drug susceptibility in vitro. Antivir Ther. 2010;15(8):1151-9. doi: 10.3851/IMP1678. PubMed PMID: 21149922.

7: Abed Y, Nehmé B, Baz M, Boivin G. Activity of the neuraminidase inhibitor A-315675 against oseltamivir-resistant influenza neuraminidases of N1 and N2 subtypes. Antiviral Res. 2008 Feb;77(2):163-6. Epub 2007 Sep 10. PubMed PMID: 17919743.

8: Molla A, Kati W, Carrick R, Steffy K, Shi Y, Montgomery D, Gusick N, Stoll VS, Stewart KD, Ng TI, Maring C, Kempf DJ, Kohlbrenner W. In vitro selection and characterization of influenza A (A/N9) virus variants resistant to a novel neuraminidase inhibitor, A-315675. J Virol. 2002 Jun;76(11):5380-6. PubMed PMID: 11991966; PubMed Central PMCID: PMC137025.

9: Nguyen HT, Sheu TG, Mishin VP, Klimov AI, Gubareva LV. Assessment of pandemic and seasonal influenza A (H1N1) virus susceptibility to neuraminidase inhibitors in three enzyme activity inhibition assays. Antimicrob Agents Chemother. 2010 Sep;54(9):3671-7. doi: 10.1128/AAC.00581-10. Epub 2010 Jun 28. PubMed PMID: 20585136; PubMed Central PMCID: PMC2934949.

10: Kati WM, Montgomery D, Carrick R, Gubareva L, Maring C, McDaniel K, Steffy K, Molla A, Hayden F, Kempf D, Kohlbrenner W. In vitro characterization of A-315675, a highly potent inhibitor of A and B strain influenza virus neuraminidases and influenza virus replication. Antimicrob Agents Chemother. 2002 Apr;46(4):1014-21. PubMed PMID: 11897583; PubMed Central PMCID: PMC127111.

11: Rungrotmongkol T, Udommaneethanakit T, Frecer V, Miertus S. Combinatorial design of avian influenza neuraminidase inhibitors containing pyrrolidine core with a reduced susceptibility to viral drug resistance. Comb Chem High Throughput Screen. 2010 Mar;13(3):268-77. PubMed PMID: 20015013.

12: Okomo-Adhiambo M, Nguyen HT, Sleeman K, Sheu TG, Deyde VM, Garten RJ, Xu X, Shaw MW, Klimov AI, Gubareva LV. Host cell selection of influenza neuraminidase variants: implications for drug resistance monitoring in A(H1N1) viruses. Antiviral Res. 2010 Feb;85(2):381-8. doi: 10.1016/j.antiviral.2009.11.005. Epub 2009 Nov 13. PubMed PMID: 19917319.

13: Okomo-Adhiambo M, Demmler-Harrison GJ, Deyde VM, Sheu TG, Xu X, Klimov AI, Gubareva LV. Detection of E119V and E119I mutations in influenza A (H3N2) viruses isolated from an immunocompromised patient: challenges in diagnosis of oseltamivir resistance. Antimicrob Agents Chemother. 2010 May;54(5):1834-41. doi: 10.1128/AAC.01608-09. Epub 2010 Mar 1. PubMed PMID: 20194700; PubMed Central PMCID: PMC2863645.

14: Gubareva LV. Molecular mechanisms of influenza virus resistance to neuraminidase inhibitors. Virus Res. 2004 Jul;103(1-2):199-203. PubMed PMID: 15163510.

15: Zhang Q, Zhao QJ, Xiong RS, Li JF, Shen JS. [Research progress of anti-influenza virus agents]. Yao Xue Xue Bao. 2010 Mar;45(3):289-99. Review. Chinese. PubMed PMID: 21351503.

16: Mishin VP, Hayden FG, Gubareva LV. Susceptibilities of antiviral-resistant influenza viruses to novel neuraminidase inhibitors. Antimicrob Agents Chemother. 2005 Nov;49(11):4515-20. PubMed PMID: 16251290; PubMed Central PMCID: PMC1280118.

17: Barnes DM, McLaughlin MA, Oie T, Rasmussen MW, Stewart KD, Wittenberger SJ. Synthesis of an influenza neuraminidase inhibitor intermediate via a highly diastereoselective coupling reaction. Org Lett. 2002 May 2;4(9):1427-30. PubMed PMID: 11975595.