L-696229

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

MedKoo CAT#: 526983

CAS#: 135525-71-2

Description: L-696229 is a specific inhibitor of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) activity that possesses antiviral activity in cell culture. L-696,229 inhibited RT activity in a mutually exclusive manner with respect to either phosphonoformate or azidothymidine triphosphate and was a weak partial inhibitor of the RNase H activity associated with HIV-1 RT. L-696,229 inhibited the spread of HIV-1 infection in cell cultures with all cell types and viral isolates tested, including human peripheral blood mononuclear cells and a virus isolate resistant to azidothymidine.


Price and Availability

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L-696229 is not in stock, but 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#: 526983
Name: L-696229
CAS#: 135525-71-2
Chemical Formula: C17H18N2O2
Exact Mass: 282.1368
Molecular Weight: 282.343
Elemental Analysis: C, 72.32; H, 6.43; N, 9.92; O, 11.33


Synonym: L-696229; L 696229; L696229; L-696,229; L 696,229; L696,229.

IUPAC/Chemical Name: 3-(2-(Benzoxazol-2-yl)ethyl)-5-ethyl-6-methylpyridin-2(1H)-one

InChi Key: MHUVLRNBDLFMHQ-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H18N2O2/c1-3-12-10-13(17(20)18-11(12)2)8-9-16-19-14-6-4-5-7-15(14)21-16/h4-7,10H,3,8-9H2,1-2H3,(H,18,20)

SMILES Code: O=C1C(CCC2=NC3=CC=CC=C3O2)=CC(CC)=C(C)N1


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: Lee LL, Herold ML, Zacchei AG. High-performance liquid chromatographic method for the determination of an HIV-1 non-nucleoside reverse transcriptase inhibitor (L-696,229) in plasma samples from animals. J Chromatogr B Biomed Appl. 1996 Oct 25;685(2):323-8. PubMed PMID: 8953174.

2: Prueksaritanont T, Dwyer LM, Balani SK, Theoharides AD. In vitro metabolism of L-696,229, an HIV-1 reverse transcriptase inhibitor in rats and humans. Hepatic and extrahepatic metabolism and identification of enzymes involved in the hepatic metabolism. Drug Metab Dispos. 1994 Mar-Apr;22(2):281-8. PubMed PMID: 7516854.

3: Balani SK, Kauffman LR, Arison BH, Olah TV, Goldman ME, Varga SL, O'Brien JA, Ramjit HG, Rooney CS, Hoffman JM, et al. Metabolism of 3-[2-(benzoxazol-2-yl)ethyl]-5-ethyl-6-methylpyridin-2 (1H)-one (L-696,229), an HIV-1 reverse transcriptase inhibitor, by rat liver slices and in humans. Drug Metab Dispos. 1994 Mar-Apr;22(2):200-5. PubMed PMID: 7516852.

4: Emini EA, Byrnes VW, Condra JH, Schleif WA, Sardana VV. The genetic and functional basis of HIV-1 resistance to nonnucleoside reverse transcriptase inhibitors. Arch Virol Suppl. 1994;9:11-7. Review. PubMed PMID: 7518271.

5: Schleif WA, Murthy KK, Sardana VV, Schneider CL, Byrnes VW, Cobb KE, Roth E, Wolfgang JA, Hoffman JM, Smith AM, et al. Attempted prophylaxis of human immunodeficiency virus type 1 infection in chimpanzees with a nonnucleoside reverse transcriptase inhibitor. AIDS Res Hum Retroviruses. 1994 Jan;10(1):107-10. PubMed PMID: 7514014.

6: Goldman ME, O'Brien JA, Ruffing TL, Schleif WA, Sardana VV, Byrnes VW, Condra JH, Hoffman JM, Emini EA. A nonnucleoside reverse transcriptase inhibitor active on human immunodeficiency virus type 1 isolates resistant to related inhibitors. Antimicrob Agents Chemother. 1993 May;37(5):947-9. PubMed PMID: 7685996; PubMed Central PMCID: PMC187857.

7: Hoffman JM, Smith AM, Rooney CS, Fisher TE, Wai JS, Thomas CM, Bamberger DL, Barnes JL, Williams TM, Jones JH, et al. Synthesis and evaluation of 2-pyridinone derivatives as HIV-1-specific reverse transcriptase inhibitors. 4. 3-[2-(Benzoxazol-2-yl)ethyl]-5-ethyl-6-methylpyridin-2(1H)-one and analogues. J Med Chem. 1993 Apr 16;36(8):953-66. PubMed PMID: 7683054.

8: Carroll SS, Olsen DB, Bennett CD, Gotlib L, Graham DJ, Condra JH, Stern AM, Shafer JA, Kuo LC. Inhibition of HIV-1 reverse transcriptase by pyridinone derivatives. Potency, binding characteristics, and effect of template sequence. J Biol Chem. 1993 Jan 5;268(1):276-81. PubMed PMID: 7677997.

9: Woolf EJ, Matuszewski BK. Column-switching high-performance liquid chromatographic determination of a 2-pyridinone-based human immunodeficiency virus type 1 (HIV-1)-specific reverse transcriptase inhibitor in human plasma. Pharm Res. 1993 Jan;10(1):56-60. PubMed PMID: 7679213.

10: O'Brien JA, Ostovic D, Schorn TW, Smith SJ, Ruffing TL, Siegl PK, Goldman ME. A rapid bioassay for the determination of non-nucleoside HIV-1 reverse transcriptase inhibitor plasma levels. Life Sci. 1993;52(3):243-9. PubMed PMID: 7678687.

11: Balani SK, Pitzenberger SM, Kauffman LR, Arison BH, Ramjit HG, Goldman ME, O'Brien JA, King JD, Hoffman JM, Rooney CS, et al. Metabolism of a new HIV-1 reverse transcriptase inhibitor, 3-[2-(benzoxazol-2-yl)ethyl]-5-ethyl-6-methylpyridin-2(1H)-one (L-696,229), in rat and liver slices. Drug Metab Dispos. 1992 Nov-Dec;20(6):869-76. PubMed PMID: 1283569.

12: Sardana VV, Emini EA, Gotlib L, Graham DJ, Lineberger DW, Long WJ, Schlabach AJ, Wolfgang JA, Condra JH. Functional analysis of HIV-1 reverse transcriptase amino acids involved in resistance to multiple nonnucleoside inhibitors. J Biol Chem. 1992 Sep 5;267(25):17526-30. PubMed PMID: 1381350.

13: Goldman ME, O'Brien JA, Ruffing TL, Nunberg JH, Schleif WA, Quintero JC, Siegl PK, Hoffman JM, Smith AM, Emini EA. L-696,229 specifically inhibits human immunodeficiency virus type 1 reverse transcriptase and possesses antiviral activity in vitro. Antimicrob Agents Chemother. 1992 May;36(5):1019-23. PubMed PMID: 1380788; PubMed Central PMCID: PMC188828.