L-696229 | CAS#135525-71-2

MedKoo Cat#: 526983 | Name: L-696229

Description:

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

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.

Chemical Structure

L-696229

CAS#135525-71-2

Theoretical Analysis

MedKoo Cat#: 526983

Name: L-696229

CAS#: 135525-71-2

Chemical Formula: C17H18N2O2

Exact Mass: 282.1368

Molecular Weight: 282.34

Elemental Analysis: C, 72.32; H, 6.43; N, 9.92; O, 11.33

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

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

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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 282.34 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

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.