L 689502

We are open as normal during COVID-19 pandemic. Order online, same day shipping out.

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

MedKoo CAT#: 596642

CAS#: 138483-63-3

Description: L 689502 is a potent inhibitor of HIV-l protease with an IC50 of 1 nM. IC50 & Target: IC50: 1 nM (HIV-l protease) In Vitro: Both L694746 and L-689502 inhibit HIV-l ptotease activity in a concentration-dependent manner. Pepstatin is much less potent than either compound exhibiting an IC50 of 2 μM. L694746 is as potent as L-689502 in inhibiting the HIV-l protease despite being structurally different from L-689502.


Price and Availability

Size Price Shipping out time Quantity
Inquire bulk and customized quantity

Pricing updated 2020-03-29. Prices are subject to change without notice.

L 689502 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

img

Theoretical Analysis

MedKoo Cat#: 596642
Name: L 689502
CAS#: 138483-63-3
Chemical Formula: C39H51N3O7
Exact Mass: 673.3727
Molecular Weight: 673.85
Elemental Analysis: C, 69.52; H, 7.63; N, 6.24; O, 16.62


Synonym: L 689502; L-689502; L689502; L-689,502; L 689,502; L689,502;

IUPAC/Chemical Name: tert-butyl ((2R,3S,5R)-3-hydroxy-6-((2-hydroxy-2,3-dihydro-1H-inden-1-yl)amino)-5-(4-(2-morpholinoethoxy)benzyl)-6-oxo-1-phenylhexan-2-yl)carbamate

InChi Key: IYLCQJSWFWQHCD-ZBSZNRNQSA-N

InChi Code: InChI=1S/C39H51N3O7/c1-39(2,3)49-38(46)40-33(24-27-9-5-4-6-10-27)34(43)26-30(37(45)41-36-32-12-8-7-11-29(32)25-35(36)44)23-28-13-15-31(16-14-28)48-22-19-42-17-20-47-21-18-42/h4-16,30,33-36,43-44H,17-26H2,1-3H3,(H,40,46)(H,41,45)/t30-,33-,34+,35?,36?/m1/s1

SMILES Code: O=C(OC(C)(C)C)N[C@H](CC1=CC=CC=C1)[C@@H](O)C[C@@H](CC2=CC=C(OCCN3CCOCC3)C=C2)C(NC4C(O)CC5=C4C=CC=C5)=O


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).

HS Tariff Code:
2934.99.9001


References

1: Vieth M, Cummins DJ. DoMCoSAR: a novel approach for establishing the docking mode that is consistent with the structure-activity relationship. Application to HIV-1 protease inhibitors and VEGF receptor tyrosine kinase inhibitors. J Med Chem. 2000 Aug 10;43(16):3020-32. PubMed PMID: 10956210.

2: Franchetti P, Perlini P, Abu Sheikha G, Cappellacci L, Grifantini M, Loi AG, De Montis A, Pani A, Marongiu ME, La Colla P. Potent and selective inhibitors of human immunodeficiency virus protease structurally related to L-694,746. Antivir Chem Chemother. 1998 Jul;9(4):303-9. PubMed PMID: 9875409.

3: Grossman SJ, Reinford N, Anderson C, Eydelloth RS, Alberts DW, Smith PF, Patrick DH. Hepatotoxicity of an HIV protease inhibitor in dogs and rats. Toxicol Appl Pharmacol. 1997 Sep;146(1):40-52. PubMed PMID: 9299595.

4: Pretzer E, Flasher D, Düzgüneş N. Inhibition of human immunodeficiency virus type-1 replication in macrophages and H9 cells by free or liposome-encapsulated L-689,502, an inhibitor of the viral protease. Antiviral Res. 1997 Mar;34(1):1-15. PubMed PMID: 9107381.

5: Wu X, Liu H, Xiao H, Kappes JC. Proteolytic activity of human immunodeficiency virus Vpr- and Vpx-protease fusion proteins. Virology. 1996 May 1;219(1):307-13. PubMed PMID: 8623547.

6: Balani SK, Pitzenberger SM, Schwartz MS, Ramjit HG, Thompson WJ. Metabolism of L-689,502 by rat liver slices to potent HIV-1 protease inhibitors. Drug Metab Dispos. 1995 Feb;23(2):185-9. PubMed PMID: 7736909.

7: Sardana VV, Schlabach AJ, Graham P, Bush BL, Condra JH, Culberson JC, Gotlib L, Graham DJ, Kohl NE, LaFemina RL, et al. Human immunodeficiency virus type 1 protease inhibitors: evaluation of resistance engendered by amino acid substitutions in the enzyme's substrate binding site. Biochemistry. 1994 Mar 1;33(8):2004-10. PubMed PMID: 8117657.

8: Lin JH, Chen IW, King J. Dose-dependent toxicokinetics of L-689,502, a potent human immunodeficiency virus protease inhibitor, in rats and dogs. J Pharmacol Exp Ther. 1992 Oct;263(1):105-11. PubMed PMID: 1403775.

9: Thompson WJ, Fitzgerald PM, Holloway MK, Emini EA, Darke PL, McKeever BM, Schleif WA, Quintero JC, Zugay JA, Tucker TJ, et al. Synthesis and antiviral activity of a series of HIV-1 protease inhibitors with functionality tethered to the P1 or P1' phenyl substituents: X-ray crystal structure assisted design. J Med Chem. 1992 May 15;35(10):1685-701. PubMed PMID: 1588551.

10: Lingham RB, Arison BH, Colwell LF, Hsu A, Dezeny G, Thompson WJ, Garrity GM, Gagliardi MM, Hartner FW, Darke PL, et al. HIV-1 protease inhibitory activity of L-694,746, a novel metabolite of L-689,502. Biochem Biophys Res Commun. 1991 Dec 31;181(3):1456-61. PubMed PMID: 1764098.