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MedKoo Cat#: 596642 | Name: L 689502

Description:

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

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.

Chemical Structure

L 689502
L 689502
CAS#138483-63-3

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

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 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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 673.85 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
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.

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