WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 596689
CAS#: 160729-91-9
Description: L 754394 is a potent and specific inhibitor of the HIV-1 protease.
MedKoo Cat#: 596689
Name: L 754394
CAS#: 160729-91-9
Chemical Formula: C38H47N5O5
Exact Mass: 653.3577
Molecular Weight: 653.82
Elemental Analysis: C, 69.81; H, 7.25; N, 10.71; O, 12.23
Synonym: L 754394; L-754394; L754394; L-754,394; L 754,394; L754,394;
IUPAC/Chemical Name: (S)-1-((2S,4R)-4-benzyl-2-hydroxy-5-(((1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl)amino)-5-oxopentyl)-N-(tert-butyl)-4-(furo[2,3-b]pyridin-5-ylmethyl)piperazine-2-carboxamide
InChi Key: UBUFVRJUGFJQSI-PPJSLLJVSA-N
InChi Code: InChI=1S/C38H47N5O5/c1-38(2,3)41-36(47)32-24-42(22-26-18-28-13-16-48-37(28)39-21-26)14-15-43(32)23-30(44)19-29(17-25-9-5-4-6-10-25)35(46)40-34-31-12-8-7-11-27(31)20-33(34)45/h4-13,16,18,21,29-30,32-34,44-45H,14-15,17,19-20,22-24H2,1-3H3,(H,40,46)(H,41,47)/t29-,30+,32+,33-,34+/m1/s1
SMILES Code: O=C(N[C@@H]1[C@H](O)CC2=C1C=CC=C2)[C@H](CC3=CC=CC=C3)C[C@H](O)CN4[C@H](C(NC(C)(C)C)=O)CN(CC5=CN=C(OC=C6)C6=C5)CC4
1: Bateman KP, Baker J, Wilke M, Lee J, Leriche T, Seto C, Day S, Chauret N, Ouellet M, Nicoll-Griffith DA. Detection of covalent adducts to cytochrome P450 3A4 using liquid chromatography mass spectrometry. Chem Res Toxicol. 2004 Oct;17(10):1356-61. PubMed PMID: 15487896.
2: Achira M, Suzuki H, Ito K, Sugiyama Y. Comparative studies to determine the selective inhibitors for P-glycoprotein and cytochrome P4503A4. AAPS PharmSci. 1999;1(4):E18. PubMed PMID: 11741214; PubMed Central PMCID: PMC2751348.
3: Kawahara I, Kato Y, Suzuki H, Achira M, Ito K, Crespi CL, Sugiyama Y. Selective inhibition of human cytochrome P450 3A4 by N-[2(R)-hydroxy-1(S)-indanyl]-5-[2(S)-(1, 1-dimethylethylaminocarbonyl)-4-[(furo[2, 3-b]pyridin-5-yl)methyl]piperazin-1-yl]-4(S)-hydroxy-2(R)-phenylmethy lpentanamide and P-glycoprotein by valspodar in gene transfectant systems. Drug Metab Dispos. 2000 Oct;28(10):1238-43. PubMed PMID: 10997946.
4: Lightning LK, Jones JP, Friedberg T, Pritchard MP, Shou M, Rushmore TH, Trager WF. Mechanism-based inactivation of cytochrome P450 3A4 by L-754,394. Biochemistry. 2000 Apr 18;39(15):4276-87. PubMed PMID: 10757976.
5: Lin JH, Chen IW, Chiba M, Nishime JA, Deluna FA. Route-dependent nonlinear pharmacokinetics of a novel HIV protease inhibitor: involvement of enzyme inactivation. Drug Metab Dispos. 2000 Apr;28(4):460-6. PubMed PMID: 10725315.
6: Nishime JA, Wang RW, Lin JH, Chiba M. Modulation of rat cytochrome P-450 by an investigational HIV protease inhibitor. Drug Metab Dispos. 1999 Sep;27(9):972-6. PubMed PMID: 10460793.
7: Sahali-Sahly Y, Balani SK, Lin JH, Baillie TA. In vitro studies on the metabolic activation of the furanopyridine L-754,394, a highly potent and selective mechanism-based inhibitor of cytochrome P450 3A4. Chem Res Toxicol. 1996 Sep;9(6):1007-12. PubMed PMID: 8870989.
8: Chiba M, Nishime JA, Lin JH. Potent and selective inactivation of human liver microsomal cytochrome P-450 isoforms by L-754,394, an investigational human immune deficiency virus protease inhibitor. J Pharmacol Exp Ther. 1995 Dec;275(3):1527-34. PubMed PMID: 8531125.
9: Lin JH, Chiba M, Chen IW, Vastag KJ, Nishime JA, Dorsey BD, Michelson SR, McDaniel SL. Time- and dose-dependent pharmacokinetics of L-754,394, an HIV protease inhibitor, in rats, dogs and monkeys. J Pharmacol Exp Ther. 1995 Jul;274(1):264-9. PubMed PMID: 7616407.