L 754394

    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.

Chemical Structure

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L 754394
CAS# 160729-91-9
Instruction

Theoretical Analysis

MedKoo Cat#: 596689
Name: L 754394
CAS#: 160729-91-9
Chemical Formula: C38H47N5O5
Exact Mass: 653.36
Molecular Weight: 653.820
Elemental Analysis: C, 69.81; H, 7.25; N, 10.71; O, 12.23

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 653.82 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.