Lixazinone | CAS#94192-59-3 | cAMP PDE inhibitor

MedKoo Cat#: 599047 | Name: Lixazinone

Description:

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

Lixazinone is a cyclic AMP phosphodiesterase (cAMP PDE) inhibitor and cardiotonic agent.

Chemical Structure

Lixazinone

CAS#94192-59-3 (free base)

Theoretical Analysis

MedKoo Cat#: 599047

Name: Lixazinone

CAS#: 94192-59-3 (free base)

Chemical Formula: C21H28N4O3

Exact Mass: 384.2161

Molecular Weight: 384.48

Elemental Analysis: C, 65.60; H, 7.34; N, 14.57; O, 12.48

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 #

101626-67-9 (sulfate) 94192-59-3 (free base) 108609-34-3 (sulfate anhydrous)

Synonym

Lixazinone; Lixazinonum;

IUPAC/Chemical Name

N-cyclohexyl-N-methyl-4-((2-oxo-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-7-yl)oxy)butanamide

InChi Key

WUECXCBONAGRSA-UHFFFAOYSA-N

InChi Code

InChI=1S/C21H28N4O3/c1-24(16-6-3-2-4-7-16)20(27)8-5-11-28-17-9-10-18-15(12-17)13-25-14-19(26)23-21(25)22-18/h9-10,12,16H,2-8,11,13-14H2,1H3,(H,22,23,26)

SMILES Code

O=C(N(C1CCCCC1)C)CCCOC2=CC3=C(N=C(NC(C4)=O)N4C3)C=C2

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

>3 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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 384.48 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: Cheng J, Thompson MA, Walker HJ, Gray CE, Warner GM, Zhou W, Grande JP. Lixazinone stimulates mitogenesis of Madin-Darby canine kidney cells. Exp Biol Med (Maywood). 2006 Mar;231(3):288-95. PubMed PMID: 16514175. 2: Venuti MC, Alvarez R, Bruno JJ, Strosberg AM, Gu L, Chiang HS, Massey IJ, Chu N, Fried JH. Inhibitors of cyclic AMP phosphodiesterase. 4. Synthesis and evaluation of potential prodrugs of lixazinone (N-cyclohexyl-N-methyl-4-[(1,2,3,5-tetrahydro-2- oxoimidazo[2,1-b]quinazolin-7-yl)-oxy]butyramide, RS-82856). J Med Chem. 1988 Nov;31(11):2145-52. PubMed PMID: 2846840. 3: Venuti MC, Stephenson RA, Alvarez R, Bruno JJ, Strosberg AM. Inhibitors of cyclic AMP phosphodiesterase. 3. Synthesis and biological evaluation of pyrido and imidazolyl analogues of 1,2,3,5-tetrahydro-2-oxoimidazo[2,1-b]quinazoline. J Med Chem. 1988 Nov;31(11):2136-45. PubMed PMID: 2846839. 4: Kenan Y, Murata T, Shakur Y, Degerman E, Manganiello VC. Functions of the N-terminal region of cyclic nucleotide phosphodiesterase 3 (PDE 3) isoforms. J Biol Chem. 2000 Apr 21;275(16):12331-8. PubMed PMID: 10766874. 5: Dickinson NT, Jang EK, Haslam RJ. Activation of cGMP-stimulated phosphodiesterase by nitroprusside limits cAMP accumulation in human platelets: effects on platelet aggregation. Biochem J. 1997 Apr 15;323 ( Pt 2):371-7. PubMed PMID: 9163326; PubMed Central PMCID: PMC1218329. 6: Matousovic K, Tsuboi Y, Walker H, Grande JP, Dousa TP. Inhibitors of cyclic nucleotide phosphodiesterase isozymes block renal tubular cell proliferation induced by folic acid. J Lab Clin Med. 1997 Nov;130(5):487-95. PubMed PMID: 9390636. 7: Dousa TP. Signaling role of PDE isozymes in pathobiology of glomerular mesangial cells. Studies in vitro and in vivo. Cell Biochem Biophys. 1998;29(1-2):19-34. PubMed PMID: 9631236. 8: Chini CC, Grande JP, Chini EN, Dousa TP. Compartmentalization of cAMP signaling in mesangial cells by phosphodiesterase isozymes PDE3 and PDE4. Regulation of superoxidation and mitogenesis. J Biol Chem. 1997 Apr 11;272(15):9854-9. PubMed PMID: 9092521. 9: Tang KM, Jang EK, Haslam RJ. Photoaffinity labelling of cyclic GMP-inhibited phosphodiesterase (PDE III) in human and rat platelets and rat tissues: effects of phosphodiesterase inhibitors. Eur J Pharmacol. 1994 Jun 15;268(1):105-14. PubMed PMID: 7925608. 10: Tsuboi Y, Shankland SJ, Grande JP, Walker HJ, Johnson RJ, Dousa TP. Suppression of mesangial proliferative glomerulonephritis development in rats by inhibitors of cAMP phosphodiesterase isozymes types III and IV. J Clin Invest. 1996 Jul 15;98(2):262-70. PubMed PMID: 8755633; PubMed Central PMCID: PMC507426. 11: Visor GC, Lin LH, Benjamin E, Strickley RG, Gu L. Parenteral formulation development for the positive inotropic agent RS-82856: solubility and stability enhancement through complexation and lyophilization. J Parenter Sci Technol. 1987 Jul-Aug;41(4):120-5. PubMed PMID: 3668754. 12: Tang KM, Jang EK, Haslam RJ. Expression and mutagenesis of the catalytic domain of cGMP-inhibited phosphodiesterase (PDE3) cloned from human platelets. Biochem J. 1997 Apr 1;323 ( Pt 1):217-24. PubMed PMID: 9173884; PubMed Central PMCID: PMC1218297. 13: Strosberg AM, Johnson L, Montgomery W, Lee CH, Alvarez R, Bruno JJ, Jones GH, Venuti MC. RS-82856, a selective phosphodiesterase inhibitor with inotropic, afterload reduction and antithrombotic properties. Proc West Pharmacol Soc. 1987;30:5-10. PubMed PMID: 3628319. 14: Alvarez R, Banerjee GL, Bruno JJ, Jones GL, Littschwager K, Strosberg AM, Venuti MC. A potent and selective inhibitor of cyclic AMP phosphodiesterase with potential cardiotonic and antithrombotic properties. Mol Pharmacol. 1986 Jun;29(6):554-60. PubMed PMID: 3012320. 15: Visor GC, Lin LH, Kenley RA, Venuti MC, Alvarez R. Electrochemical evaluation of the interaction between ascorbic acid and the cardiotonic drug RS-82856. Drug Des Deliv. 1987 Dec;2(2):121-8. PubMed PMID: 2855568. 16: Venuti MC, Jones GH, Alvarez R, Bruno JJ. Inhibitors of cyclic AMP phosphodiesterase. 2. Structural variations of N-cyclohexyl-N-methyl-4-[(1,2,3,5-tetrahydro- 2-oxoimidazo[2,1-b]quinazolin-7-yl)-oxy]butyramide (RS-82856). J Med Chem. 1987 Feb;30(2):303-18. PubMed PMID: 3027339. 17: Artman M, Robertson DW, Mahony L, Thompson WJ. Analysis of the binding sites for the cardiotonic phosphodiesterase inhibitor [3H]LY186126 in ventricular myocardium. Mol Pharmacol. 1989 Aug;36(2):302-11. PubMed PMID: 2505059. 18: Matousovic K, Grande JP, Chini CC, Chini EN, Dousa TP. Inhibitors of cyclic nucleotide phosphodiesterase isozymes type-III and type-IV suppress mitogenesis of rat mesangial cells. J Clin Invest. 1995 Jul;96(1):401-10. PubMed PMID: 7615811; PubMed Central PMCID: PMC185213.