LIXAZINONE SULFATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H28N4O3.H2O.H2O4S
Molecular Weight	500.566
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.OS(O)(=O)=O.CN(C1CCCCC1)C(=O)CCCOC2=CC=C3NC4=NC(=O)CN4CC3=C2

InChI

InChIKey=IXJGUUXNDBSBPT-UHFFFAOYSA-N

InChI=1S/C21H28N4O3.H2O4S.H2O/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;1-5(2,3)4;/h9-10,12,16H,2-8,11,13-14H2,1H3,(H,22,23,26);(H2,1,2,3,4);1H2

HIDE SMILES / InChI

Molecular Formula	H2O4S
Molecular Weight	98.078
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C21H28N4O3
Molecular Weight	384.472
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://adisinsight.springer.com/drugs/800000346 | https://www.ncbi.nlm.nih.gov/pubmed/16514175 | https://www.ncbi.nlm.nih.gov/pubmed/3012320

Lixazinone selectively inhibits the high-affinity form of cyclic AMP phosphodiesterase (type IV) isolated from human platelets with only weak effects on both the nonspecific and cyclic GMP-sensitive phosphodiesterases. The inhibitor reduces both maximum velocity and substrate affinity of the type IV enzyme. Lixazinone exhibits marked selectively for the platelet high-affinity enzyme. It also has significant inhibitory effects on cardiac membrane-bound phosphodiesterase. Lixazinone may be useful as an agent to increase cardiac output in the treatment of congestive heart failure. It is a potent PDE3 inhibitor. Lixazinone suppresses folic acid-induced proliferation of rat tubular epithelial cells in vivo.

Approval Year

PubMed

Title	Date	PubMed
A potent and selective inhibitor of cyclic AMP phosphodiesterase with potential cardiotonic and antithrombotic properties.	1986 Jun	3012320
RS-82856, a selective phosphodiesterase inhibitor with inotropic, afterload reduction and antithrombotic properties.	1987	3628319
Electrochemical evaluation of the interaction between ascorbic acid and the cardiotonic drug RS-82856.	1987 Dec	2855568
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).	1987 Feb	3027339
Parenteral formulation development for the positive inotropic agent RS-82856: solubility and stability enhancement through complexation and lyophilization.	1987 Jul-Aug	3668754
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).	1988 Nov	2846840
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.	1988 Nov	2846839
Analysis of the binding sites for the cardiotonic phosphodiesterase inhibitor [3H]LY186126 in ventricular myocardium.	1989 Aug	2505059
Photoaffinity labelling of cyclic GMP-inhibited phosphodiesterase (PDE III) in human and rat platelets and rat tissues: effects of phosphodiesterase inhibitors.	1994 Jun 15	7925608
Inhibitors of cyclic nucleotide phosphodiesterase isozymes type-III and type-IV suppress mitogenesis of rat mesangial cells.	1995 Jul	7615811
Suppression of mesangial proliferative glomerulonephritis development in rats by inhibitors of cAMP phosphodiesterase isozymes types III and IV.	1996 Jul 15	8755633
Expression and mutagenesis of the catalytic domain of cGMP-inhibited phosphodiesterase (PDE3) cloned from human platelets.	1997 Apr 1	9173884
Compartmentalization of cAMP signaling in mesangial cells by phosphodiesterase isozymes PDE3 and PDE4. Regulation of superoxidation and mitogenesis.	1997 Apr 11	9092521
Activation of cGMP-stimulated phosphodiesterase by nitroprusside limits cAMP accumulation in human platelets: effects on platelet aggregation.	1997 Apr 15	9163326
Inhibitors of cyclic nucleotide phosphodiesterase isozymes block renal tubular cell proliferation induced by folic acid.	1997 Nov	9390636
Signaling role of PDE isozymes in pathobiology of glomerular mesangial cells. Studies in vitro and in vivo.	1998	9631236
Functions of the N-terminal region of cyclic nucleotide phosphodiesterase 3 (PDE 3) isoforms.	2000 Apr 21	10766874
Lixazinone stimulates mitogenesis of Madin-Darby canine kidney cells.	2006 Mar	16514175

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:43:45 GMT 2023` Edited by `admin` on `Fri Dec 15 15:43:45 GMT 2023`
Record UNII	50S40MPD5U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LIXAZINONE SULFATE

Official Name

English

LIXAZINONE SULFATE [USAN]

Common Name

English

RS-82856

Code

English

N-CYCLOHEXYL-N-METHYL-4-((1,2,3,5-TETRAHYDRO-2-OXOIMIDAZO(2,1-B)QUINAZOLIN-7-YL)OXY)BUTYRAMIDE SULPHATE (1:1), MONOHYDRATE

Common Name

English

LIXAZINONE SULPHATE

Common Name

English

N-Cyclohexyl-N-methyl-4-[(1,2,3,5-tetrahydro-2-oxoimidazo[2,1-b]quinazolin-7-yl)oxy]butyramide sulfate (1:1), monohydrate

Common Name

English

BUTANAMIDE, N-CYCLOHEXYL-N-METHYL-4-((1,2,3,5-TETRAHYDRO-2-OXOIMIDAZO(2,1-B)QUINAZOLIN-7-YL)OXY)-, SULFATE, HYDRATE (1:1:1)

Systematic Name

English

BUTANAMIDE, N-CYCLOHEXYL-N-METHYL-4-((1,2,3,5-TETRAHYDRO-2-OXOIMIDAZO(2,1-B)QUINAZOLIN-7-YL)OXY)-, SULFATE (1:1), MONOHYDRATE

Common Name

English

BUTANAMIDE, N-CYCLOHEXYL-N-METHYL-4-((1,2,3,5-TETRAHYDRO-2-OXOIMIDAZO(2,1-B)QUINAZOLIN-7-YL)OXY)-, SULPHATE (1:1), MONOHYDRATE

Common Name

English

Code System Code Type Description

FDA UNII

50S40MPD5U