Mozavaptan

Names

[ Name ]:
Mozavaptan

[Synonym ]:
5-dimethylamino-1-[4-[(2-methylbenzoyl)amino]benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine
N-(4-(((5RS)-5-(Dimethylamino)-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl)phenyl)-2-methylbenzamide
Mozavaptan
Mozavaptan [INN]
N-(4-((5-(Dimethylamino)-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl)phenyl)-2-methylbenzamide
(+/-)-5-dimethylamino-1-[4-(2-methylbenzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzazepin
Benzamide,N-(4-((5-(dimethylamino)-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl)phenyl)-2-methyl
N-(4-{[5-(Dimethylamino)-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl]carbonyl}phenyl)-2-methylbenzamide
Benzamide, N-[4-[[5-(dimethylamino)-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl]carbonyl]phenyl]-2-methyl-

Biological Activity

[Description]:

Mozavaptan (OPC31260) is a orally effective, nonpeptide vasopressin V2 receptor antagonist with an IC50 of 14 nM.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Vasopressin Receptor

Research Areas >> Cancer

[Target]

IC50: 14 nM (vasopressin receptor)[1]

[In Vitro]

Mozavaptan causes a competitive displacement of [3H]-arginine vasopressin (AVP) binding to both V1 and V2 receptors with IC50 values of 1.2 μM and 14 nM, respectively. The Kd of [3H]-AVP is reduced significantly in both rat liver and kidney in the presence of mozavaptan (Kd=1.1 nM in liver, Kd=1.38 nM in kidney)[1].

[In Vivo]

Mozavaptan at doses of 10 to 100 μg/kg, i.v., inhibits the antidiuretic action of exogenously administered arginine vasopressin in water-loaded, alcohol-anaesthetized rats in a dose-dependent manner. Mozavaptan does not exert an antidiuretic activity suggesting that it is not a partial V2 receptor agonist. Mozavaptan dose-dependently increases urine flow and decreases urine osmolality after oral administration at doses of 1 to 30 mg/kg in normal conscious rats[1].

[Kinase Assay]

To determine binding kinetic constants, liver or kidney plasma membranes are incubated with increasing concentrations of [3H]-AVP with or without excess (1 μM) unlabelled AVP to obtain a saturation curve. To investigate whether mozavaptan interacts competitively or noncompetitively, the saturation binding of [3H]-AVP is examined in the absence and presence of mozavaptan at concentrations of 0.3 μM and 1 μM in liver membranes and 3 nM, and 10 nM in kidney membranes. Data on the saturation curve are plotted according to the method of Scatchard and fitted by a regression analysis[1].

[Animal admin]

Rats: Mozavaptan is dissolved in DMSO at a concentration of 10 mM and diluted with assay buffer. Female Brattleboro rats homozygous for hypothalamic diabetes insipidus and weighing between 180 and 280g are used. Mozavaptan (30 mg/kg) and vehicle (5% gum arabic) are administered orally in a volume of 2 mL/kg and d(CH2)5Tyr(Et)VAVP (10pgkg-1) is administered in a volume of 1 mL/kg. Spontaneously voided urine is collected for 6h with metabolic cages. Both before and during the study, the rats received water and food ad libitum[1].

[References]

[1]. Yamamura Y, et al. Characterization of a novel aquaretic agent, OPC-31260, as an orally effective, nonpeptide vasopressin V2 receptor antagonist. Br J Pharmacol. 1992 Apr;105(4):787-91.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
543.0±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₇H₂₉N₃O₂

[ Molecular Weight ]:
427.538

[ Flash Point ]:
282.2±30.1 °C

[ Exact Mass ]:
427.225983

[ PSA ]:
52.65000

[ LogP ]:
3.83

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.647

Safety Information

[ Hazard Codes ]:
Xi

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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