(2S,4R)-1-[(R)-5-CHLORO-1-(2,4-DIMETHOXY-BENZENESULFONYL)-3-(2-METHOXY-PHENYL)-2-OXO-2,3-DIHYDRO-1H-INDOL-3-YL]-4-HYDROXY-PYRROLIDINE-2-CARBOXYLIC ACID DIMETHYLAMIDE CAS#: 439687-69-1

(2S,4R)-1-[(R)-5-CHLORO-1-(2,4-DIMETHOXY-BENZENESULFONYL)-3-(2-METHOXY-PHENYL)-2-OXO-2,3-DIHYDRO-1H-INDOL-3-YL]-4-HYDROXY-PYRROLIDINE-2-CARBOXYLIC ACID DIMETHYLAMIDE Basic information

Product Name:

(2S,4R)-1-[(R)-5-CHLORO-1-(2,4-DIMETHOXY-BENZENESULFONYL)-3-(2-METHOXY-PHENYL)-2-OXO-2,3-DIHYDRO-1H-INDOL-3-YL]-4-HYDROXY-PYRROLIDINE-2-CARBOXYLIC ACID DIMETHYLAMIDE

Synonyms:

(2S,4R)-1-[(R)-5-CHLORO-1-(2,4-DIMETHOXY-BENZENESULFONYL)-3-(2-METHOXY-PHENYL)-2-OXO-2,3-DIHYDRO-1H-INDOL-3-YL]-4-HYDROXY-PYRROLIDINE-2-CARBOXYLIC ACID DIMETHYLAMIDE
2-PYRROLIDINECARBOXAMIDE, 1-[(3R)-5-CHLORO-1-[(2,4-DIMETHOXYPHENYL)SULFONYL]-2,3-DIHYDRO-3-(2-METHOXYPHENYL)-2-OXO-1H-INDOL-3-YL]-4-HYDROXY-N,N-DIMETHYL-, (2S,4R)-
Nelivaptan
Nelivaptan(SSR-149,415)
(2S,4R)-1-[(3R)-5-chloro-1-(2,4-dimethoxyphenyl)sulfonyl-3-(2-methoxyphenyl)-2-oxoindol-3-yl]-4-hydroxy-N,N-dimethylpyrrolidine-2-carboxamide
SSR 149415
(2S,4R)-1-[(3R)-5-Chloro-1-[(2,4-dimethoxyphenyl)sulfonyl]-2,3-dihydro-3-(2-methoxyphenyl)-2-oxo-1H-indol-3-yl]-4-hydroxy-N,N-dimethyl-2-pyrrolidinecarboxamide
SSR 149415 - Nelivaptan

CAS:

439687-69-1

MF:

C30H32ClN3O8S

MW:

630.11

Mol File:

439687-69-1.mol

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(2S,4R)-1-[(R)-5-CHLORO-1-(2,4-DIMETHOXY-BENZENESULFONYL)-3-(2-METHOXY-PHENYL)-2-OXO-2,3-DIHYDRO-1H-INDOL-3-YL]-4-HYDROXY-PYRROLIDINE-2-CARBOXYLIC ACID DIMETHYLAMIDE Chemical Properties

Boiling point:: 799.7±70.0 °C(Predicted)
Density: 1.414±0.06 g/cm3(Predicted)
storage temp.: Store at -20°C
solubility: 63.01mg/ml in DMSO; 63.01mg/ml in ethanol
pka: 14.14±0.40(Predicted)
form: Solid
color: White to off-white

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(2S,4R)-1-[(R)-5-CHLORO-1-(2,4-DIMETHOXY-BENZENESULFONYL)-3-(2-METHOXY-PHENYL)-2-OXO-2,3-DIHYDRO-1H-INDOL-3-YL]-4-HYDROXY-PYRROLIDINE-2-CARBOXYLIC ACID DIMETHYLAMIDE Usage And Synthesis

Uses

SSR 149415 is a vasopressin V1b receptor antagonist.

Biological Activity

SSR149415 is an orally active, selective vasopressin V1b receptor antagonist (human/r at Ki in nM = 1.5/1.3/V1b, 91/1050/V1a, 1412/2897/V2, 174/270/OT) th at inhibits 30 nM AVP-induced Ca2+ response in human and r at V1b CHO transfectants (Ki = 1.26/2.0 nM). SSR149415 suppresses AVP-mediated physiological responses in vivo, including corticotropin secretion (1-30 mg/kg p.o. or i.p. in rats) upon exogenous AVP administration (0.3 μg/kg alone or 0.03 μg/kg with 0.1 μg corticoliberin/kg via i.v.), restraint stress-Induced corticotropin secretion (EC50 = 10 mg/kg i.p. in rats), and in a murine model of anxiety (four-plate test; 1-10 mg/kg i.p. or 3-10 mg/kg p.o. acute or 10 mg/kg/day p.o.).

in vivo

Nelivaptan (1-30 mg/kg; 30 min i.p. or 2 h p.o. before an exogenous AVP injection) inhibits exogenous AVP-induced increase in plasma corticotropin in Sprague-Dawley rats^[1].
Nelivaptan (1-10 mg/kg; p.o.; 1, 2, 3, 4, and 6 h before the AVP challenge) produces powerful dose-dependent inhibition of the corticotropin increase in response to exogenous AVP plus corticotropin-releasing factor (CRF) in Sprague-Dawley rats^[1].
Nelivaptan (1-10 mg/kg; i.p. 30 min or 60 min before test; or p.o. for 7 days) displays anxiolytic-like activity after acute and 7-day repeated administrations in male NMRI mice ^[1].
Nelivaptan (30 mg/kg; i.p.; daily for two weeks) retains efficacy in reducing both measured indices of depression-like behavior (learned helplessness and anhedonia), even when neurogenesis is blocked in male Wistar rats with chronic mild stress^[2].

Animal Model:	Male Wistar rats (300-400 g, aged 3 months) with chronic mild stress^[2]
Dosage:	30 mg/kg
Administration:	Intraperitoneal injection (i.p.); daily for two weeks
Result:	Chronic administration reversed learned helplessness and anhedonia even when methylazoxymethanol (MAM) was administered. Attenuated these depressive-like behaviors after 1 week. Restored the density of Ki-67-positive cells to control levels.

Animal Model:	Male Sprague-Dawley CD rats (275-300 g)^[1]
Dosage:	1, 3, 10, 30 mg/kg
Administration:	Intraperitoneal injection (i.p.) or Oral gavage (p.o.); 30 min i.p. or 2 h p.o. before an exogenous AVP injection
Result:	Antagonized AVP-induced corticotropin secretion in a dose-dependent manner by both intraperitoneal and oral routes. The inhibition was significant from 10 mg/kg p.o. and 3 mg/kg i.p. upwards. The inhibitory action lasted significantly for more than 2 h at 10 mg/kg i.p. and up to 4 h at 10 mg/kg p.o.. Had no effect on basal corticotropin plasma levels up to 30 mg/kg p.o..

Animal Model:	Male Sprague-Dawley CD rats (275-300 g)^[1]
Dosage:	1, 3, 10 mg/kg
Administration:	Oral gavage (p.o.); 1, 2, 3, 4, and 6 h before the AVP challenge (10 mg/kg)
Result:	Produced powerful dose-dependent inhibition of the corticotropin increase in response to exogenous AVP plus corticoliberin; the effect was significant from the dose of 3 mg/kg p.o.. Complete blockade was achieved at 10 mg/kg. Showed a fast onset of action, the inhibitory effect was maximal at 1 h after administration. The inhibitory effect on corticotropin secretion lasted significantly more than 4 h, demonstrating a long-lasting oral effect in a specific V_1b-related model.

Animal Model:	Male NMRI mice (20 g)^[1]
Dosage:	1, 3, 10 mg/kg
Administration:	Intraperitoneal injection (i.p.) or Oral gavage (p.o.); i.p. (1, 3, 10 mg/kg) 30 min or 60 min befeore; p.o. (10 mg/kg) for 7 days,
Result:	In the acute experiments, i.p. and p.o. compound increased the number of punished crossings showing marked anxiolytic effects. Post hoc analysis revealed that these effects reached statistical significance from 3 mg/kg p.o. and i.p. The anxiolytic-like activity was still significantly maintained when given repeatedly at 10 mg/kg p.o. for 7 days. The oral time course of the anxiolytic-like action performed at 10 mg/kg indicated that effects lasted for more than 4 h.

storage

Store at -20°C

(2S,4R)-1-[(R)-5-CHLORO-1-(2,4-DIMETHOXY-BENZENESULFONYL)-3-(2-METHOXY-PHENYL)-2-OXO-2,3-DIHYDRO-1H-INDOL-3-YL]-4-HYDROXY-PYRROLIDINE-2-CARBOXYLIC ACID DIMETHYLAMIDESupplier

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(2S,4R)-1-[(R)-5-CHLORO-1-(2,4-DIMETHOXY-BENZENESULFONYL)-3-(2-METHOXY-PHENYL)-2-OXO-2,3-DIHYDRO-1H-INDOL-3-YL]-4-HYDROXY-PYRROLIDINE-2-CARBOXYLIC ACID DIMETHYLAMIDE(439687-69-1)Related Product Information