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(2S)-1-[[(2R,3S)-5-CHLORO-3-(2-CHLOROPHENYL)-1-[(3,4-DIMETHOXYPHENYL)SULFONYL]-2,3-DIHYDRO-3-HYDROXY-1H-INDOL-2-YL]CARBONYL]-2-PYRROLIDINECARBOXAMIDE

Basic information Safety Supplier Related

(2S)-1-[[(2R,3S)-5-CHLORO-3-(2-CHLOROPHENYL)-1-[(3,4-DIMETHOXYPHENYL)SULFONYL]-2,3-DIHYDRO-3-HYDROXY-1H-INDOL-2-YL]CARBONYL]-2-PYRROLIDINECARBOXAMIDE Basic information

Product Name:
(2S)-1-[[(2R,3S)-5-CHLORO-3-(2-CHLOROPHENYL)-1-[(3,4-DIMETHOXYPHENYL)SULFONYL]-2,3-DIHYDRO-3-HYDROXY-1H-INDOL-2-YL]CARBONYL]-2-PYRROLIDINECARBOXAMIDE
Synonyms:
  • (2S)-1-[[(2R,3S)-5-CHLORO-3-(2-CHLOROPHENYL)-1-[(3,4-DIMETHOXYPHENYL)SULFONYL]-2,3-DIHYDRO-3-HYDROXY-1H-INDOL-2-YL]CARBONYL]-2-PYRROLIDINECARBOXAMIDE
  • INDOL-2-YLCARBONYL)-L-PROLINAMIDE
  • Relcovaptan
  • reclovaptan
  • SR 49059
  • Relcovaptan (SR-49059)
  • 2-Pyrrolidinecarboxamide, 1-[[(2R,3S)-5-chloro-3-(2-chlorophenyl)-1-[(3,4-dimethoxyphenyl)sulfonyl]-2,3-dihydro-3-hydroxy-1H-indol-2-yl]carbonyl]-, (2S)-
CAS:
150375-75-0
MF:
C28H27Cl2N3O7S
MW:
620.5
Mol File:
150375-75-0.mol
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(2S)-1-[[(2R,3S)-5-CHLORO-3-(2-CHLOROPHENYL)-1-[(3,4-DIMETHOXYPHENYL)SULFONYL]-2,3-DIHYDRO-3-HYDROXY-1H-INDOL-2-YL]CARBONYL]-2-PYRROLIDINECARBOXAMIDE Chemical Properties

Melting point:
158-160oC
Boiling point:
868.0±75.0 °C(Predicted)
Density 
1.499±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO: ≥10mg/mL
form 
powder
pka
10.95±0.40(Predicted)
color 
white to off-white
optical activity
[α]/D -180 to -190°, c = 0.3 in chloroform-d
Stability:
Hygroscopic
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Safety Information

WGK Germany 
nwg
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(2S)-1-[[(2R,3S)-5-CHLORO-3-(2-CHLOROPHENYL)-1-[(3,4-DIMETHOXYPHENYL)SULFONYL]-2,3-DIHYDRO-3-HYDROXY-1H-INDOL-2-YL]CARBONYL]-2-PYRROLIDINECARBOXAMIDE Usage And Synthesis

Uses

Relcovaptan is a selective vasopressin-1a receptor antagonist that prevents cellular swelling and provides treatment for post-traumatic brain edema.

Definition

ChEBI: (2S)-1-[[(2R,3S)-5-chloro-3-(2-chlorophenyl)-1-(3,4-dimethoxyphenyl)sulfonyl-3-hydroxy-2H-indol-2-yl]-oxomethyl]-2-pyrrolidinecarboxamide is a proline derivative.

Biological Activity

Potent and selective non-peptide vasopressin V 1A receptor antagonist; devoid of agonist activity. Displays high affinity and efficacy at both rat (K i = 1.6 nM) and human (K i = 1.1-6.3 nM) V 1A receptors. Potently antagonizes arginine vasopressin-induced effects in vitro (IC 50 = 3.7 nM for inhibition of human platelet aggregation) and is orally active in vivo .

Biochem/physiol Actions

SR 49059 is a potent and selective Arginine Vasopressin (AVP) V1a-receptor antagonist. AVP is a hormone that plays an important part in circulatory and water homoeostasis and is important in renal hemodynamic alterations, water retention, and cardiac remodeling in congestive heart failure (CHF). There are three AVP receptor subtypes V1a, V1b, and V2. All belong to the large rhodopsin-like G-protein-coupled receptor family. V(1a) antagonists improve water balance and cardiac hypertrophy in CHF and might be beneficial for the treatment of water retention and cardiac remodeling in CHF. SR 49059 has also shown initial positive results in the treatment of Raynaud′s disease, dysmenorrhoea, and tocolysis.

storage

Store at +4°C

(2S)-1-[[(2R,3S)-5-CHLORO-3-(2-CHLOROPHENYL)-1-[(3,4-DIMETHOXYPHENYL)SULFONYL]-2,3-DIHYDRO-3-HYDROXY-1H-INDOL-2-YL]CARBONYL]-2-PYRROLIDINECARBOXAMIDESupplier

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