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S5701

Sigma-Aldrich

SR 49059

≥97% (HPLC)

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Synonym(s):
(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, SR49059
Empirical Formula (Hill Notation):
C28H27Cl2N3O7S
CAS Number:
150375-75-0
Molecular Weight:
620.50
MDL number:
MFCD00922133
UNSPSC Code:
51111800
PubChem Substance ID:
329824460
NACRES:
NA.77

Quality Level

100

Assay

≥97% (HPLC)

form

powder

optical activity

[α]/D -180 to -190°, c = 0.3 in chloroform-d

color

white to off-white

solubility

DMSO: ≥10 mg/mL

originator

Sanofi Aventis

storage temp.

2-8°C

SMILES string

COc1ccc(cc1OC)S(=O)(=O)N2[C@@H](C(=O)N3CCC[C@H]3C(N)=O)[C@@](O)(c4ccccc4Cl)c5cc(Cl)ccc25

InChI

1S/C28H27Cl2N3O7S/c1-39-23-12-10-17(15-24(23)40-2)41(37,38)33-21-11-9-16(29)14-19(21)28(36,18-6-3-4-7-20(18)30)25(33)27(35)32-13-5-8-22(32)26(31)34/h3-4,6-7,9-12,14-15,22,25,36H,5,8,13H2,1-2H3,(H2,31,34)/t22-,25-,28+/m0/s1

InChI key

CEBYCSRFKCEUSW-NAYZPBBASA-N

Gene Information

human ... AVPR1A(552) , OXTR(5021)

Application

SR 49059 has been used to study the V1AR (vasopressin type 1A receptor) signaling mediated β adrenergic receptor responsiveness and its contribution to the development of heart failure.
SR 49059 may be used in Arginine Vasopressin (AVP) V1a-receptor-mediated cell signaling studies.

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.

Features and Benefits

This compound was developed by Sanofi Aventis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

WGK

nwg

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Piotr Pierzynski
Reproductive biomedicine online, 22(1), 9-16 (2010-12-07)
Embryo transfer, the final stage of IVF/embryo transfer (IVF/ET) treatment, independently influences treatment outcome.Successful embryo implantation following embryo transfer, among other factors, is also dependant on uterine receptivity.Uterine contractile activity may adversely affect the implantation. Although increased contractions have been
Atsuo Tahara et al.
European journal of pharmacology, 538(1-3), 32-38 (2006-05-09)
Mesangial cells are centrally-located glomerular pericytes with contractile, endocrine, and immunity-regulating functions. These cells are thought to maintain normal glomerular function, since mesangial cell proliferation and extracellular matrix formation are hallmarks of chronic glomerular disease. Vasopressin causes mesangial cell contraction
Anatol Manaenko et al.
Neurochemistry international, 58(4), 542-548 (2011-01-25)
Cerebral edema is a devastating consequence of brain injury leading to cerebral blood flow compromise and worsening parenchyma damage. In the present study, we investigated the effects of arginine-vasopressin (AVP) V(1a) receptor inhibition following an intracerebral hemorrhagic (ICH) brain injury
Daniela Braida et al.
Psychopharmacology, 220(2), 319-330 (2011-10-01)
Oxytocin (OT) and arginine-vasopressin (AVP) regulate social behavior in mammals. Zebrafish (Danio rerio) allows higher throughput and ease in studying human brain disorders. This study investigated in zebrafish the effect of non-mammalian homologs isotocin (IT) and vasotocin (AVT) in comparison
Stuart R Hawtin
The Journal of biological chemistry, 281(21), 14604-14614 (2006-03-28)
Pharmacological chaperones represent a new class of ligand with the potential to facilitate the delivery of misfolded, but still active, G-protein-coupled receptors to the cell surface. Using transfected HEK 293T cells, treatment with a nonpeptide antagonist, SR49059, dramatically increased (
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