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S5701

SR 49059

Name: SR 49059
Brand: SIGMA

≥97% (HPLC), Arginine Vasopressin (AVP) V1a-receptor antagonist, powder

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

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About This Item

Empirical Formula (Hill Notation):

C₂₈H₂₇Cl₂N₃O₇S

CAS Number:

150375-75-0

Molecular Weight:

620.50

UNSPSC Code:

51111800

PubChem Substance ID:

329824460

NACRES:

NA.77

MDL number:

MFCD00922133

Assay:

≥97% (HPLC)

Form:

powder

Quality level:

100

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Properties

Product Name

SR 49059, ≥97% (HPLC)

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)

Description

Application

SR 49059 may be used in Arginine Vasopressin (AVP) V1a-receptor-mediated cell signaling studies.

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.

Biochem/physiol Actions

SR 49059 is a potent and selective Arginine Vasopressin (AVP) V1a-receptor antagonist.

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.

Storage Class

11 - Combustible Solids

wgk

nwg

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number

026M4758V

052M4613V

040M4607

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cAMP/PKA-dependent increases in Ca Sparks, oscillations and SR Ca stores in retinal arteriolar myocytes after exposure to vasopressin.

Owen Jeffries et al.

Investigative ophthalmology & visual science, 51(3), 1591-1598 (2009-12-05)

To investigate the effects of arginine vasopressin (AVP) on Ca(2+) sparks and oscillations and on sarcoplasmic reticulum (SR) Ca(2+) content in retinal arteriolar myocytes. Fluo-4-loaded smooth muscle in intact segments of freshly isolated porcine retinal arteriole was imaged by confocal

The effect of relcovaptan (SR 49059), an orally active vasopressin V1a receptor antagonist, on uterine contractions in preterm labor.

Margareta Steinwall et al.

Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology, 20(2), 104-109 (2005-04-13)

Relcovaptan (SR 49059) is a non-peptide, orally active vasopressin V1a receptor inhibitor. The effect on uterine contractions in 18 women with preterm labor in pregnancy weeks 32-36 was assessed in a double-blind investigation. The inclusion criterion was at least four

Evidence for a role of vasopressin in the control of aldosterone secretion in primary aldosteronism: in vitro and in vivo studies.

Véronique Perraudin et al.

The Journal of clinical endocrinology and metabolism, 91(4), 1566-1572 (2006-02-02)

Arginine vasopressin (AVP) stimulates steroid secretion from the normal human adrenal gland and some cortisol-producing adrenocortical tumors or hyperplasia through activation of the V(1a) receptor. The objective of the study was to investigate in vitro and in vivo the possible

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Global Trade Item Number

SKU	GTIN
S5701-25MG	04061832867847
S5701-5MG	04061832867854