Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C28H27Cl2N3O7S |
Molecular Weight | 620.501 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(OC)C=C(C=C1)S(=O)(=O)N2[C@@H](C(=O)N3CCC[C@H]3C(N)=O)[C@](O)(C4=CC(Cl)=CC=C24)C5=C(Cl)C=CC=C5
InChI
InChIKey=CEBYCSRFKCEUSW-NAYZPBBASA-N
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
Molecular Formula | C28H27Cl2N3O7S |
Molecular Weight | 620.501 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/12436936Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/15823830 | https://www.ncbi.nlm.nih.gov/pubmed/14678081 | https://www.ncbi.nlm.nih.gov/pubmed/11035135
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12436936
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/15823830 | https://www.ncbi.nlm.nih.gov/pubmed/14678081 | https://www.ncbi.nlm.nih.gov/pubmed/11035135
Relcovaptan is a potent, orally active nonpeptide vasopressin V1a antagonist that was undergoing clinical development with Sanofi-Synthélabo (formerly Sanofi) in France. SR49059 is specifically and selectively antagonizes the effect of vasopressin on the V1a receptor in animals’ and in humans. The drug has been shown to have an excellent safety profile in single and repeated dose toxicological studies in animals. In the human uterus in vitro, SR49059 caused a dose-dependent inhibition of vasopressin V1a receptor-mediated activity of myometrial strips and isolated uterine arteries. In vivo in nonpregnant women, an inhibition of vasopressin-induced uterine activity has been observed.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1889 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21885275 |
13.0 nM [IC50] | ||
Target ID: CHEMBL1790 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12036368 |
178.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Binding of [3H] SR 49059, a potent nonpeptide vasopressin V1a antagonist, to rat and human liver membranes. | 1994 Feb 28 |
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Mapping peptide-binding domains of the human V1a vasopressin receptor with a photoactivatable linear peptide antagonist. | 1997 Oct 17 |
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Pharmacological characterization of the human vasopressin receptor subtypes stably expressed in Chinese hamster ovary cells. | 1998 Dec |
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Receptor binding of oxytocin and vasopressin antagonists and inhibitory effects on isolated myometrium from preterm and term pregnant women. | 1999 Oct |
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Vasopressin does not effect hypertension caused by long-term nitric oxide inhibition. | 2000 Feb |
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Conserved aromatic residues in the transmembrane region VI of the V1a vasopressin receptor differentiate agonist vs. antagonist ligand binding. | 2000 Jul |
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Binding properties of a selective tritiated vasopressin V2 receptor antagonist, [H]-SR 121463. | 2000 Oct |
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High concentrations of oxytocin cause vasoconstriction by activating vasopressin V1A receptors in the isolated perfused rat kidney. | 2001 Apr |
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Effects of YM471, a nonpeptide AVP V(1A) and V(2) receptor antagonist, on human AVP receptor subtypes expressed in CHO cells and oxytocin receptors in human uterine smooth muscle cells. | 2001 Jul |
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Vasopressin-induced facilitation of adrenergic responses in the rat mesenteric artery is V1-receptor dependent. | 2003 Feb |
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Oxytocin and fetal membranes in preterm labor: current concepts and clinical implication. | 2003 Jun |
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Identification of the binding sites of the SR49059 nonpeptide antagonist into the V1a vasopressin receptor using sulfydryl-reactive ligands and cysteine mutants as chemical sensors. | 2003 Oct 10 |
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Vasotocin and vasopressin stimulation of the chloride secretion in the human bronchial epithelial cell line, 16HBE14o-. | 2005 Apr |
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The effect of relcovaptan (SR 49059), an orally active vasopressin V1a receptor antagonist, on uterine contractions in preterm labor. | 2005 Feb |
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Pharmacologic properties of YM218, a novel, potent, nonpeptide vasopressin V1A receptor-selective antagonist. | 2005 Jan |
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Selectivity of d[Cha4]AVP and SSR149415 at human vasopressin and oxytocin receptors: evidence that SSR149415 is a mixed vasopressin V1b/oxytocin receptor antagonist. | 2005 Nov |
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Protective effect of the V1a receptor antagonist SR49059 on brain edema formation following middle cerebral artery occlusion in the rat. | 2006 |
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Vasopressin receptor antagonists: pharmacological tools and potential therapeutic agents. | 2006 Apr |
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Evidence for a role of vasopressin in the control of aldosterone secretion in primary aldosteronism: in vitro and in vivo studies. | 2006 Apr |
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Pharmacologic chaperones as a potential treatment for X-linked nephrogenic diabetes insipidus. | 2006 Jan |
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Pharmacological chaperone activity of SR49059 to functionally recover misfolded mutations of the vasopressin V1a receptor. | 2006 May 26 |
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Functional rescue of vasopressin V2 receptor mutants in MDCK cells by pharmacochaperones: relevance to therapy of nephrogenic diabetes insipidus. | 2007 Jan |
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The modulation of aquaporin-4 by using PKC-activator (phorbol myristate acetate) and V1a receptor antagonist (SR49059) following middle cerebral artery occlusion/reperfusion in the rat. | 2008 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14678081
25, 75 or 200 mg
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16926443
MDCK II cells were seeded on 12 multiwell filters (Costar) at a density of 150,000 cells/cm2 and grown for 3 days. Cells were subsequently treated with the antagonists for 16 h, followed by three washes with ice-cold phosphate-buffered saline containing 1 mM MgCl2 and 0.1 mM CaCl2 (PBS-CM). The cells were then incubated for 1 h on ice with [3H]AVP (PerkinElmer Life Sciences, Boston, MA) and the antagonist (Relcovaptan) diluted in PBS-CM. Cells were washed three times with ice-cold PBS-CM, followed by excision of the filters and counting of the radioactivity
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 16:48:32 UTC 2023
by
admin
on
Sat Dec 16 16:48:32 UTC 2023
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Record UNII |
C1GL8G6G0O
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Record Status |
Validated (UNII)
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Record Version |
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-
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NCI_THESAURUS |
C2180
Created by
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Code System | Code | Type | Description | ||
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RELCOVAPTAN
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7809
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60943
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C1497
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300000034447
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150375-75-0
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C1GL8G6G0O
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CHEMBL419667
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DTXSID1045746
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DB13929
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
BINDING
IC50
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TARGET -> INHIBITOR |
BINDING
IC50
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TARGET -> INHIBITOR |
Ki
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TARGET->WEAK INHIBITOR |
BINDING
IC50
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TARGET -> INHIBITOR |
AVP-induced human platelet aggregation.
IC50
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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