SATAVAPTAN

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C33H45N3O8S
Molecular Weight	643.791
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC1=CC=C2N(C(=O)[C@@]3(CC[C@@H](CC3)OCCN4CCOCC4)C2=C1)S(=O)(=O)C5=CC=C(C=C5OC)C(=O)NC(C)(C)C

InChI

InChIKey=QKXJWFOKVQWEDZ-VCCCEUOBSA-N

InChI=1S/C33H45N3O8S/c1-6-43-25-8-9-27-26(22-25)33(13-11-24(12-14-33)44-20-17-35-15-18-42-19-16-35)31(38)36(27)45(39,40)29-10-7-23(21-28(29)41-5)30(37)34-32(2,3)4/h7-10,21-22,24H,6,11-20H2,1-5H3,(H,34,37)/t24-,33+

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24259510 / https://clinicaltrials.gov/ct2/show/NCT00359437 / https://www.ncbi.nlm.nih.gov/pubmed/11890358

Sanofi-Synthélabo has developed satavaptan (previously known as SR121463) as a non-peptidic vasopressin V2 receptor antagonist for the potential treatment for cardiovascular indications such as congestive heart failure (CHF) and hypertension. The drug reached phase II for these indications before the studies were discontinued. Satavaptan was also studied for the potential treatment of glaucoma. In addition, this drug was involved in phase III clinical trials in patients with ascites due to cirrhosis of the liver and in in patients with dilutional hyponatremia. However, the further development of the satavaptan was discontinued in 2009.

Originator

Approval Year

PubMed

Title	Date	PubMed
Successful long-term treatment of hyponatremia in syndrome of inappropriate antidiuretic hormone secretion with satavaptan (SR121463B), an orally active nonpeptide vasopressin V2-receptor antagonist.	2006-11	17699341
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.	2001-07	11429400
Binding properties of a selective tritiated vasopressin V2 receptor antagonist, [H]-SR 121463.	2000-10	11012895
Conserved aromatic residues in the transmembrane region VI of the V1a vasopressin receptor differentiate agonist vs. antagonist ligand binding.	2000-07	10866830
Receptor binding of oxytocin and vasopressin antagonists and inhibitory effects on isolated myometrium from preterm and term pregnant women.	1999-10	10519430
Pharmacological characterization of the human vasopressin receptor subtypes stably expressed in Chinese hamster ovary cells.	1998-12	9884074
Identification of residues responsible for the selective binding of peptide antagonists and agonists in the V2 vasopressin receptor.	1998-11-06	9792651
Characterization of SR 121463A, a highly potent and selective, orally active vasopressin V2 receptor antagonist.	1996-12-15	8981918

Patents

Sample Use Guides

In Vivo Use Guide

oral administration once daily

Route of Administration: Oral

Name

Type

Language

AQUILDA

Preferred Name

English

SATAVAPTAN

Official Name

English

BENZAMIDE, N-(1,1-DIMETHYLETHYL)-4-((CIS-5'-ETHOXY-4-(2-(4-MORPHOLINYL)ETHOXY)-2'-OXOSPIRO(CYCLOHEXANE-1,3'-(3H)INDOL)-1'(2'H)-YL)SULFONYL)-3-METHOXY-

Common Name

English

SR-121463

Code

English

satavaptan [INN]

Common Name

English

SATAVAPTAN [MART.]

Common Name

English

BENZAMIDE, N-(1,1-DIMETHYLETHYL)-4-((5'-ETHOXY-4-(2-(4-MORPHOLINYL)ETHOXY)-2'-OXOSPIRO(CYCLOHEXANE-1,3'-(3H)INDOL)-1'(2'H)-YL)SULFONYL)-3-METHOXY-, CIS-

Common Name

English

Satavaptan [WHO-DD]

Common Name

English

N-TERT-BUTYL-4-(((1S,4S)-5'-ETHOXY-4-(2-MORPHOLIN-4-YLETHOXY)-2'-OXOSPIRO(CYCLOHEXANE-1,3'-INDOL)-1'(2'H)-YL)SULFONYL)-3-METHOXYBENZAMIDE

Common Name

English

SR-121463A

Code

English

SR121463

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C2180