satavaptan   Click here for help

GtoPdb Ligand ID: 2199

Synonyms: SR 121463A | SR-121463B | SR-121463F | SR121463A
Compound class: Synthetic organic
Comment: This compound was being tested in clinical trials for the prevention of ascites, but in 2008 the pharmaceutical company withdrew its application for marketing authorisation from the European Medicines Agency (EMA). There is some ambiguity in the literature and on other databases as to the exact stereochemistry of Satavaptan. The structure shown here matches the INN document, while the compound is represented on ChEMBL by CHEMBL2107777 and on PubChem by CID 158348.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 1
Rotatable bonds 12
Topological polar surface area 132.09
Molecular weight 643.29
XLogP 3.53
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CCOc1ccc2c(c1)C1(CCC(CC1)OCCN1CCOCC1)C(=O)N2S(=O)(=O)c1ccc(cc1OC)C(=O)NC(C)(C)C
Isomeric SMILES CCOc1ccc2c(c1)[C@@]1(CC[C@H](CC1)OCCN1CCOCC1)C(=O)N2S(=O)(=O)c1ccc(cc1OC)C(=O)NC(C)(C)C
InChI 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+
InChI Key QKXJWFOKVQWEDZ-VCCCEUOBSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
4-{[(1s,4s)-5'-Ethoxy-4-[2-(4-morpholinyl)ethoxy]-2'-oxospiro[cyclohexane-1,3'-indol]-1'(2'H)-yl]sulfonyl}-3-methoxy-N-(2-methyl-2-propanyl)benzamide
International Nonproprietary Names Click here for help
INN number INN
8591 satavaptan
Synonyms Click here for help
SR 121463A | SR-121463B | SR-121463F | SR121463A
Database Links Click here for help
CAS Registry No. 185913-78-4 (source: Scifinder)
GtoPdb PubChem SID 135651071
PubChem CID 158348
Search Google for chemical match using the InChIKey QKXJWFOKVQWEDZ-VCCCEUOBSA-N
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Search UniChem for chemical match using the InChIKey QKXJWFOKVQWEDZ-VCCCEUOBSA-N
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Wikipedia Satavaptan