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150683-30-0 molecular structure
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N-[4-(7-chloro-5-hydroxy-2,3,4,5-tetrahydro-1H-1-benzazepine-1-carbonyl)-3-methylphenyl]-2-methylbenzamide

ChemBase ID: 73268
Molecular Formular: C26H25ClN2O3
Molecular Mass: 448.9413
Monoisotopic Mass: 448.15537035
SMILES and InChIs

SMILES:
C(=O)(c1c(cc(cc1)NC(=O)c1ccccc1C)C)N1CCCC(c2c1ccc(c2)Cl)O
Canonical SMILES:
Clc1ccc2c(c1)C(O)CCCN2C(=O)c1ccc(cc1C)NC(=O)c1ccccc1C
InChI:
InChI=1S/C26H25ClN2O3/c1-16-6-3-4-7-20(16)25(31)28-19-10-11-21(17(2)14-19)26(32)29-13-5-8-24(30)22-15-18(27)9-12-23(22)29/h3-4,6-7,9-12,14-15,24,30H,5,8,13H2,1-2H3,(H,28,31)
InChIKey:
GYHCTFXIZSNGJT-UHFFFAOYSA-N

Cite this record

CBID:73268 http://www.chembase.cn/molecule-73268.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-[4-(7-chloro-5-hydroxy-2,3,4,5-tetrahydro-1H-1-benzazepine-1-carbonyl)-3-methylphenyl]-2-methylbenzamide
IUPAC Traditional name
tolvaptan
N-[4-(7-chloro-5-hydroxy-2,3,4,5-tetrahydro-1-benzazepine-1-carbonyl)-3-methylphenyl]-2-methylbenzamide
Synonyms
N-(4-(7-Chloro-5-hydroxy-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide
N-[4-[(7-Chloro-2,3,4,5-tetrahydro-5-hydroxy-1H-1-benzazepin-1-yl)carbonyl]-3-methylphenyl]-2-methylbenzamide
OPC 41061
Tolvaptan
OPC-41061
Samsca
Tolvaptan
CAS Number
150683-30-0
MDL Number
MFCD09838782
PubChem SID
162038188
PubChem CID
216237

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 11.755283  H Acceptors
H Donor LogD (pH = 5.5) 5.3501835 
LogD (pH = 7.4) 5.3501654  Log P 5.3501835 
Molar Refractivity 129.1552 cm3 Polarizability 48.183975 Å3
Polar Surface Area 69.64 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO: ≥15 mg/mL expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
white to tan powder expand Show data source
Melting Point
219-222°C expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥98% (HPLC) expand Show data source
95+% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C26H25ClN2O3 expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
Selleck Chemicals - S2593 external link
Biological Activity:
Tolvaptan (OPC-41061) is a selective, competitive arginine vasopressin receptor 2 antagonist with an IC50 of 1.28µM for the inhibition of AVP-induced platelet aggregation. Tolvaptan (OPC-41061) is used to treat hyponatremia (low blood sodium levels) associated with congestive heart failure, cirrhosis, and the syndrome of inappropriate antidiuretic hormone (SIADH). Tolvaptan (OPC-41061) is also in fast-track clinical trials for polycystic kidney disease. Treatment with t tolvaptan (OPC-41061) causes rapid and sustained body weight reductions concurrent with increases in urine output, improves and/or normalizes serum sodium in hyponatremic patients, reduces signs and symptoms of congestion and increases thirst. However, tolvaptan (OPC-41061) has not been shown to decrease heart failure re-hospitalization or mortality. As an adjunct to standard therapy, tolvaptan (OPC-41061) is unique in that it is virtually the only novel agent tested in patients hospitalized for acute heart failure syndrome (AHFS) to reach its primary end point for short-term efficacy without causing deleterious side effects. [1][2][3]References on Tolvaptan (OPC-41061)[1] http://en.wikipedia.org/wiki/Tolvaptan, , [2] Eur J Endocrinol. , 2011 Feb 11, [3] Expert Opin Pharmacother., 2011 Apr, 12(6):961-76
Sigma Aldrich - T7455 external link
Biochem/physiol Actions
Tolvaptan (OPC 41061) is a potent, orally active non-peptide vasopressin V2 selective antagonist. IC50 = 3 nM at the rat V2 receptor; 29 times more selective for the V2 than for V1a. Tolvaptan has also been shown to inhibit the development of polycystic kidney disease in several animal models.
Toronto Research Chemicals - T536650 external link
It is a selective, competitive arginine vasopressin V2 receptor antagonist used to treat hyponatremia (low blood sodium levels) associated with congestive heart failure, cirrhosis, and the syndrome of inappropriate antidiuretic hormone (SIADH).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Paterna, S., et al.: Eur. J. Heart Fail, 2, 305 (2000)
  • • Udelson, J., et al.: Circulation, 104, 2417 (2000)
  • • Goldsmith, S., et al.: J. Am. Coll Cardiol., 46, 1785 (2000)
  • • Schrier, R., et al.: N. Engl. J. Med., 355, 2099 (2000)
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PATENTS

PATENTS

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INTERNET

INTERNET

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