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: 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 150683-30-0
• MDL Number: MFCD09838782
• PubChem SID: 162038188
• PubChem CID: 216237

CALCULATED PROPERTIES

• Acid pKa: 11.755283
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.3501835
• LogD (pH = 7.4): 5.3501654
• Log P: 5.3501835
• Molar Refractivity: 129.1552 cm^3
• Polarizability: 48.183975 Å^3
• Polar Surface Area: 69.64 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥15 mg/mL; Methanol
• Apperance: White Solid; white to tan powder
• Melting Point: 219-222°C

Safety Information

• Storage Condition: -20°C; Refrigerator
• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC); 95+%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C26H25ClN2O3

DETAILS

Selleck Chemicals - S2593

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

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

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

• 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)