Tolvaptan
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| Systematic (IUPAC) name | |
| N-(4-{[(5R)-7-chloro-5-hydroxy-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl]carbonyl}-3-methylphenyl)-2-methylbenzamide | |
| Clinical data | |
| Trade names | Samsca |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a609033 |
| Licence data | US FDA:link |
| Pregnancy cat. | C(US) |
| Legal status | ℞-only (US) |
| Routes | Oral |
| Pharmacokinetic data | |
| Bioavailability | Unknown (40% absorbed) |
| Protein binding | 99% |
| Metabolism | Hepatic (CYP3A4-mediated)[1] |
| Half-life | 12 hours (terminal) |
| Identifiers | |
| CAS number | 150683-30-0  |
| ATC code | C03XA01 |
| PubChem | CID 216237 |
| ChemSpider | 187438  |
| UNII | 21G72T1950 |
| ChEMBL | CHEMBL344159 |
| Synonyms | N-{4-[(6R)-9-chloro-6-hydroxy-2-azabicyclo[5.4.0]undeca-8,10,12-triene-2-carbonyl]-3-methyl-phenyl}-2-methyl-benzamide |
| Chemical data | |
| Formula | C26H25ClN2O3 |
| Mol. mass | 448.941 g/mol |
| SMILES | eMolecules & PubChem |
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Tolvaptan (INN), also known as OPC-41061, is a selective, competitive vasopressin receptor 2 antagonist used to treat hyponatremia (low blood sodium levels) associated with congestive heart failure, cirrhosis, and the syndrome of inappropriate antidiuretic hormone (SIADH). Tolvaptan was approved by the U.S. Food and Drug Administration on May 19, 2009, and is sold by Otsuka Pharmaceutical Co. under the trade name Samsca.
Tolvaptan is also in fast-track clinical trials[2] for polycystic kidney disease. In a 2004 trial, tolvaptan, when administered with traditional diuretics, was noted to increase excretion of excess fluids and improve blood sodium levels in patients with heart failure without producing side effects such as hypotension (low blood pressure) or hypokalemia (decreased blood levels of potassium) and without having an adverse effect on kidney function.[3]
[edit] Chemistry
Chemical synthesis:[4]
[edit] References
- ^ Shoaf S, Elizari M, Wang Z et al. (2005). "Tolvaptan administration does not affect steady state amiodarone concentrations in patients with cardiac arrhythmias". J Cardiovasc Pharmacol Ther 10 (3): 165–71. doi:10.1177/107424840501000304. PMID 16211205.
- ^ Otsuka Maryland Research Institute, Inc.
- ^ Gheorghiade M, Gattis W, O'Connor C et al. (2004). "Effects of tolvaptan, a vasopressin antagonist, in patients hospitalized with worsening heart failure: a randomized controlled trial". JAMA 291 (16): 1963–71. doi:10.1001/jama.291.16.1963. PMID 15113814.
- ^ Kondo, K.; Ogawa, H.; Yamashita, H.; Miyamoto, H.; Tanaka, M.; Nakaya, K.; Kitano, K.; Yamamura, Y.; Nakamura, S.; Onogawa, T.; et al.; Bioor. Med. Chem. 1999, 7, 1743.
- Gheorghiade M, Niazi I, Ouyang J et al. (2003). "Vasopressin V2-receptor blockade with tolvaptan in patients with chronic heart failure: results from a double-blind, randomized trial". Circulation 107 (21): 2690–6. doi:10.1161/01.CIR.0000070422.41439.04. PMID 12742979.
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