tolvaptan

{{short description|Chemical compound}}

{{Infobox drug

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 470611744

| IUPAC_name = N-(4-{[(5R)-7-Chloro-5-hydroxy-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl]carbonyl}-3-methylphenyl)-2-methylbenzamide

| image = (RS)-Tolvaptan Structural Formula V1.svg

| image_class = skin-invert-image

| image2 = Tolvaptan ball-and-stick model.png

| tradename = Samsca, Jinarc, Jynarque, others

| Drugs.com = {{drugs.com|monograph|tolvaptan}}

| MedlinePlus = a609033

| DailyMedID = Tolvaptan

| pregnancy_AU =

| pregnancy_category = UK: Contraindicated

| routes_of_administration = By mouth

| ATC_prefix = C03

| ATC_suffix = XA01

| ATC_supplemental =

| legal_AU = S4

| legal_AU_comment = {{cite web | title=Tolvaptan GH (Lupin Australia Pty Limited) | website=Therapeutic Goods Administration (TGA) | date=14 January 2025 | url=https://www.tga.gov.au/resources/prescription-medicines-registrations/tolvaptan-gh-lupin-australia-pty-limited | access-date=20 January 2025}}

| legal_CA =

| legal_UK = POM

| legal_UK_comment = {{cite web | title=Samsca 15 mg tablets - Summary of Product Characteristics (SmPC) | website=(emc) | url=https://www.medicines.org.uk/emc/product/6635/smpc | access-date=14 December 2020}}{{cite web | title=Jinarc 15 mg tablets - Summary of Product Characteristics (SmPC) | website=(emc) | date=21 April 2020 | url=https://www.medicines.org.uk/emc/product/6849/smpc | access-date=14 December 2020}}

| legal_US = Rx-only

| legal_US_comment = {{cite web | title=Jynarque- tolvaptan kit Jynarque- tolvaptan tablet | website=DailyMed | date=31 March 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3febc0a1-9e5a-4ce0-843d-210f21d862c4 | access-date=14 December 2020}}{{cite web | title=Samsca- tolvaptan tablet | website=DailyMed | date=26 October 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=5526617c-c7b9-4556-886d-729bbabbc566 | access-date=14 December 2020}}

| legal_EU = Rx-only

| legal_EU_comment = {{cite web | title=Samsca EPAR | website=European Medicines Agency (EMA) | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/samsca | access-date=14 December 2020}}{{cite web | title=Jinarc EPAR | website=European Medicines Agency (EMA) | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/jinarc | access-date=14 December 2020}}

| legal_status =

| protein_bound = 99%

| metabolism = Liver (CYP3A4-mediated){{cite journal |vauthors=Shoaf S, Elizari M, Wang Z, etal | title = Tolvaptan administration does not affect steady state amiodarone concentrations in patients with cardiac arrhythmias | journal = J Cardiovasc Pharmacol Ther | volume = 10 | issue = 3 | pages = 165–71 | year = 2005 | pmid = 16211205 | doi = 10.1177/107424840501000304| s2cid = 39158242 | doi-access = free }}

| elimination_half-life = 12 hours (terminal)

| excretion =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 150683-30-0

| PubChem = 216237

| IUPHAR_ligand = 2226

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB06212

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 187438

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 21G72T1950

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 344159

| ChEBI = 32246

| KEGG = D01213

| C = 26

| H = 25

| Cl = 1

| N = 2

| O = 3

| smiles = Cc1ccccc1C(=O)Nc2cc(C)c(cc2)C(=O)N3c4ccc(Cl)cc4[C@H](O)CCC3

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = GYHCTFXIZSNGJT-UHFFFAOYSA-N

| synonyms = OPC-41061

}}

Tolvaptan, sold under the brand name Samsca among others, is an aquaretic drug that functions as a selective, competitive vasopressin receptor 2 (V₂) 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 (FDA) on May 19, 2009, and is sold by Otsuka Pharmaceutical Co. under the trade name Samsca.{{cite web | title=Drug Approval Package: Samsca (Tolvaptan) Tablets NDA #022275 | website=U.S. Food and Drug Administration (FDA) | date=21 July 2009 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022275s000TOC.cfm | archive-url=https://web.archive.org/web/20170119030937/http://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022275s000TOC.cfm | url-status=dead | archive-date=January 19, 2017 | access-date=15 August 2020}} Tolvaptan, as Jynarque, was granted approval for medical use in the United States in April 2018.{{cite web | title=Drug Approval Package: Jynarque (tolvaptan) | website=U.S. Food and Drug Administration (FDA) | date=8 June 2018 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/204441Orig1s000TOC.cfm | archive-url=https://web.archive.org/web/20190330121657/https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/204441Orig1s000TOC.cfm | url-status=dead | archive-date=March 30, 2019 | access-date=15 August 2020}}

The U.S. Food and Drug Administration (FDA) granted tolvaptan a fast track designation for clinical trials investigating its use for the treatment of polycystic kidney disease.{{cite web |title=Otsuka Maryland Research Institute, Inc. Granted Fast Track Designation For Tolvaptan In PKD |url=https://www.medicalnewstoday.com/releases/38392.php |website=Medical News Today |publisher=Healthline Media UK Ltd |access-date=6 December 2018 }} The FDA granted Jynarque an orphan drug designation in April 2012, for the treatment of autosomal dominant polycystic kidney disease.{{cite web | title=Tolvaptan Orphan Drug Designations and Approvals | website=U.S. Food and Drug Administration (FDA) | date=6 April 2012 | url=https://www.accessdata.fda.gov/scripts/opdlisting/oopd/detailedIndex.cfm?cfgridkey=20113473 | archive-url=https://web.archive.org/web/20210829090956/https://www.accessdata.fda.gov/scripts/opdlisting/oopd/detailedIndex.cfm?cfgridkey=20113473 | url-status=dead | archive-date=August 29, 2021 | access-date=15 August 2020}}

Tolvaptan is available as a generic medication.{{cite web | title=Drugs@FDA: FDA-Approved Drugs | website=U.S. Food and Drug Administration (FDA) | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=211891 | archive-url=https://web.archive.org/web/20201020120636/https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=211891 | url-status=dead | archive-date=October 20, 2020 | access-date=15 August 2020}}{{cite web | title=Tolvaptan Accord: Pending EC decision | website=European Medicines Agency (EMA) | date=26 January 2023 | url=https://www.ema.europa.eu/en/medicines/human/summaries-opinion/tolvaptan-accord | access-date=28 January 2023 | archive-date=27 January 2023 | archive-url=https://web.archive.org/web/20230127225415/https://www.ema.europa.eu/en/medicines/human/summaries-opinion/tolvaptan-accord | url-status=dead }}