Tolvaptan

---

title: "Tolvaptan" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["diuretics", "chloroarenes", "secondary-alcohols", "benzazepanes", "benzamides", "benzanilides", "vasopressin-receptor-antagonists", "otsuka-pharmaceutical", "world-anti-doping-agency-prohibited-substances", "orphan-drugs", "2-tolyl-compounds", "systemic-hormonal-preparations"] description: "Chemical compound" topic_path: "general/diuretics" source: "https://en.wikipedia.org/wiki/Tolvaptan" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

::data[format=table title="Infobox drug"]

Field	Value
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
image_class2	bg-transparent
	tradename
Drugs.com
MedlinePlus	a609033
DailyMedID	Tolvaptan
pregnancy_AU
pregnancy_category	UK: Contraindicated
routes_of_administration	By mouth
ATC_prefix	C03
ATC_suffix	XA01
legal_AU	S4
legal_AU_comment
legal_CA
legal_UK	POM
legal_UK_comment
legal_US	Rx-only
legal_US_comment
legal_EU	Rx-only
legal_EU_comment
legal_status
protein_bound	99%
metabolism	Liver (CYP3A4-mediated)
elimination_half-life	12 hours (terminal)
excretion
CAS_number_Ref
CAS_number	150683-30-0
PubChem	216237
IUPHAR_ligand	2226
DrugBank_Ref
DrugBank	DB06212
ChemSpiderID_Ref
ChemSpiderID	187438
UNII_Ref
UNII	21G72T1950
ChEMBL_Ref
ChEMBL	344159
ChEBI	32246
KEGG	D01213
	C
H	25
Cl	1
N	2
O	3
smiles	Cc1ccccc1C(=O)Nc2cc(C)c(cc2)C(=O)N3c4ccc(Cl)cc4C@HCCC3
StdInChI_Ref
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
StdInChIKey	GYHCTFXIZSNGJT-UHFFFAOYSA-N
synonyms	OPC-41061
::

| 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 | image_class2 = bg-transparent

| tradename = Samsca, Jinarc, Jynarque, others | Drugs.com = | 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 = | legal_CA = | legal_UK = POM | legal_UK_comment = | legal_US = Rx-only | legal_US_comment = | legal_EU = Rx-only | legal_EU_comment = | legal_status = | protein_bound = 99% | metabolism = Liver (CYP3A4-mediated) | elimination_half-life = 12 hours (terminal) | excretion = | CAS_number_Ref = | CAS_number = 150683-30-0 | PubChem = 216237 | IUPHAR_ligand = 2226 | DrugBank_Ref = | DrugBank = DB06212 | ChemSpiderID_Ref = | ChemSpiderID = 187438 | UNII_Ref = | UNII = 21G72T1950 | ChEMBL_Ref = | 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)cc4C@HCCC3 | StdInChI_Ref = | 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 = | 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. Tolvaptan, as Jynarque, was granted approval for medical use in the United States in April 2018.

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. The FDA granted Jynarque an orphan drug designation in April 2012, for the treatment of autosomal dominant polycystic kidney disease.

Tolvaptan is available as a generic medication.

Medical uses

Tolvaptan (Samsca) is indicated for the treatment of clinically significant hypervolemic and euvolemic hyponatremia.

Tolvaptan (Jynarque) is indicated for slow kidney-function decline in adults at risk of rapidly progressing autosomal dominant polycystic kidney disease (ADPKD).

Tolvaptan phosphate is a prodrug of tolvaptan, developed for intravenous administration. Tolvaptan phosphate is converted into the active drug tolvaptan in the human body following administration.

Side effects

The FDA has determined that tolvaptan should not be used for longer than 30 days and should not be used in patients with underlying liver disease because it can cause liver injury, potentially leading to liver failure. When using to treat hyponatremia, it may cause too rapid correction of hyponatremia resulting in fatal osmotic demyelination syndrome.

Pharmacology

Tolvaptan is a selective vasopressin V2 receptor antagonist.

Chemistry

Tolvaptan is a racemate, a 1:1 mixture of the following two enantiomers: ::data[format=table]

Enantiomers of tolvaptan
[[File:(R)-Tolvaptan Structural Formula V1.svg
(R)-Tolvaptan
CAS number: 331947-66-1
::

References

References

1. (14 January 2025). "Tolvaptan GH (Lupin Australia Pty Limited)".
2. "Samsca 15 mg tablets - Summary of Product Characteristics (SmPC)".
3. (21 April 2020). "Jinarc 15 mg tablets - Summary of Product Characteristics (SmPC)".
4. (31 March 2020). "Jynarque- tolvaptan kit Jynarque- tolvaptan tablet".
5. (26 October 2020). "Samsca- tolvaptan tablet".
6. (17 September 2018). "Samsca EPAR".
7. (17 September 2018). "Jinarc EPAR".
8. (2005). "Tolvaptan administration does not affect steady state amiodarone concentrations in patients with cardiac arrhythmias". J Cardiovasc Pharmacol Ther.
9. (21 July 2009). "Drug Approval Package: Samsca (Tolvaptan) Tablets NDA #022275".
10. (8 June 2018). "Drug Approval Package: Jynarque (tolvaptan)".
11. "Otsuka Maryland Research Institute, Inc. Granted Fast Track Designation For Tolvaptan In PKD". Healthline Media UK Ltd.
12. (6 April 2012). "Tolvaptan Orphan Drug Designations and Approvals".
13. "Drugs@FDA: FDA-Approved Drugs".
14. (26 January 2023). "Tolvaptan Accord: Pending EC decision".
15. (28 May 2019). "Samsca- tolvaptan tablet".
16. (31 March 2020). "Jynarque- tolvaptan kit Jynarque- tolvaptan tablet".
17. (March 28, 2022). "Otsuka Obtains Approval in Japan for SAMTASU® for I.V. Infusion, a V2 -Receptor Antagonist for the Treatment of Cardiac Edema".
18. "U.S. Food and Drug Administration." Samsca (Tolvaptan): Drug Safety Communication. N.p., 30 Apr. 2013. Web. 1 June 2014. <[https://web.archive.org/web/20130504040023/http://www.fda.gov/Safety/MedWatch/SafetyInformation/SafetyAlertsforHumanMedicalProducts/ucm350185.htm]
19. (5 December 2017). "Goodman & Gilman's the pharmacological basis of therapeutics".
20. Rote Liste Service GmbH (Hrsg.): ''Rote Liste 2017 - Arzneimittelverzeichnis für Deutschland (einschließlich EU-Zulassungen und bestimmter Medizinprodukte)''. Rote Liste Service GmbH, Frankfurt/Main, 2017, Aufl. 57, {{ISBN. 978-3-946057-10-9, S. 222.

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