Torasemide
{{Short description|Diuretic medication}}
{{Use dmy dates|date=February 2024}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 470611857
| image = Torasemide.svg
| alt =
| image2 =
| alt2 =
| USAN = Torsemide
| tradename = Demadex, Tortas, Wator
| Drugs.com = {{drugs.com|monograph|torsemide}}
| MedlinePlus = a601212
| DailyMedID = Torsemide
| routes_of_administration = By mouth, intraveneous
| class = Loop diuretic
| ATC_prefix = C03
| ATC_suffix = CA04
| ATC_supplemental =
| legal_US = Rx-only
| bioavailability = 80-90%
| protein_bound = Highly bound (>99%).
| metabolism = Liver (80%)
| elimination_half-life = 3.5 hours; Cirrhosis: 7-8 hours
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 56211-40-6
| PubChem = 41781
| IUPHAR_ligand = 7312
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00214
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 38123
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = W31X2H97FB
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00382
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 9637
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1148
| synonyms = Torsemide
| IUPAC_name = N-[(isopropylamino)carbonyl]-4-[(3-methylphenyl)amino]pyridine-3-sulfonamide
| C = 16
| H = 20
| N = 4
| O = 3
| S = 1
| smiles = CC(C)NC(=O)NS(=O)(=O)c1cnccc1Nc2cc(C)ccc2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C16H20N4O3S/c1-11(2)18-16(21)20-24(22,23)15-10-17-8-7-14(15)19-13-6-4-5-12(3)9-13/h4-11H,1-3H3,(H,17,19)(H2,18,20,21)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NGBFQHCMQULJNZ-UHFFFAOYSA-N
}}
Torasemide, also known as torsemide, is a diuretic medication used to treat fluid overload due to heart failure, kidney disease, and liver disease. It is a less preferred treatment for high blood pressure. It is taken by mouth or by injection into a vein.{{cite web |title=Torsemide Monograph for Professionals |url=https://www.drugs.com/monograph/torsemide.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |accessdate=18 March 2019 }}
Common side effects include headache, increased urination, diarrhea, cough, and dizziness. Other side effects may include hearing loss and low blood potassium. Torasemide is a sulfonamide and loop diuretic. Use is not recommended in pregnancy or breastfeeding. It works by decreasing the reabsorption of sodium by the kidneys.
Torasemide was patented in 1974 and came into medical use in 1993.{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=978-3-527-60749-5 |page=458 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA458 }} It is on the World Health Organization's List of Essential Medicines.{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }} It is available as a generic medication.{{cite book|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=978-0-85711-338-2|pages=227–228|edition=76}} In 2022, it was the 184th most commonly prescribed medication in the United States, with more than 2{{nbsp}}million prescriptions.{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}{{cite web | title = Torsemide Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Torsemide | access-date = 30 August 2024 }}
Medical uses
It is used to treat fluid overload due to heart failure. It is sometimes used to treat high blood pressure. Compared with furosemide, torasemide is associated with a lower risk of rehospitalization for heart failure and an improvement in New York Heart Association class of heart failure.{{cite journal |vauthors=Abraham B, Megaly M, Sous M, Fransawyalkomos M, Saad M, Fraser R, Topf J, Goldsmith S, Simegn M, Bart B, Azzo Z, Mesiha N, Sharma R |title=Meta-Analysis Comparing Torsemide Versus Furosemide in Patients With Heart Failure |journal=Am. J. Cardiol. |volume=125 |issue=1 |pages=92–99 |date=January 2020 |pmid=31699358 |doi=10.1016/j.amjcard.2019.09.039 |doi-access= |s2cid=207937875 }}{{cite journal |vauthors=Täger T, Fröhlich H, Seiz M, Katus HA, Frankenstein L |title=READY: relative efficacy of loop diuretics in patients with chronic systolic heart failure-a systematic review and network meta-analysis of randomised trials |journal=Heart Fail Rev |volume= 24|issue= 4|pages= 461–472|date=March 2019 |pmid=30874955 |doi=10.1007/s10741-019-09771-8 |s2cid=77394851 }}{{cite journal |vauthors=Miles JA, Hanumanthu BK, Patel K, Chen M, Siegel RM, Kokkinidis DG |title=Torsemide versus furosemide and intermediate-term outcomes in patients with heart failure: an updated meta-analysis |journal=J Cardiovasc Med (Hagerstown) |volume=20 |issue=6 |pages=379–388 |date=June 2019 |pmid=30950982 |doi=10.2459/JCM.0000000000000794 |s2cid=96436158 }} In heart failure it may be safer and more effective than furosemide.{{cite journal |vauthors=Wargo KA, Banta WM |title=A comprehensive review of the loop diuretics: should furosemide be first line? |journal=Ann Pharmacother |volume=43 |issue=11 |pages=1836–47 |date=November 2009 |pmid=19843838 |doi=10.1345/aph.1M177 |s2cid=43339236 }}{{cite journal|pmid=24243991 | doi=10.1177/1074248413497257 | volume=19 | issue=1 | title=Diuretics: a review and update | year=2014 | journal=J. Cardiovasc. Pharmacol. Ther. | pages=5–13 | vauthors=Roush GC, Kaur R, Ernst ME| s2cid=21204143 }}{{cite journal|pmid=25728721 | doi=10.1016/j.ahj.2014.12.009 | volume=169 | issue=3 | title=A reappraisal of loop diuretic choice in heart failure patients | pmc=4346710 | year=2015 | journal=Am. Heart J. | pages=323–33 | vauthors=Buggey J, Mentz RJ, Pitt B, Eisenstein EL, Anstrom KJ, Velazquez EJ, O'Connor CM}} Long-term outcomes with torasemide may be better than with furosemide in patients with heart failure.{{cite journal | vauthors = Ozierański K, Balsam P, Kapłon-Cieślicka A, Tymińska A, Kowalik R, Grabowski M, Peller M, Wancerz A, Marchel M, Crespo-Leiro MG, Maggioni AP, Drożdż J, Filipiak KJ, Opolski G | title = Comparative Analysis of Long-Term Outcomes of Torasemide and Furosemide in Heart Failure Patients in Heart Failure Registries of the European Society of Cardiology | journal = Cardiovascular Drugs and Therapy | volume = 33 | issue = 1 | pages = 77–86 | date = February 2019 | pmid = 30649675 | doi = 10.1007/s10557-018-6843-5 | hdl-access = free | s2cid = 58014640 | hdl = 2183/22704 }}
Adverse effects
No evidence of torasemide-induced ototoxicity has been demonstrated in humans.{{cite journal |vauthors =Dunn CJ, Fitton A, Brogden RN |title=Torasemide. An update of its pharmacological properties and therapeutic efficacy |journal=Drugs |volume=49 |issue=1 |pages=121–42 |date=January 1995 |pmid=7705212 |doi= 10.2165/00003495-199549010-00009|s2cid=261404564 }}
Loop diuretics, including torsemide, may decrease total body thiamine, particularly in people with poor thiamine intake, and this depletion may worsen heart failure. It is therefore reasonable to either also give thiamine supplements or to check blood thiamine levels in those being treated with chronic loop diuretics.{{cite journal |vauthors=Kattoor AJ, Goel A, Mehta JL |title=Thiamine Therapy for Heart Failure: a Promise or Fiction? |journal=Cardiovasc Drugs Ther |volume=32 |issue=4 |pages=313–317 |date=August 2018 |pmid=30022355 |doi=10.1007/s10557-018-6808-8 |doi-access=free }}
Chemistry
Compared with other loop diuretics, torasemide has a more prolonged diuretic effect than equipotent doses of furosemide and relatively decreased potassium loss.{{cite journal|url=https://link.springer.com/article/10.2165/00003495-199549010-00009|journal=Drugs|author=Christopher J. Dunn|title=Torasemide: An Update of its Pharmacological Properties and Therapeutic Efficacy|date=1995|volume=49 |issue=1 |pages=121–142 |doi=10.2165/00003495-199549010-00009 |pmid=7705212 |accessdate=8 March 2024}}
Names
{{unreferenced section|date=February 2024}}
Torasemide is the recommended name of the drug (rINN) according to the (INN), which is the drug naming system coordinated by the World Health Organization. Torsemide is the official name of the drug according to the (USAN), which is the drug naming system coordinated by the USAN Council, which is co-sponsored by the American Medical Association (AMA), the United States Pharmacopeial Convention (USP), and the American Pharmacists Association (APhA).
Veterinary uses
In May 2024, the US FDA conditionally approved the first torsemide animal medication for dogs. UpCard-CA1 (torsemide oral solution) was conditionally approved for use with concurrent therapy with pimobendan, spironolactone, and an angiotensin-converting enzyme (ACE) inhibitor for the management of pulmonary edema (fluid build-up in lungs) in dogs with congestive heart failure caused by myxomatous mitral valve disease (MMVD).{{cite press release | title=FDA Conditionally Approves First Torsemide Animal Drug for Dogs | website=U.S. Food and Drug Administration | date=10 May 2024 | url=https://www.fda.gov/animal-veterinary/cvm-updates/fda-conditionally-approves-first-torsemide-animal-drug-dogs | access-date=15 May 2024}} {{PD-notice}}{{cite press release | title=FDA Roundup: May 14, 2024 | website=U.S. Food and Drug Administration | date=14 May 2024 | url=https://www.fda.gov/news-events/press-announcements/fda-roundup-may-14-2024 | access-date=15 May 2024}} {{PD-notice}}