Terfenadine

Jump to navigation Jump to search
The printable version is no longer supported and may have rendering errors. Please update your browser bookmarks and please use the default browser print function instead.
Terfenadine
Clinical data
Trade namesSeldane, Triludan, Teldane
AHFS/Drugs.comMultum Consumer Information
MedlinePlusa600034
Pregnancy
category
  • US: C (Risk not ruled out)
ATC code
Legal status
Legal status
  • Withdrawn
Pharmacokinetic data
Protein binding70%
Elimination half-life3.5 hours
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC32H41NO2
Molar mass471.673 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

WikiDoc Resources for Terfenadine

Articles

Most recent articles on Terfenadine

Most cited articles on Terfenadine

Review articles on Terfenadine

Articles on Terfenadine in N Eng J Med, Lancet, BMJ

Media

Powerpoint slides on Terfenadine

Images of Terfenadine

Photos of Terfenadine

Podcasts & MP3s on Terfenadine

Videos on Terfenadine

Evidence Based Medicine

Cochrane Collaboration on Terfenadine

Bandolier on Terfenadine

TRIP on Terfenadine

Clinical Trials

Ongoing Trials on Terfenadine at Clinical Trials.gov

Trial results on Terfenadine

Clinical Trials on Terfenadine at Google

Guidelines / Policies / Govt

US National Guidelines Clearinghouse on Terfenadine

NICE Guidance on Terfenadine

NHS PRODIGY Guidance

FDA on Terfenadine

CDC on Terfenadine

Books

Books on Terfenadine

News

Terfenadine in the news

Be alerted to news on Terfenadine

News trends on Terfenadine

Commentary

Blogs on Terfenadine

Definitions

Definitions of Terfenadine

Patient Resources / Community

Patient resources on Terfenadine

Discussion groups on Terfenadine

Patient Handouts on Terfenadine

Directions to Hospitals Treating Terfenadine

Risk calculators and risk factors for Terfenadine

Healthcare Provider Resources

Symptoms of Terfenadine

Causes & Risk Factors for Terfenadine

Diagnostic studies for Terfenadine

Treatment of Terfenadine

Continuing Medical Education (CME)

CME Programs on Terfenadine

International

Terfenadine en Espanol

Terfenadine en Francais

Business

Terfenadine in the Marketplace

Patents on Terfenadine

Experimental / Informatics

List of terms related to Terfenadine

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Terfenadine is an antihistamine formerly used for the treatment of allergic conditions. It was brought to market by Hoechst Marion Roussel (now Sanofi-Aventis) and marketed under various brand names, including Seldane in the United States, Triludan in the United Kingdom, and Teldane in Australia. According to its manufacturer, terfenadine had been used by over 100 million patients worldwide as of 1990.It was superseded by fexofenadine in the 1990s due to the risk of a particular type of disruption of the electrical rhythms of the heart (specifically cardiac arrhythmia caused by QT interval prolongation).

Terfenadine is a prodrug, generally completely metabolized to the active form fexofenadine in the liver by the enzyme cytochrome P450 CYP3A4 isoform. Due to its near complete metabolism by the liver immediately after leaving the gut, terfenadine normally is not measurable in the plasma. Terfenadine itself, however, is cardiotoxic at higher doses, while its major active metabolite is not. Terfenadine, in addition to its antihistamine effects, also acts as a potassium channel blocker (Kv11.1 encoded by the gene hERG). Since its active metabolite is not a potassium channel blocker, no cardiotoxicity is associated with fexofenadine.Toxicity is possible after years of continued use with no previous problems as a result of an interaction with other medications such as erythromycin, or foods such as grapefruit. The addition of, or dosage change in, these CYP3A4 inhibitors makes it harder for the body to metabolize and remove terfenadine. In larger plasma concentrations, it may lead to toxic effects on the heart's rhythm (e.g. ventricular tachycardia and torsades de pointes).

History

In the United States, Seldane was brought to market in 1985 as the first nonsedating antihistamine for the treatment of allergic rhinitis.In June 1990, evidence of serious ventricular arrhythmias among those taking Seldane prompted the FDA to issue a report on the risk factors associated with concomitant use of the drug with macrolide antibiotics and ketoconazole.Two months later, the FDA required the manufacturer to send a letter to all physicians, alerting them to the problem; in July 1992, the existing precautions were elevated to a black box warningand the issue attracted mass media attention in reports that people with liver disease or who took ketoconazole, an antifungal agent, or the antibiotic erythromycin, could suffer cardiac arrhythmia if they also took Seldane.

In January 1997, the same month when the U.S. Food and Drug Administration (FDA) had earlier approved a generic version of Seldane made by IVAX Corporation of Miami, the FDA recommended terfenadine-containing drugs be removed from the market and physicians consider alternative medications for their patients.Seldane (and Seldane-D, terfenadine combined with the decongestant pseudoephedrine) were removed from the U.S. market by their manufacturer in late 1997 after the FDA approval of Allegra-D (fexofenadine/pseudoephedrine). >"FDA Approves Allegra-D, Manufacturer To Withdraw Seldane From Marketplace". Food and Drug Administration. Archived from <refs/topics/ANSWERS/ANS00843.html the original on 2008-02-23. Retrieved 2010-11-11.</ref> Terfenadine-containing drugs were subsequently removed from the Canadian market in 1999,[1]

See also

References

Synthesis

Terfenadine synthesis:Richardson-Merrell Inc., U.S. Patent 3,878,217 DE 2303305  DE 2303306  DE 2503362  GB 1412605 

[1]

External links

  1. Arzneimittel-Forsch 32, 1157 (1982).