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T9652 Sigma

Terfenadine

Synonym: α-[4-(1,1-Dimethylethyl)phenyl]-4-(hydroxydiphenylmethyl)-1-piperidinebutanol

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Properties

Related Categories Application Index, Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Biochemicals and Reagents,
InChI Key   GUGOEEXESWIERI-UHFFFAOYSA-N
solubility   chloroform: soluble250 mg plus 5 ml of solvent, clear, colorless to faintly yellow
  H2O: soluble0.01 mg/mL at 30 °C
  1 M HCl: soluble0.12  mg/mL at 30 °C
  hexane: soluble0.34  mg/mL at 30 °C
  0.1 M tartaric acid: soluble0.45  mg/mL
  0.1 M citric acid: soluble1.1  mg/mL
  methanol: soluble37.5  mg/mL at 30 °C
  ethanol: soluble in salt form37.8  mg/mL at 30 °C
originator   Sanofi Aventis
storage temp.   2-8°C
Gene Information   human ... ABCB1(5243), CYP2C8(1558), CYP3A4(1576), HRH1(3269), IL4(3565), IL5(3567), KCNH1(3756), KCNH2(3757)
mouse ... Abcb1a(18671), Abcb1b(18669)
rat ... Hrh1(24448)

Description

Biochem/physiol Actions

Terfenadine inhibits HERG (human ether-a-gogo-related gene) K+ channels. It also blocks the delayed rectifier potassium current (IK) of rat isolated ventricular myocytes with IC50 value of 5.96 μM.

Non-sedating second generation H1 histamine receptor antagonist. Mainly metabolized by Cyp3A4, 5, 7. Inhibits CYP2C8.

Packaging

5, 25 g in poly bottle

Preparation Note

250 mg of Terfenadine dissolves in 5ml of chloroform to yield a clear, colorless solution. Terfenadine is also soluble at 30° C in 0.1 M citric acid (1.1 mg/ml), water (0.01 mg/ml), methanol (37.5 mg/ml), hexane (0.34 mg/ml), ethanol (37.8 mg/ml), 1 M hydrochloric acid (0.12 mg/ml), and 0.1 M tartaric acid (0.45 mg/ml).

Application

Terfenadine has been used to study the role of histamine in itch related to proteinase-activated receptors (PARs) in mice. Terfenadine has also been used to block histamine receptor type 1 to study the pathogenesis of 2,4-dinitrobenzene sulfonic acid (DNBS)-induced ulcerative colitis in rats.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

This compound is featured on the Potassium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

This compound was developed by Sanofi Aventis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. T9652.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

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Safety & Documentation

Safety Information

Hazard statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
2
Protocols & Articles

Articles

Discover Bioactive Small Molecules for ADME/Tox

A significant number of drugs that fail in clinical trials have been associated with safety issues, including unexpected drug-drug interactions (DDI) or lack of efficacy due to poor pharmacokinetics....
Keywords: Absorption, Bioactive small molecules, Clinical, Metabolism

HPLC Analysis of Terfenadine Enantiomers on Astec® Cellulose DMP

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of Terfenadine Enantiomers on Astec® Cellulose DMP
Keywords: Chromatography, High performance liquid chromatography, Pharmaceutical

Peer-Reviewed Papers
15

References

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