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T9652

Sigma-Aldrich

Terfenadine

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Synonym(s):
α-[4-(1,1-Dimethylethyl)phenyl]-4-(hydroxydiphenylmethyl)-1-piperidinebutanol
Empirical Formula (Hill Notation):
C32H41NO2
CAS Number:
50679-08-8
Molecular Weight:
471.67
EC Number:
256-710-8
MDL number:
MFCD00079622
PubChem Substance ID:
24277779
NACRES:
NA.77

Quality Level

200

solubility

chloroform: soluble 250 mg plus 5 ml of solvent, clear to very slightly hazy, colorless to faintly yellow
H2O: soluble 0.01 mg/mL at 30 °C
1 M HCl: soluble 0.12 mg/mL at 30 °C
hexane: soluble 0.34 mg/mL at 30 °C
0.1 M tartaric acid: soluble 0.45 mg/mL
0.1 M citric acid: soluble 1.1 mg/mL
methanol: soluble 37.5 mg/mL at 30 °C
ethanol: soluble in salt form 37.8 mg/mL at 30 °C

originator

Sanofi Aventis

storage temp.

2-8°C

SMILES string

CC(C)(C)c1ccc(cc1)C(O)CCCN2CCC(CC2)C(O)(c3ccccc3)c4ccccc4

InChI

1S/C32H41NO2/c1-31(2,3)26-18-16-25(17-19-26)30(34)15-10-22-33-23-20-29(21-24-33)32(35,27-11-6-4-7-12-27)28-13-8-5-9-14-28/h4-9,11-14,16-19,29-30,34-35H,10,15,20-24H2,1-3H3

InChI key

GUGOEEXESWIERI-UHFFFAOYSA-N

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)

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Application

Terfenadine has been used as a positive control in electrophysiology recordings. It has also been used as a constituent of internal standard solution in liquid chromatography-mass spectrometry (LC-MS).
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.

Biochem/physiol Actions

Non-sedating second generation H1 histamine receptor antagonist. Mainly metabolized by Cyp3A4, 5, 7. Inhibits CYP2C8.
Terfenadine acts a potential anti-histamine and is used in the treatment of allergic rhinitis and chronic urticaria.

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 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.

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).

Hazard Statements

H413

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Marine algal toxin azaspiracid is an open-state blocker of hERG potassium channels
Twiner MJ, et al.
Chemical Research in Toxicology, 25(9), 1975-1984 (2012)
M Taglialatela et al.
Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology, 29 Suppl 3, 182-189 (1999-08-12)
Despite the enormous success of second generation antihistamines, in the mid-1980s, about 10 years after their introduction in the market, several reports appeared in the literature indicating the rare occurrence of a form of polymorphic ventricular dysrhythmia, the 'torsade de
H Ohtani et al.
The Journal of pharmacy and pharmacology, 51(9), 1059-1063 (1999-10-21)
We examined and compared the inhibitory effects of three non-sedating antihistamines, terfenadine, ebastine, and epinastine, on delayed rectifier potassium current (IK) and transient outward potassium current (Ito) of rat isolated ventricular myocytes, using a patch clamp technique. Terfenadine, ebastine and
Terfenadine
McTavish D, et al.
Drugs, 39, 552-574 (1990)
Hiroyuki Kusuhara et al.
Drug metabolism and disposition: the biological fate of chemicals, 41(1), 206-213 (2012-11-02)
The effect of rifampicin on the pharmacokinetics of fexofenadine enantiomers was examined in healthy subjects who received fexofenadine alone or with single or multiple doses of rifampicin (600 mg). A single coadministered dose of rifampicin significantly decreased the oral clearance
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