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T9652

Terfenadine

≥97.5% (HPLC), powder, H1 histamine receptor antagonist

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C32H41NO2
CAS Number:
50679-08-8
Molecular Weight:
471.67
NACRES:
NA.77
PubChem Substance ID:
24277779
UNSPSC Code:
12161501
EC Number:
256-710-8
MDL number:
MFCD00079622
Quality level:
200
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Product Name

Terfenadine,

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)

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

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

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).

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hcodes

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ7665
MKCM5456
MKCJ2949
MKCC6581
MKBX6318V

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Articles

Discover Bioactive Small Molecules for ADME/Tox

Discover Bioactive Small Molecules for ADME/Tox

Terfenadine
McTavish D, et al.
Drugs, 39, 552-574 (1990)
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
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
View All Related Papers

Global Trade Item Number

SKUGTIN
T9652-5G04061837381768
T9652-25G04061832931609