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1643805

USP

Terfenadine

United States Pharmacopeia (USP) Reference Standard

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
MDL number:
MFCD00079622
UNSPSC Code:
41116107
PubChem Substance ID:
329751237
NACRES:
NA.24

grade

pharmaceutical primary standard

manufacturer/tradename

USP

application(s)

pharmaceutical (small molecule)

format

neat

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 ... HRH1(3269)

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General description

Terfenadine is a non-sedating antagonist of histamine receptor. It has pharmacodynamic property and therapeutic efficiency which accounts for its anti-histamine profile.[1]

Application

It was studied to understand its solubility enhancement when aqueous multi-basic organic acids like citric, glutaric, malic, malonic, or tartaric acids were added.[2] It may be used as a standard during determination of terfenadine using spectrophotometric procedure.[1]

Biochem/physiol Actions

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

Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Other Notes

USP issued SDS can be found here.
Sales restrictions may apply.

hcodes

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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Solubilization of terfenadine, riboflavin, and sudan III by aqueous multi-basic organic acids.
Abdoh, A. A., M. B. Zughul, and A. A. Badwan.
Journal of Dispersion Science and Technology, 23.6, 759-768 (2002)
Utility of the ion-pair formation for spectrophotometric determination of terfenadine in pure form and in some pharmaceutical formulations.
Amin, Alaa S., and Yousry M. Issa.
Microchimica Acta, 130.3, 173-179 (1999)
D W Aaronson
Drug safety, 8(4), 321-329 (1993-04-01)
Sedation and impairment of psychomotor performance are well known adverse effects of the traditional antihistamines. These effects appear to be caused by different mechanisms, but both may have potentially dangerous consequences. while several of the newer antihistamines, such as terfenadine
M Q Zhang et al.
Pharmacy world & science : PWS, 15(5), 186-192 (1993-10-15)
Terfenadine was the first non-sedating histamine H1 receptor antagonist and one of the most frequently prescribed H1 antihistamines. Terfenadine has one asymmetric centre in the molecule and is currently used as a racemate. Different methods and approaches for obtaining pure
D McTavish et al.
Drugs, 39(4), 552-574 (1990-04-01)
Terfenadine is a selective histamine H1-receptor antagonist which, in pharmacodynamic studies, is devoid of central nervous system depressant activity. In clinical studies terfenadine is well tolerated and at a dose of 60mg administered twice daily the drug provides effective relief
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