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ChemicalBook--->CAS DataBase List--->50679-08-8

50679-08-8

50679-08-8 Structure

50679-08-8 Structure
IdentificationMore
[Name]

Terfenadine
[CAS]

50679-08-8
[Synonyms]

ALPHA-[4-(1,1-DIMETHYLETHYL)PHENYL]-4-(HYDROXYDIPHENYLMETHYL)-1-PIPERIDINEBUTANOL
TERFENADINE
1-(4-tert-butylphenyl)-4-(4-(alpha-hydroxybenzhydryl)piperidino)-butan-1-ol
1-(4-tert-Butylphenyl)-4-(4-[hydroxy(diphenyl)methyl]-1-piperidinyl)-1-butanol
1-(p-tert-butylphenyl)-4-(4’-(alpha-hydroxydiphenylmethyl)-1’-piperidyl)-butan
1-Piperidinebutanol, alpha-[4-(1,1-dimethylethyl)phenyl]-4-(hydroxydiphenylmethyl)-
1-piperidinebutanol,alpha-(4-(1,1-dimethylethyl)phenyl)-4-(hydroxydiphenylmeth
Aldaban
Allerplus
alpha-(4-(1,1-dimethylethyl)phenyl)-4-(hydroxydiphenylmethyl)-1-piperidinebu
alpha-(4-(1,1-dimethylethyl)phenyl)-4-(hydroxydiphenylmethyl)-1-piperidinebuta
alpha-(p-tert-butylphenyl)-4-(alpha-hydroxy-alpha-phenylbenzyl)-1-piperidinebu
alpha-(p-tert-Butylphenyl)-4-(hydroxydiphenylmethyl)-1-piperidinebutanol
Cyater
mdl9918
MDL-9918
Nebralin
RMI 9918
rmi9918
rmi-9918
[EINECS(EC#)]

256-710-8
[Molecular Formula]

C32H41NO2
[MDL Number]

MFCD00079622
[Molecular Weight]

471.67
[MOL File]

50679-08-8.mol
Chemical PropertiesBack Directory
[Appearance]

White Solid
[Melting point ]

145-152 °C
[Boiling point ]

572.76°C (rough estimate)
[density ]

1.0488 (rough estimate)
[refractive index ]

1.6310 (estimate)
[storage temp. ]

2-8°C
[solubility ]

chloroform: soluble250 mg plus 5 ml of solvent, clear to very slightly hazy, colorless to faintly yellow
[form ]

neat
[pka]

pKa 9.21(H2O t = 25 I = 0.025) (Uncertain)
[color ]

White to Off-White
[Water Solubility ]

0.001 g/100 mL (30 ºC)
[Usage]

Nonsedating-type histamine H1-receptor antagonist. Antihistaminic
[CAS DataBase Reference]

50679-08-8(CAS DataBase Reference)
[NIST Chemistry Reference]

Seldane(50679-08-8)
Safety DataBack Directory
[Safety Statements ]

S24/25:Avoid contact with skin and eyes .
[WGK Germany ]

2
[RTECS ]

TM4969000
[HS Code ]

29333999
[Hazardous Substances Data]

50679-08-8(Hazardous Substances Data)
[Toxicity]

LD50 orally in mice: >2000 mg/kg (Carr, Meyer)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Hydrochloric acid-->Methanol-->Toluene-->Potassium hydroxide-->Acetone-->Aluminum chloride-->Sodium borohydride-->Isopropyl alcohol-->Potassium iodide-->Potassium borohydride-->Potassium bicarbonate-->Isobutylbenzene-->4-Piperidinemethanol-->4-Chlorobutyryl chloride-->Difenidol hydrochloride-->alpha,alpha-Diphenyl-4-piperidinomethanol
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Terfenadine(50679-08-8).msds
Hazard InformationBack Directory
[Chemical Properties]

White Solid
[Originator]

Histafen,Berk
[Uses]

H1 antihistamine
[Uses]

It is used for relieving symptoms associated with seasonal allergic rhinitis and conjunctivitis, for angioneurotic edema and allergic skin reaction, and also as an ingredient of complex therapy for bronchial asthma. Synonyms of this drug are seldane, hystadin, trexil, and others.
[Uses]

Nonsedating-type histamine H1-receptor antagonist. Antihistaminic
[Definition]

ChEBI: Terfenadine is a diarylmethane.
[Manufacturing Process]

A mixture of 107 g (0.4 mole) of α,α-diphenyl-4-piperidinemethanol, 105 g (0.44 mole) of 4'-tert-butyl-4-chlorobutyrophenone, 70 g (0.7 mole) of potassium bicarbonate, and a small amount of potassium iodide in 600 ml of toluene was refluxed and stirred for 2.5 days then filtered. The filtrate was treated with charcoal, filtered through celite then treated with ethereal HCl. The resulting solid was recrystallized from methanol and isopropyl alcohol to give the 4'-tert-butyl-4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]- butyrophenone hydrochloride, melting point 234°-235°C.
To a mixture of 4.2 g (0.0083 mole) of 4'-tert-butyl-4-[4-(α-hydroxy-α- phenylbenzyl)piperidino]-butyrophenone hydrochloride and 0.54 g (0.01 mole) of sodium methoxide in 25 ml of methanol is added 2.16 g (0.04 mole) of potassium borohydride. The reaction mixture is stirred overnight, diluted with water and the methanol removed under reduced pressure. The remaining material is extracted with chloroform, washed with water, dried over magnesium sulfate and filtered. The filtrate is concentrated, and the residue is recrystallized from acetone-water to give 4-[α-(p-tert-butylphenyl)-α- hydroxybenzyl]-α-phenyl-1-piperidinebutanol, melting point 161°-163°C.
[Brand name]

Antifen;Fenadin.
[Therapeutic Function]

Antihistaminic, Bronchodilator
[World Health Organization (WHO)]

The first clinically interesting histamine H-receptor1 antagonists were introduced in the late 1940s and early 1950s. Several H-antihistaminics have a similar cardiac effect to that seen with astemizole1 and terfenadine. Serious cardiovascular adverse reactions have been reported when used concomitantly with imidazole antifungals and macrolide antibiotics. See also under astemizole.
[Biological Activity]

Histamine H 1 receptor antagonist. Also blocks hERG and K ATP channels (IC 50 values are 204 nM and 1.2 μ M respectively). Inhibits the delayed rectifier K + current (I Kr ) in guinea pig ventricular myocytes (IC 50 = 50 nM). Activity prolongs QT and induces Torsades de pointes (TdP); cardiotoxic in vivo .
[Biochem/physiol Actions]

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

Terfenadine not only differs from the other antihistamine drugs in its chemical structure, but also in that its action begins within 1–2 h and last approximately 12 h, reaching its peak of action in 3–4 h.
[Synthesis]

Terfenadine, |á-(4-tert-butylphenyl) -4-hydroxydiphenylmethyl)- 1-piperidinebutanol (16.1.24), is synthesized in two ways. According to the first, benzyl-4- magnesiumchloropiperidine is reacted with benzophenone, giving (1-benzyl-4-piperidyl) diphenylcarbinol (16.2.22), which undergoes further debenzylation by reduction with hydrogen using a palladium over carbon catalyst, giving (4-piperidyl)diphenylcarbinol (16.2.22). This product is alkylated by either 1-(4-tert-butylphenyl)-4-chlorobutanol, which forms terfenadine (16.1.24), or by alkylating with (4-tert-butylphenyl-3-chloropropiophenone, which forms the product (16.1.25), the carbonyl group of which is reduced to an alcohol group, thus giving the desired terfenadine (16.1.24).

Synthesis_50679-08-8

[storage]

Store at +4°C
Spectrum DetailBack Directory
[Spectrum Detail]

Terfenadine(50679-08-8)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Terfenadine(50679-08-8)
[Sigma Aldrich]

50679-08-8(sigmaaldrich)
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