TERFENADINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C32H41NO2
Molecular Weight	471.6734
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CC(C)(C)C1=CC=C(C=C1)C(O)CCCN2CCC(CC2)C(O)(C3=CC=CC=C3)C4=CC=CC=C4

InChI

InChIKey=GUGOEEXESWIERI-UHFFFAOYSA-N

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

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Description

Terfenadine under brand name Seldane was used for the treatment of allergic rhinitis and allergic skin disorders but was withdrawn because of the serious side effect, heart rhythm problems. Terfenadine is a potent antagonist of histamine H1-receptor-mediated responses.

Approval Year

Targets

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 316	Antagonist 2,849		40.0 nM [Ki]

C_max

Value	Dose	Analyte	Population
406.9 ng/mL	120 mg single, oral	FEXOFENADINE plasma	Homo sapiens
458.1 ng/mL	120 mg single, oral	FEXOFENADINE plasma	Homo sapiens
1.544 ng/mL	60 mg single, oral	TERFENADINE plasma	Homo sapiens
4.519 ng/mL	180 mg single, oral	TERFENADINE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
2720.1 ng × h/mL	120 mg single, oral	FEXOFENADINE plasma	Homo sapiens
2712.1 ng × h/mL	120 mg single, oral	FEXOFENADINE plasma	Homo sapiens
11.864 ng × h/mL	60 mg single, oral	TERFENADINE plasma	Homo sapiens
44.341 ng × h/mL	180 mg single, oral	TERFENADINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
12.6 h	120 mg single, oral		FEXOFENADINE plasma	Homo sapiens
11.6 h	120 mg single, oral		FEXOFENADINE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
180 mg 2 times / day multiple, oral Highest studied dose	healthy, 18-40	Other AEs: Electrocardiogram QTc interval prolonged...
60 mg 2 times / day multiple, oral Recommended	unhealthy, 18-45	Disc. AE: Headache... Other AEs: Somnolence...
120 mg 1 times / day multiple, oral Recommended	unhealthy, 19-66	Disc. AE: Nausea, Headache...
60 mg single, oral Recommended	healthy, 23-40
240 mg single, oral Highest studied dose	healthy, 23-47	Other AEs: Driving ability disturbed...

Showing 1 to 5 of 5 entries

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AEs

Show entries

AE	Significance	Dose	Population
Electrocardiogram QTc interval prolonged	12.5%	180 mg 2 times / day multiple, oral Highest studied dose	healthy, 18-40
Somnolence	grade 1, 4.15%	60 mg 2 times / day multiple, oral Recommended	unhealthy, 18-45
Headache	grade 2-3, 8.3% Disc. AE	60 mg 2 times / day multiple, oral Recommended	unhealthy, 18-45
Headache	2.4% Disc. AE	120 mg 1 times / day multiple, oral Recommended	unhealthy, 19-66
Nausea	2.4% Disc. AE	120 mg 1 times / day multiple, oral Recommended	unhealthy, 19-66

Showing 1 to 5 of 6 entries

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Sourcing

Sourcing

Show entries

Vendor/Aggregator	ID	URL
001 Chemical	DY107635	https://www.001chemical.com/chem/50679-08-8
3B Scientific (Wuhan) Corp	3B1-00163	http://www.3bsc.com/index/pro_info.php?id=20375
3B Scientific (Wuhan) Corp	3B2-0907	http://www.3bsc.com/index/pro_info.php?id=41812
AA Blocks	AA003UFS	https://www.aablocks.com/goods/Goods/detail?id=AA003UFS
Aaron Chemicals	AR003V7K	http://www.aaronchem.com/50679-08-8

Showing 1 to 5 of 46 entries

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PubMed

Show entries

Title	Date	PubMed
Mechanism of terfenadine block of ATP-sensitive K(+) channels.	2000 Aug	10928959
Redox state dependency of HERGS631C channel pharmacology: relation to C-type inactivation.	2000 May 26	10828461
Effect of oxatomide, an antiallergic agent, on QT interval in dogs.	2001	11799844
Impact of rhinitis on airway inflammation: biological and therapeutic implications.	2001	11737929
Safety of antihistamines in children.	2001	11235817

Showing 1 to 5 of 23 entries

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Patents

Sample Use Guides

In Vivo Use Guide

Terfenadine 20 mg 3 times a day

Route of Administration: Oral

Show entries

Name

Type

Language

SELDANE

Preferred Name

English

TERFENADINE

Official Name

English

TERFENADINE [MART.]

Common Name

English

NSC-758627

Code

English

Terfenadine [WHO-DD]

Common Name

English

Showing 1 to 5 of 17 entries

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Classification Tree

Code System

Code

Immunotherapeutic Agent

NCI_THESAURUS

C29578

Other antihistamines for systemic use

WHO-ATC

R06AX12

Other antihistamines for systemic use

WHO-VATC

QR06AX12

Allergy symptoms

LIVERTOX

939

Subpart B--Compounded Drug Products

CFR

21 CFR 216.24

Showing 1 to 5 of 5 entries

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Code System

Code

Type

Description

MESH

D016593

PRIMARY

ECHA (EC/EINECS)

256-710-8

PRIMARY

NSC

758627

PRIMARY

WIKIPEDIA

Terfenadine

PRIMARY

CAS

50679-08-8

PRIMARY

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ACTIVE MOIETY


					7BA5G9Y06Q

TERFENADINE

METABOLITE (PARENT)


					YY2UN66CBE

4-(1-HYDROXY-4-(4-(HYDROXYDIPHENYLMETHYL)-1-PIPERIDINYL)BUTYL)-.ALPHA.,.ALPHA.-DIMETHYLBENZENEACETALDEHYDE

SMILES

InChI

Approval Year

Targets

Cmax

AUC

T1/2

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2