SynCED: Terfenadine

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:39 UTC

Update Date

2026-05-14 16:35:59 UTC

Accession Number

CHEM002176

Identification

Common Name

Terfenadine

Class

Small Molecule

Description

Terfenadine is only found in individuals that have used or taken this drug. In the U.S., Terfenadine was superseded by fexofenadine in the 1990s due to the risk of cardiac arrhythmia caused by QT interval prolongation.Terfenadine competes with histamine for binding at H1-receptor sites in the GI tract, uterus, large blood vessels, and bronchial muscle. This reversible binding of terfenadine to H1-receptors suppresses the formation of edema, flare, and pruritus resulting from histaminic activity. As the drug does not readily cross the blood-brain barrier, CNS depression is minimal.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Anti-Allergic Agent
Anti-Arrhythmia Agent
Drug
Histamine Antagonist
Histamine H1 Antagonist, Non-Sedating
Human Neurotoxin
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Seldane	Kegg
Ternadin	HMDB
Heumann brand OF terfenadine	HMDB
Merck dura brand OF terfenadine	HMDB
Stadapharm brand OF terfenadine	HMDB
Terfemundin	HMDB
Terfenadin heumann	HMDB
Terfenidine	HMDB
Terfenadin von CT	HMDB
Aliud brand OF terfenadine	HMDB
Cantabria brand OF terfenadine	HMDB
Mundipharma brand OF terfenadine	HMDB
Rapidal	HMDB
Teldane	HMDB
Terfenadin al	HMDB
Triludan	HMDB
CT Arzneimittel brand OF terfenadine	HMDB
Balkis saft spezial	HMDB
Cyater	HMDB
Hisfedin	HMDB
Hoechst brand OF terfenadine	HMDB
Terfedura	HMDB
alpha-(4-(1,1-Dimethylethyl)phenyl)-4-(hydroxydiphenylmethyl)-1-piperdinebutanol	HMDB
CT-Arzneimittel brand OF terfenadine	HMDB
Ratiopharm brand OF terfenadine	HMDB
Bial brand OF terfenadine	HMDB
Dolorgiet brand OF terfenadine	HMDB
Sigma tau brand OF terfenadine	HMDB
Sigma-tau brand OF terfenadine	HMDB
Terfenadin stada	HMDB
Terfenadin-ratiopharm	HMDB
Wolff brand OF terfenadine	HMDB
Terfenadin ratiopharm	MeSH

Chemical Formula

C₃₂H₄₁NO₂

Average Molecular Mass

471.673 g/mol

Monoisotopic Mass

471.314 g/mol

CAS Registry Number

50679-08-8

IUPAC Name

1-(4-tert-butylphenyl)-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butan-1-ol

Traditional Name

terfenadine

SMILES

CC(C)(C)C1=CC=C(C=C1)C(O)CCCN1CCC(CC1)C(O)(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Phenylbutylamine
Phenylpropane
Aralkylamine
Piperidine
Tertiary alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Organoheterocyclic compound
Azacycle
Aromatic alcohol
Alcohol
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

diarylmethane (CHEBI:9453 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Blood
Heart
Liver

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	147°C
Boiling Point	Not Available
Solubility	0.0963 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.00046 g/L	ALOGPS
logP	5.89	ALOGPS
logP	6.48	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	13.2	ChemAxon
pKa (Strongest Basic)	9.02	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	43.7 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	146.27 m³·mol⁻¹	ChemAxon
Polarizability	56.45 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

Oral. On the basis of a mass balance study using 14C labeled terfenadine the oral absorption of terfenadine was estimated to be at least 70%

Mechanism of Toxicity

Terfenadine competes with histamine for binding at H1-receptor sites in the GI tract, uterus, large blood vessels, and bronchial muscle. This reversible binding of terfenadine to H1-receptors suppresses the formation of edema, flare, and pruritus resulting from histaminic activity. As the drug does not readily cross the blood-brain barrier, CNS depression is minimal.

Metabolism

Terfenadine is a prodrug, generally completely metabolized to the active form fexofenadine in the liver by the enzyme cytochrome P450 CYP3A4 isoform. Due to its near complete metabolism by the liver immediately after leaving the gut, terfenadine normally is not measurable in the plasma. (Wikipedia) Half Life: 3.5 hours

Toxicity Values

LD50: 5000 mg/kg (Oral, mouse)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the treatment of allergic rhinitis, hay fever, and allergic skin disorders.

Minimum Risk Level

Not Available

Health Effects

Cardiotoxic at higher doses. In larger plasma concentrations, it may lead to toxic effects on the heart's rhythm (e.g. ventricular tachycardia and torsades de pointes). (Wikipedia)

Symptoms

Mild (e.g., headache, nausea, confusion), but adverse cardiac events including cardiac arrest, ventricular arrhythmias including torsades de pointes and QT prolongation have been reported.

Treatment

in cases of overdosage, cardiac monitoring for at least 24 hours is recommended and for as long as QTc is prolonged, along with standard measures to remove any unabsorbed drug. Treatment of the signs and symptoms of overdosage should be symptomatic and supportive after the acute stage. (2)

Concentrations

Not Available

External Links

DrugBank ID

DB00342

HMDB ID

HMDB0014486

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Timothy G. Fawcett, Christian T. Goralski, David W. Ziettlow, “Preparation of polymorphically pure terfenadine.” U.S. Patent US4742175, issued April, 1975.

MSDS

Link

General References

Terfenadine (CHEM002176)

Structure for CHEM002176: Terfenadine