CAS 50679-08-8|terfenadine|Terfenadine|1-(4-tert-butylphenyl)-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butan-1-ol|Terfenadine|α-[4-(1,1-Dimethylethyl)phenyl]-4-(hydroxydiphenylmethyl)-1-piperidin...

General Information

Structure

Molecular Formula

C₃₂H₄₁NO₂

Molecular Mass

471.67344

Exact Mass

471.31372956

Charge

InChI

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

InChIKey

GUGOEEXESWIERI-UHFFFAOYSA-N

Canonic Smiles

OC(c1ccc(cc1)C(C)(C)C)CCCN1CCC(CC1)C(c1ccccc1)(c1ccccc1)O

Isomeric Smiles

OC(C1CCN(CC1)CCCC(O)c1ccc(C(C)(C)C)cc1)(c1ccccc1)c1ccccc1

Calculated Properties

JChem

Acid pKa

13.197068

H Acceptors

H Donor

LogD (pH = 5.5)

3.2679386

LogD (pH = 7.4)

4.8515763

Log P

6.4791093

Molar Refractivity

146.2674

Polarizability

57.32755

Polar Surface Area

43.7

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

5.89

LOG S

-6.01

Solubility (Water)

4.58e-04 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

IUPAC Traditional name

terfenadine

IUPAC name

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

Synonyms

TerfenadineTerfenadineα-[4-(1,1-Dimethylethyl)phenyl]-4-(hydroxydiphenylmethyl)-1-piperidinebutanolTernadinAllerplusHistadinα-[4-(1,1-Dmethylethyl)phenyl]-4-(hydroxydiphenylmethyl)-1-piperidinebutanolα-(p-tert-Butylphenyl)-4-(α-hydroxy-α-phenylbenzyl)-1-piperidinebutanolCyater(±)-TerfenadineMDL 9918NSC 665802

Brand Name

TriludanTeldaneTeldanexAldabanAllerplusTerdinTerfexCyaterSeldane

Names and Identifiers

Registration numbers

CAS Number

50679-08-8

PubChem CID

5405

PubChem SID

4650700716096368924277779

EC Number

256-710-8

MDL Number

MFCD00079622

Registration numbers

Properties

Pharmacology Properties

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)

Others

Product Information

Download link

Free Base

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00342

Drug Groups

approved; withdrawn

Description

In the U.S., Terfenadine was superseded by fexofenadine in the 1990s due to the risk of cardiac arrhythmia caused by QT interval prolongation.

Indication

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

Pharmacology

Terfenadine, an H1-receptor antagonist antihistamine, is similar in structure to astemizole and haloperidol, a butyrophenone antipsychotic. The active metabolite of terfenadine is fexofenadine.

Toxicity

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. LD₅₀=mg/kg (orally in mice)

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic

Absorption

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

Half Life

3.5 hours

Protein Binding

70%

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Sigma Aldrich

T9652

Biochem/physiol Actions
Non-sedating second generation H1 histamine receptor antagonist. Mainly metabolized by Cyp3A4, 5, 7. Inhibits CYP2C8.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. T9652.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

TRC

T114500

Nonsedating-type histamine H1-receptor antagonist. Antihistaminic.

Molecule Details

References

PubChem Literature

From Data Sources

• Badwan, A.A., et al.: Anal. Profiles Drug Subs., 19, 627 (1982)

• Jurima-Romet, M., et al.: Drug Metab. Dispos., 22, 849 (1982)

• Carr, A.A., et al.: Arzneim. Forsch., 32, 1157 (1982)

• Masheter, H.C., et al.: Clin. Rev. Allergy, 11, 5 (1982)

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Academic Data

Commercial Catalog

Names and Identifiers

IUPAC Traditional name

terfenadine

IUPAC name

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

Synonyms

Brand Name

TriludanTeldaneTeldanexAldabanAllerplusTerdinTerfexCyaterSeldane

Registration numbers

CAS Number

50679-08-8

PubChem CID

5405

PubChem SID

4650700716096368924277779

EC Number

256-710-8

MDL Number

MFCD00079622

Molecule Details

DrugBank

DB00342

Drug Groups

approved; withdrawn

Description

In the U.S., Terfenadine was superseded by fexofenadine in the 1990s due to the risk of cardiac arrhythmia caused by QT interval prolongation.

Indication

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

Pharmacology

Terfenadine, an H1-receptor antagonist antihistamine, is similar in structure to astemizole and haloperidol, a butyrophenone antipsychotic. The active metabolite of terfenadine is fexofenadine.

Toxicity

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic

Absorption

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

Half Life

3.5 hours

Protein Binding

70%

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Sigma Aldrich

T9652

TRC

T114500

Nonsedating-type histamine H1-receptor antagonist. Antihistaminic.

References

PubChem Literature

From Data Sources

• Badwan, A.A., et al.: Anal. Profiles Drug Subs., 19, 627 (1982)

• Jurima-Romet, M., et al.: Drug Metab. Dispos., 22, 849 (1982)

• Carr, A.A., et al.: Arzneim. Forsch., 32, 1157 (1982)

• Masheter, H.C., et al.: Clin. Rev. Allergy, 11, 5 (1982)

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

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)

Others

Product Information

Download link

Free Base

Molecule

ID:226