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

• ChemBase ID: 226
• Molecular Formular: C32H41NO2
• Molecular Mass: 471.67344
• Monoisotopic Mass: 471.31372956
• SMILES: OC(C1CCN(CC1)CCCC(O)c1ccc(C(C)(C)C)cc1)(c1ccccc1)c1ccccc1
• Canonical SMILES: OC(c1ccc(cc1)C(C)(C)C)CCCN1CCC(CC1)C(c1ccccc1)(c1ccccc1)O
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(4-tert-butylphenyl)-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butan-1-ol
• IUPAC Traditional name: terfenadine
• Brand Name: Aldaban; Allerplus; Cyater; Seldane; Teldane; Teldanex; Terdin; Terfex; Triludan
• Synonyms: α-[4-(1,1-Dimethylethyl)phenyl]-4-(hydroxydiphenylmethyl)-1-piperidinebutanol; Terfenadine; α-[4-(1,1-Dmethylethyl)phenyl]-4-(hydroxydiphenylmethyl)-1-piperidinebutanol; α-(p-tert-Butylphenyl)-4-(α-hydroxy-α-phenylbenzyl)-1-piperidinebutanol; Allerplus; Cyater; Histadin; MDL 9918; NSC 665802; (±)-Terfenadine; Ternadin; Terfenadine

Database IDs

• CAS Number: 50679-08-8
• EC Number: 256-710-8
• MDL Number: MFCD00079622
• PubChem SID: 160963689; 24277779; 46507007
• PubChem CID: 5405

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.197068
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.2679386
• LogD (pH = 7.4): 4.8515763
• Log P: 6.4791093
• Molar Refractivity: 146.2674 cm^3
• Polarizability: 57.32755 Å^3
• Polar Surface Area: 43.7 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.89
• LOG S: -6.01
• Solubility (Water): 4.58e-04 g/l

PROPERTIES

Physical Property

• Solubility: 10 mg/L; Chloroform
• Apperance: White Solid
• Melting Point: 130-140°C
• Hydrophobicity(logP): 7.1

Safety Information

• Storage Condition: Refrigerator
• RTECS: TM4969000
• German water hazard class: 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Others
• Gene Information: 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)

Product Information

• Salt Data: Free Base

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• Drug Groups: approved; withdrawn
• Description: In the U.S., Terfenadine was superseded by fexofenadine in the 1990s due to the risk of cardiac arrhythmia caused by QT interval prolongation.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.

Toronto Research Chemicals - T114500

Nonsedating-type histamine H1-receptor antagonist. Antihistaminic.

REFERENCES

• Carr, A.A., et al.: Arzneim. Forsch., 32, 1157 (1982)
• Badwan, A.A., et al.: Anal. Profiles Drug Subs., 19, 627 (1982)
• Masheter, H.C., et al.: Clin. Rev. Allergy, 11, 5 (1982)
• Jurima-Romet, M., et al.: Drug Metab. Dispos., 22, 849 (1982)