1-(4-tert-butylphenyl)-4-[4-(diphenylmethoxy)piperidin-1-yl]butan-1-one

• ChemBase ID: 124976
• Molecular Formular: C32H39NO2
• Molecular Mass: 469.65756
• Monoisotopic Mass: 469.29807949
• SMILES: C(OC1CCN(CC1)CCCC(=O)c1ccc(C(C)(C)C)cc1)(c1ccccc1)c1ccccc1
• Canonical SMILES: O=C(c1ccc(cc1)C(C)(C)C)CCCN1CCC(CC1)OC(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C32H39NO2/c1-32(2,3)28-18-16-25(17-19-28)30(34)15-10-22-33-23-20-29(21-24-33)35-31(26-11-6-4-7-12-26)27-13-8-5-9-14-27/h4-9,11-14,16-19,29,31H,10,15,20-24H2,1-3H3
• InChIKey: MJJALKDDGIKVBE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(4-tert-butylphenyl)-4-[4-(diphenylmethoxy)piperidin-1-yl]butan-1-one
• IUPAC Traditional name: 1-(4-tert-butylphenyl)-4-[4-(diphenylmethoxy)piperidin-1-yl]butan-1-one; kestin
• Synonyms: Estivan; Ebastel; Ebastin; Kestine; LAS-W 090; RP 64305; Ebastine; 1-[4-(1,1-Dimethylethyl)phenyl]-4-[4-(diphenylmethoxy)-1-piperidinyl]-1-butanone; Ebastine; Bastel; 4-(4-(benzhydryloxy)piperidin-1-yl)-1-(4-(tert-butyl)phenyl)butan-1-one

Database IDs

• CAS Number: 90729-43-4
• MDL Number: MFCD00865661
• PubChem SID: 162219329
• PubChem CID: 3191

CALCULATED PROPERTIES

• Acid pKa: 16.450401
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.1321745
• LogD (pH = 7.4): 5.8916144
• Log P: 6.9630213
• Molar Refractivity: 145.381 cm^3
• Polarizability: 56.836548 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO: >10 mg/mL; H2O: insoluble
• Apperance: white solid; White to Off-White Powder
• Melting Point: 80-82°C

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: EL8140000
• German water hazard class: 3
• GHS Hazard statements: H413
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: room temp

Pharmacology Properties

• Target: Others
• Mechanism of Action: Antihistamine; Calcium entry blocker

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Description: 2 Isomers
• Application(s): Antiallergic agent
• Empirical Formula (Hill Notation): C32H39NO2

DETAILS

InterBioScreen - BB_SC-9897

2 Isomers

Sigma Aldrich - E9531

Biochem/physiol Actions
Ebastine is a non-sedating histamine H1 receptor antagonist, which inhibits allergen-induced bronchospasm in conscious guinea pigs. Unlike other compounds in this category, ebastine does not prolong the QT interval at up to five times the recommended therapeutic dose.

Toronto Research Chemicals - E320000

A nonsedating type histamine H1-receptor antagonist. Antihistaminic.

REFERENCES

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• Hurst, M. et al., Drugs, 2000, 59, 981-1006