2-(4-{1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butyl}phenyl)-2-methylpropanoic acid hydrochloride

• ChemBase ID: 70514
• Molecular Formular: C32H40ClNO4
• Molecular Mass: 538.1173
• Monoisotopic Mass: 537.26458645
• SMILES: C(=O)(C(C)(C)c1ccc(cc1)C(CCCN1CCC(CC1)C(c1ccccc1)(c1ccccc1)O)O)O.Cl
• Canonical SMILES: OC(=O)C(c1ccc(cc1)C(CCCN1CCC(CC1)C(c1ccccc1)(c1ccccc1)O)O)(C)C.Cl
• InChI: InChI=1S/C32H39NO4.ClH/c1-31(2,30(35)36)25-17-15-24(16-18-25)29(34)14-9-21-33-22-19-28(20-23-33)32(37,26-10-5-3-6-11-26)27-12-7-4-8-13-27;/h3-8,10-13,15-18,28-29,34,37H,9,14,19-23H2,1-2H3,(H,35,36);1H
• InChIKey: RRJFVPUCXDGFJB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-{1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butyl}phenyl)-2-methylpropanoic acid hydrochloride
• IUPAC Traditional name: fexofenadine hydrochloride
• Synonyms: 2-(4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butyl)phenyl)-2-methylpropanoic acid hydrochloride; 4-[1-Hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]butyl]-α,α-dimethylbenzeneacetic Acid Hydrochloride; Carboxyterfenadine Hydrochloride; Terfenadinecarboxylate Hydrochloride; Alernex; Allegra; Feksine; Fexadyne; Fexo; Fexofen; MDL 16455A; Telfast; Telfast BD; Vivafeks; Fexofenadine Hydrochloride; Fexofenadine HCl; Fexofenidine hydrochloride; MDL 16455 hydrochloride; Terfenidine carboxylate hydrochloride; Fexofenadine hydrochloride; 2-(4-{1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butyl}phenyl)-2-methylpropanoic acid hydrochloride

Database IDs

• CAS Number: 153439-40-8
• MDL Number: MFCD00865710
• PubChem SID: 162036229; 24278447
• PubChem CID: 63002

CALCULATED PROPERTIES

• Acid pKa: 4.040438
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.9300497
• LogD (pH = 7.4): 2.9334483
• Log P: 2.938501
• Molar Refractivity: 147.9846 cm^3
• Polarizability: 57.84285 Å^3
• Polar Surface Area: 81.0 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble ≥5 mg/mL; Methanol
• Apperance: Off-White Solid; white to beige powder
• Melting Point: 190-192°C
• Hydrophobicity(logP): 1.957

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Target: Histamine Receptor
• Gene Information: human ... HRH1(3269)

Product Information

• Purity: >98% (HPLC); 95%; 95+%; 97%
• Salt Data: HCl
• Empirical Formula (Hill Notation): C32H39NO4 · HCl

DETAILS

Sigma Aldrich - F9427

Biochem/physiol Actions
Fexofenadine is a non-sedating H1 histamine receptor antagonist.

Toronto Research Chemicals - F322490

The active metabolite of Terfenadine (T114500), a H1-histamine receptor antagonist.

REFERENCES

• Pratt, E., et al.: Diabet Med., 18, 515 (2001)
• Mizutani, N., et al.: J. Pharmacol. Sci., 93, 437 (2001)
• Scadding, G., et al.: Clin. Drug Invest., 25, 153 (2001)
• Asai, M., et al.: N. Engl. J. Med., 354, 307 (2001)