Fexofenadine

Base Information

• Chemical Name: Fexofenadine
• CAS No.: 83799-24-0
• Deprecated CAS: 159389-12-5,76815-58-2
• Molecular Formula: C32H39NO4
• Molecular Weight: 501.666
• Hs Code.: 2933399090
• European Community (EC) Number: 801-893-7
• UNII: E6582LOH6V
• DSSTox Substance ID: DTXSID00861411
• Nikkaji Number: J413.164I
• Wikipedia: Fexofenadine
• Wikidata: Q415122
• NCI Thesaurus Code: C61764
• RXCUI: 87636
• Pharos Ligand ID: MLSC7Q81T2RD
• Metabolomics Workbench ID: 38712
• ChEMBL ID: CHEMBL914
• Mol file: 83799-24-0.mol

Synonyms:Allegra;alpha-(4-(1-carboxy-1-methylethyl)phenyl)-4-hydroxydiphenylmethyl-1-piperidinebutanol;fexofenadine;fexofenadine hydrochloride;MDL 16,455A;MDL 16.455;MDL 16455;MDL-16455;Telfast

Chemical Property of Fexofenadine

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 2.08E-20mmHg at 25°C
• Melting Point: 218-220 °C
• Refractive Index: 1.596
• Boiling Point: 697.3 °C at 760 mmHg
• PKA: 4.43±0.10(Predicted)
• Flash Point: 375.5 °C
• PSA: 81.00000
• Density: 1.171 g/cm³
• LogP: 5.44840
• Storage Temp.: -20°C Freezer
• Solubility.: Methanol (Slightly, Heated, Sonicated)
• XLogP3: 3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 501.28790873
• Heavy Atom Count: 37
• Complexity: 678

Purity/Quality:

99% ^*data from raw suppliers

Fexofenadine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antihistamines
• Canonical SMILES: CC(C)(C1=CC=C(C=C1)C(CCCN2CCC(CC2)C(C3=CC=CC=C3)(C4=CC=CC=C4)O)O)C(=O)O
• Recent ClinicalTrials: Efficacy and Safety of Subcutaneous Dupilumab for the Treatment of Adult Participants With Chronic Pruritus of Unknown Origin (CPUO) (LIBERTY-CPUO-CHIC)
• Recent EU Clinical Trials: Master protocol of two randomized, double blind, placebo-controlled, multicenter, parallel group studies to evaluate the efficacy and safety of dupilumab in adult patients with chronic pruritus of unknown origin (CPUO)
• Recent NIPH Clinical Trials: Evaluation study for the effect of dl-methylephedrine and pseudoephedrine.
• Description: Fexofenadine, the carboxylic acid metabolite of terfenadine, is widely available. It accounts for the antihistaminic properties of terfenadine, which is very rapidly metabolized via CYP3A4-catalyzed processes. Members of the organic anion transporter protein family and the drug efflux transporter P-glycoprotein are involved in the disposition of fexofenadine. Fexofenadine does not have the antiarrhythmic side effects of terfenadine.
• Therapeutic Function: Antihistaminic

Technology Process of Fexofenadine

There total 78 articles about Fexofenadine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

fexofenadine methyl ester (154825-96-4) → fexofenadine (83799-24-0,139965-11-0)

Guidance literature:

With water; potassium hydroxide; In ethanol; for 3h; Reagent/catalyst; Solvent; Reflux;

Reference yield: 92.0%

terfenadine (50679-08-8) → fexofenadine (83799-24-0,139965-11-0)

Guidance literature:

With Absidia corymbifera LCP 62 1800; YM medium cultured with soybean peptones; In N,N-dimethyl-formamide; at 30 ℃; for 120h;

DOI:10.1016/j.bmcl.2004.07.076

Reference yield: 90.0%

ethyl 4-[4[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-α,α-dimethylbenzeneacetate (174483-06-8) → fexofenadine (83799-24-0,139965-11-0)

Guidance literature:

With sodium hydroxide; In methanol;

DOI:10.1016/S0040-4039(98)00410-9

upstream raw materials:

fexofenadine methyl ester

ethyl 4-[4[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-α,α-dimethylbenzeneacetate

2-(4-bromophenyl)-2-methylpropionic acid

4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butyraldehyde

Downstream raw materials:

4-(4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)-1-hydroxybutyl)-α,α-dimethylphenylacetic acid, salt with formic acid

fexofenadine hydrochloride

Refernces

• 1、 -. "A fexofenadine and method for synthesizing intermediate". Paragraph 0047; 0053; 0064; 0065. . Retrieved 2018/04/26.
• 2、 -. "METHODS AND COMPOSITIONS FOR TREATING INFECTION". Paragraph 0242. . Retrieved 2015/09/28.