Terfenadine

Base Information

• Chemical Name: Terfenadine
• CAS No.: 50679-08-8
• Molecular Formula: C32H41NO2
• Molecular Weight: 471.683
• Hs Code.: 29333999
• European Community (EC) Number: 256-710-8
• NSC Number: 758627,665802
• UNII: 7BA5G9Y06Q
• DSSTox Substance ID: DTXSID2023642
• Nikkaji Number: J434.879F,J9.749G
• Wikipedia: Terfenadine
• Wikidata: Q417909
• NCI Thesaurus Code: C29494
• Pharos Ligand ID: MGQPMCMHRN4T
• Metabolomics Workbench ID: 42719
• ChEMBL ID: CHEMBL17157
• Mol file: 50679-08-8.mol

Synonyms:alpha-(4-(1,1-Dimethylethyl)phenyl)-4-(hydroxydiphenylmethyl)-1-piperdinebutanol;Balkis Saft Spezial;Cyater;Hisfedin;Rapidal;RMI 9918;RMI-9918;RMI9918;Seldane;Teldane;Terfedura;Terfemundin;Terfenadin AL;Terfenadin Heumann;Terfenadin Ratiopharm;Terfenadin Stada;terfenadin von ct;Terfenadin-ratiopharm;Terfenadine;Terfenidine;Ternadin;Triludan

Chemical Property of Terfenadine

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 1.41E-16mmHg at 25°C
• Melting Point: 145-152 °C
• Refractive Index: 1.6310 (estimate)
• Boiling Point: 626.8 °C at 760 mmHg
• PKA: pKa 9.21(H2O t = 25 I = 0.025) (Uncertain)
• Flash Point: 306.9 °C
• PSA: 43.70000
• Density: 1.088 g/cm³
• LogP: 6.38370
• Storage Temp.: 2-8°C
• Solubility.: chloroform: soluble250 mg plus 5 ml of solvent, clear to very sl
• Water Solubility.: 0.001 g/100 mL (30 ºC)
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 471.313729551
• Heavy Atom Count: 35
• Complexity: 582

Purity/Quality:

98%min ^*data from raw suppliers

Terfenadine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)C1=CC=C(C=C1)C(CCCN2CCC(CC2)C(C3=CC=CC=C3)(C4=CC=CC=C4)O)O
• Uses: Nonsedating-type histamine H1-receptor antagonist. Antihistaminic H1 antihistamine It is used for relieving symptoms associated with seasonal allergic rhinitis and conjunctivitis, for angioneurotic edema and allergic skin reaction, and also as an ingredient of complex therapy for bronchial asthma. Synonyms of this drug are seldane, hystadin, trexil, and others. Terfenadine has been used to study the role of histamine in itch related to proteinase-activated receptors (PARs) in mice. Terfenadine has also been used to block histamine receptor type 1 to study the pathogenesis of 2,4-dinitrobenzene sulfonic acid (DNBS)-induced ulcerative colitis in rats.
• Therapeutic Function: Antihistaminic, Bronchodilator

Technology Process of Terfenadine

There total 9 articles about Terfenadine 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: 97.0%

→ terfenadine (50679-08-8)

Guidance literature:

Reference yield: 96.0%

4'-tert-butyl-4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]butyrophenone (43076-30-8,76815-60-6) → terfenadine (50679-08-8)

Guidance literature:

With sodium tetrahydroborate; In methanol;

DOI:10.1016/0223-5234(93)90009-4

Reference yield: 90.0%

racemic α-[4-(1,1-dimethylethyl)phenyl]-4-(hydroxydiphenylmethyl)-1-piperidinebutanol (terfenadine) + Di-p-toluoyl-L-tartaric acid monohydrate (71607-31-3) → terfenadine (50679-08-8) + (+)-Terfenadine

Guidance literature:

In acetone;

upstream raw materials:

4'-tert-butyl-4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]butyrophenone

1-<4-(1,1-Dimethylethyl)phenyl>-4-<4-(hydroxydiphenylmethyl)-1-piperidinyl>-1-butanone Hydrochloride

C₁₈H₂₁NO

4'-tert-butyl-4-chlorobutyrophenone

Downstream raw materials:

4'-tert-butyl-4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]butyrophenone

fexofenadine

Refernces

Synthesis of useful fragments in drug discovery: 2-Amino-5-tert- butylpyridine and its oxidised analogues

10.1016/j.bmcl.2011.05.066

The study presents a novel and robust synthesis of the fragment 2-amino-5-tert-butylpyridine, which is proposed as a replacement for 4-tert-butylaniline in drug discovery. The authors, Christopher G. Thomson, John Reilly, and David A. Sandham, from the Novartis Institutes for Biomedical Research, aimed to improve the drug-like properties of compounds containing the tert-butyl phenyl moiety, which is often associated with higher affinity but can lead to issues such as poor solubility and metabolic side effects. The study describes a synthesis route that not only produces 2-amino-5-tert-butylpyridine but also yields intermediates that can be used to synthesize putative oxidative metabolites of the lead molecules. These intermediates include a methyl ester and an alcohol derivative. The synthesized fragment is shown to have improved physicochemical properties, such as reduced lipophilicity, increased polar surface area, and enhanced solubility, compared to 4-tert-butylaniline. The study also highlights the potential of this fragment to aid in understanding the metabolic clearance processes of pharmaceutical compounds, as the tert-butyl group is prone to oxidation via CYP450 enzymes, similar to the well-documented case of terfenadine. The synthesis is scalable, with the production of up to 60 grams of the compound within Novartis laboratories.

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