Ebastine

Title: Ebastine
CAS Registry Number: 90729-43-4
CAS Name: 1-[4-(1,1-Dimethylethyl)phenyl]-4-[4-(diphenylmethoxy)-1-piperidinyl]-1-butanone
Additional Names: 4¢-tert-butyl-4-[4-(diphenylmethoxy)piperidino]butyrophenone; 4-diphenylmethoxy-1-[3-(4-tert-butylbenzoyl)propyl]piperidine
Manufacturers' Codes: LAS-W-090
Trademarks: Ebastel (Almirall); Estivan (Almirall); Evastel (Almirall); Kestin (Almirall); Kestine (Almirall)
Molecular Formula: C32H39NO2
Molecular Weight: 469.66
Percent Composition: C 81.83%, H 8.37%, N 2.98%, O 6.81%
Literature References: Nonsedating type histamine H1-receptor antagonist. Prepn: J. M. P. Soto et al., EP 134124; eidem, US 4550116 (both 1985 to Fordonal). Metabolized in vivo to carebastine, its active carboxylic acid metabolite. Clinical pharmacology, pharmacokinetics: J. Vincent et al., Br. J. Clin. Pharmacol. 26, 497 (1988). Effect on psychomotor performance: J. Vincent et al., ibid. 503.
Derivative Type: Fumarate
Molecular Formula: C32H39NO2.C4H4O4
Molecular Weight: 585.73
Percent Composition: C 73.82%, H 7.40%, N 2.39%, O 16.39%
Properties: Crystals from ethanol, mp 197-198°.
Melting point: mp 197-198°
Therap-Cat: Antihistaminic.
Keywords: Antihistaminic.
Ebimar? Ebselen Eburnamonine Ecabapide Ecabet

Ebastine
Ebastine.svg
Systematic (IUPAC) name
4-(4-benzhydryloxy-1-piperidyl)-1-(4-tert-butylphenyl)butan-1-one
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Routes Oral
Pharmacokinetic data
Protein binding Greater than 95%
Metabolism Hepatic (CYP3A4-mediated), to carebastine
Half-life 15 to 19 hours (carebastine)
Identifiers
CAS number 90729-43-4 YesY
ATC code R06AX22
PubChem CID 3191
ChemSpider 3079 YesY
UNII TQD7Q784P1 YesY
ChEMBL CHEMBL305660 YesY
Chemical data
Formula C32H39NO2 
Mol. mass 469.658 g/mol
 YesY (what is this?)  (verify)

Ebastine (trade names Evastin, Kestine, Ebastel, Aleva, Ebatrol) is a non-sedating H1 antihistamine.

It does not penetrate the blood–brain barrier to a significant amount and thus allows an effective block of the H1 receptor in peripheral tissue without a central side effect, i.e. not causing sedation or drowsiness.[1][2]

The patent in which the structure of ebastine is first mentioned is EP 134124  in Europe and US 4550116  in the US. The substance is often provided in micronised form due to poor water solubility.