| Identification | Back Directory | [Name]
BEPOTASTINE BESILATE | [CAS]
190786-44-8 | [Synonyms]
BB
CS-645
CS-487
Talion
TAU 284
Bepreve
Talion (TN)
Benzestatine
Bepotastine Beslilat
Bepotastine Besylate
BEPOTASTINE BESILATE
Bepotastine Beslilate
Benzenesulfonate salt
(S)-Bepotastine Besylate
Bepotastine Benzenesulfonate
BEPOTASTINE BESILATE USP/EP/BP
bepotastine benzenesulfonate salt
Bepotastine Besilate (This product is only available in Japan.)
4-[4-[(R)-(4-chlorophenyl)-pyridin-2-yl-methoxy]-1-piperidyl]butanoic acid
(S)-4-[4-(4-Chlorophenyl-2-pyridylMethoxy)piperidinyl]butyric Acid Benzenesulfonate
4-[(S)-(4-Chlorophenyl)-2-pyridinylMethoxy]-1-piperidinebutanoic Acid Benzenesulfonate
4-[4-[(4-chlorophenyl)-pyridin-2-ylMethoxy]piperidin-1-yl]butanoic acid benzenesulfonate
4-((4-Chlorophenyl)-2-pyridinylmethoxy)- (S)-1-piperidinebutanoic acid monobenzenesulfonate
4-[4-[(S)-(4-Chlorophenyl)(2-pyridinyl)methoxy]-1-piperidinyl]butanoic Acid Benzenesulfonate
(S)-4-[4-[(4-Chlorophenyl)(pyridin-2-yl)methoxy]piperidin-1-yl]butanoic Acid Benzenesulfonate
1-Piperidinebutanoic acid, 4-[(S)-(4-chlorophenyl)-2-pyridinylmethoxy]-, monobenzenesulfonate
(+)-(S)-4-(4-((4-Chlorophenyl)(2-pyridyl)methoxy)piperidino)butyric acid monobenzenesulfonate
1-Piperidinebutanoic acid, 4-[(4-chlorophenyl)-2-pyridinylmethoxy]-, (S)-, monobenzenesulfonate
1-Piperidinebutanoic acid, 4-[(S)-(4-chlorophenyl)-2-pyridinylmethoxy]-, benzenesulfonate (1:1)
(+)-(S)-4-[4-[1-(4-Chlorophenyl)-1-(2-pyridyl)methoxy]piperidin-1-yl]butyric acid benzenesulfonate | [EINECS(EC#)]
1806241-263-5 | [Molecular Formula]
C27H31ClN2O6S | [MDL Number]
MFCD01938491 | [MOL File]
190786-44-8.mol | [Molecular Weight]
547.07 |
| Chemical Properties | Back Directory | [Melting point ]
161-163° | [alpha ]
D20 +6.0° (c = 5 in methanol) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
DMSO (Slightly, Heated), Methanol (Slightly, Heated) | [form ]
Solid | [color ]
White to Light Beige | [optical activity]
[α]/D 4.5 to 6.5°, c =1 in methanol | [Stability:]
Hygroscopic |
| Hazard Information | Back Directory | [Description]
Betotastine was introduced in Japan for the treatment of allergic rhinitis. This
structurally-related derivative of chlorpheniramine and ebastine is prepared by
condensation of optically-resolved 4-[1-(4-chlorophenyl)-1-(2-pyridyl)-methoxy]piperidine
with ethyl 4-bromobutyrate followed by ester hydrolysis. Betotastine is the seventh
marketed non-sedating histamine H1 antagonist. Its very low sedative side effect is due to
very poor penetration in the central nervous system. Besides its potent and long-acting
activity in models of allergic rhinitis, betotastine was also shown to act as a PAF antagonist and inhibit LTD4 in tracheal smooth muscle and ileum, IL-5 production by human peripheral
blood mononuclear cells as well as eosinophil infiltration in the airway and peripheral
blood. As a consequence, it is currently being developed against other allergic and
respiratory disorders. | [Chemical Properties]
Off-White to Light Beige Solid | [Originator]
UBE (Japan) | [Uses]
Bepotastine is a histamine H1 receptor anatagonist. Bepotastine suppresses some allergic inflammatory processes such as allergic rhinitis, chronic urticaria or pruritus associated with skin conditions
(eczema/dermatitis, prurigo or pruritus cutaneus). | [Uses]
Bepotastine is a non-sedating, selective antagonist of histamine 1 (H1) receptor with pIC50 of 5.7 | [Definition]
ChEBI: An organosulfonate salt obtained by combining equimolar amounts of bepotastine and benzenesulfonic acid. A topical, selective and non-sedating histamine (H1) receptor antagonist used for treatment of itching associated with allergic co
junctivitis. | [Manufacturing Process]
Manufacturing process for BEPOTASTINE BESILATE includes these steps as follows: Step A: Synthesis of Methyl 2-endo-hydroxy-1-exo-hydroxymethyl-3a,8b-cis-2,3,3a,8b-tetrahydro-
1H-5-cyclopenta[b]benzofurancarboxylate,Step B: Synthesis of Methyl 3-methyl-trans-4a-cisoid-4a,5a-cis-5a-1,4a,5,5a,10b,10c-hexahydro-7-
dioxin o[5,4-a]cyclopenta[b]benzofurancarboxylate,Step C: Synthesis of 3-Methyl-trans-4a-cosoid-4a,5a-cis-5a-1,4a,5,5a,10b,10c-hexahydro-7-
dioxino[5,4-a]cyclopenta[b]benzofuranylmethanol,Step D: Synthesis of 7-Chloromethyl-3-methyl-trans-4a-cisoid-4a,5a-cis-5a-1,4a,5,5a,10b,10chexahydrodioxino[5,4-a]cyclopenta[b]benzofuran,Step E: Synthesis of 4-[3-Methyl-trans-4a-cisoid-4a,5a-cis-5a-1,4a,5,5a,10b,10c-hexahydro-7-
dioxino[5,4-a]cyclopenta[b]benzofuranyl]butyric acid, Step F: Synthesis of Methyl 4-[2-endo-hydroxy-1-exo-hydroxymethyl-3a,8b-cis-2,3,3a,8btetrahydro-1H-5- cyclopenta[b]benzofuranyl]butyrate, Step G: Synthesis of Methyl 4-[2-endo-acetoxy-1-exo-hydroxymethyl-3a,8b-cis-2,3,3a,8btetrahydro-1H-5-cyclopenta[b]benzofuranyl]butyrate, Step H: Synthesis of Methyl ester of 11,15-dideoxy-11-acetoxy-16-methyl-15-oxo-18,19-
tetradehydro-5,6,7-trinor-4,8-inter-m-phenylene PGI2,Step I: Synthesis of 11-Deoxy-11-acetoxy-16-methyl-18,19-tetradehydro-5,6,7-trinor-4,8-inter-mphenylene PGI2.To a solution of 54 mg of methyl ester of 11-deoxy-11-acetoxy-16-methyl-
18,19-tetradehydro-5,6,7-trinor-4,8-inter-m-phenylene PGI2 in 4.5 ml of
anhydrous methanol was added 0.001 ml of 4.8 N sodium methoxide under
argon, and the reaction mixture was stirred for 1.5 hours at room
temperature.
After addition of acetic acid to the reaction mixture and concentration of the
mixture, the residue was dissolved in 20 ml of ethyl acetate, and the solution
was washed with aqueous saturated solution of sodium hydrogen carbonate,
water and aqueous saturated solution of sodium chloride, dried and
concentrated to afford 55 mg of an oily material.
This oily material was purified by column chromatography using ethyl acetate
and cyclohexane (3:1) as eluent to give 48 mg of the methyl ester of 16-
methyl-18,19-tetradehydro-5,6,7-trinor-4,8-inter-m-phenylene PGI2. | [Brand name]
Talion | [Therapeutic Function]
Antiallergic |
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