CAS 125602-71-3 Bepotastine (HCID 164522)

概要

Bepotastine is an ether that is (S)-(4-chlorophenyl)(pyridin-2-yl)methanol in which the hydroxyl hydrogen is substituted by a 1-(3-carboxypropyl)piperidin-4-yl group. A topical, selective and non-sedating histamine (H1) receptor antagonist used (as its benzenesulfonate salt) for treatment of itching associated with allergic conjunctivitis. It has a role as a H1-receptor antagonist and an anti-allergic agent. It is a monocarboxylic acid, an ether, a member of piperidines, a member of pyridines and a member of monochlorobenzenes. It is a conjugate base of a bepotastine(1+).

名称と識別子

優先名称: Bepotastine
IUPAC: 4-[4-[(S)-(4-chlorophenyl)-pyridin-2-ylmethoxy]piperidin-1-yl]butanoic acid
現地名: ベポタスチン
英語名: BEPOTASTINE
分子式: C21H25ClN2O3
分子量: 388.89

名称と別名

Bepotastine125602-71-3BetotastinebepotastinaTau 284bepotastinum4-[4-[(S)-(4-chlorophenyl)-pyridin-2-ylmethoxy]piperidin-1-yl]butanoic acidHYD2U48IASCHEBI:71204DTXSID90904947(S)-4-(4-((4-Chlorophenyl)(2-pyridil)methoxy)piperidino)butylic acid(+)-4-(((S)-p-Chloro-alpha-2-pyridylbenzyl)oxy)-1-piperidinebutyric acid

名称をさらに表示

ベポタスチン4-[4-[(S)-(4-クロロフェニル)(2-ピリジニル)メトキシ]ピペリジノ]酪酸4-[4-[[(S)-α-(2-ピリジニル)-4-クロロベンジル]オキシ]ピペリジン-1-イル]ブタン酸4-[4-[[(αS)-α-(2-ピリジル)-4-クロロベンジル]オキシ]ピペリジノ]酪酸4-[4-[[(S)-4-クロロ-α-(2-ピリジル)ベンジル]オキシ]ピペリジノ]酪酸ベトタスチン4-[4-[(S)-4-クロロ-α-(2-ピリジル)ベンジルオキシ]ピペリジノ]酪酸4-{4-[(S)-(4-クロロフェニル)(ピリジン-2-イル)メトキシ]ピペリジン-1-イル}ブタン酸Bestatin (i.eBepotastine >(S)-BepotastineBepotastine >90%betotastine besilateBepotastine free baseBepotastine (Standard)-4-(4-((4-Chlorophenyl)Bepotastine, 10 mM in DMSO

TAU-2841-Piperidinebutanoic acid, 4-((4-chlorophenyl)-2-pyridinylmethoxy)-4-(4-((S)-(4-chlorophenyl)-pyridin-2-ylmethoxy)piperidin-1-yl)butanoic acidRefChem:56382DTXCID201334062(S)-4-(4-((4-chlorophenyl)(2-pyridil)methoxy)piperidino)butylic acid monobenzenesulfonate4-(4-((4-chlorophenyl)(pyridin-2-yl)methoxy)piperidin-1-yl)butanoic acid(S)-4-(4-((4-Chlorophenyl)(pyridin-2-yl)methoxy)piperidin-1-yl)butanoic acid

データベース識別子

CAS: 125602-71-3
PubChem CID: 164522
DTXSID: DTXSID90904947
ChEMBL: CHEMBL1201758
ChEBI: CHEBI:71204
UNII: HYD2U48IAS
Nikkaji: J824.035C

物性

構造計算による物性

XLogP: 1
極性表面積: 62.7 Å²
水素結合供与体数: 1
水素結合受容体数: 5
回転可能結合数: 8
重原子数: 27
形式電荷: 0
複雑度: 449

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15

Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Allergic Agents; Antihistamines

物理化学的性質

融点: 56 · 56 - 58°C
沸点: 546.8 · 546.8±50.0 °C(Predicted)
比重(密度): 1.26 · 1.26
貯蔵温度: -20 °C · -20°C Freezer, Under inert atmosphere
溶解性: DMSO（微量）、メタノール（微量）
酸解離定数(Pka): 4.44 · 4.44±0.10(Predicted)
外見: 個体
色: ホワイト～ペールベージュ
InChIKey: YWGDOWXRIALTES-NRFANRHFSA-N
SMILES: [C@@H](C1N=CC=CC=1)(C1C=CC(=CC=1)Cl)OC1CCN(CC1)CCCC(=O)O

安全と法規制

毒性情報

Exposure Routes · 1 件

Oral, Ophthalmic. Tmax, after single dose, opthalmic = 1.2 hours; Cmax, 1.5%, opthalmic dose = 7.3 ± 1.9 ng/mL; After 24 hours post-installation, levels of bepotastine are below quantifiable limit of 2 ng/mL. Minimal systemic absorption with opthalmic dosage form.

Toxicity Summary · 1 件

Because of a type 1 hypersensitivity reaction cascade that is triggered by antigen exposure, allergic conjunctivitis occurs. Allergen exposure is followed by conjunctival mast cell degranulation and histamine released as a result of the formation of complementary IgE cross-links on the conjunctiva. Due to the release of histamine, symptoms such as itching can be observed. Bepotastine works to relieve itchy eyes by three primary mechanisms of action. It is a non-sedating, selective antagonist of the histamine 1 (H1) receptor, a mast cell stabilizer, and it suppresses the migration of eosinophils into inflamed tissues to prevent tissue damage and worsening of allergic inflammation of the conjunctiva.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

化学と産業

薬理情報

Protein Binding55.4% mean plasma protein binding with 10 mg oral dose. Extent of protein binding is independent of plasma drug concentration.

Pharmacodynamics · 1 件

Bepotastine is a non-sedating, selective antagonist of the histamine 1 (H1) receptor. It belongs to the second-generation piperidine chemical class. It is a mast cell stabilizer and suppresses the migration of eosinophils into inflamed tissues. Furthermore, bepotastine does not interact with serotonin, muscarinic, benzodiazepine, and beta-adrenergic receptor that would otherwise result in adverse reactions such as dry mouth or sonmolence. Onset of action = 0.25 hours; Duration of action = 12-24 hours;

Mechanism of Action · 1 件

Because of a type 1 hypersensitivity reaction cascade that is triggered by antigen exposure, allergic conjunctivitis occurs. Allergen exposure is followed by conjunctival mast cell degranulation and histamine released as a result of the formation of complementary IgE cross-links on the conjunctiva. Due to the release of histamine, symptoms such as itching can be observed. Bepotastine works to relieve itchy eyes by three primary mechanisms of action. It is a non-sedating, selective antagonist of the histamine 1 (H1) receptor, a mast cell stabilizer, and it suppresses the migration of eosinophils into inflamed tissues to prevent tissue damage and worsening of allergic inflammation of the conjunctiva.

Biological Half-LifeElimination half life = 2.5 hours

Metabolism/Metabolites · 2 件

Minimal metabolism via CYP enzymes

Minimal metabolism via CYP enzymes Route of Elimination: When a oral dose of 2.5 - 40 mg bepotastine is given, 75%-90% of the dose was excreted unchanged in the urine by 24 hours. Half Life: Elimination half life = 2.5 hours

FDA Pharmacological Classification · 4 件

HYD2U48IAS

BEPOTASTINE

Established Pharmacologic Class [EPC] - Histamine-1 Receptor Antagonist

Bepotastine is a Histamine-1 Receptor Antagonist.

用途と製造

UsesFor the symptomatic treatment of itchy eyes (caused by IgE-induced mast cell degranulation) due to allergic conjunctivitis. Used in the treatment of allergic rhinitis and uriticaria/puritus. [Wikipedia]

応用分野

用途ヒスタミンH 拮抗薬アレルギー性鼻炎，蕁麻疹，アトピー性皮膚炎

サプライヤー88 社

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Sinco Pharmachem (ShenZhen) R&D Co., Ltd.+86-18603013401 · [email protected]

補足説明 · 1 件

定義ChEBI: An ether that is (S)-(4-chlorophenyl)(pyridin-2-yl)methanol in which the hydroxyl hydrogen is substituted by a 1-(3-carboxypropyl)piperidin-4-yl group. A topical, selective and non-sedating histamine (H1) receptor anta onist used (as its benzenesulfonate salt) for treatment of itching associated with allergic conjunctivitis.