CAS 125602-71-3 Bepotastine (HCID 164522)

Überblick

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+).

Namen und Bezeichner

Bevorzugter Name: Bepotastine
IUPAC: 4-[4-[(S)-(4-chlorophenyl)-pyridin-2-ylmethoxy]piperidin-1-yl]butanoic acid
Englischer Name: BEPOTASTINE
Summenformel: C21H25ClN2O3
Molmasse: 388.89

Namen und Synonyme

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

Weitere Namen anzeigen

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 1
Polarare Oberfläche (TPSA): 62,7 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 5
Frei drehbare Bindungen: 8
Schwere Atome: 27
Formalladung: 0
Komplexität: 449

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15

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

Physikochemische Eigenschaften

Schmelzpunkt: 56 · 56 - 58°C
Siedepunkt: 546.8 · 546.8±50.0 °C(Predicted)
Dichte: 1.26 · 1.26
storage temp.: -20 °C · -20°C Freezer, Under inert atmosphere
Löslichkeit: DMSO (Slightly), Methanol (Slightly)
pka: 4.44 · 4.44±0.10(Predicted)
Aggregatzustand: Solid
Farbe: White to Pale Beige
InChIKey: YWGDOWXRIALTES-NRFANRHFSA-N
SMILES: [C@@H](C1N=CC=CC=1)(C1C=CC(=CC=1)Cl)OC1CCN(CC1)CCCC(=O)O

Sicherheit und Regulatorisches

Toxikologische Informationen

Exposure Routes · 1 Eintrag

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 Eintrag

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

Chemie und Industrie

Pharmakologische Informationen

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

Pharmacodynamics · 1 Eintrag

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 Eintrag

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 Einträge

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 Einträge

HYD2U48IAS

BEPOTASTINE

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

Bepotastine is a Histamine-1 Receptor Antagonist.

Verwendung und Herstellung

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]

Anbieter88 Anbieter

广州佳途科技股份有限公司81960175 18933936954 · [email protected]

上海康恩博科技有限公司（科小研试剂）400-1388-521 17673770086 · [email protected]

上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]

四川星优天下医药科技有限公司18328380615 · [email protected]

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

Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: 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.