4-((4-Chlorophenyl)-2-pyridinylmethoxy)-1-piperidinebutanoic Acid (HCID 2350)

Overview

Bepotastine is a non-sedating, selective antagonist of the histamine 1 (H1) receptor. Bepotastine was approved in Japan for use in the treatment of allergic rhinitis and uriticaria/puritus in July 2000 and January 2002, respectively, and is marketed by Tanabe Seiyaku Co., Ltd. under the brand name Talion. It is available in oral and opthalmic dosage forms in Japan. The opthalmic solution is FDA approved since Sept 8, 2009 and is under the brand name Bepreve.

Names & identifiers

Preferred name: 4-((4-Chlorophenyl)-2-pyridinylmethoxy)-1-piperidinebutanoic Acid
IUPAC: 4-[4-[(4-chlorophenyl)-pyridin-2-ylmethoxy]piperidin-1-yl]butanoic acid
English name: 4-[(4-Chlorophenyl)-2-pyridinylmethoxy]-1-piperidinebutanoic acid
Molecular formula: C21H25ClN2O3
Molecular weight: 388.89

Names & synonyms

1070505-53-1DTXSID708697274-((4-Chlorophenyl)-2-pyridinylmethoxy)-1-piperidinebutanoic acid4-[(4-Chlorophenyl)-2-pyridinylmethoxy]-1-piperidinebutanoic acidRefChem:1069653DTXCID60208727rac Bepotastine190786-43-7TAU-284DS4-[(4-Chlorophenyl)-2-pyridinylmethoxy]-1-piperidinebutanoic Acid;4-[4-[(4-Chlorophenyl)(2-pyridyl)methoxy]piperidino]butanoic Acid;DB 185SCHEMBL726880CHEMBL4877190

Show more names

Rac-Bepotastine-d61-Piperidinebutanoic acid, 4-[(4-chlorophenyl)-2-pyridinylmethoxy]-

SCHEMBL30200949YWGDOWXRIALTES-UHFFFAOYSA-NHMS5085J19(+)-(S)-4-[4-[1-(4-chlorophenyl)-1-(2-pyridyl)methoxy]piperidin-1-yl]butyric acid4-[4-[(S)-(4-chlorophenyl)-pyridin-2-ylmethoxy]piperidin-1-yl]butanoic acid4-[4-[(4-chlorophenyl)-(2-pyridyl)methoxy]-1-piperidyl]butanoic acidEBC-26902MFCD00887421s5940

Database identifiers

CAS: 1070505-53-1、190786-44-8
PubChem CID: 2350
DTXSID: DTXSID70869727
ChEMBL: CHEMBL4877190

Properties

Computed structural properties

XLogP: 1
Topological polar surface area: 62.7 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 5
Rotatable bonds: 8
Heavy atoms: 27
Formal charge: 0
Complexity: 449

Experimental & physicochemical properties

Solubility5.03e-02 g/L

Physical DescriptionSolid

Physicochemical properties

Density: 1.26 · 1.26

Safety & regulation

Toxicology

Exposure Routes · 1 item

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 item

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).

Chemistry & industry

Pharmacology

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

Pharmacodynamics · 1 item

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 item

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 items

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

Absorption, Distribution and Excretion · 2 items

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.

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.

Uses & manufacturing

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]

Applications · 1 item

Usesrac Bepotastine is the free form of Bepotastine Besylate (B317025), the racemate of (S)-Bepotastine Besylate (B317000); a histamine H1 receptor antagonist. Bepotastine suppresses some allergic inflammatory processes such as allergic rhinitis, chronic urticaria or pruritus associated with skin conditions (eczema/dermatitis, prurigo or pruritus cutaneus).