CAS 125602-71-3 Bepotastine (HCID 164522)

Overview

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+).

Names & identifiers

Preferred name: Bepotastine
IUPAC: 4-[4-[(S)-(4-chlorophenyl)-pyridin-2-ylmethoxy]piperidin-1-yl]butanoic acid

Names & synonyms

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

Show more names

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

Database identifiers

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

Properties

Computed structural propertiesFilling in

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

DrugsPharmaceuticals -> Listed in ZINC15

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

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).

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

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

FDA Pharmacological Classification · 4 items

HYD2U48IAS

BEPOTASTINE

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

Bepotastine is a Histamine-1 Receptor Antagonist.

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]