Epinastine

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Structural formula
Structure of epinastine
1: 1 mixture of ( R ) -form (left) and ( S ) -form (right)
General
Non-proprietary name Epinastine
other names
  • 9,13b-dihydro-1 H -dibenz [ c, f ] imidazo [1,5- a ] azepin-3-amine
  • ( RS ) -3-Amino-9,13b-dihydro-1 H -dibenz [ c, f ] imidazo [1,5- a ] azepine
  • (±) -3-Amino-9,13b-dihydro-1 H -dibenz [ c, f ] imidazo [1,5- a ] azepine
  • Epinastinum ( Latin )
Molecular formula
External identifiers / databases
CAS number
  • 80012-43-7 ( epinastine )
  • 108929-04-0 ( epinastine monohydrochloride)
  • 127786-29-2 ( epinastine monohydrobromide)
PubChem 3241
DrugBank DB00751
Wikidata Q632405
Drug information
ATC code
Drug class

H 1 antihistamines

Mechanism of action

Antagonist at H 1 receptors

properties
Molar mass
  • 249.32 g · mol -1 (epinastine)
  • 285.77 g mol −1 (epinastine monohydrochloride)
Melting point
  • 205-208 ° C
  • 273–275 ° C (epinastine monohydrochloride)
  • 284–286 ° C (epinastine monohydrobromide)
solubility

almost insoluble in water (1.86 mg l −1 at 25 ° C)

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
06 - Toxic or very toxic

danger

H and P phrases H: 301
P: 301 + 310
Toxicological data

192 mg kg −1 ( LD 50ratoral , monohydrochloride)

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Epinastine is a drug that is used as an antihistamine to relieve the symptoms of allergic conjunctivitis .

effect

The active ingredient occupies the histamine binding sites in the body and thus reduces the allergy reaction. It is a potent antagonist (more precisely: an inverse agonist ) at H 1 receptors (H 1 antihistamine) and does not penetrate the blood-brain barrier . The drug is also mast cell stabilizing .

Side effects

The observed side effect is irritation to the eyes . It does not affect the central nervous system .

Stereochemistry

Medicinal products contain the medicinal substance as a racemate (1: 1 mixture of enantiomers ), with the use of the enantiomer which is more effective or which has fewer side effects would be preferred for fundamental reasons.

Trade names

Epinastin is commercially available in Germany, Austria and Switzerland under the name Relestat .

Individual evidence

  1. a b Entry on epinastine in the DrugBank of the University of Alberta .
  2. a b The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, pp. 617-618, ISBN 978-0-911910-00-1 .
  3. a b c Data sheet Epinastine hydrochloride ≥ 98% (HPLC), solid from Sigma-Aldrich , accessed on March 30, 2011 ( PDF ).
  4. EJ Ariëns, Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology , European Journal of Clinical Pharmacology 26 (1984) 663-668, PMID 6092093 .