Epinastine

Epinastine (brand names Alesion, Elestat, Purivist, Relestat) is a second-generation antihistamine and mast cell stabilizer that is used in eye drops to treat allergic conjunctivitis. It is produced by Allergan and marketed by Inspire in the United States.[1] It is highly selective for the H1 receptor and does not cross the blood-brain-barrier.[2]

Epinastine
Clinical data
Trade namesAlesion, Elestat, Purivist, Relestat
AHFS/Drugs.comMonograph
MedlinePlusa604011
Pregnancy
category
  • C
Routes of
administration		Eye drops
ATC code
Pharmacokinetic data
Protein binding64%
Elimination half-life12 hours
Identifiers
IUPAC name
  • (RS)-3-amino-9,13b-dihydro-1H-dibenz(c,f)imidazo(1,5-a)azepine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.120.187
Chemical and physical data
FormulaC16H15N3
Molar mass249.317 g·mol−1
3D model (JSmol)
SMILES
  • N\4=C(\N3c1c(cccc1)Cc2c(cccc2)C3C/4)N
InChI
  • InChI=1S/C16H15N3/c17-16-18-10-15-13-7-3-1-5-11(13)9-12-6-2-4-8-14(12)19(15)16/h1-8,15H,9-10H2,(H2,17,18) Y
  • Key:WHWZLSFABNNENI-UHFFFAOYSA-N Y
  (verify)

It was patented in 1980 and came into medical use in 1994.[3]

References
  1. Pradhan, S; Abhishek, K; Mah, F (2009). "Epinastine: topical ophthalmic second generation antihistamine without significant systemic side effects". Expert Opinion on Drug Metabolism & Toxicology. 5 (9): 1135–40. doi:10.1517/17425250903117284. PMID 19630694. S2CID 207490591.
  2. Walther G, Daniel H, Bechtel WD, Brandt K (April 1990). "New tetracyclic guanidine derivatives with H1-antihistaminic properties. Chemistry of epinastine". Arzneimittel-Forschung. 40 (4): 440–6. PMID 1972625.
  3. Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 549. ISBN 9783527607495.
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