Epinastine
Grundinformationen
- CAS
80012-43-7- Standard-SMILES
NC1=NCC2c3ccccc3Cc3ccccc3N12- InChIKey
WHWZLSFABNNENI-UHFFFAOYSA-N- Summenformel
- C16H15N3
- Durchschnittliche Molmasse
- 249,31 g/mol
- Monoisotopische Masse
- 249,12659749
Überblick
Epinastine is a benzazepine that is 6,11-dihydro-5H-dibenzo[b,e]azepine in which the azepine ring is fused to the e side of 4,5-dihydro-1H-imidazol-2-amine. It has a role as a H1-receptor antagonist, a histamine antagonist, an anti-allergic agent and an ophthalmology drug. It is a member of guanidines and a benzazepine.
Namen und Bezeichner
- Bevorzugter Name
- Epinastine
- IUPAC
- 2,4-diazatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),3,7,9,11,14,16-heptaen-3-amine
- Englischer Name
- Epinastine
- Summenformel
- C16H15N3
- Molmasse
- 249.31
Namen und Synonyme
epinastine80012-43-7EpinastinaEpinastinum(+-)-EpinastinePurivist3-Amino-9,13b-dihydro-1H-dibenz(c,f)imidazo(1,5-a)azepine3-Amino-9,13b-dihydro-1H-dibenz[c,f]imidazo[1,5-a]azepineQ13WX941EFCHEBI:51032WAL-8013-amino-9,13b-dihydro-1H-benz(c,f)imidazo(1,5a)azepine
Weitere Namen anzeigen
WAL801CS-1366EpastineELESTATWAL801Apinastine BaseEPINASTINE BASEEpinastine (WAL801)Epinastine USP/EP/BPEpinastine in methanol
DTXSID2048371R06AX241H-Dibenz(c,f)imidazo(1,5-a)azepin-3-amino, 9,13b-dihydro-RefChem:56561DTXCID8028345S01GX102,4-diazatetracyclo(12.4.0.02,?.0?,12)octadeca-1(18),3,7,9,11,14,16-heptaen-3-amine616-785-3
Datenbank-Bezeichner
- CAS
80012-43-7- PubChem CID
- 3241
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,5
- Polarare Oberfläche (TPSA)
- 41,6 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 1
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 19
- Formalladung
- 0
- Komplexität
- 378
Experimentelle und physikochemische Eigenschaften
LogP3.1
Solubility1.63e-01 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Antihistamines
Melting Point
205-208 °C
205 - 208 °C
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 205 · 205-208°
- Siedepunkt
- 428 · 428.0±55.0 °C(Predicted)
- Dichte
- 1.32 · 1.32±0.1 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- Löslichkeit
- 50 mg/mL · DMSO : ≥ 50 mg/mL (200.55 mM);Water : < 0.1 mg/mL (insoluble)
- pka
- 11.2 · 11.2(at 25℃)
- Aggregatzustand
- Solid
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory InformationREACH registered substance: 2,4-diazatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),3,7,9,11,14,16-heptaen-3-amine (EC: 616-785-3)
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxikologische Informationen
Adverse Effects
Epinastine is a safe and well-tolerated drug. It is used topically as an eye drop, and it does not cause any systemic side effects. However, it can cause a burning sensation in the eyes, hyperemia, increased lacrimation, folliculitis, and pruritus.
Toxicity SummaryThere are no reported cases of overdose with epinastine to date. However, in case of an overdose, the institution and health care providers must act promptly to ensure airway patency and that there is no circulatory collapse.
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Epinastine
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Chemie und Industrie
Pharmakologische Informationen
ATC Code
S01GX10
S - Sensory organs
R - Respiratory system
QR - Respiratory system
QS - Sensory organs
Protein Binding64%
Pharmacodynamics
Epinastine is an antihistamine and an inhibitor of histamine release from the mast cell for topical administration to the eyes. Epinastine is indicated for the prevention of itching associated with allergic conjunctivitis. Epinastine is a topically active, direct H<sub>1</sub>-receptor antagonist and an inhibitor of the release of histamine from the mast cell. Epinastine is selective for the histamine H<sub>1</sub>-receptor and has affinity for the histamine H2 receptor. Epinastine also possesses affinity for the a1-, a2-, and 5-HT<sub>2</sub> -receptors. Epinastine does not penetrate the blood/brain barrier and, therefore, is not expected to induce side effects of the central nervous system.
Mechanism of Action
Epinastine has a multiaction effect that inhibits the allergic response in 3 ways: 1. stabilizes mast cells by preventing mast cell degranulation to control the allergic response, 2. prevents histamine binding to both the H1- and H<sub>2</sub>-receptors to stop itching and provide lasting protection, and 3. prevents the release of proinflammatory chemical mediators from the blood vessel to halt progression of the allergic response.
Biological Half-Life12 hours
Metabolism/MetabolitesMainly excreted unchanged, less than 10% metabolized.
FDA Pharmacological Classification
Q13WX941EF
EPINASTINE
Mechanisms of Action [MoA] - Adrenergic Agonists
Established Pharmacologic Class [EPC] - Adrenergic Receptor Agonist
Physiologic Effects [PE] - Decreased Histamine Release
Mechanisms of Action [MoA] - Histamine H1 Receptor Antagonists
Zugehörige Reaktionen
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