Introduction：Basic information about Epinastine CAS 80012-43-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Epinastine Basic information
| Product Name: | Epinastine |
| Synonyms: | 3-amino-9,13b-dihydro-1h-dibenz[c,f]imidazo[1,5-a]azepine;EPINASTINE;EPINASTINE BASE;9,13b-Dihydro-1H-dibenz[c,f]imidazo[1,5-a]azepin-3- amine;Apinastine Base;3-Amino-9,13b-dihydro-1H-dibenzo[c,f]imidazo[1,5-a]azepine;CS-1366;ELESTAT;WAL801 |
| CAS: | 80012-43-7 |
| MF: | C16H15N3 |
| MW: | 249.31 |
| EINECS: | 616-785-3 |
| Product Categories: | |
| Mol File: | 80012-43-7.mol |
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Epinastine Chemical Properties
| Melting point | 205-208° |
| Boiling point | 428.0±55.0 °C(Predicted) |
| density | 1.32±0.1 g/cm3(Predicted) |
| storage temp. | Keep in dark place,Inert atmosphere,Room temperature |
| solubility | DMSO : ≥ 50 mg/mL (200.55 mM);Water : < 0.1 mg/mL (insoluble) |
| pka | 11.2(at 25℃) |
| form | Solid |
| color | White to off-white |
| CAS DataBase Reference | 80012-43-7(CAS DataBase Reference) |
Safety Information
Epinastine Usage And Synthesis
| Description | Epinastine hydrochloride, an orally active antihistaminic agent, was marketed inJapan for the treatment of bronchial asthma, allergic rhinitis, urticaria, eczema,dermatitis, and psoriasis vulgaris.Epinastine is one of the most effectiveperipherally acting histamine H1-receptor antagonists without sedative effects.Inaddition, it exhibits potent anti-PAF and anti-LT activity which may also contributesignificantly to its antiallergic activity. Chronic epinastine has been reported toeffectively inhibit airway hyper-responsiveness in rats. Potent inhibitory effects ofepinastine on bronchoconstriction induced by histamine and bradykinin, but not byother chemical mediators, has also been reported. Studies have indicated that thereare no significant differences in pharmacological properties among D-, L-, andracemic epinastine. |
| Originator | Boehringerlngelheim (Germany) |
| Uses | Epinastine is antihistamine and mast cell stabilize that is used in eye drops for the treatment of allergic conjunctivitis. |
| Definition | ChEBI: 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. |
| Brand name | Aleslon |
| Clinical Use | Epinastine is a potent, long-acting H1 antihistamine and an inhibitor of the release ofhistamine and other transmitters from mast cells. It has some affinity for H2 receptors as well.It is used as an eye drop for allergic conjunctivitis. It does not penetrate into the CNS and isclassified as a nonsedating antihistamine. |
| Synthesis | Several patents on the synthesis ofepinastin (VIII) have appeared in Europe and Japan.The synthesis described below is taken partly from the USpatent and a Japanese patent. All the synthesesutilized 6-aminomethyl-6,11-dihydro-5H-dibenzo[b.e]azepine(80) as the key intermediate which was converted to the finalguanidine epinastine by reacting with cyanogen bromide.The solution of 80 in ethanol was treated with a solution ofcyanogen bromide in THF at room temperature and stirredovernight. The hydrobromide salt was collected in 79%yield after adding ether to the reaction mixture. The salt wasfree based with a solution of sodium hydroxide and thentreated with an ethereal solution of HCl to obtain theepinastine hydrochloride salt VIII. For the preparation of thekey intermediate, chloroimine 78, presumably obtained fromketone 77 via Beckmann rearrangement, was reactedwith sodium cyanide in DMSO to give the nitrile 79 in 70%yield. Reduction of the imino nitrile was carried out in THFin the presence of an acid with LAH to give the keyintermediate 80 in 67% yield.
An alternate approach to preparation of 80 is shown inScheme 8 as well. Reaction of the commercially availablechloride 81 with phthalimide in the presence of abase gave the phthalimide 82. Reduction of the imine withsodium borohydride gave 83, which was then reacted withhydrazine hydrate to free up the amine in 90% yield. Theamine intermediate was isolated as the fumarate salt. |
Epinastine Preparation Products And Raw materials
| Preparation Products | EPINASTINE HYDROCHLORIDE |
