147084-10-4 Usage
Description
Alcaftadine is a histamine H1/H2 receptor antagonist, specifically an imidazobenzazepine derivative, which was approved in the United States in 2010. It is characterized by a 6,11-dihydro-5H-imidazo[2,1-b][3]benzazepine structure, with a formyl group at position 3 and a 1-methylpiperidin-4-ylidene group at position 11. Alcaftadine is primarily used for the treatment of allergic conjunctivitis, a condition that affects up to 40% of the global population. It is known for its effectiveness in preventing itching and redness associated with this condition, and the pharmaceutical market for conjunctivitis treatments is substantial and growing.
Uses
Used in Pharmaceutical Industry:
Alcaftadine is used as an antihistamine for the prevention of itching and redness associated with allergic conjunctivitis. It is particularly effective in treating both seasonal and perennial forms of the condition, which can significantly impact the quality of life for those affected.
Used in Ophthalmology:
In the field of ophthalmology, Alcaftadine is used as a H1 histamine receptor antagonist to treat the signs and symptoms of allergic conjunctivitis. This includes ocular itching and conjunctival redness, which are primary symptoms of the condition. As a topical antihistamine, Alcaftadine offers an effective therapy for managing these symptoms and improving patient comfort.
Brand Name:
Alcaftadine is marketed under the brand name Lastacaft?, which is specifically formulated to address the needs of patients suffering from allergic conjunctivitis.
Originator
Janssen Research Foundation (United States)
Clinical Use
Alcaftadine, an ophthalmic histamine H1 receptor antagonist,
was approved by the FDA for the prevention of itching associated
with allergic conjunctivitis and was launched under the trade
name Lastacaft in early 2011. Alcaftadine was discovered by
Janssen Pharmaceuticals and marketed by Vistakon Pharmaceuticals,
both subsidiaries of Johnson & Johnson. However, unlike other marketed drugs, the synthesis of alcaftadine was only mentioned
in the patents filed by Janssen’s scientists approximately twenty
years ago.
Synthesis
The synthetic route described in the scheme is based on
the discovery route disclosed in those patents. 1-(2-Phenylethyl)-
1H-imidazole 7 is now commercially available, otherwise
it could be prepared by reacting imidazole (5) with 2-phenylethyl
bromide (6). With pyridine and triethylamine as base, imidazole
7 was reacted with acyl chloride 8 to provide piperidinecarboxylate
9 in 34% yield, followed by acid hydrolysis with 48% HBr
aqueous solution to obtain piperidine dihydrobromide 10 in 98%
yield. The N-methylation of 10 was acheived by Leuckart reaction
with formaldehyde and formic acid to give 4-methylpiperidine 11
in 82% yield. Treatment of 11 with trifluoromethanesulfonic acid
followed by subsequent basification triggered an intramolecular
alkylation–dehydration reaction to generate benzazepine 12. Next,
alcohol 13 was obtained by prolonged exposure (7 days) of 12 to
hydroxymethylation conditions using 40% aqueous formaldehyde.
Oxidation of 13 with manganese (IV) oxide provided alcaftadine
(II). The yields of last three steps from compound 11 to alcaftadine
(II) were not provided in the patent.
Check Digit Verification of cas no
The CAS Registry Mumber 147084-10-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,7,0,8 and 4 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 147084-10:
(8*1)+(7*4)+(6*7)+(5*0)+(4*8)+(3*4)+(2*1)+(1*0)=124
124 % 10 = 4
So 147084-10-4 is a valid CAS Registry Number.