58581-89-8 Usage
Description
Azelastine is a phthalazine compound characterized by an oxo substituent at the 1-position, a 1-methylazepan-4-yl group at the 2-position, and a 4-chlorobenzyl substituent at the 4-position. It is known by the brand names Astelin and Optivar, both manufactured by Medpointe. Azelastine is primarily used for its pharmacological properties, which include acting as an anesthetic and anticonvulsant.
Uses
Used in Pharmaceutical Industry:
Azelastine is used as an anesthetic for its ability to reduce pain and discomfort in various medical conditions. Its anesthetic properties make it a valuable component in the development of medications aimed at alleviating pain.
Azelastine is also used as an anticonvulsant to help prevent and control seizures in patients suffering from epilepsy or other conditions that cause convulsions. Its anticonvulsant properties contribute to its effectiveness in managing these medical issues.
Clinical Use
Azelastine, although not a close structural analogue to the benzimidazoles, has some
structural similarities to them. It is used as a nasal spray for allergic rhinitis and as eye drops
for allergic conjunctivitis.Like olopatadine, azelastine also stabilizes mast cells, preventing
degranulation and subsequent release of histamine, leukotrienes, and PGD2. It is available in
Europe for systemic use in the treatment of asthma and seasonal allergies. Besides
antihistaminic effects, it also may block release of histamine and other inflammatory
mediators from mast cells. When administered orally, the N-dealkylated metabolite appears to
contribute significantly to its pharmacological effects.
Safety Profile
Poison by ingestion,subcutaneous, intravenous, and intraperitoneal routes.Experimental reproductive effects. When heated todecomposition it emits toxic fumes of NOx and Cl- .
Check Digit Verification of cas no
The CAS Registry Mumber 58581-89-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,8,5,8 and 1 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 58581-89:
(7*5)+(6*8)+(5*5)+(4*8)+(3*1)+(2*8)+(1*9)=168
168 % 10 = 8
So 58581-89-8 is a valid CAS Registry Number.
InChI:InChI=1/C22H25ClN3O/c1-25-13-4-5-18(12-14-25)26-22(27)20-7-3-2-6-19(20)21(24-26)15-16-8-10-17(23)11-9-16/h2-3,6-11,18,21H,4-5,12-15H2,1H3/q+1
58581-89-8Relevant articles and documents
Synthesis and structure of azelastine-N-oxides
Brandes, Benjamin,Halz, Jan H.,Merzweiler, Kurt,Deigner, Hans-Peter,Csuk, René
, (2021/12/10)
Azelastine is among the most frequently used drugs; however, knowledge and solid data about its metabolites are scarcely found in literature. Thus, microsomal oxidation of azelastine is thought to produce the corresponding N-oxides, However, until now these products had never been produced in significant amounts. By oxidation of azelastine with H2O2, these N-oxides were now prepared in racemic form for the first time and were fully characterized. Their structure was additionally confirmed by a single crystal X-ray analysis. Both N-oxides were found to be non-cytotoxic in SRB assays.
Contra-thermodynamic Hydrogen Atom Abstraction in the Selective C-H Functionalization of Trialkylamine N-CH3 Groups
Barham, Joshua P.,John, Matthew P.,Murphy, John A.
supporting information, p. 15482 - 15487 (2016/12/09)
We report a simple one-pot protocol that affords functionalization of N-CH3 groups in N-methyl-N,N-dialkylamines with high selectivity over N-CH2R or N-CHR2 groups. The radical cation DABCO+?, prepared in situ by oxidation of DABCO with a triarylaminium salt, effects highly selective and contra-thermodynamic C-H abstraction from N-CH3 groups. The intermediates that result react in situ with organometallic nucleophiles in a single pot, affording novel and highly selective homologation of N-CH3 groups. Chemoselectivity, scalability, and recyclability of reagents are demonstrated, and a mechanistic proposal is corroborated by computational and experimental results. The utility of the transformation is demonstrated in the late-stage site-selective functionalization of natural products and pharmaceuticals, allowing rapid derivatization for investigation of structure-activity relationships.
Synthesis and X-ray-structure analysis of azelastine
Scheffler,Engel,Kutscher,Sheldrick,Bell
, p. 205 - 208 (2007/10/02)
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