85650-56-2 Usage
Description
Asenapine, a dual antagonist of dopamine D2and serotonin 5-HT2receptors, was launched for the acute treatment of schizophreniaand manic or mixed episodes associated with bipolar I disorder in adults. Asenapine exhibits high affinity for serotonin 5-HT1A, 5-HT1B, 5-HT2A, 5-HT2B, 5-HT2C, 5-HT5, 5-HT6, and 5-HT7 receptors (Ki = 2.5, 4.0, 0.06, 0.16, 0.03, 1.6, 0.25, and 0.13 nM, respectively); dopamine D1, D2, D3, and D4 receptors (Ki = 1.4, 0.42, 1.1, and 1.3 nM, respectively); a1- and a2-adrenergic receptors (Ki = 1.2 and 1.2 nM, respectively); and histamine H1 receptors (Ki = 1.0 nM), and moderate affinity for H2 receptors (Ki = 6.2 nM). In in vitro assays, asenapine acts as an antagonist at these receptors. Asenapine has no appreciable affinity for muscarinic cholinergic receptors (e.g., Ki = 8128 nM for M1). Despite its potent binding affinity for multiple receptors, the efficacy of asenapine in schizophrenia is thought to be primarily mediated through a combination of antagonist activity at D2 and 5-HT2A receptors.
Chemical Properties
White Solid
Originator
Organon (US)
Uses
Different sources of media describe the Uses of 85650-56-2 differently. You can refer to the following data:
1. Antipsychotic;serotonin 5-HT receptors
2. Asenapine Maleate is a 5-HT receptor antagonist developed for the treatment of acute schizophrenia and bipolar mania.
3. Asenapine maleate has been used as a stressor in studying the Fos expression in forebrain structures of rat models.
Brand name
Saphris
General Description
Asenapine is a new atypical antipsychotic developed for the treatment of schizophrenia and acute mania associated with bipolar disorder. The drug is marketed under the trade names Saphris? and Sycrest. This certified solution standard is suitable for LC/MS or GC/MS applications in clinical toxicology, forensic testing, or pharmaceutical research.
Biochem/physiol Actions
Asenapine maleate is a 5-HT receptor antagonist (5-HT1A,1B, 5-HT2A, 2B, 2C, 5-HT5A, 5-HT6 and 5-HT7), a D2 antagonist, and an antipsychotic.
Side effects
The most common adverse effects associated with asenapine treatment include insomnia, somnolence, nausea, anxiety, agitation, headache, vomiting, constipation, and psychosis. In placebo-controlled trials with risperidone, aripiprazole, and olanzapine in elderly subjects with dementia, there was a higher incidence of cerebrovascular adverse reactions (cerebrovascular accidents and transient ischemic attacks) including fatalities compared to placebo-treated subjects. Asenapine is not approved for the treatment of patients with dementia-related psychosis.
Synthesis
The chemical synthesis of asenapine can be achieved by several different methods. A concise synthesis of asenapine begins with the Horner-Emmons condensation of diethyl (5-chloro-2-fluoro)benzyl phosphonate with salicylaldehyde to produce the corresponding stilbene derivative, which undergoes a 1,3-dipolar cycloaddition reaction with trimethylamine-N-oxide in the presence of lithium diisopropylamide to furnish a trans-3,4-diarylpyrrolidine intermediate. Then, a base-catalyzed intramolecular cyclization involving the nucleophilic displacement of the fluoro group by the phenolic hydroxyl group affords asenapine, which
is finally treated with maleic acid in ethanol to yield the corresponding
maleate salt.
Check Digit Verification of cas no
The CAS Registry Mumber 85650-56-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,5,6,5 and 0 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 85650-56:
(7*8)+(6*5)+(5*6)+(4*5)+(3*0)+(2*5)+(1*6)=152
152 % 10 = 2
So 85650-56-2 is a valid CAS Registry Number.
InChI:InChI=1/C17H16ClNO.C4H4O4/c1-19-9-14-12-4-2-3-5-16(12)20-17-7-6-11(18)8-13(17)15(14)10-19;5-3(6)1-2-4(7)8/h2-8,14-15H,9-10H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-,15-;/m1./s1
85650-56-2Relevant articles and documents
CRYSTAL FORM OF ASENAPINE MALEATE
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Page/Page column 17; 18, (2013/04/10)
The present invention relates to a form of Asenapine Maleate with XRPD peaks at about 5.5,12.5,19.0 and 25.3 and to methods for the preparation thereof. Furthermore the invention relates to a reproducible process for the preparation of pure monoclinic form of Asenapine Maleate in crystalline form and to pharmaceutical compositions comprising the pure monoclinic form of asenapine maleate.
COMPRESSED ORAL DOSAGE FORM FOR ASENAPINE MALEATE
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Page/Page column 28, (2013/04/10)
The present invention relates to a compressed pharmaceutical dosage form intended for sublingual or buccal administration and capable of being rapidly disintegrated, the compressed pharmaceutical dosage form containing asenapine maleate in a microcrystalline monoclinic form. It further relates to a method of preparing the same and to a container comprising the dosage form.
CRYSTALLINE SALTS OF ASENAPINE
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Page/Page column 14, (2012/11/14)
Disclosed is asenapine phosphate of formula (I) and its enantiomer (I) which can be used to prepare asenapine maleate. Further disclosed is a monoclinic crystalline form of asenapine maleate.
