Basic information
- CAS
98206-10-1- Standard SMILES
O=C(NCCN1CCN(c2cccc3c2OC[C@H](CO)O3)CC1)c1ccc(F)cc1- InChIKey
NYSDRDDQELAVKP-SFHVURJKSA-N- Molecular formula
- C22H26FN3O4
- Average molar mass
- 415.5 g/mol
- Monoisotopic mass
- 415.19073448
Overview
Flesinoxan is a small molecule drug. The usage of the INN stem '-oxan(e)' in the name indicates that Flesinoxan is a benzodioxane derivative. Flesinoxan has a monoisotopic molecular weight of 415.19 Da.
Names & identifiers
- Preferred name
- Flesinoxan
- IUPAC
- 4-fluoro-N-[2-[4-[(2S)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-5-yl]piperazin-1-yl]ethyl]benzamide
- English name
- Flesinoxan
- Molecular formula
- C22H26FN3O4
- Molecular weight
- 415.46
Names & synonyms
Flesinoxan98206-10-1flesinoxano3V574S89E1flesinoxanum4-fluoro-N-(2-(4-((3S)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-8-yl)piperazin-1-yl)ethyl)benzamide4-fluoro-N-[2-[4-[(3S)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-8-yl]piperazin-1-yl]ethyl]benzamideRefChem:140696p-fluoro-N-(2-(4-(2-(hydroxymethyl)-1,4-benzodioxan-5-yl)-1-piperazinyl)ethyl)benzamideFlesinoxan [INN]4-fluoro-N-[2-[4-[(2S)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-5-yl]piperazin-1-yl]ethyl]benzamideFlesinoxan (INN)
Show more names
N-[2-[4-[[(S)-2,3-Dihydro-2β-hydroxymethyl-1,4-benzodioxin]-5-yl]-1-piperazinyl]ethyl]-4-fluorobenzamideN-[2-[4-[[(R)-2,3-Dihydro-2α-hydroxymethyl-1,4-benzodioxin]-5-yl]-1-piperazinyl]ethyl]-4-fluorobenzamideN-(2-(4-((2R)-2,3-Dihydro-2-(hydroxymethyl)-1,4-benzodioxin-5-yl)-1-piperazinyl)ethyl)-4-fluorobenzamideBenzamide, N-[2-[4-[(2R)-2,3-dihydro-2-(hydroxymethyl)-1,4-benzodioxin-5-yl]-1-piperazinyl]ethyl]-4-fluoro-
(+)-(S)-p-Fluoro-N-(2-(4-(2-(hydroxymethyl)-1,4-benzodioxan-5-yl)-1-piperazinyl)ethyl)benzamide4-fluoro-N-[2-[4-[2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-5-yl]piperazin-1-yl]ethyl]benzamideUNII-3V574S89E1(+)-flesinoxanFLESINOXAN [MI]GTPL1SCHEMBL220401CHEMBL1742477
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 74.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 6
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 553
Physicochemical properties
- alpha
- 26 ° · D +26° (c = 1 in methanol)
- Boiling point
- 635.8 · 635.8±55.0 °C(Predicted)
- Density
- 1.271 · 1.271±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 31.25 mg/mL · DMSO: 31.25 mg/mL (75.22 mM)
- pka
- 14.09 · 14.09±0.10(Predicted)
- form
- Solid
- color
- Off-white to light yellow
- FDA UNII
- 3 V574S89E1 · 3V574S89E1
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems.
Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here.
Endogenous compounds and drugs that bind to and activate SEROTONIN RECEPTORS. Many serotonin receptor agonists are used as ANTIDEPRESSANTS; ANXIOLYTICS; and in the treatment of MIGRAINE DISORDERS.
Applications
DescriptionFlesinoxan is a new heterobicyclic-aryl-piperazine, chemically different from buspirone-like compounds. In vitro, flesinoxan is a highly selective 5-HT1A receptor agonist and has much weaker affinity for α1-adrenergic, dopamine 2, and dopamine 3 receptors compared with buspirone (Duphar, unpublished data). The highest density of flesinoxan binding sites in brain is observed in the hippocampus, dentate gyrus, lateral septum, and entorrhinal cortex (Duphar, unpublished data). In several animal paradigms of anxiety, flesinoxan is more potent in reducing anxiety than are buspirone and ipsapirone (Duphar, unpublished data). Phase II studies have shown that flesinoxan is clearly effective in relieving symptoms of generalized anxiety disorder and better than placebo (Duphar, unpublished data). Generally, a low dose (0.4 mg) of flesinoxan is well tolerated. Higher doses (4.0 mg) are associated with treatment emergent adverse events, such as nausea, vomiting, nervousness, dizziness, and headache (Duphar, unpublished data). Currently, flesinoxan is under clinical development as a treatment both for generalized anxiety disorder and for major depressive disorder.
Related reactions
1 records
Compound notes
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