Azabon

Last updated
Azabon
Azabon.svg
Identifiers
  • 4-(3-Azabicyclo[3.2.2]non-3-ylsulfonyl)aniline
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C14H20N2O2S
Molar mass 280.386
3D model (JSmol)
  • c1cc(ccc1N)S(=O)(=O)N2CC3CCC(C2)CC3
  • InChI=1S/C14H20N2O2S/c15-13-5-7-14(8-6-13)19(17,18)16-9-11-1-2-12(10-16)4-3-11/h5-8,11-12H,1-4,9-10,15H2
  • Key:RQBNXPJPWKUTOG-UHFFFAOYSA-N

  • InChI=1/C14H20N2O2S/c15-13-5-7-14(8-6-13)19(17,18)16-9-11-1-2-12(10-16)4-3-11/h5-8,11-12H,1-4,9-10,15H2
  • Key:RQBNXPJPWKUTOG-UHFFFAOYAL

Azabon is a central nervous system stimulant of the sulfonamide class [1] that is also used as a nootropic. [2] It has poor antibacterial potency, as is common in benzenesulfonamides with two substituents on N1. It is synthesized from 3-azabicyclo-[2.2.2]nonane, itself prepared by pyrolysis of aliphatic diamine. [3]

Related Research Articles

<span class="mw-page-title-main">Amitriptyline</span> Tricyclic antidepressant

Amitriptyline, sold under the brand name Elavil among others, is a tricyclic antidepressant primarily used to treat major depressive disorder, and a variety of pain syndromes such as neuropathic pain, fibromyalgia, migraine and tension headaches. Due to the frequency and prominence of side effects, amitriptyline is generally considered a second-line therapy for these indications.

In the physical sciences, a partition coefficient (P) or distribution coefficient (D) is the ratio of concentrations of a compound in a mixture of two immiscible solvents at equilibrium. This ratio is therefore a comparison of the solubilities of the solute in these two liquids. The partition coefficient generally refers to the concentration ratio of un-ionized species of compound, whereas the distribution coefficient refers to the concentration ratio of all species of the compound.

<span class="mw-page-title-main">Benzimidazole</span> Chemical compound

Benzimidazole is a heterocyclic aromatic organic compound. This bicyclic compound may be viewed as fused rings of the aromatic compounds benzene and imidazole. It is a white solid that appears in form of tabular crystals.

hERG Mammalian protein found in humans

hERG is a gene that codes for a protein known as Kv11.1, the alpha subunit of a potassium ion channel. This ion channel is best known for its contribution to the electrical activity of the heart: the hERG channel mediates the repolarizing IKr current in the cardiac action potential, which helps coordinate the heart's beating.

<span class="mw-page-title-main">Huperzine A</span> Chemical compound

Huperzine A is a naturally-occurring sesquiterpene alkaloid compound found in the firmoss Huperzia serrata and in varying quantities in other food Huperzia species, including H. elmeri, H. carinat, and H. aqualupian. Huperzine A has been investigated as a treatment for neurological conditions such as Alzheimer's disease, but a 2013 meta-analysis of those studies concluded that they were of poor methodological quality and the findings should be interpreted with caution. Huperzine A inhibits the breakdown of the neurotransmitter acetylcholine (ACh) by the enzyme acetylcholinesterase. It is also an antagonist of the NMDA-receptor. It is commonly available over the counter as a nutritional supplement and marketed as a memory and concentration enhancer.

<span class="mw-page-title-main">Efflux pump</span> Protein complexes that move compounds, generally toxic, out of bacterial cells

An efflux pump is an active transporter in cells that moves out unwanted material. Efflux pumps are an important component in bacteria in their ability to remove antibiotics. The efflux could also be the movement of heavy metals, organic pollutants, plant-produced compounds, quorum sensing signals, bacterial metabolites and neurotransmitters. All microorganisms, with a few exceptions, have highly conserved DNA sequences in their genome that encode efflux pumps. Efflux pumps actively move substances out of a microorganism, in a process known as active efflux, which is a vital part of xenobiotic metabolism. This active efflux mechanism is responsible for various types of resistance to bacterial pathogens within bacterial species - the most concerning being antibiotic resistance because microorganisms can have adapted efflux pumps to divert toxins out of the cytoplasm and into extracellular media.

<span class="mw-page-title-main">Picamilon</span> Chemical compound

Picamilon is a drug formed by a synthetic combination of niacin and γ-aminobutyric acid (GABA). It was developed in the Soviet Union in 1969 and further studied in both Russia and Japan as a prodrug of GABA.

<span class="mw-page-title-main">Isradipine</span> Antihypertensive drug of the calcium channel blocker class

Isradipine is a calcium channel blocker of the dihydropyridine class. It is usually prescribed for the treatment of high blood pressure in order to reduce the risk of stroke and heart attack.

<span class="mw-page-title-main">NMDA receptor antagonist</span> Class of anesthetics

NMDA receptor antagonists are a class of drugs that work to antagonize, or inhibit the action of, the N-Methyl-D-aspartate receptor (NMDAR). They are commonly used as anesthetics for humans and animals; the state of anesthesia they induce is referred to as dissociative anesthesia.

<span class="mw-page-title-main">Metabotropic glutamate receptor 2</span> Mammalian protein found in humans

Metabotropic glutamate receptor 2 (mGluR2) is a protein that, in humans, is encoded by the GRM2 gene. mGluR2 is a G protein-coupled receptor (GPCR) that couples with the Gi alpha subunit. The receptor functions as an autoreceptor for glutamate, that upon activation, inhibits the emptying of vesicular contents at the presynaptic terminal of glutamatergic neurons.

<span class="mw-page-title-main">MEOX2</span> Protein-coding gene in the species Homo sapiens

Homeobox protein MOX-2 is a protein that in humans is encoded by the MEOX2 gene.

<span class="mw-page-title-main">Blonanserin</span> Atypical antipsychotic

Blonanserin, sold under the brand name Lonasen, is a relatively new atypical antipsychotic commercialized by Dainippon Sumitomo Pharma in Japan and Korea for the treatment of schizophrenia. Relative to many other antipsychotics, blonanserin has an improved tolerability profile, lacking side effects such as extrapyramidal symptoms, excessive sedation, or hypotension. As with many second-generation (atypical) antipsychotics it is significantly more efficacious in the treatment of the negative symptoms of schizophrenia compared to first-generation (typical) antipsychotics such as haloperidol.

<span class="mw-page-title-main">Baicalein</span> Polyphenol compound

Baicalein (5,6,7-trihydroxyflavone) is a flavone, a type of flavonoid, originally isolated from the roots of Scutellaria baicalensis and Scutellaria lateriflora. It is also a constituent of Oroxylum indicum and thyme. It is the aglycone of baicalin.

A self-microemulsifying drug delivery system (SMEDDS) is a drug delivery system that uses a microemulsion achieved by chemical rather than mechanical means. That is, by an intrinsic property of the drug formulation, rather than by special mixing and handling. It employs the familiar ouzo effect displayed by anethole in many anise-flavored liquors. Microemulsions have significant potential for use in drug delivery, and SMEDDS are the best of these systems identified to date. SMEDDS are of particular value in increasing the absorption of lipophilic drugs taken by mouth.

In pharmacology, a GABA transaminase inhibitor is an enzyme inhibitor that acts upon GABA transaminase. Inhibition of GABA transaminase enzymes reduces the degradation of GABA, leading to increased neuronal GABA concentrations.

<span class="mw-page-title-main">Plasma membrane monoamine transporter</span> Protein-coding gene in the species Homo sapiens

The plasma membrane monoamine transporter (PMAT) is a low-affinity monoamine transporter protein which in humans is encoded by the SLC29A4 gene. It is known alternatively as the human equilibrative nucleoside transporter-4 (hENT4). It was discovered in 2004 and has been identified as a potential alternate target for treating various conditions.

<span class="mw-page-title-main">PF-03654746</span> Chemical compound

PF-03654746 is a potent and selective histamine H3 receptor antagonist developed by Pfizer and currently undergoing clinical trials for the treatment of ADHD, Tourette syndrome as well as potential anti-allergy applications.

<span class="mw-page-title-main">Antibody–drug conjugate</span> Class of biopharmaceutical drugs

Antibody–drug conjugates or ADCs are a class of biopharmaceutical drugs designed as a targeted therapy for treating cancer. Unlike chemotherapy, ADCs are intended to target and kill tumor cells while sparing healthy cells. As of 2019, some 56 pharmaceutical companies were developing ADCs.

<span class="mw-page-title-main">Resistance Database Initiative</span> Not-for-profit organisation

HIV Resistance Response Database Initiative (RDI) was formed in 2002 to use artificial intelligence (AI) to predict how patients will respond to HIV drugs using data from more 250,000 patients from around 50 countries around the world.

Lindsay H. Burns is an American neuroscientist and rower who won a silver medal at the 1996 Summer Olympics. She was a senior vice president of the pharmaceutical company Cassava Sciences until July 2024 and married to its CEO Remi Barbier.

References

  1. WO 2011089215,Vetter D, Rau H,"Dipeptide-based prodrug linkers for aromatic amine-containing drugs",published 28 July 2011, assigned to Ascendis Pharma AS
  2. Mao F, Ni W, Xu X, Wang H, Wang J, Ji M, Li J (January 2016). "Chemical Structure-Related Drug-Like Criteria of Global Approved Drugs". Molecules. 21 (1): 75. doi: 10.3390/molecules21010075 . PMC   6273477 . PMID   26771590.
  3. Lednicer D, Mitscher LA (1980). The Organic Chemistry of Drug Synthesis (PDF). Vol. 2. Wiley Interscience. p. 115. ISBN   0-471-04392-3.