Tolazamide

Last updated
Tolazamide
Tolazamide.svg
Tolazamide ball-and-stick.png
Clinical data
Trade names Tolinase
AHFS/Drugs.com Monograph
MedlinePlus a682482
License data
Pregnancy
category
  • AU:C
Routes of
administration
Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability ?
Metabolism metabolized in the liver to active metabolites
Elimination half-life 7 hours
Excretion Renal (85%) and fecal (7%)
Identifiers
  • N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.013.262 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C14H21N3O3S
Molar mass 311.40 g·mol−1
3D model (JSmol)
  • O=S(=O)(c1ccc(cc1)C)NC(=O)NN2CCCCCC2
  • InChI=1S/C14H21N3O3S/c1-12-6-8-13(9-7-12)21(19,20)16-14(18)15-17-10-4-2-3-5-11-17/h6-9H,2-5,10-11H2,1H3,(H2,15,16,18) Yes check.svgY
  • Key:OUDSBRTVNLOZBN-UHFFFAOYSA-N Yes check.svgY
   (verify)

Tolazamide is an oral blood glucose lowering drug used for people with Type 2 diabetes. It is part of the sulfonylurea family (ATC A10BB).

Contents

Synthesis

Tolazemide synthesis: U.S. Patent 3,063,903
.mw-parser-output .citation{word-wrap:break-word}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}
GB 887886
DE 1196200 Tolazamide synthesis.png
Tolazemide synthesis: U.S. Patent 3,063,903 GB 887886   DE 1196200  

para-Toluenesulfonamide is converted to its carbamate with ethyl chloroformate in the presence of a base. Heating that intermediate with 1-amino-azepane leads to the displacement of the ethoxy group and the formation of tolazemide: [1]

Azepane proper would lead to [13078-23-4].

Related Research Articles

<span class="mw-page-title-main">Cat</span> Small domesticated carnivorous mammal

The cat is a domestic species of small carnivorous mammal. It is the only domesticated species in the family Felidae and is commonly referred to as the domestic cat or house cat to distinguish it from the wild members of the family. Cats are commonly kept as house pets but can also be farm cats or feral cats; the feral cat ranges freely and avoids human contact. Domestic cats are valued by humans for companionship and their ability to kill rodents. About 60 cat breeds are recognized by various cat registries.

<span class="mw-page-title-main">Earth</span> Third planet from the Sun

Earth is the third planet from the Sun and the only place in the universe known to harbor life. While large volumes of water can be found throughout the Solar System, only Earth sustains liquid surface water. Approximately 70.8% of Earth's surface is made up of the ocean, dwarfing Earth's polar ice, lakes, and rivers. The remaining 29.2% of Earth's surface is land, consisting of continents and islands. Earth's surface layer is formed of several slowly moving tectonic plates, which interact to produce mountain ranges, volcanoes, and earthquakes. Earth's liquid outer core generates the magnetic field that shapes the magnetosphere of the Earth, deflecting destructive solar winds.

<span class="mw-page-title-main">ISBN</span> Unique numeric book identifier (introduced 1970)

The International Standard Book Number (ISBN) is a numeric commercial book identifier that is intended to be unique. Publishers purchase ISBNs from an affiliate of the International ISBN Agency.

An Internet Protocol address is a numerical label such as 192.0.2.1 that is connected to a computer network that uses the Internet Protocol for communication. An IP address serves two main functions: network interface identification and location addressing.

macOS Operating system for Apple computers

macOS is a Unix operating system developed and marketed by Apple Inc. since 2001. It is the primary operating system for Apple's Mac computers. Within the market of desktop and laptop computers it is the second most widely used desktop OS, after Microsoft Windows and ahead of ChromeOS.

<span class="mw-page-title-main">Periodic table</span> Tabular arrangement of the chemical elements ordered by atomic number

The periodic table, also known as the periodic table of the (chemical) elements, is a rows and columns arrangement of the chemical elements. It is widely used in chemistry, physics, and other sciences, and is generally seen as an icon of chemistry. It is a graphic formulation of the periodic law, which states that the properties of the chemical elements exhibit an approximate periodic dependence on their atomic numbers. The table is divided into four roughly rectangular areas called blocks. The rows of the table are called periods, and the columns are called groups. Elements from the same group of the periodic table show similar chemical characteristics. Trends run through the periodic table, with nonmetallic character increasing from left to right across a period, and from down to up across a group, and metallic character increasing in the opposite direction. The underlying reason for these trends is electron configurations of atoms. The periodic table exclusively lists electrically neutral atoms that have an equal number of positively charged protons and negatively charged electrons and puts isotopes at the same place. Other atoms, like nuclides and isotopes, are graphically collected in other tables like the tables of nuclides.

<span class="mw-page-title-main">Russia</span> Country spanning Europe and Asia

Russia, or the Russian Federation, is a transcontinental country spanning Eastern Europe and Northern Asia. It is the largest country in the world, with its internationally recognised territory covering 17,098,246 square kilometres (6,601,670 sq mi), and encompassing one-eighth of Earth's inhabitable landmass. Russia extends across eleven time zones and shares land boundaries with fourteen countries. It is the world's ninth-most populous country and Europe's most populous country, with a population of 146 million people. The country's capital and largest city is Moscow. Saint Petersburg is Russia's cultural centre and second-largest city. Other major urban areas include Novosibirsk, Yekaterinburg, Nizhny Novgorod, and Kazan.

<span class="mw-page-title-main">Midfielder</span> Association football position

midfielder is an outfield position in association football. Midfielders may play an exclusively defensive role, breaking up attacks, and are in that case known as defensive midfielders. As central midfielders often go across boundaries, with mobility and passing ability, they are often referred to as deep-lying midfielders, play-makers, box-to-box midfielders, or holding midfielders. There are also attacking midfielders with limited defensive assignments.

<span class="mw-page-title-main">Human</span> Species of hominid in the genus Homo

Humans are the most abundant and widespread species of primate, characterized by bipedalism and exceptional cognitive skills due to a large and complex brain. This has enabled the development of advanced tools, culture, and language. Humans are highly social and tend to live in complex social structures composed of many cooperating and competing groups, from families and kinship networks to political states. Social interactions between humans have established a wide variety of values, social norms, and rituals, each of which bolster human society. Its intelligence and its desire to understand and influence the environment and to explain and manipulate phenomena have motivated humanity's development of science, philosophy, mythology, religion, and other fields of study.

<span class="mw-page-title-main">Sulfonylurea</span> Class of organic compounds used in medicine and agriculture

Sulfonylureas are a class of organic compounds used in medicine and agriculture, for example as antidiabetic drugs widely used in the management of diabetes mellitus type 2. They act by increasing insulin release from the beta cells in the pancreas. A number of sulfonylureas are also used as herbicides, because they can interfere with plant biosynthesis of certain amino acids. Sulfonylureas are also used experimentally to inhibit interleukin 1 beta release from the NALP3 inflammasome.

ATC code A10Drugs used in diabetes is a therapeutic subgroup of the Anatomical Therapeutic Chemical Classification System, a system of alphanumeric codes developed by the World Health Organization (WHO) for the classification of drugs and other medical products. Subgroup A10 is part of the anatomical group A Alimentary tract and metabolism.

<span class="mw-page-title-main">Doxepin</span> Medication to treat depressive disorder, anxiety disorders, chronic hives, and trouble sleeping

Doxepin is a medication belonging to the tricyclic antidepressant (TCA) class of drugs used to treat major depressive disorder, anxiety disorders, chronic hives, and insomnia. For hives it is a less preferred alternative to antihistamines. It has a mild to moderate benefit for sleeping problems. It is used as a cream for itchiness due to atopic dermatitis or lichen simplex chronicus.

<span class="mw-page-title-main">HIV/AIDS</span> Spectrum of conditions caused by HIV infection

Human immunodeficiency virus infection and acquired immunodeficiency syndrome (HIV/AIDS) is a spectrum of conditions caused by infection with the human immunodeficiency virus (HIV), a retrovirus. Following initial infection an individual may not notice any symptoms, or may experience a brief period of influenza-like illness. Typically, this is followed by a prolonged incubation period with no symptoms. If the infection progresses, it interferes more with the immune system, increasing the risk of developing common infections such as tuberculosis, as well as other opportunistic infections, and tumors which are rare in people who have normal immune function. These late symptoms of infection are referred to as acquired immunodeficiency syndrome (AIDS). This stage is often also associated with unintended weight loss.

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

Azepines are unsaturated heterocycles of seven atoms, with a nitrogen replacing a carbon at one position.

<span class="mw-page-title-main">Animal</span> Kingdom of living things

Animals are multicellular, eukaryotic organisms in the biological kingdom Animalia. With few exceptions, animals consume organic material, breathe oxygen, are able to move, can reproduce sexually, and go through an ontogenetic stage in which their body consists of a hollow sphere of cells, the blastula, during embryonic development. Over 1.5 million living animal species have been described—of which around 1 million are insects—but it has been estimated there are over 7 million animal species in total. Animals range in length from 8.5 micrometres (0.00033 in) to 33.6 metres (110 ft). They have complex interactions with each other and their environments, forming intricate food webs. The scientific study of animals is known as zoology.

The molecular formula C6H13N (molar mass: 99.17 g/mol, exact mass: 99.1048 u) may refer to:

<span class="mw-page-title-main">Michael Smith (darts player)</span> English darts player (born 1990)

Michael Smith is an English professional darts player. Nicknamed "Bully Boy", he plays in Professional Darts Corporation (PDC) events, where he is the reigning World Champion and World No. 1, having won the 2023 World Championship.

<span class="mw-page-title-main">Balanol</span> Fungal metabolite

Balanol is a fungal metabolite produced by the fungus Verticillium balanoides. It is a potent inhibitor of the serine/threonine kinases protein kinase A (PKA) and protein kinase C (PKC), binding in a similar manner with that of ATP. Balanol was discovered in 1993 in the search for novel inhibitors of PKC, a member of a family of serine/threonine kinases whose overactivation is associated with numerous human diseases of signal transduction including cancer. However, much of the research on balanol focuses on how chemical modifications of the molecular structure affect binding to PKA. Indeed, balanol, its chemically altered analogs, and their interactions with PKA in particular are used to illuminate the roles of selectivity and protein flexibility in the inhibition of kinases. For instance, the X-ray crystal structure of balanol in complex with PKA was used in order to confer selectivity and to improve pharmacological efficacy of inhibitors of the H. sapiens Akt (PKB), another serine/threonine protein kinase implicated in the proper functioning of many cellular processes.

<span class="mw-page-title-main">PlayStation 4</span> Sonys fourth home video game console, part of the eighth generation of consoles

The PlayStation 4 (PS4) is a home video game console developed by Sony Interactive Entertainment. Announced as the successor to the PlayStation 3 in February 2013, it was launched on November 15, 2013, in North America, November 29, 2013 in Europe, South America and Australia, and on February 22, 2014 in Japan. A console of the eighth generation, it competes with Microsoft's Xbox One and Nintendo's Wii U and Switch.

References

  1. 1 2 Wright JB, Willette RE (July 1962). "Antidiabetic Agents. N4-Arylsulfonylsemicarbazides". Journal of Medicinal and Pharmaceutical Chemistry. 91 (4): 815–22. doi:10.1021/jm01239a016. PMID   14056414.