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Other names Sodium 3,3'-diamino-4,4'-dihydroxyarsenobenzene-N-formaldehydesulfoxylate; Neoarsphenamine;914 | |
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3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.006.613 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C13H13As2N2NaO4S | |
Molar mass | 466.15 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Neosalvarsan is a synthetic chemotherapeutic that is an organoarsenic compound. It became available in 1912 and superseded the more toxic and less water-soluble Salvarsan as an effective treatment for syphilis. Because both of these arsenicals carried considerable risk of side effects, they were replaced for this indication by penicillin in the 1940s.
Both Salvarsan and Neosalvarsan were developed in the laboratory of Paul Ehrlich in Frankfurt, Germany. Their discoveries were the result of the first organized team effort to optimize the biological activity of a lead compound through systematic chemical modifications. [1] This scheme is the basis for most modern pharmaceutical research. Both Salvarsan and Neosalvarsan are prodrugs –that is, they are metabolised into the active drug in the body.
Although, like Salvarsan, it was originally believed to contain an arsenic-arsenic double bond, this is now known to be incorrect for Salvarsan. [2] Presumably, Neosalvarsan also exists as a mixture of differently sized rings with arsenic-arsenic single bonds.
Arsenic is a chemical element with the symbol As and the atomic number 33. It is a metalloid and one of the pnictogens, and therefore shares many properties with its group 15 neighbors phosphorus and antimony. Arsenic is a notoriously toxic heavy metal. It occurs naturally in many minerals, usually in combination with sulfur and metals, but also as a pure elemental crystal. It has various allotropes, but only the grey form, which has a metallic appearance, is important to industry.
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms. Study of structure determines their structural formula. Study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical study.
Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and sometimes broadened to include metalloids like boron, silicon, and selenium, as well. Aside from bonds to organyl fragments or molecules, bonds to 'inorganic' carbon, like carbon monoxide, cyanide, or carbide, are generally considered to be organometallic as well. Some related compounds such as transition metal hydrides and metal phosphine complexes are often included in discussions of organometallic compounds, though strictly speaking, they are not necessarily organometallic. The related but distinct term "metalorganic compound" refers to metal-containing compounds lacking direct metal-carbon bonds but which contain organic ligands. Metal β-diketonates, alkoxides, dialkylamides, and metal phosphine complexes are representative members of this class. The field of organometallic chemistry combines aspects of traditional inorganic and organic chemistry.
Paul Ehrlich was a Nobel Prize-winning German physician and scientist who worked in the fields of hematology, immunology and antimicrobial chemotherapy. Among his foremost achievements were finding a cure for syphilis in 1909 and inventing the precursor technique to Gram staining bacteria. The methods he developed for staining tissue made it possible to distinguish between different types of blood cells, which led to the ability to diagnose numerous blood diseases.
Arsenic poisoning is a medical condition that occurs due to elevated levels of arsenic in the body. If arsenic poisoning occurs over a brief period of time, symptoms may include vomiting, abdominal pain, encephalopathy, and watery diarrhea that contains blood. Long-term exposure can result in thickening of the skin, darker skin, abdominal pain, diarrhea, heart disease, numbness, and cancer.
Arsphenamine, also known as Salvarsan or compound 606, is an antibiotic drug that was introduced at the beginning of the 1910s as the first effective treatment for the deadly infectious diseases syphilis, relapsing fever, and African trypanosomiasis. This organoarsenic compound was the first modern antimicrobial agent.
Bioinorganic chemistry is a field that examines the role of metals in biology. Bioinorganic chemistry includes the study of both natural phenomena such as the behavior of metalloproteins as well as artificially introduced metals, including those that are non-essential, in medicine and toxicology. Many biological processes such as respiration depend upon molecules that fall within the realm of inorganic chemistry. The discipline also includes the study of inorganic models or mimics that imitate the behaviour of metalloproteins.
Arsanilic acid, also known as aminophenyl arsenic acid or aminophenyl arsonic acid, is an organoarsenic compound, an amino derivative of phenylarsonic acid whose amine group is in the 4-position. A crystalline powder introduced medically in the late 19th century as Atoxyl, its sodium salt was used by injection in the early 20th century as the first organic arsenical drug, but it was soon found prohibitively toxic for human use.
Arsenic trioxide is an inorganic compound with the formula As
2O
3. As an industrial chemical, its major uses include the manufacture of wood preservatives, pesticides, and glass. It is sold under the brand name Trisenox among others when used as a medication to treat a type of cancer known as acute promyelocytic leukemia. For this use it is given by injection into a vein.
Pierre Jacques Antoine Béchamp was a French scientist now best known for breakthroughs in applied organic chemistry and for a bitter rivalry with Louis Pasteur.
Sahachirō Hata was a prominent Japanese bacteriologist who researched the bubonic plague under Kitasato Shibasaburō and assisted in developing the antisyphilitic drug arsphenamine in 1909 in the laboratory of Paul Ehrlich.
In organic synthesis the Béchamp reaction is used for producing arsonic acids from activated aromatic substrates. The reaction is an electrophilic aromatic substitution, using arsenic acid as the electrophile. The reaction proceeds according to this idealized stoichiometry for the preparation of arsanilic acid:
William John Young was an English biochemist.
Potassium arsenite (KAsO2) is an inorganic compound that exists in two forms, potassium meta-arsenite (KAsO2) and potassium ortho-arsenite (K3AsO3). It is composed of arsenite ions (AsO33− or AsO2−) with arsenic always existing in the +3 oxidation state. Like many other arsenic containing compounds, potassium arsenite is highly toxic and carcinogenic to humans. Potassium arsenite forms the basis of Fowler’s solution, which was historically used as a medicinal tonic, but due to its toxic nature its use was discontinued. Potassium arsenite is still, however, used as a rodenticide.
Organoarsenic chemistry is the chemistry of compounds containing a chemical bond between arsenic and carbon. A few organoarsenic compounds, also called "organoarsenicals," are produced industrially with uses as insecticides, herbicides, and fungicides. In general these applications are declining in step with growing concerns about their impact on the environment and human health. The parent compounds are arsane and arsenic acid. Despite their toxicity, organoarsenic biomolecules are well known.
Pharmaceutical engineering is a branch of engineering focused on discovering, formulating, and manufacturing medication, analytical and quality control processes, and on designing, building, and improving manufacturing sites that produce drugs. It utilizes the fields of chemical engineering, biomedical engineering, pharmaceutical sciences, and industrial engineering.
Arsenic biochemistry refers to biochemical processes that can use arsenic or its compounds, such as arsenate. Arsenic is a moderately abundant element in Earth's crust, and although many arsenic compounds are often considered highly toxic to most life, a wide variety of organoarsenic compounds are produced biologically and various organic and inorganic arsenic compounds are metabolized by numerous organisms. This pattern is general for other related elements, including selenium, which can exhibit both beneficial and deleterious effects. Arsenic biochemistry has become topical since many toxic arsenic compounds are found in some aquifers, potentially affecting many millions of people via biochemical processes.
Alfred Bertheim was a German chemist, best known for his research on arsenic compounds with Paul Ehrlich.
The magic bullet is a scientific concept developed by the German Nobel laureate Paul Ehrlich in 1907. While working at the Institute of Experimental Therapy, Ehrlich formed an idea that it could be possible to kill specific microbes, which cause diseases in the body, without harming the body itself. He named the hypothetical agent as Zauberkugel, and used the English translation "magic bullet" in The Harben Lectures at London. The name itself is a reference to an old German myth about a bullet that cannot miss its target. Ehrlich had in mind Carl Maria von Weber's popular 1821 opera Der Freischütz, in which a young hunter is required to hit an impossible target in order to marry his bride.
Carl Voegtlin, also Karl Voegtlin, was a Swiss-American pharmacologist, organic chemist, and the first director of the U.S. National Cancer Institute. He is known for his research into the biochemical effects of cancer, contributions to the pharmacology of arsenicals and the discovery, with Homer Smith, of mapharsen as the active agent in Paul Ehrlich's Salvarsan.