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Encyclopedia > Sulfonamide (medicine)
Sulfonamide (medicine) chemical structure
Sulfonamide (medicine)
Systematic (IUPAC) name
sulfanilamide
Identifiers
CAS number 63-74-1
ATC code J01EB06 D06BA05
PubChem 5333
DrugBank APRD00438
Chemical data
Formula C6H8N2O2S
Mol. weight 172.206 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

? Image File history File links Download high resolution version (1100x490, 14 KB) File links The following pages link to this file: Sulfa drug User:Benjah-bmm27/Gallery ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules . ... DrugBank is a database available at the University of Alberta that provides information about thousands of products. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Santorio Santorio (1561-1636) in his steelyard balance, from Ars de statica medecina, first published 1614 Metabolism (from μεταβολισμος (metabolismos)) is the biochemical modification of chemical compounds in living organisms anggjgjhnd cell (b). ... The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ... Excretion is the biological process by which an organism chemically separates waste products from its body. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...

Legal status
Routes  ?

There are several sulphonamide-based groups of drugs. The original antibacterial sulfonamides (sometimes called simply sulfa drugs) are synthetic antimicrobial agents that contain the sulfonamide group. The sulfonylureas (main article: sulfonylureas) and thiazide diuretics (main article thiazide) are newer drug groups based on the antibacterial sulfonamides. The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... The structure of the sulfonamide group In chemistry, the sulfonamide functional group is -S(=O)2-NH2, a sulfone group connected to an amine group. ... Sulfonylurea derivatives are a class of antidiabetic drugs that are used in the management of diabetes mellitus type 2 (adult-onset). They act by increasing insulin release from the beta cells in the pancreas. ... Thiazides are a class of drug that promote water loss from the body ((diuretics)). They inhibit Na+/Cl- reabsorption from the distal convoluted tubules in the kidneys. ...


In bacteria, antibacterial sulfonamides act as competitive inhibitors of the enzyme dihydropteroate synthetase, DHPS. DHPS catalyses the coversion of PABA (para-aminobenzoate) to dihydropteroate, a key step in folate synthesis. Folate is necessary for the cell to synthesize nucleic acids (nucleic acids are essential building blocks of DNA and RNA), and in its absence cells will be unable to divide. Hence the sulfonamide antibacterials exhibit a bacteriostatic rather than bactericidal effect. Phyla/Divisions Actinobacteria Aquificae Bacteroidetes/Chlorobi Chlamydiae/Verrucomicrobia Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Nitrospirae Omnibacteria Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Bacteria (singular, bacterium) are a major group of living organisms. ... In biochemistry there are three ways in which certain chemical substances may reduce or prevent the activities of enzymes: competitive, non-competitive and uncompetitive inhibition. ... Para-Aminobenzoic acid (PABA) is a chemical used in sunscreen that is an essential nutrient for some bacteria. ... Folic acid (the anion form is called folate) is a B-complex vitamin (once called vitamin M) that is important in preventing neural tube defects (NTDs) in the developing human fetus. ... Schematic diagram of a double-stranded nucleic acid. ... The general structure of a section of DNA Deoxyribonucleic acid (DNA) is a nucleic acid that contains the genetic instructions for the biological development of a cellular form of life or a virus. ... Ribonucleic acid (RNA) is a nucleic acid polymer consisting of nucleotide monomers. ... Bacteriostatic antibiotics hamper the growth of bacteria by interfering with bacteria protein production, interfering with bacteria DNA production interfering with bacteria cellular metabolism Bacteriostatic antibiotics inhibit growth and repoduction of the bacteria, though do not kill it, while bactericidal antibiotics kill bacteria. ... A bacteriocide or bactericide is a substance that kills bacteria and, preferably, nothing else. ...


Folate is not synthesized in mammalian cells, but is instead a dietary requirement. This explains the selective toxicity to bacterial cells of these drugs.


Sulfa allergies are common, hence medications containing sulfonamides are prescribed carefully.

Contents


History

The first sulfonamide was trade named prontosil, which is a prodrug. The first experiments with prontosil began in 1932 by the German chemist Gerhard Domagk, and the results were published in 1935 (after his employer, IG Farben, had obtained a patent on the compound). Prontosil was a red azo dye, and in mice had a protective action against streptococci. It had no effect in the test tube, and only exerted an antibacterial effect in the live animal itself. The drug is connected with an azo bond, which is a N=N bond. This bond is easily broken in the GI tract to release the active drug sulfanilamide. And, with war on the horizon, there was interest among the Allies to break the German patent. Prontosil is the first successful oral antibiotic developed by Gerhard Domagk, who received the 1939 Nobel Prize in Medicine. ... A prodrug is a pharmacological substance (drug) which is administered in an inactive (or significantly less active) form. ... 1932 (MCMXXXII) was a leap year starting on Friday (the link will take you to a full 1932 calendar). ... Gerhard Johannes Paul Domagk (October 30, 1895 - April 24, 1964) was a German pathologist and bacteriologist and Nobel laureate. ... 1935 (MCMXXXV) was a common year starting on Tuesday (link will take you to calendar). ... IG Farben (short for Interessen-Gemeinschaft Farbenindustrie AG) was a German conglomerate of companies formed in 1925 and even earlier during World War I. IG Farben held nearly a total monopoly on the chemical production, later during the time of Nazi Germany. ... In chemistry, azo compounds generally have a molecular formula of the form R-N=N-R, in which R and R can be either aromatic or aliphatic. ... Species S. agalactiae S. bovis S. mutans S. pneumoniae S. pyogenes S. salivarius S. sanguinis S. suis Streptococcus viridans group etc. ... When spelt with a capital A, Allies usually denotes the countries supporting the Triple Entente who fought together against the Central Powers in World War I and against the Axis Powers in World War II. For more information, see the related articles: Allies of World War I and Allies of...


Soon it was discovered (1936) that prontosil's active agent was a smaller, more effective compound known as sulfanilamide. 1936 (MCMXXXVI) was a leap year starting on Wednesday (link will take you to calendar). ... Sulfonamides, also known as sulfa drugs, are synthetic antimicrobial agents derived from sulfonic acid. ...


Sulfanilamide had a central role in preventing infection during World War II. American soldiers were issued a first aid kit containing sulfa powder and were told to sprinkle sulfa on any open wound. During the years 1942 to 1943, Nazi doctors conducted sulfanilamide experiments on prisoners in [[on the US Food and Drug Administration. A preparation called Elixir Sulfanilamide contained diethylene glycol as a solvent, which is toxic. This preparation killed over one hundred people, mostly children, and led to the passage of the 1938 Food, Drug, and Cosmetic Act. This article is becoming very long. ... This article or section is in need of attention from an expert on the subject. ... Diethylene glycol (DEG, 3-oxa-1,5-pentanediol, diglycol, ethylene diglycol, or dihydroxy diethyl ether) is a diol, an alcohol with two -OH groups, a dimer of ethylene glycol. ... The United States Federal Food, Drug, and Cosmetic Act (FD&C) is a set of laws passed by Congress in 1938 giving authority to the Food and Drug Administration to oversee the safety of food, drugs, and cosmetics. ...


The Sulfanilamide compound is more active in the protonated form, which in case of the acid works better in a basic environment. The solubility of the drug is very low and sometimes can crystalize in the kidneys, due to its first pKa of around 10. This is a very painful experience so patients are told to take the medication with copious amounts of water. Newer compounds have a pKa of around 5-6 so the problem is avoided.


Many thousands of permutations of the sulfanilamide structure have been created since its discovery (by one account, over 5400 permutations by 1945), usually by the substitution of another functional group for a single amide hydrogen. 1945 (MCMVL) was a common year starting on Monday (the link is to a full 1945 calendar). ...


Sulpha is an alternate (UK English) spelling of the common name for Sulfonamide antibiotics.


Preparation

Certain sulfonamides (sulfadiazine or sulfamethoxazole) are sometimes mixed with the drug trimethoprim, which acts against dihydrofolate reductase. Sulfamethoxazole is a sulfonamide antibiotic. ... Trimethoprim is a bacteriostatic antibiotic mainly used in the prophylaxis and treatment of urinary tract infections (cystitis). ... Categories: Biochemistry stubs | EC 1. ...


Side Effects

Sulfonamides have the potential to cause a variety of untoward reactions, including urinary tract disorders, haemopoietic disorders and hypersensitivity reactions.


See also

An antibiotic is a drug that kills or slows the growth of bacteria. ... This is the timeline of antimicrobial (anti-infective) therapy. ... Sulfa drugs are synthetic antimicrobial agents that contain the sulfonamide group. ...

External links


 
 

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