Clofibric acid

Last updated
Clofibric acid
Clofibric acid.png
Names
Preferred IUPAC name
2-(4-Chlorophenoxy)-2-methylpropanoic acid
Other names
Clofibrin
Chlorofibrinic acid
Chlorophenoxyisobutyric acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.011.751 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C10H11ClO3/c1-10(2,9(12)13)14-8-5-3-7(11)4-6-8/h3-6H,1-2H3,(H,12,13) Yes check.svgY
    Key: TXCGAZHTZHNUAI-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C10H11ClO3/c1-10(2,9(12)13)14-8-5-3-7(11)4-6-8/h3-6H,1-2H3,(H,12,13)
    Key: TXCGAZHTZHNUAI-UHFFFAOYAP
  • Clc1ccc(OC(C(=O)O)(C)C)cc1
Properties
C10H11ClO3
Molar mass 214.645 g/mol
AppearanceWhite to yellow solid
Melting point 118 to 123 °C (244 to 253 °F; 391 to 396 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Clofibric acid is a biologically active metabolite of the lipid-lowering drugs clofibrate, etofibrate and theofibrate [1] [2] with the molecular formula C10H11ClO3. It has been found in the environment following use of these drugs, for example in Swiss lakes and the North Sea. [2] [3]

Some derivatives of clofibric acid are in a drug class called fibrates.

See also

Related Research Articles

<span class="mw-page-title-main">Tetrahydrocannabinol</span> Psychoactive component of cannabis

Tetrahydrocannabinol (THC) is a cannabinoid found in cannabis. It is the principal psychoactive constituent of cannabis and one of at least 113 total cannabinoids identified on the plant. Although the chemical formula for THC (C21H30O2) describes multiple isomers, the term THC usually refers to the delta-9-THC isomer with chemical name (−)-trans9-tetrahydrocannabinol. It is a colorless oil.

<span class="mw-page-title-main">Water pollution</span> Contamination of water bodies

Water pollution is the contamination of water bodies, with a negative impact on their uses. It is usually a result of human activities. Water bodies include lakes, rivers, oceans, aquifers, reservoirs and groundwater. Water pollution results when contaminants mix with these water bodies. Contaminants can come from one of four main sources. These are sewage discharges, industrial activities, agricultural activities, and urban runoff including stormwater. Water pollution may affect either surface water or groundwater. This form of pollution can lead to many problems. One is the degradation of aquatic ecosystems. Another is spreading water-borne diseases when people use polluted water for drinking or irrigation. Water pollution also reduces the ecosystem services such as drinking water provided by the water resource.

A xenobiotic is a chemical substance found within an organism that is not naturally produced or expected to be present within the organism. It can also cover substances that are present in much higher concentrations than are usual. Natural compounds can also become xenobiotics if they are taken up by another organism, such as the uptake of natural human hormones by fish found downstream of sewage treatment plant outfalls, or the chemical defenses produced by some organisms as protection against predators. The term "xenobiotic" is also used to refer to organs transplanted from one species to another.

<span class="mw-page-title-main">Esomeprazole</span> Medication which reduces stomach acid

Esomeprazole, sold under the brand name Nexium [or Neksium] among others, is a medication which reduces stomach acid. It is used to treat gastroesophageal reflux disease, peptic ulcer disease, and Zollinger–Ellison syndrome. Its effectiveness is similar to that of other proton pump inhibitors (PPIs). It is taken by mouth or injection into a vein.

<span class="mw-page-title-main">Aniracetam</span> Medication

Aniracetam, also known as N-anisoyl-2-pyrrolidinone, is a racetam which is sold in Europe as a prescription drug. It is not approved by the Food and Drug Administration for use in the United States as a prescription medication or dietary supplement. Despite the FDA's lack of approval, the drug is readily available over-the-counter in misbranded dietary supplements.

Drug metabolism is the metabolic breakdown of drugs by living organisms, usually through specialized enzymatic systems. More generally, xenobiotic metabolism is the set of metabolic pathways that modify the chemical structure of xenobiotics, which are compounds foreign to an organism's normal biochemistry, such as any drug or poison. These pathways are a form of biotransformation present in all major groups of organisms and are considered to be of ancient origin. These reactions often act to detoxify poisonous compounds. The study of drug metabolism is the object of pharmacokinetics. Metabolism is one of the stages of the drug's transit through the body that involves the breakdown of the drug so that it can be excreted by the body.

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

Sulfamethoxazole is an antibiotic. It is used for bacterial infections such as urinary tract infections, bronchitis, and prostatitis and is effective against both gram negative and positive bacteria such as Escherichia coli and Listeria monocytogenes.

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

Mefenamic acid is a member of the anthranilic acid derivatives class of nonsteroidal anti-inflammatory drugs (NSAIDs), and is used to treat mild to moderate pain.

<span class="mw-page-title-main">Natural product</span> Chemical compound or substance produced by a living organism, found in nature

A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical synthesis and have played a central role in the development of the field of organic chemistry by providing challenging synthetic targets. The term natural product has also been extended for commercial purposes to refer to cosmetics, dietary supplements, and foods produced from natural sources without added artificial ingredients.

Shikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid. It is an important biochemical metabolite in plants and microorganisms. Its name comes from the Japanese flower shikimi, from which it was first isolated in 1885 by Johan Fredrik Eykman. The elucidation of its structure was made nearly 50 years later.

<span class="mw-page-title-main">Ellagic acid</span> Natural phenol antioxidant

Ellagic acid is a polyphenol found in numerous fruits and vegetables. It is the dilactone of hexahydroxydiphenic acid.

<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">Paramethadione</span> Chemical compound

Paramethadione is an anticonvulsant drug of the chemical class called oxazolidinediones developed by the Illinois-based pharmaceutical company Abbott Laboratories, and approved by the Food and Drug Administration in 1949 for the treatment of absence seizures, also called partial seizures.

<span class="mw-page-title-main">Flutazolam</span> Benzodiazepam

Flutazolam is a drug which is a benzodiazepine derivative. It was invented in Japan, and this is the main country in which it has been used medically. It has sedative, muscle relaxant, anticonvulsant, and anxiolytic effects similar to those produced by other benzodiazepine derivatives, and though it is around the same potency as diazepam, it produces a more marked sedation and impaired coordination. It is indicated for the treatment of insomnia. Its major active metabolite is n-desalkylflurazepam, also known as norflurazepam, which is also a principal metabolite of flurazepam. While flutazolam has a very short half-life of only 3.5 hours, n-desalkylflurazepam has a long half-life of between 47–100 hours.

<span class="mw-page-title-main">Dinoseb</span> Chemical compound used as a herbicide

Dinoseb is a common industry name for 6-sec-butyl-2,4-dinitrophenol, a herbicide in the dinitrophenol family. It is a crystalline orange solid which does not readily dissolve in water. Dinoseb is banned as an herbicide in the European Union (EU) and the United States because of its toxicity.

<span class="mw-page-title-main">Environmental impact of pharmaceuticals and personal care products</span> Effects of drugs on the environment

The environmental effect of pharmaceuticals and personal care products (PPCPs) is being investigated since at least the 1990s. PPCPs include substances used by individuals for personal health or cosmetic reasons and the products used by agribusiness to boost growth or health of livestock. More than twenty million tons of PPCPs are produced every year. The European Union has declared pharmaceutical residues with the potential of contamination of water and soil to be "priority substances".[3]

4-Hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors are a class of herbicides that prevent growth in plants by blocking 4-Hydroxyphenylpyruvate dioxygenase, an enzyme in plants that breaks down the amino acid tyrosine into molecules that are then used by plants to create other molecules that plants need. This process of breakdown, or catabolism, and making new molecules from the results, or biosynthesis, is something all living things do. HPPD inhibitors were first brought to market in 1980, although their mechanism of action was not understood until the late 1990s. They were originally used primarily in Japan in rice production, but since the late 1990s have been used in Europe and North America for corn, soybeans, and cereals, and since the 2000s have become more important as weeds have become resistant to glyphosate and other herbicides. Genetically modified crops are under development that include resistance to HPPD inhibitors. There is a pharmaceutical drug on the market, nitisinone, that was originally under development as an herbicide as a member of this class and is used to treat an orphan disease, type I tyrosinemia.

Drug pollution or pharmaceutical pollution is pollution of the environment with pharmaceutical drugs and their metabolites, which reach the aquatic environment through wastewater. Drug pollution is therefore mainly a form of water pollution.

Molecular Operating Environment (MOE) is a drug discovery software platform that integrates visualization, modeling and simulations, as well as methodology development, in one package. MOE scientific applications are used by biologists, medicinal chemists and computational chemists in pharmaceutical, biotechnology and academic research. MOE runs on Windows, Linux, Unix, and macOS. Main application areas in MOE include structure-based design, fragment-based design, ligand-based design, pharmacophore discovery, medicinal chemistry applications, biologics applications, structural biology and bioinformatics, protein and antibody modeling, molecular modeling and simulations, virtual screening, cheminformatics & QSAR. The Scientific Vector Language (SVL) is the built-in command, scripting and application development language of MOE.

Lichen products, also known as lichen substances, are organic compounds produced by a lichen. Specifically, they are secondary metabolites. Lichen products are represented in several different chemical classes, including terpenoids, orcinol derivatives, chromones, xanthones, depsides, and depsidones. Over 800 lichen products of known chemical structure have been reported in the scientific literature, and most of these compounds are exclusively found in lichens. Examples of lichen products include usnic acid, atranorin, lichexanthone, salazinic acid, and isolichenan, an α-glucan. Many lichen products have biological activity, and research into these effects is ongoing.

References

  1. Salgado, R.; Oehmen, A.; Carvalho, G.; Noronha, J.P.; Reis, M.A.M. (2012). "Biodegradation of clofibric acid and identification of its metabolites". Journal of Hazardous Materials. 241–242: 182–189. doi:10.1016/j.jhazmat.2012.09.029. PMID   23062606.
  2. 1 2 Packer, Jennifer L; Werner, Jeffrey J; Latch, Douglas E; McNeill, Kristopher; Arnold, William A (2003). "Photochemical fate of pharmaceuticals in the environment: Naproxen, diclofenac, clofibric acid, and ibuprofen". Aquatic Sciences. 65 (4): 342–351. doi:10.1007/s00027-003-0671-8. S2CID   24063392.
  3. Buser, Hans-Rudolf; Müller, Markus D; Theobald, Norbert (1998). "Occurrence of the Pharmaceutical Drug Clofibric Acid and the Herbicide Mecoprop in Various Swiss Lakes and in the North Sea". Environmental Science & Technology. 32 (1): 188–192. Bibcode:1998EnST...32..188B. doi:10.1021/es9705811.