Glucuronide

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Morphine-6-glucuronide, a major metabolite of morphine Morphine 6-glucuronide.png
Morphine-6-glucuronide, a major metabolite of morphine

A glucuronide, also known as glucuronoside, is any substance produced by linking glucuronic acid to another substance via a glycosidic bond. [1] The glucuronides belong to the glycosides.

Glucuronidation, the conversion of chemical compounds to glucuronides, is a method that animals use to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys. [2]

Enzymes that cleave the glycosidic bond of a glucuronide are called glucuronidases.

Examples

Related Research Articles

A glycosidic bond or glycosidic linkage is a type of covalent bond that joins a carbohydrate (sugar) molecule to another group, which may or may not be another carbohydrate.

Glucuronolactone

Glucuronolactone is a naturally occurring substance that is an important structural component of nearly all connective tissues. It is frequently used in energy drinks to increase energy levels and improve alertness, and can also be used to reduce "brain fog" cause by various medical conditions. Glucuronolactone is also found in many plant gums.

Glycoside Molecule in which a sugar is bound to another functional group

In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of Heliconius butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.

Desloratadine Allergy medication

Desloratadine (trade name Clarinex and Aerius) is a tricyclic H1 antagonist that is used to treat allergies. It is an active metabolite of loratadine.

Enterohepatic circulation

Enterohepatic circulation refers to the circulation of biliary acids, bilirubin, drugs or other substances from the liver to the bile, followed by entry into the small intestine, absorption by the enterocyte and transport back to the liver. Enterohepatic circulation is an especially important concept in the field of toxicology as many lipophilic xenobiotics undergo this process causing repeated liver damage.

Glucuronidation is often involved in drug metabolism of substances such as drugs, pollutants, bilirubin, androgens, estrogens, mineralocorticoids, glucocorticoids, fatty acid derivatives, retinoids, and bile acids. These linkages involve glycosidic bonds.

Glucuronic acid

Glucuronic acid is a uronic acid that was first isolated from urine. It is found in many gums such as gum arabic, xanthan, and Kombucha tea and is important for the metabolism of microorganisms, plants and animals.

Glucuronosyltransferase

Uridine 5'-diphospho-glucuronosyltransferase is a microsomal glycosyltransferase that catalyzes the transfer of the glucuronic acid component of UDP-glucuronic acid to a small hydrophobic molecule. This is a glucuronidation reaction.

Toluene toxicity refers to the harmful effects caused by toluene on the body.

4-Aminobiphenyl (4-APB) is an organic compound with the formula C6H5C6H4NH2. It is an amine derivative of biphenyl. It is a colorless solid, although aged samples can appear colored. 4-Aminobiphenyl was commonly used in the past as a rubber antioxidant and an intermediate for dyes. Exposure to this aryl-amine can happen through contact with chemical dyes and from inhalation of cigarette smoke. Researches showed that 4-aminobiphenyl is responsible for bladder cancer in humans and dogs by damaging DNA. Due to its carcinogenic effects, commercial production of 4-aminobiphenyl ceased in the United States in the 1950s.

UGT2B7

UGT2B7 (UDP-Glucuronosyltransferase-2B7) is a phase II metabolism isoenzyme found to be active in the liver, kidneys, epithelial cells of the lower gastrointestinal tract and also has been reported in the brain. In humans, UDP-Glucuronosyltransferase-2B7 is encoded by the UGT2B7 gene.

UGT2B17

UDP-glucuronosyltransferase 2B17 is an enzyme that in humans is encoded by the UGT2B17 gene.

Eslicarbazepine acetate Anticonvulsant medication

Eslicarbazepine acetate (ESL), sold under the brand names Aptiom and Zebinix among others, is an anticonvulsant medication approved for use in Europe and the United States as monotherapy or as additional therapy for partial-onset seizures epilepsy.

Ethyl glucuronide

Ethyl glucuronide (EtG) is a metabolite of ethanol which is formed in the body by glucuronidation following exposure to ethanol, usually from drinking alcoholic beverages. It is used as a biomarker to test for ethanol use and to monitor alcohol abstinence in situations where drinking is prohibited, such as by the military, in alcohol treatment programs, in professional monitoring programs, in schools, liver transplant clinics, or in recovering alcoholic patients. In addition to its use to monitor abstinence and detect drinking, EtG also has potential for monitoring the amount of alcohol use over time because it can be detected in hair and nails, though the effectiveness of this has not yet been proven.

Naldemedine

Naldemedine is a medication that is used for the treatment of opioid-induced constipation in adults with chronic non-cancer pain. It is a peripherally acting μ-opioid receptor antagonist and was developed by Shionogi. Clinical studies have found it to possess statistically significant effectiveness for these indications and to be generally well tolerated, with predominantly mild to moderate gastrointestinal side effects. Effects indicative of central opioid withdrawal or impact on the analgesic or miotic effects of co-administered opioids have only been observed in a small number of patients.

Mycophenolic acid acyl-glucuronide esterase, mitochondrial, also called abhydrolase domain-containing protein 10, mitochondrial (ABHD10), is in humans encoded by the ABHD10 gene. This enzyme catalyses the following chemical reaction

Estriol glucuronide

Estriol glucuronide (E3G), or oestriol glucuronide, also known as estriol monoglucuronide, as well as estriol 16α-β-D-glucosiduronic acid, is a natural, steroidal estrogen and the glucuronic acid conjugate of estriol. It occurs in high concentrations in the urine of pregnant women as a reversibly formed metabolite of estriol. Estriol glucuronide is a prodrug of estriol, and was the major component of Progynon and Emmenin, estrogenic products manufactured from the urine of pregnant women that were introduced in the 1920s and 1930s and were the first orally active estrogens. Emmenin was succeeded by Premarin, which is sourced from the urine of pregnant mares and was introduced in 1941. Premarin replaced Emmenin due to the fact that it was easier and less expensive to produce.

Estradiol glucuronide

Estradiol glucuronide, or estradiol 17β-D-glucuronide, is a conjugated metabolite of estradiol. It is formed from estradiol in the liver by UDP-glucuronyltransferase via attachment of glucuronic acid and is eventually excreted in the urine by the kidneys. It has much higher water solubility than does estradiol. Glucuronides are the most abundant estrogen conjugates.

Estradiol 3-glucuronide

Estradiol 3-glucuronide (E2-3G), also known as 17β-estradiol 3-(β-D-glucuronide), is a naturally occurring and endogenous estrogen conjugate. It is specifically the C3 glucuronide conjugate of estradiol, the major estrogen in the body. It is formed from estradiol in the liver by UDP-glucuronosyltransferase via attachment of glucuronic acid and is eventually excreted in urine and bile. Similarly to estrogen sulfates like estrone sulfate, estrogen glucuronides have much higher water solubility than do unconjugated estrogens like estradiol.

Bilirubin glucuronide A reaction intermediate over the process of conjugation of indirect bilirubin. A conjugated bilirubin.

Bilirubin glucuronide is a water-soluble reaction intermediate over the process of conjugation of indirect bilirubin. Bilirubin glucuronide itself belongs to the category of conjugated bilirubin along with bilirubin di-glucuronide. However, only the latter one is primarily excreted into the bile in the normal setting.

References

  1. The American Heritage Medical Dictionary, 2007, Houghton Mifflin Company
  2. Yang G, Ge S, Singh R, Basu S, Shatzer K, Zen M, et al. (May 2017). "Glucuronidation: driving factors and their impact on glucuronide disposition". Drug Metabolism Reviews. 49 (2): 105–138. doi:10.1080/03602532.2017.1293682. PMC   7660525 . PMID   28266877.