Galegine

Last updated
Galegine
Galegine.svg
Names
IUPAC name
2-(3-Methylbut-2-enyl)guanidine
Other names
  • Isopentenyl guanidine
  • Dimethylallylguanidine
  • Isoamylene guanidine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C6H13N3/c1-5(2)3-4-9-6(7)8/h3H,4H2,1-2H3,(H4,7,8,9)
    Key: UVMLHMAIUVSYOL-UHFFFAOYSA-N
  • CC(=CCN=C(N)N)C
Properties
C6H13N3
Molar mass 127.191 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Galegine is a toxic chemical compound that has been isolated from Galega officinalis . [1] It has also been found to be the principal cause of the toxicity of poison sedge (Schoenus asperocarpus). [2]

Galegine was used in the 1920s as a pharmaceutical treatment for diabetes; [3] however, because of its toxicity, its use was soon supplanted by superior alternatives. Research on galegine eventually led to the development of metformin which is used today for treatment of type 2 diabetes. [3]

See also

Related Research Articles

<span class="mw-page-title-main">Polycystic ovary syndrome</span> Set of symptoms caused by abnormal hormones in females

Polycystic ovary syndrome, or polycystic ovarian syndrome (PCOS), is the most common endocrine disorder in women of reproductive age. The syndrome is named after cysts which form on the ovaries of some people with this condition, though this is not a universal symptom, and not the underlying cause of the disorder.

<span class="mw-page-title-main">Type 2 diabetes</span> Type of diabetes mellitus with high blood sugar and insulin resistance

Type 2 diabetes (T2D), formerly known as adult-onset diabetes, is a form of diabetes mellitus that is characterized by high blood sugar, insulin resistance, and relative lack of insulin. Common symptoms include increased thirst, frequent urination, fatigue and unexplained weight loss. Symptoms may also include increased hunger, having a sensation of pins and needles, and sores (wounds) that do not heal. Often symptoms come on slowly. Long-term complications from high blood sugar include heart disease, strokes, diabetic retinopathy which can result in blindness, kidney failure, and poor blood flow in the limbs which may lead to amputations. The sudden onset of hyperosmolar hyperglycemic state may occur; however, ketoacidosis is uncommon.

<span class="mw-page-title-main">Lactic acidosis</span> Metabolic medical condition

Lactic acidosis is a medical condition characterized by a build-up of lactate in the body, with formation of an excessively low pH in the bloodstream. It is a form of metabolic acidosis, in which excessive acid accumulates due to a problem with the body's oxidative metabolism.

<span class="mw-page-title-main">Metformin</span> Medication used to treat diabetes by reducing glucose levels

Metformin, sold under the brand name Glucophage, among others, is the main first-line medication for the treatment of type 2 diabetes, particularly in people who are overweight. It is also used in the treatment of polycystic ovary syndrome. It is sometimes used as an off-label adjunct to lessen the risk of metabolic syndrome in people who take antipsychotics. Metformin is not associated with weight gain and is taken by mouth.

Drugs used in diabetes treat diabetes mellitus by decreasing glucose levels in the blood. With the exception of insulin, most GLP-1 receptor agonists, and pramlintide, all diabetes medications are administered orally and are thus called oral hypoglycemic agents or oral antihyperglycemic agents. There are different classes of hypoglycemic drugs, and selection of the appropriate agent depends on the nature of diabetes, age, and situation of the person, as well as other patient factors.

<i>Galega officinalis</i> Species of leguminous plant

Galega officinalis, commonly known as galega or goat's-rue, is a herbaceous plant in the subfamily Faboideae of the legume family Fabaceae. It is native to parts of northern Africa, western Asia and Europe, but is widely cultivated and naturalised elsewhere. The plant has been extensively cultivated as a forage crop, an ornamental, a bee plant, and as green manure.

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

Pioglitazone, sold under the brand name Actos among others, is an anti-diabetic medication used to treat type 2 diabetes. It may be used with metformin, a sulfonylurea, or insulin. Use is recommended together with exercise and diet. It is not recommended in type 1 diabetes. It is taken by mouth.

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

Sulfonylureas or sulphonylureas are a class of organic compounds used in medicine and agriculture. The functional group consists of a sulfonyl group (-S(=O)2) with its sulphur atom bonded to a nitrogen atom of a ureylene group (N,N-dehydrourea, a dehydrogenated derivative of urea). The side chains R1 and R2 distinguish various sulfonylureas. Sulfonylureas are the most widely used herbicide.

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

Biguanide is the organic compound with the formula HN(C(NH)NH2)2. It is a colorless solid that dissolves in water to give highly basic solution. These solutions slowly hydrolyse to ammonia and urea.

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

Vildagliptin, sold under the brand name Galvus and others, is an oral anti-hyperglycemic agent of the dipeptidyl peptidase-4 (DPP-4) inhibitor class of drugs. Vildagliptin inhibits the inactivation of GLP-1 and GIP by DPP-4, allowing GLP-1 and GIP to potentiate the secretion of insulin in the beta cells and suppress glucagon release by the alpha cells of the islets of Langerhans in the pancreas.

<span class="mw-page-title-main">Dipeptidyl peptidase-4 inhibitor</span> Enzyme blocker and diabetes treatment drug

Inhibitors of dipeptidyl peptidase 4 are a class of oral hypoglycemics that block the enzyme dipeptidyl peptidase-4 (DPP-4). They can be used to treat diabetes mellitus type 2.

<span class="mw-page-title-main">Sitagliptin</span> Diabetes medication

Sitagliptin, sold under the brand name Januvia among others, is an anti-diabetic medication used to treat type 2 diabetes. In the United Kingdom it is listed as less preferred than metformin or a sulfonylurea. It is taken by mouth. It is also available in the fixed-dose combination medication sitagliptin/metformin.

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

Saxagliptin, sold under the brand name Onglyza, is an oral hypoglycemic of the dipeptidyl peptidase-4 (DPP-4) inhibitor class. Early development was solely by Bristol-Myers Squibb; in 2007 AstraZeneca joined with Bristol-Myers Squibb to co-develop the final compound and collaborate on the marketing of the drug.

<span class="mw-page-title-main">Dapagliflozin</span> Diabetes medication

Dapagliflozin, sold under the brand names Farxiga (US) and Forxiga (EU) among others, is a medication used to treat type 2 diabetes. It is also used to treat adults with heart failure and chronic kidney disease. It reversibly inhibits sodium-glucose co-transporter 2 (SGLT-2) in the renal proximal convoluted tubule to reduce glucose reabsorption and increase urinary glucose excretion.

<i>N</i>-Nitrosodimethylamine Chemical compound

N-Nitrosodimethylamine (NDMA), also known as dimethylnitrosamine (DMN), is an organic compound with the formula (CH3)2NNO. It is one of the simplest members of a large class of nitrosamines. It is a volatile yellow oil. NDMA has attracted wide attention as being highly hepatotoxic and a known carcinogen in laboratory animals.

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

Remogliflozin etabonate (INN/USAN) is a drug of the gliflozin class for the treatment of non-alcoholic steatohepatitis ("NASH") and type 2 diabetes. Remogliflozin was discovered by the Japanese company Kissei Pharmaceutical and is currently being developed by BHV Pharma, a wholly owned subsidiary of North Carolina, US-based Avolynt, and Glenmark Pharmaceuticals through a collaboration with BHV. In 2002, GlaxoSmithKline (GSK) received a license to use it. From 2002 to 2009, GSK carried out a significant clinical development program for the treatment of type-2 diabetes mellitus in various nations across the world and obesity in the UK. Remogliflozin etabonate's pharmacokinetics, pharmacodynamics, and clinical dose regimens were characterized in 18 Phase I and 2 Phase II investigations. Due to financial concerns, GSK stopped working on remogliflozin and sergliflozin, two further SGLT2 inhibitors that were licensed to the company, in 2009. Remogliflozin was commercially launched first in India by Glenmark in May 2019.

Synthalin was an oral anti-diabetic drug. Discovered in 1926 it was marketed in Europe by Schering AG of Berlin as a synthetic drug with insulin-like properties that could be taken orally. However, it was toxic to the liver and kidney and was withdrawn from the market in the early 1940s.

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

Trelagliptin is a pharmaceutical drug used for the treatment of type 2 diabetes.

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

Gosogliptin is a drug for the treatment of type II diabetes. It is in the class of dipeptidyl peptidase-4 (DPP-4) inhibitors. It was discovered and developed through Phase 1 and Phase 2 by Pfizer. The crystal structure of DPP-4 in complex with gosogliptin is available. Its metabolism, excretion and pharmacokinetics in rat, dog and human have been described. A cost efficient route has been published. Other studies including Phase 3 studies were conducted in Russia. It is approved for use in Russia.

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

Ertugliflozin, sold under the brand name Steglatro, is a medication for the treatment of type 2 diabetes.

References

  1. Oldham, Michelle; Ransom, Corey V.; Ralphs, Michael H.; Gardner, Dale R. (2011). "Galegine Content in Goatsrue (Galega officinalis) Varies by Plant Part and Phenological Growth Stage". Weed Science. 59 (3): 349–352. doi:10.1614/WS-D-10-00169.1.
  2. Huxtable, C. R.; Dorling, P. R.; Colegate, S. M. (1993). "Identification of galegine, an isoprenyl guanidine, as the toxic principle of Schoenus asperocarpus (poison sedge)". Australian Veterinary Journal. 70 (5): 169–71. doi:10.1111/j.1751-0813.1993.tb06120.x. PMID   8343085.
  3. 1 2 Bailey, CJ; Day, C. (2004). "Metformin: Its botanical background". Practical Diabetes International. 21 (3): 115–117. doi:10.1002/pdi.606.