Glimepiride

Last updated
Glimepiride
Glimepiride.svg
Clinical data
Trade names Amaryl, others
AHFS/Drugs.com Monograph
MedlinePlus a696016
License data
Pregnancy
category
  • AU:C
Routes of
administration 		By mouth (tablets)
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability 100%
Protein binding >99.5%
Metabolism Complete Liver (1st stage through CYP2C9)
Elimination half-life 5–8 hours
Excretion Urine (~60%), feces (~40%)
Identifiers
  • 3-Ethyl-4-methyl-N-[2-(4-{[(trans-4-methylcyclohexyl)carbamoyl]sulfamoyl}phenyl)ethyl]-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.170.771 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C24H34N4O5S
Molar mass 490.62 g·mol−1
3D model (JSmol)
Melting point 207 °C (405 °F)
  • O=C3C(/CC)=C(/C)CN3C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)N[C@H]2CC[C@H](C)CC2
  • InChI=1S/C24H34N4O5S/c1-4-21-17(3)15-28(22(21)29)24(31)25-14-13-18-7-11-20(12-8-18)34(32,33)27-23(30)26-19-9-5-16(2)6-10-19/h7-8,11-12,16,19H,4-6,9-10,13-15H2,1-3H3,(H,25,31)(H2,26,27,30)/t16-,19- Yes check.svgY
  • Key:WIGIZIANZCJQQY-RUCARUNLSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Glimepiride, is an anti-diabetic medication used to treat type 2 diabetes. [1] [2] It is less preferred than metformin. [1] Use is recommended together with diet and exercise. [1] It is taken by mouth. [1] Glimepiride takes up to three hours for maximum effect and lasts for about a day. [1]

Contents

Common side effects include headache, nausea, and dizziness. [1] Serious side effects may include low blood sugar. [1] Use during pregnancy and breastfeeding is not recommended. [3] It works mainly by increasing the amount of insulin released from the pancreas. [1] It is classified as a second-generation sulfonylurea. [4]

Glimepiride was patented in 1979 and approved for medical use in 1995. [5] It is available as a generic medication. [2] In 2019, it was the 62nd most commonly prescribed medication in the United States, with more than 11 million prescriptions. [6] [7]

Medical uses

Two generic oral tablets of glimepiride, 2 mg each Glimepiride 2 MG Oral Tablet.jpg
Two generic oral tablets of glimepiride, 2 mg each

Glimepiride is indicated to treat type 2 diabetes mellitus; its mode of action is to increase insulin secretion by the pancreas. However it requires adequate insulin synthesis as prerequisite to treat appropriately. It is not used for type 1 diabetes because in type 1 diabetes the pancreas is not able to produce insulin. [8]

Contraindications

Its use is contraindicated in patients with hypersensitivity to glimepiride or other sulfonylureas.

Adverse effects

Side effects from taking glimepiride include gastrointestinal tract (GI) disturbances, occasional allergic reactions, and rarely blood production disorders including thrombocytopenia, leukopenia, and hemolytic anemia. In the initial weeks of treatment, the risk of hypoglycemia may be increased. Alcohol consumption and exposure to sunlight should be restricted because they can worsen side effects. [8]

Interactions

Nonsteroidal anti-inflammatory drugs (such as salicylates), sulfonamides, chloramphenicol, coumadin and probenecid may potentiate the hypoglycemic action of glimepiride. Thiazides, other diuretics, phothiazides, thyroid products, oral contraceptives, and phenytoin tend to produce hyperglycemia.

Mechanism of action

Like all sulfonylureas, glimepiride acts as an insulin secretagogue. [9] It lowers blood sugar by stimulating the release of insulin by pancreatic beta cells and by inducing increased activity of intracellular insulin receptors.

Not all secondary sulfonylureas have the same risk of hypoglycemia. Glibenclamide (glyburide) is associated with an incidence of hypoglycemia of up to 20–30%, compared to as low as 2% to 4% with glimepiride. Glibenclamide also interferes with the normal homeostatic suppression of insulin secretion in reaction to hypoglycemia, whereas glimepiride does not. Also, glibenclamide diminishes glucagon secretion in reaction to hypoglycemia, whereas glimepiride does not. [10]

Pharmacokinetics

Gastrointestinal absorption is complete, with no interference from meals. Significant absorption can occur within one hour, and distribution is throughout the body, 99.5% bound to plasma protein. Metabolism is by oxidative biotransformation, it is hepatic and complete. First, the medication is metabolized to M1 metabolite by CYP2C9. M1 possesses about 1⁄3 of pharmacological activity of glimepiride, yet it is unknown if this results in clinically meaningful effect on blood glucose. M1 is further metabolized to M2 metabolite by cytosolic enzymes. M2 is pharmacologically inactive. Excretion in the urine is about 65%, and the remainder is excreted in the feces.

Related Research Articles

Hypoglycemia Not enough blood sugar, usually because of temporary overcorrection of diabetes

Hypoglycemia, also called low blood sugar, is a fall in blood sugar to levels below normal, typically below 70 mg/dL (3.9 mmol/L). Whipple's triad is used to properly identify hypoglycemic episodes. It is defined as blood glucose below 70 mg/dL (3.9 mmol/L), symptoms associated with hypoglycemia, and resolution of symptoms when blood sugar returns to normal. Hypoglycemia may result in headache, tiredness, clumsiness, trouble talking, confusion, fast heart rate, sweating, shakiness, nervousness, hunger, loss of consciousness, seizures, or death. Symptoms typically come on quickly.

Glipizide Chemical compound

Glipizide, sold under the brand name Glucotrol among others, is an anti-diabetic medication of the sulfonylurea class used to treat type 2 diabetes. It is used together with a diabetic diet and exercise. It is not indicated for use by itself in type 1 diabetes. It is taken by mouth. Effects generally begin within half an hour and can last for up to a day.

Drugs used in diabetes treat diabetes mellitus by altering the glucose level in the blood. With the exceptions of insulin, most GLP receptor agonists, and pramlintide, all are administered orally and are thus also called oral hypoglycemic agents or oral antihyperglycemic agents. There are different classes of anti-diabetic drugs, and their selection depends on the nature of the diabetes, age and situation of the person, as well as other factors.

Sulfonylureas are a class of organic compounds used in medicine and agriculture, for example as antidiabetic drugs widely used in the management of diabetes mellitus type 2. They act by increasing insulin release from the beta cells in the pancreas. A number of sulfonylureas are also used as herbicides, because they can interfere with plant biosynthesis of certain amino acids. Sulfonylureas are also used experimentally to inhibit interleukin 1 beta release from the NALP3 inflammasome.

Hyperinsulinemic hypoglycemia describes the condition and effects of low blood glucose caused by excessive insulin. Hypoglycemia due to excess insulin is the most common type of serious hypoglycemia. It can be due to endogenous or injected insulin.

Chlorpropamide Chemical compound

Chlorpropamide is a drug in the sulfonylurea class used to treat diabetes mellitus type 2. It is a long-acting first-generation sulfonylurea.

Diazoxide Medication used to treat low blood sugar and high blood pressure

Diazoxide, sold under the brand name Proglycem and Balila(India), is a medication used to treat low blood sugar due to a number of specific causes. This includes islet cell tumors that cannot be removed and leucine sensitivity. It can also be used in refractory cases of sulfonylurea toxicity. It is generally taken by mouth.

Diabetic hypoglycemia Medical condition

Diabetic hypoglycemia is a low blood glucose level occurring in a person with diabetes mellitus. It is one of the most common types of hypoglycemia seen in emergency departments and hospitals. According to the National Electronic Injury Surveillance System-All Injury Program (NEISS-AIP), and based on a sample examined between 2004 and 2005, an estimated 55,819 cases involved insulin, and severe hypoglycemia is likely the single most common event.

Tolbutamide

Tolbutamide is a first-generation potassium channel blocker, sulfonylurea oral hypoglycemic medication. This drug may be used in the management of type 2 diabetes if diet alone is not effective. Tolbutamide stimulates the secretion of insulin by the pancreas.

Glibenclamide Chemical compound

Glibenclamide, also known as glyburide, is a medication used to treat diabetes mellitus type 2. It is recommended that it be taken together with diet and exercise. It may be used with other antidiabetic medication. It is not recommended for use by itself in diabetes mellitus type 1. It is taken by mouth.

Exenatide

Exenatide, sold under the brand name Byetta and Bydureon among others, is a medication used to treat diabetes mellitus type 2. It is used together with diet, exercise, and potentially other antidiabetic medication. It is a treatment option after metformin and sulfonylureas. It is given by injection under the skin within an hour before the first and last meal of the day. A once-weekly injection version is also available.

Repaglinide

Repaglinide is an antidiabetic drug in the class of medications known as meglitinides, and was invented in 1983. Repaglinide is an oral medication used in addition to diet and exercise for blood sugar control in type 2 diabetes mellitus. The mechanism of action of repaglinide involves promoting insulin release from β-islet cells of the pancreas; like other antidiabetic drugs, a main side effect concern is hypoglycemia. It is sold by Novo Nordisk under the name of Prandin in the United States, GlucoNorm in Canada, Surepost in Japan, Repaglinide in Egypt by EIPICO, and NovoNorm elsewhere. In Japan it is produced by Dainippon Sumitomo Pharma.

Gliclazide Chemical compound

Gliclazide, sold under the brand name Diamicron among others, is a sulfonylurea type of anti-diabetic medication, used to treat type 2 diabetes. It is used when dietary changes, exercise, and weight loss are not enough. It is taken by mouth.

Sitagliptin 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.

Gliquidone Chemical compound

Gliquidone is an anti-diabetic medication in the sulfonylurea class. It is classified as a second-generation sulfonylurea. It is used in the treatment of diabetes mellitus type 2. It is marketed by the pharmaceutical company Boehringer Ingelheim (Germany).

Linagliptin

Linagliptin, sold under the brand name Trajenta among others, is a medication used to treat diabetes mellitus type 2. It is generally less preferred than metformin and sulfonylureas as an initial treatment. It is used together with exercise and diet. It is not recommended in type 1 diabetes. It is taken by mouth.

Sitagliptin/metformin, sold under the brand name Janumet among others, is a fixed-dose combination anti-diabetic medication used to treat type 2 diabetes. It may be used in those whose blood sugar is not controlled with metformin and a sulfonylurea. It is taken by mouth.

Dulaglutide Diabetes medication

Dulaglutide, sold under the brand name Trulicity among others, is a medication used for the treatment of type 2 diabetes in combination with diet and exercise. It is also approved in the United States for the reduction of major adverse cardiovascular events in adults with type 2 diabetes who have established cardiovascular disease or multiple cardiovascular risk factors. It is a once-weekly injection.

Pioglitazone/glimepiride, sold under the brand name Duetact among others, is a fixed-dose combination anti-diabetic medication for the treatment of type 2 diabetes. It contains the thiazolidinedione pioglitazone and the sulfonylurea glimepiride. It is taken by mouth.

References

  1. 1 2 3 4 5 6 7 8 "Glimepiride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
  2. 1 2 British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 693. ISBN   9780857113382.
  3. ↑ "Glimepiride Pregnancy and Breastfeeding Warnings". Drugs.com. Retrieved 3 March 2019.
  4. ↑ Davis SN (2004). "The role of glimepiride in the effective management of Type 2 diabetes". J. Diabetes Complicat. 18 (6): 367–76. doi:10.1016/j.jdiacomp.2004.07.001. PMID   15531188.
  5. ↑ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 449. ISBN   9783527607495.
  6. ↑ "The Top 300 of 2019". ClinCalc. Retrieved 16 October 2021.
  7. ↑ "Glimepiride - Drug Usage Statistics". ClinCalc. Retrieved 16 October 2021.
  8. 1 2 "Glimepiride: MedlinePlus Drug Information". nih.gov.
  9. ↑ Nissen SE, Nicholls SJ, Wolski K, et al. (April 2008). "Comparison of pioglitazone vs glimepiride on progression of coronary atherosclerosis in patients with type 2 diabetes: the PERISCOPE randomized controlled trial". JAMA. 299 (13): 1561–73. doi: 10.1001/jama.299.13.1561 . PMID   18378631.
  10. ↑ Davis, Stephen N. (2005). "60. Insulin, oral hypoglycemic agents, and the pharmacology of the endocrine pancreas". In Brunton, Laurence L.; Lazo, John S.; Parker, Keith L. (eds.). Goodman & Gilman's The Pharmacological Basis of Therapeutics . New York: McGraw-Hill. p. 1636. ISBN   0-07-142280-3.
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