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Wikipedia

Glimepiride

December 14, 2023

Glimepiride is an antidiabetic medication within the sulfonylurea class, primarily prescribed for the management of type 2 diabetes.[1][2] It is regarded as a second-line option compared to metformin, due to metformin's well-established safety and efficacy.[1] Use of glimepiride is recommended in conjunction with lifestyle modifications such as diet and exercise.[1] It is taken by mouth,[1] reaching a peak effect within three hours and lasting for about a day.[1]

Glimepiride
Clinical data
Trade namesAmaryl, others
AHFS/Drugs.comMonograph
MedlinePlusa696016
License data
Pregnancy
category
  • AU: C
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability100%
Protein binding>99.5%
MetabolismComplete Liver (1st stage through CYP2C9)
Onset of action2–3 hours
Elimination half-life5–8 hours
Duration of action24 hours
ExcretionUrine (~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
  • 93479-97-1 Y
PubChem CID
  • 3476
IUPHAR/BPS
  • 6820
DrugBank
  • DB00222 N
ChemSpider
  • 16740595 Y
UNII
  • 6KY687524K
KEGG
  • D00593 Y
ChEBI
  • CHEBI:5383 N
ChEMBL
  • ChEMBL1481 Y
CompTox Dashboard (EPA)
  • DTXSID5040675
ECHA InfoCard100.170.771
Chemical and physical data
FormulaC24H34N4O5S
Molar mass490.62 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point207 °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- Y
  • Key:WIGIZIANZCJQQY-RUCARUNLSA-N Y
 NY (what is this?)  (verify)

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 predominantly 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 2020, it was the 87th most commonly prescribed medication in the United States, with more than 8 million prescriptions.[6][7]

Medical uses edit

 
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 edit

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

Adverse effects edit

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 edit

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 edit

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 edit

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.

References edit

  1. ^ a b c d e f g h "Glimepiride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
  2. ^ a b 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 J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 449. ISBN 9783527607495.
  6. ^ "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
  7. ^ "Glimepiride - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.
  8. ^ a b "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.

External links edit

  • "Glimepiride". Drug Information Portal. U.S. National Library of Medicine.

December 14, 2023
glimepiride, antidiabetic, medication, within, sulfonylurea, class, primarily, prescribed, management, type, diabetes, regarded, second, line, option, compared, metformin, metformin, well, established, safety, efficacy, glimepiride, recommended, conjunction, w. Glimepiride is an antidiabetic medication within the sulfonylurea class primarily prescribed for the management of type 2 diabetes 1 2 It is regarded as a second line option compared to metformin due to metformin s well established safety and efficacy 1 Use of glimepiride is recommended in conjunction with lifestyle modifications such as diet and exercise 1 It is taken by mouth 1 reaching a peak effect within three hours and lasting for about a day 1 GlimepirideClinical dataTrade namesAmaryl othersAHFS Drugs comMonographMedlinePlusa696016License dataEU EMA by INN US DailyMed GlimepiridePregnancycategoryAU CRoutes ofadministrationBy mouthATC codeA10BB12 WHO Legal statusLegal statusAU S4 Prescription only US only In general Prescription only Pharmacokinetic dataBioavailability100 Protein binding gt 99 5 MetabolismComplete Liver 1st stage through CYP2C9 Onset of action2 3 hoursElimination half life5 8 hoursDuration of action24 hoursExcretionUrine 60 feces 40 IdentifiersIUPAC name 3 Ethyl 4 methyl N 2 4 trans 4 methylcyclohexyl carbamoyl sulfamoyl phenyl ethyl 2 oxo 2 5 dihydro 1H pyrrole 1 carboxamideCAS Number93479 97 1 YPubChem CID3476IUPHAR BPS6820DrugBankDB00222 NChemSpider16740595 YUNII6KY687524KKEGGD00593 YChEBICHEBI 5383 NChEMBLChEMBL1481 YCompTox Dashboard EPA DTXSID5040675ECHA InfoCard100 170 771Chemical and physical dataFormulaC 24H 34N 4O 5SMolar mass490 62 g mol 13D model JSmol Interactive imageMelting point207 C 405 F SMILES O C3C CC C C CN3C O NCCc1ccc cc1 S O O NC O N C H 2CC C H C CC2InChI 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 YKey WIGIZIANZCJQQY RUCARUNLSA N Y N Y what is this verify 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 predominantly 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 2020 it was the 87th most commonly prescribed medication in the United States with more than 8 million prescriptions 6 7 Contents 1 Medical uses 2 Contraindications 3 Adverse effects 4 Interactions 5 Mechanism of action 6 Pharmacokinetics 7 References 8 External linksMedical uses edit nbsp Two generic oral tablets of glimepiride 2 mg eachGlimepiride 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 editIts use is contraindicated in patients with hypersensitivity to glimepiride or other sulfonylureas Adverse effects editSide 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 editNonsteroidal 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 editLike 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 editGastrointestinal 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 References edit a b c d e f g h Glimepiride Monograph for Professionals Drugs com American Society of Health System Pharmacists Retrieved 3 March 2019 a b British national formulary BNF 76 76 ed Pharmaceutical Press 2018 p 693 ISBN 9780857113382 Glimepiride Pregnancy and Breastfeeding Warnings Drugs com Retrieved 3 March 2019 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 Fischer J Ganellin CR 2006 Analogue based Drug Discovery John Wiley amp Sons p 449 ISBN 9783527607495 The Top 300 of 2020 ClinCalc Retrieved 7 October 2022 Glimepiride Drug Usage Statistics ClinCalc Retrieved 7 October 2022 a b Glimepiride MedlinePlus Drug Information nih gov 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 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 amp Gilman s The Pharmacological Basis of Therapeutics New York McGraw Hill p 1636 ISBN 0 07 142280 3 External links edit Glimepiride Drug Information Portal U S National Library of Medicine Portal nbsp Medicine Retrieved from https en wikipedia org w index php title Glimepiride amp oldid 1168800926, wikipedia, wiki, book, books, library,

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