Glimepiride

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
IUPAC name
  • 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 InfoCard100.170.771
Chemical and physical data
FormulaC24H34N4O5S
Molar mass490.62 g·mol−1
3D model (JSmol)
Melting 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)CC2
InChI
  • 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)

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]

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 2022, it was the 64th most commonly prescribed medication in the United States, with more than 10 million prescriptions.[6][7]

  1. ^ a b c d e f g h "Glimepiride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 6 March 2019. 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. Archived from the original on 6 March 2019. 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. Archived from the original on 10 January 2023. Retrieved 7 September 2020.
  6. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  7. ^ "Glimepiride Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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