Glimepiride

Glimepiride
Clinical data
Trade names	Amaryl, others
AHFS/Drugs.com	Monograph
MedlinePlus	a696016
License data	US DailyMed: Glimepiride;
Pregnancy; category	AU: C; ;
Routes of; administration	By mouth
ATC code	A10BB12 (WHO) ;
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)
Onset of action	2–3 hours
Elimination half-life	5–8 hours
Duration of action	24 hours
Excretion	Urine (~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	93479-97-1 ;
PubChem CID	3476;
IUPHAR/BPS	6820;
DrugBank	DB00222 ;
ChemSpider	16740595 ;
UNII	6KY687524K;
KEGG	D00593 ;
ChEBI	CHEBI:5383 ;
ChEMBL	ChEMBL1481 ;
CompTox Dashboard (EPA)	DTXSID20861130 DTXSID5040675, DTXSID20861130 ;
ECHA InfoCard	100.170.771
Chemical and physical data
Formula	C24H34N4O5S
Molar mass	490.62 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	207 °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- ; Key:WIGIZIANZCJQQY-RUCARUNLSA-N ;
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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]

^ ^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.
^ ^a ^b British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 693. ISBN 9780857113382.
^ "Glimepiride Pregnancy and Breastfeeding Warnings". Drugs.com. Archived from the original on 6 March 2019. 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 & Sons. p. 449. ISBN 9783527607495. Archived from the original on 10 January 2023. Retrieved 7 September 2020.
^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
^ "Glimepiride Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.

[AHFS2019-1] ^ ^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.

[BNF76-2] British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 693. ISBN 9780857113382.

[Preg2019-3] "Glimepiride Pregnancy and Breastfeeding Warnings". Drugs.com. Archived from the original on 6 March 2019. Retrieved 3 March 2019.

[pmid15531188-4] 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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Glimepiride

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