グリメピリド

Glimepiride/ja
Clinical data
Trade names	アマリール, その他
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	完全な肝臓（第1段階からCYP2C9まで）
Onset of action	2–3時間
Elimination half-life	5–8時間
Duration of action	24時間
Excretion	尿中 (~60%), 糞中 (~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 ;
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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グリメピリド（Glimepiride）は、スルホニルウレア薬クラスの抗糖尿病薬であり、主に2型糖尿病の管理に処方される。メトホルミンの安全性と有効性が確立されているため、メトホルミンと比較して第二選択薬とみなされている。グリメピリドは、食事療法や運動療法などの生活習慣の改善と併用することが推奨されている。経口で服用し、3時間以内に効果がピークに達し、約1日間持続する。

Common side effects include headache, nausea, and dizziness. Serious side effects may include low blood sugar. Use during pregnancy and breastfeeding is not recommended. It is classified as a second-generation sulfonylurea.

Glimepiride was patented in 1979 and approved for medical use in 1995. It is available as a generic medication. In 2021, it was the 74th most commonly prescribed medication in the United States, with more than 8 million prescriptions.

Medical uses

Glimepiride is indicated to treat type 2 diabetes; 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.

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.

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. 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.

薬物動態

消化管吸収は完全で、食事による影響はない。有意な吸収は1時間以内に起こり、全身に分布し、99.5％が血漿タンパク質に結合する。代謝は酸化的生体内変換によるもので、肝臓で完全に行われる。まず、医薬品はCYP2C9によってM₁代謝物に代謝される。M₁はグリメピリドの薬理活性の¹⁄₃程度を有するが、これが血糖に対して臨床的に意味のある効果をもたらすかどうかは不明である。M₁は細胞質酵素によってさらにM₂代謝物に代謝される。M₂は薬理学的に不活性である。尿中への排泄率は約65％で、残りは糞便中に排泄される。