同: glibenclamide

WordNet

an oral antidiabetic drug (trade names DiaBeta and Micronase) that stimulates the release of insulin from the pancreas (同)DiaBeta, Micronase

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/01/22 17:37:43」(JST)

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Glibenclamide (AAN, BAN, INN), also known as glyburide (USAN), is an antidiabetic drug in a class of medications known as sulfonylureas, closely related to sulfa drugs. It was developed in 1966 in a cooperative study between Boehringer Mannheim (now part of Roche) and Hoechst (now part of Sanofi-Aventis).^[1]

It is sold in doses of 1.25, 2.5, and 5 mg, under the trade names Diabeta, Glynase, and Micronase in the United States and Daonil, Semi-Daonil, and Euglucon in the United Kingdom, and Delmide, Glybovin in India. It is also sold in combination with metformin under the trade names Glucovance, Benimet, and Glibomet, as well as Glucored and Glucored Forte (by Sun Pharmaceutical) in Russia, Belarus and other countries of the CIS.

Medical uses

It is used in the treatment of type 2 diabetes. As of 2011^[update], it is one of only two oral antidiabetics in the World Health Organization Model List of Essential Medicines (the other being metformin).^[2] As of 2003, in the United States, it was the most popular sulfonylurea.^[3]

Side effects and contraindications

This drug is a major cause of drug-induced hypoglycemia. The risk is increased against other sulfonylureas.^[4] Cholestatic jaundice is noted.

Glibenclamide may be contraindicated in those with G6PD deficiency, as it may cause acute haemolysis.^[5]

Recently published data suggest glibenclamide is associated with significantly higher annual mortality when combined with metformin than other insulin-secreting medications, after correcting for other potentially confounding patient characteristics. The safety of this combination has been questioned.^[6] Glibenclamide causes cholestasis as the major side effect.

Mechanism of action

The drug works by binding to and activating the ATP-sensitive potassium channels (K_ATP) inhibitory regulatory subunit sulfonylurea receptor 1 (SUR1) ^[7] in pancreatic beta cells. This inhibition causes cell membrane depolarization, opening voltage-dependent calcium channels. This results in an increase in intracellular calcium in the beta cell and subsequent stimulation of insulin release.

After a cerebral ischemic insult, the blood–brain barrier is broken and glibenclamide can reach the central nervous system. Glibenclamide has been shown to bind more efficiently to the ischemic hemisphere.^[8] Moreover, under ischemic conditions SUR1, the regulatory subunit of the K_ATP- and the NC_Ca-ATP-channels, is expressed in neurons, astrocytes, oligodendrocytes, endothelial cells^[9] and by reactive microglia.^[8]

Analogs

Additional glibenclamide structural analogs have been prepared by Ahmadi et al.^[10]

Research

Glibenclamide improves outcome in animal stroke models by preventing brain swelling^[11] and enhancing neuroprotection.^[7] A retrospective study showed, in type 2 diabetic patients already taking glyburide, NIH stroke scale scores on were improved on discharge compared to diabetic patients not taking glyburide.^[12]

References

^ Marble A (1971). "Glibenclamide, a new sulphonylurea: whither oral hypoglycaemic agents?". Drugs 1 (2): 109–15. doi:10.2165/00003495-197101020-00001. PMID 4999930.
^ WHO Expert Committee (March 2011). "The selection and use of essential medicines". World Health Organ Tech Rep Ser (965): i–xiv, 1–249. PMID 22891532.
^ Riddle MC (February 2003). "Editorial: sulfonylureas differ in effects on ischemic preconditioning--is it time to retire glyburide?". J. Clin. Endocrinol. Metab. 88 (2): 528–30. doi:10.1210/jc.2002-021971. PMID 12574174.
^ Gangji, A. S.; Cukierman, T.; Gerstein, H. C.; Goldsmith, C. H.; Clase, C. M. (1 February 2007). "A Systematic Review and Meta-Analysis of Hypoglycemia and Cardiovascular Events: A comparison of glyburide with other secretagogues and with insulin". Diabetes Care 30 (2): 389–394. doi:10.2337/dc06-1789.
^ Meloni G, Meloni T (January 1996). "Glyburide-induced acute haemolysis in a G6PD-deficient patient with NIDDM". Br. J. Haematol. 92 (1): 159–60. doi:10.1046/j.1365-2141.1996.275810.x. PMID 8562390.
^ Monami M, Luzzi C, Lamanna C, Chiasserini V, Addante F, Desideri CM, Masotti G, Marchionni N, Mannucci E (2006). "Three-year mortality in diabetic patients treated with different combinations of insulin secretagogues and metformin". Diabetes Metab Res Rev 22 (6): 477–82. doi:10.1002/dmrr.642. PMID 16634115.
^ ^a ^b Serrano-Martín X, Payares G, Mendoza-León A (December 2006). "Glibenclamide, a blocker of K+(ATP) channels, shows antileishmanial activity in experimental murine cutaneous leishmaniasis". Antimicrob. Agents Chemother. 50 (12): 4214–6. doi:10.1128/AAC.00617-06. PMC 1693980. PMID 17015627.
^ ^a ^b Ortega FJ, Gimeno-Bayon J, Espinosa-Parrilla JF, Carrasco JL, Batlle M, Pugliese M, Mahy N, Rodríguez MJ (May 2012). "ATP-dependent potassium channel blockade strengthens microglial neuroprotection after hypoxia-ischemia in rats". Exp. Neurol. 235 (1): 282–96. doi:10.1016/j.expneurol.2012.02.010. PMID 22387180.
^ Simard JM, Woo SK, Schwartzbauer GT, Gerzanich V (September 2012). "Sulfonylurea receptor 1 in central nervous system injury: a focused review". J. Cereb. Blood Flow Metab. 32 (9): 1699–717. doi:10.1038/jcbfm.2012.91. PMC 3434627. PMID 22714048.
^ Ahmadi, A; Khalili, M; Khatami, K; Farsadrooh, M; Nahri-Niknafs, B (2014). "Synthesis and investigating hypoglycemic and hypolipidemic activities of some glibenclamide analogues in rats". Mini reviews in medicinal chemistry 14 (2): 208–13. PMID 24387708. edit
^ Simard JM, Chen M, Tarasov KV, Bhatta S, Ivanova S, Melnitchenko L, Tsymbalyuk N, West GA, Gerzanich V (April 2006). "Newly expressed SUR1-regulated NC(Ca-ATP) channel mediates cerebral edema after ischemic stroke". Nat. Med. 12 (4): 433–40. doi:10.1038/nm1390. PMC 2740734. PMID 16550187.
^ Kunte H, Schmidt S, Eliasziw M, del Zoppo GJ, Simard JM, Masuhr F, Weih M, Dirnagl U (September 2007). "Sulfonylureas improve outcome in patients with type 2 diabetes and acute ischemic stroke". Stroke 38 (9): 2526–30. doi:10.1161/STROKEAHA.107.482216. PMC 2742413. PMID 17673715.

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1. 妊娠糖尿病の内科的マネージメントおよびフォローアップ medical management and follow up of gestational diabetes mellitus
2. 糖尿病の治療におけるスルホニル尿素およびメグリチニド sulfonylureas and meglitinides in the treatment of diabetes mellitus
3. スルホニル尿素剤中毒 sulfonylurea agent poisoning
4. 2型糖尿病における血糖の初期マネージメント initial management of blood glucose in type 2 diabetes mellitus
5. 高齢患者における2型糖尿病の治療 treatment of type 2 diabetes mellitus in the elderly patient

English Journal

Pharmacological Management of Gestational Diabetes Mellitus.

Bergel R1,2, Hadar E1,2, Toledano Y1,2, Hod M3,4.
Current diabetes reports.Curr Diab Rep.2016 Nov;16(11):118.
Gestational diabetes mellitus (GDM) is one of the most common morbidities complicating pregnancy, with short- and long-term consequences to the mothers, fetuses, and newborns. Management and treatment are aimed to achieve best possible glycemic control, while avoiding hypoglycemia and ensuring mater
PMID 27752931

Safety and efficacy of intravenous glyburide on brain swelling after large hemispheric infarction (GAMES-RP): a randomised, double-blind, placebo-controlled phase 2 trial.

Sheth KN1, Elm JJ2, Molyneaux BJ3, Hinson H4, Beslow LA5, Sze GK6, Ostwaldt AC7, Del Zoppo GJ8, Simard JM9, Jacobson S10, Kimberly WT11.
The Lancet. Neurology.Lancet Neurol.2016 Oct;15(11):1160-9. doi: 10.1016/S1474-4422(16)30196-X. Epub 2016 Aug 23.
BACKGROUND: Preclinical models of stroke have shown that intravenous glyburide reduces brain swelling and improves survival. We assessed whether intravenous glyburide (RP-1127; glibenclamide) would safely reduce brain swelling, decrease the need for decompressive craniectomy, and improve clinical ou
PMID 27567243

Glyburide for cerebral oedema: could an old dog have a new trick?

Hankey GJ1.
The Lancet. Neurology.Lancet Neurol.2016 Oct;15(11):1109-11. doi: 10.1016/S1474-4422(16)30198-3. Epub 2016 Aug 23.
PMID 27567242

Japanese Journal

Validation of a sensitive LC-MS assay for quantification of glyburide and its metabolite 4-transhydroxy glyburide in plasma and urine : An OPRU Network study

NARAHARISETTI Suresh Babu,KIRBY Brian J.,HEBERT Mary F.,EASTERLING Thomas R.,UNADKAT Jashvant D.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 860(1), 34-41, 2007-12-01
NAID 10027466737

セボフルランはKATPチャンネルを介して犬の気絶心筋の収縮能を改善する

関口昌人,赤澤訓,中井川泰,井上荘一郎,佐藤正章,萩原秀文,池野重雄,石井良介,瀬尾憲正
自治医科大学紀要 29, 137-146, 2006-12-01
本研究の目的は,犬の気絶心筋において,吸入麻酔薬セボフルランによって誘導される心筋保護作用が,KATPチャンネルを介して行われることを調べることにある。気絶心筋は,冠動脈左前下行枝を5回,5分間毎の結紮と解除を繰り返すことによって作成した。22頭の雑種成犬を,コントロール群(n=7),セボフルラン群(n=7),グリブライド(KATPチャンネルブロッカー)処理群(n=8)の3群に分けた。血行動態,代 …
NAID 110006457560

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リンク元

「グリブリド」

Glibenclamide
Systematic (IUPAC) name
	5-chloro-N-(4-[N-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-2-methoxybenzamide
Clinical data
Trade names	Diabeta, Glynase, Micronase Daonil, Semi-Daonil, Euglucon, Delmide, Glybovin Gilemal
AHFS/Drugs.com	International Drug Names
MedlinePlus	a684058
Licence data	US FDA:link
Pregnancy; category	AU: C; US: B;
Legal status	UK: POM; US: ℞-only;
Routes	Oral
Pharmacokinetic data
Protein binding	Extensive
Metabolism	Hepatic hydroxylation (CYP2C9-mediated)
Half-life	10 hours
Excretion	Renal and biliary
Identifiers
CAS number	10238-21-8
ATC code	A10BB01
PubChem	CID 3488
IUPHAR ligand	2414
DrugBank	DB01016
ChemSpider	3368
UNII	SX6K58TVWC
KEGG	D00336
ChEBI	CHEBI:5441
ChEMBL	CHEMBL472
Chemical data
Formula	C23H28ClN3O5S
Molecular mass	494.004 g/mol
	SMILES O=C(NC1CCCCC1)NS(=O)(=O)c2ccc(cc2)CCNC(=O)c3cc(Cl)ccc3OC;
	InChI InChI=1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29) ; Key:ZNNLBTZKUZBEKO-UHFFFAOYSA-N ;
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　　[★]

英: glyburide
同: グリベンクラミド？、glibenclamide？
関

米国における糖尿病治療薬
スルフォニル尿酸系薬

[pmid4999930-1] Marble A (1971). "Glibenclamide, a new sulphonylurea: whither oral hypoglycaemic agents?". Drugs 1 (2): 109–15. doi:10.2165/00003495-197101020-00001. PMID 4999930.

[pmid22891532-2] WHO Expert Committee (March 2011). "The selection and use of essential medicines". World Health Organ Tech Rep Ser (965): i–xiv, 1–249. PMID 22891532.

[pmid12574174-3] Riddle MC (February 2003). "Editorial: sulfonylureas differ in effects on ischemic preconditioning--is it time to retire glyburide?". J. Clin. Endocrinol. Metab. 88 (2): 528–30. doi:10.1210/jc.2002-021971. PMID 12574174.

[4] Gangji, A. S.; Cukierman, T.; Gerstein, H. C.; Goldsmith, C. H.; Clase, C. M. (1 February 2007). "A Systematic Review and Meta-Analysis of Hypoglycemia and Cardiovascular Events: A comparison of glyburide with other secretagogues and with insulin". Diabetes Care 30 (2): 389–394. doi:10.2337/dc06-1789.

[pmid8562390-5] Meloni G, Meloni T (January 1996). "Glyburide-induced acute haemolysis in a G6PD-deficient patient with NIDDM". Br. J. Haematol. 92 (1): 159–60. doi:10.1046/j.1365-2141.1996.275810.x. PMID 8562390.

[6] Monami M, Luzzi C, Lamanna C, Chiasserini V, Addante F, Desideri CM, Masotti G, Marchionni N, Mannucci E (2006). "Three-year mortality in diabetic patients treated with different combinations of insulin secretagogues and metformin". Diabetes Metab Res Rev 22 (6): 477–82. doi:10.1002/dmrr.642. PMID 16634115.

[pmid17015627-7] Serrano-Martín X, Payares G, Mendoza-León A (December 2006). "Glibenclamide, a blocker of K+(ATP) channels, shows antileishmanial activity in experimental murine cutaneous leishmaniasis". Antimicrob. Agents Chemother. 50 (12): 4214–6. doi:10.1128/AAC.00617-06. PMC 1693980. PMID 17015627.

[pmid22387180-8] Ortega FJ, Gimeno-Bayon J, Espinosa-Parrilla JF, Carrasco JL, Batlle M, Pugliese M, Mahy N, Rodríguez MJ (May 2012). "ATP-dependent potassium channel blockade strengthens microglial neuroprotection after hypoxia-ischemia in rats". Exp. Neurol. 235 (1): 282–96. doi:10.1016/j.expneurol.2012.02.010. PMID 22387180.

[pmid22714048-9] Simard JM, Woo SK, Schwartzbauer GT, Gerzanich V (September 2012). "Sulfonylurea receptor 1 in central nervous system injury: a focused review". J. Cereb. Blood Flow Metab. 32 (9): 1699–717. doi:10.1038/jcbfm.2012.91. PMC 3434627. PMID 22714048.

[10] Ahmadi, A; Khalili, M; Khatami, K; Farsadrooh, M; Nahri-Niknafs, B (2014). "Synthesis and investigating hypoglycemic and hypolipidemic activities of some glibenclamide analogues in rats". Mini reviews in medicinal chemistry 14 (2): 208–13. PMID 24387708. edit

[pmid16550187-11] Simard JM, Chen M, Tarasov KV, Bhatta S, Ivanova S, Melnitchenko L, Tsymbalyuk N, West GA, Gerzanich V (April 2006). "Newly expressed SUR1-regulated NC(Ca-ATP) channel mediates cerebral edema after ischemic stroke". Nat. Med. 12 (4): 433–40. doi:10.1038/nm1390. PMC 2740734. PMID 16550187.

[pmid17673715-12] Kunte H, Schmidt S, Eliasziw M, del Zoppo GJ, Simard JM, Masuhr F, Weih M, Dirnagl U (September 2007). "Sulfonylureas improve outcome in patients with type 2 diabetes and acute ischemic stroke". Stroke 38 (9): 2526–30. doi:10.1161/STROKEAHA.107.482216. PMC 2742413. PMID 17673715.

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glyburide