Glyburide

An orally administered sulfonylurea used to improve glycemic control in patients with type 2 diabetes mellitus. Glyburide binds to the sulfonylurea receptor SUR1 on pancreatic beta-cell ATP-sensitive potassium channels, causing channel closure, membrane depolarization, calcium influx, and insulin secretion. Its glucose-independent stimulation of insulin release can cause significant and prolonged hypoglycemia, particularly in older adults and patients with renal impairment. Other adverse effects include weight gain. Glyburide is also known as glibenclamide

CAS Number: 10238-21-8

Molecular Mass: 494.0 g/mol

Formula: C₂₃H₂₈ClN₃O₅S

Smiles: COc1ccc(Cl)cc1C(=O)NCCc1ccc(S(=O)(=O)NC(=O)NC2CCCCC2)cc1

Synonymes:

Glyburide, Glibenclamide, glyburide, 10238-21-8, Glynase, Euglucon, Semi-daonil, Libanil, Glibenclamida, Glibenclamidum, Calabren, Lederglib, HB 419, Glyburide (micronized), 1-(p-(2-(5-Chloro-2-methoxybenzamido)ethyl)benzenesulfonyl)-3-cyclohexylurea, SX6K58TVWC, 5-Chloro-N-(2-(4-((((cyclohexylamino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-methoxybenzamide, NSC-759618, 5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxybenzamide, U-26,452, 5-chloro-N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-2-methoxybenzamide, U-26452, CHEBI:5441, U-26,45, N-(4-(beta-(2-Methoxy-5-chlorbenzamido)-aethyl)-benzolsulfonyl)-N'-cyclohexyl-harnstoff, HB419, 5-Chloro-N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-2-methoxybenzamide, HB420, HB 420, Gliken, Glynase Prestab, Diabetamide 5, 5-chloro-N-(2-(4-(((cyclohexylcarbamoyl)amino)sulfonyl)phenyl)ethyl)-2-methoxybenzamide, 5-chloro-N-(2-(4-(cyclohexylcarbamoylsulfamoyl)phenyl)ethyl)-2-methoxybenzamide, Diabetamide 2.5, RefChem:5865, A10BB01, 4-(2-(5-Chloro-2-methoxybenzoylamino)ethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide, 233-570-6, Glybenclamide, Diabeta, Micronase, Daonil, Maninil, Glybenzcyclamide, Apo-Glibenclamide, Euglucon 5, Azuglucon, Bastiverit, Benclamin, Betanase, Duraglucon, Euglucan, Euglykon, Glibenil, Glucolon, Orabetic, Prodiabet, Renabetic, Yuglucon, Dibelet, Gilemal, Glibens, Glibil, Glimel, Glimide, Humedia, Suraben, Tiabet, Adiab, Melix, Pira, Med-Glionil, 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide, Glibenclamidum [INN-Latin], C23H28ClN3O5S, Glibenclamida [INN-Spanish], glyburide (glibenclamide), HB-419, MFCD00056625, UR 606, 5-Chloro-N-[2-[4-[[[(cyclohexylamino)carbonyl]-amino]sulfonyl]phenyl]-ethyl]-2-methoxybenzamide, Cirara, 1-((p-(2-(5-Chloro-o-anisamido)ethyl)phenyl)sulfonyl)-3-cyclohexylurea, Neogluconin, Glibenclamide [INN], U 26452, DTXSID0037237, Gewaglucon, Glibenbeta, Glidiabet, Glucobene, Glucohexal, Glucoremed, Hexaglucon, Lisaglucon, Normoglucon, Praeciglucon, Cytagon, Euclamin, Glamide, Glibesyn, Glibetic, Gliboral, Glisulin, Glitisol, Glubate, Glucomid, Glucoven, Glycomin, Miglucan, Debtan, Gliban, Gliben, Glibet, Glicem, Gluben, Glyben, Nadib, Sugril, CHEMBL472, Novo-Glyburide, Glibenclamid AL, Gen-Glybe, Norglicem 5, Betanese 5, N-(4-(2-(5-Chloro-2-methoxybenzamido)ethyl)phenylsulfonyl)-N'-cyclohexylurea, Glibenclamid Fabra, Benzamide, 5-chloro-N-(2-(4-((((cyclohexylamino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-methoxy-, MLS000069721, Glibenclamid Basics, Glibenclamid-Cophar, Glibenclamid Heumann, Semi-Euglucon, Glibenclamid Genericon, 5-Chloro-N-[4-(cyclohexylureidosulfonyl)phenethyl]-2-methoxybenzamide, Hemi-Daonil, Glibenclamid-Ratiopharm, 5-chloro-N-(2-{4-[(cyclohexylcarbamoyl)sulfamoyl]phenyl}ethyl)-2-methoxybenzamide, Urea, 1-(p-(2-(5-chloro-2-methoxybenzamido)ethyl)benzenesulfonyl)-3-cyclohexyl-, Benzamide, 5-chloro-N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-2-methoxy-, Glyburide [USAN], NCGC00015467-11, Abbenclamide, Diabiphage, Glibadone, SMR000058229, Semi-Gliben-Puren N, GBN 5, CAS-10238-21-8, Glibenclamid Riker M., S1716, Urea, 1-((p-(2-(chloro-o-anisamido)ethyl)phenyl)sulfonyl)-3-cyclohexyl-, Micronized glyburide, DTXCID8017237, Glycron, 1-[[p-[2-(5-Chloro-o-anisamido)ethyl]phenyl]sulfonyl]-3-cyclohexylurea, 5-chloro-N-(2-{4-[N-(N-cyclohexylcarbamoyl)sulfamoyl]phenyl}ethyl)-2-methoxybenzamide, 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)-phenethyl)-2-methoxybenzamide, Glyburide (USP), Micronase (TN), 1-{4-[2-(5-chloro-2-methoxybenzamido)ethyl]benzenesulfonyl}-3-cyclohexylurea, 1-{4-[2-(5-chloro-2-methoxybenzamido)ethyl]benzenesulfonyl}-3-cyclohexylurea, Diabeta (TN), Glynase (TN), SR-01000000196, Glyburide [USAN:USP], EINECS 233-570-6, UNII-SX6K58TVWC, BRN 2230085, Glibenclamid, Amglidia, Delmide, Diabetamide, , Glyburide, , Micronase, , Calabren, , Euglucon, , Gilemal, , Glynase, , Libanil, , Daonil, , DiaBeta, , Malix, , 5-chloro-N-(4-[N-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-2-methoxybenzamide, Glibenclamide CRS, GBM, Prestwick_569, RP-1127, Spectrum_000250, Tocris-0911, Glybenzcyclamide, 99%, Glibenclamide, Glyburide, Glyburide, Glibenclamide, Opera_ID_801, GLYBURIDE [MI], Glibenclamide (Standard), Prestwick0_000316, Prestwick1_000316, Prestwick2_000316, Prestwick3_000316, Spectrum2_001816, Spectrum3_001327, Spectrum4_001199, Spectrum5_001631, GLYBURIDE [VANDF], Lopac-G-0639, Probes1_000431, Probes2_000378, UPCMLD-DP006, G 0639, GLIBENCLAMIDE [JAN], GLYBURIDE [USP-RS], GLYBURIDE [WHO-IP], Glibenclamide (JP18/INN), CBiol_001790, Lopac0_000499, Oprea1_764617, SCHEMBL22009, BSPBio_000312, BSPBio_001351, BSPBio_003053, KBioGR_000071, KBioGR_001897, KBioSS_000071, KBioSS_000730, MLS001077262, BIDD:GT0239, DivK1c_000481, GLIBENCLAMIDE [MART.], SPECTRUM2300229, SPBio_001831, SPBio_002531, GLIBENCLAMIDE [WHO-DD], GLIBENCLAMIDE [WHO-IP], BPBio1_000344, GTPL2414, orb1307954, orb3025499, GLYBURIDE [ORANGE BOOK], SCHEMBL29355447, UPCMLD-DP006:001, HMS501I03, KBio1_000481, KBio2_000071, KBio2_000730, KBio2_002639, KBio2_003298, KBio2_005207, KBio2_005866, KBio3_000141, KBio3_000142, KBio3_002273, GLYBURIDE [USP MONOGRAPH], MSK7191, Glibenclamide - Bio-X trade mark, Glybenclamide, >=99% (HPLC), NINDS_000481, Bio1_000076, Bio1_000565, Bio1_001054, Bio2_000071, Bio2_000551, GLXC-05423, HMS1361D13, HMS1568P14, HMS1791D13, HMS1922L08, HMS1989D13, HMS2089L06, HMS2093P04, HMS2095P14, HMS3259O12, HMS3261D19, HMS3267A15, HMS3402D13, HMS3411F16, HMS3428D15, HMS3651E17, HMS3675F16, HMS3712P14, HMS5079L16, HMS6018I15, Pharmakon1600-02300229, PXB98502, GLIBENCLAMIDE [EP MONOGRAPH], Tox21_110158, Tox21_300758, Tox21_500499, BDBM50012957, CCG-39618, EBC-08611, GLUCOVANCE COMPONENT GLYBURIDE, HD 419, HY-15206R, MSK7191-100M, NSC759618, NSC813214, SBB057426, STK362992, GLIBENCLAMIDUM [WHO-IP LATIN], AKOS001487495, MSK7191-1000M, N-p-[2-(5-Chloro-2-methoxybenzamido)ethyl]benzenesulfonyl-N'-cyclohexylurea, Tox21_110158_1, DB01016, FC23675, KS-5326, LP00499, NC00566, NSC 759618, NSC-813214, SB17414, SDCCGSBI-0050483.P004, 5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxy-benzamide, IDI1_000481, IDI1_033821, Glibenclamide 1.0 mg/ml in Acetonitrile, NCGC00015467-01, NCGC00015467-02, NCGC00015467-03, NCGC00015467-04, NCGC00015467-05, NCGC00015467-06, NCGC00015467-07, NCGC00015467-08, NCGC00015467-09, NCGC00015467-10, NCGC00015467-12, NCGC00015467-13, NCGC00015467-14, NCGC00015467-15, NCGC00015467-16, NCGC00015467-17, NCGC00015467-18, NCGC00015467-20, NCGC00015467-21, NCGC00015467-36, NCGC00015467-37, NCGC00016689-01, NCGC00023447-02, NCGC00023447-04, NCGC00023447-05, NCGC00023447-06, NCGC00023447-07, NCGC00023447-08, NCGC00023447-09, NCGC00023447-10, NCGC00023447-11, NCGC00023447-12, NCGC00254662-01, NCGC00261184-01, BG166164, Glibenclamide for peak identification CRS, HY-15206, ST024780, SY057080, SBI-0050483.P003, Glyburide, meets USP testing specifications, AB00051949, EU-0100499, G0382, NS00001144, SW195828-5, Glibenclamide Solution in Methanol, 100ug/mL, C07022, D00336, D81733, EN300-117270, Glibenclamide Solution in Methanol, 1000ug/mL, M01823, AB00051949-16, AB00051949-17, AB00051949_18, AB00051949_19, Q420626, SR-01000000196-2, SR-01000000196-4, SR-01000000196-5, SR-01000000196-6, SR-01000000196-8, BRD-K36927236-001-06-0, BRD-K36927236-001-17-7, BRD-K36927236-001-30-0, BRD-K36927236-001-31-8, BRD-K36927236-001-32-6, Z277540138, Glybenclamide, European Pharmacopoeia (EP) Reference Standard, Glyburide, United States Pharmacopeia (USP) Reference Standard, 1-((p-(2-(5-Chloro-o-anisamido)ethyl)phenyl)sulfonyl)-3-cyclohexyl urea, 5-Chloro-N-[4-(3-cyclohexylureidosulfonyl)phenethyl]-2-methoxybenzamide, Glibenclamide for peak identification, European Pharmacopoeia (EP) Reference Standard, Glyburide (Glibenclamide), Pharmaceutical Secondary Standard, Certified Reference Material, N-(4-(.beta.-(2-Methoxy-5-chlorbenzamido)-aethyl)-benzolsulfonyl)-N'-cyclohexyl-harnstoff, N1-[4-({[(cyclohexylamino)carbonyl]amino}sulfonyl)phenethyl]-5-chloro-2-methoxybenzamide, (5-chloro-2-methoxyphenyl)-N-[2-(4-{[(cyclohexylamino)carbonylamino]sulfonyl}p henyl)ethyl]carboxamide, 5-Chloro-N-(2-[4-(([(cyclohexylamino)carbonyl]amino)sulfonyl)phenyl]ethyl)-2-methoxybenzamide #, 5-Chloro-N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]-sulfonyl]phenyl]ethyl]-2-methoxy-benzamide, N-[(4-{2-[(5-chloro-2-methoxyphenyl)carbonylamino]ethyl}phenyl)sulfonyl](cyclo hexylamino)carboxamide

Bioactivity: Second-generation sulfonylurea antidiabetic agent; ATP-sensitive potassium (KATP) channel blocker; insulin secretagogue

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Butanol	283.15	-	1.016	[160]
1-Butanol	288.15	-	1.21	[160]
1-Butanol	293.15	-	1.304	[160]
1-Butanol	298.15	-	1.528	[160]
1-Butanol	303.15	-	1.784	[160]
1-Butanol	308.15	-	2.371	[160]
1-Butanol	313.15	-	3.425	[160]
1-Butanol	318.15	-	4.863	[160]
1-Butanol	323.15	-	7.106	[160]
1-Propanol	283.15	-	0.6699	[160]
1-Propanol	288.15	-	1.032	[161]
1-Propanol	288.15	-	0.8304	[160]
1-Propanol	293.15	-	1.274	[161]
1-Propanol	293.15	-	1.075	[160]
1-Propanol	298.15	-	1.557	[161]
1-Propanol	298.15	-	1.482	[160]
1-Propanol	303.15	-	1.978	[161]
1-Propanol	303.15	-	1.874	[160]
1-Propanol	308.15	-	2.788	[161]
1-Propanol	308.15	-	2.482	[160]
1-Propanol	313.15	-	3.703	[161]
1-Propanol	313.15	-	3.481	[160]
1-Propanol	318.15	-	4.84	[161]
1-Propanol	318.15	-	4.701	[160]
1-Propanol	323.15	-	6.218	[161]
1-Propanol	323.15	-	6.305	[160]
2-Butanol	283.15	-	0.3449	[160]
2-Butanol	288.15	-	0.4305	[160]
2-Butanol	293.15	-	0.5583	[160]
2-Butanol	298.15	-	0.755	[160]
2-Butanol	303.15	-	0.9806	[160]
2-Butanol	308.15	-	1.312	[160]
2-Butanol	313.15	-	1.92	[160]
2-Butanol	318.15	-	2.973	[160]
2-Butanol	323.15	-	4.616	[160]
Acetone	283.15	-	3.025	[159]
Acetone	283.15	-	3.216	[160]
Acetone	288.15	-	3.789	[159]
Acetone	288.15	-	3.848	[160]
Acetone	293.15	-	4.712	[159]
Acetone	293.15	-	4.642	[160]
Acetone	298.15	-	5.883	[159]
Acetone	298.15	-	5.973	[160]
Acetone	303.15	-	7.449	[159]
Acetone	303.15	-	7.222	[160]
Acetone	308.15	-	9.21	[159]
Acetone	308.15	-	8.797	[160]
Acetone	313.15	-	11.46	[159]
Acetone	313.15	-	11.19	[160]
Acetone	318.15	-	14.22	[159]
Acetone	318.15	-	13.89	[160]
Acetone	323.15	-	17.33	[159]
Acetone	323.15	-	16.81	[160]
Acetonitrile	283.15	-	0.5014	[160]
Acetonitrile	288.15	-	0.759	[161]
Acetonitrile	288.15	-	0.6781	[160]
Acetonitrile	293.15	-	0.9932	[161]
Acetonitrile	293.15	-	0.9277	[160]
Acetonitrile	298.15	-	1.349	[161]
Acetonitrile	298.15	-	1.225	[160]
Acetonitrile	303.15	-	1.706	[161]
Acetonitrile	303.15	-	1.513	[160]
Acetonitrile	308.15	-	2.131	[161]
Acetonitrile	308.15	-	2.073	[160]
Acetonitrile	313.15	-	2.747	[161]
Acetonitrile	313.15	-	2.896	[160]
Acetonitrile	318.15	-	3.906	[161]
Acetonitrile	318.15	-	3.799	[160]
Acetonitrile	323.15	-	5.151	[161]
Acetonitrile	323.15	-	5.037	[160]
Ethanol	283.15	-	0.8844	[159]
Ethanol	283.15	-	0.925	[160]
Ethanol	288.15	-	1.233	[159]
Ethanol	288.15	-	1.279	[160]
Ethanol	293.15	-	1.661	[159]
Ethanol	293.15	-	1.591	[160]
Ethanol	298.15	-	2.179	[159]
Ethanol	298.15	-	2.1	[160]
Ethanol	303.15	-	2.792	[159]
Ethanol	303.15	-	2.649	[160]
Ethanol	308.15	-	3.642	[159]
Ethanol	308.15	-	3.434	[160]
Ethanol	313.15	-	5.141	[159]
Ethanol	313.15	-	4.893	[160]
Ethanol	318.15	-	7.359	[159]
Ethanol	318.15	-	7.123	[160]
Ethanol	323.15	-	9.98	[159]
Ethanol	323.15	-	9.531	[160]
Ethyl acetate	283.15	-	0.4415	[159]
Ethyl acetate	283.15	-	0.461	[160]
Ethyl acetate	288.15	-	0.582	[159]
Ethyl acetate	288.15	-	0.6125	[160]
Ethyl acetate	293.15	-	0.7372	[159]
Ethyl acetate	293.15	-	0.7585	[160]
Ethyl acetate	298.15	-	0.934	[159]
Ethyl acetate	298.15	-	0.9054	[160]
Ethyl acetate	303.15	-	1.178	[159]
Ethyl acetate	303.15	-	1.127	[160]
Ethyl acetate	308.15	-	1.518	[159]
Ethyl acetate	308.15	-	1.434	[160]
Ethyl acetate	313.15	-	1.934	[159]
Ethyl acetate	313.15	-	1.844	[160]
Ethyl acetate	318.15	-	2.494	[159]
Ethyl acetate	318.15	-	2.369	[160]
Ethyl acetate	323.15	-	3.134	[159]
Ethyl acetate	323.15	-	3.037	[160]
Isopropanol	283.15	-	0.5199	[159]
Isopropanol	283.15	-	0.4933	[160]
Isopropanol	288.15	-	0.691	[161]
Isopropanol	288.15	-	0.6479	[159]
Isopropanol	288.15	-	0.5776	[160]
Isopropanol	293.15	-	0.7847	[161]
Isopropanol	293.15	-	0.8409	[159]
Isopropanol	293.15	-	0.8116	[160]
Isopropanol	298.15	-	1.081	[161]
Isopropanol	298.15	-	1.13	[159]
Isopropanol	298.15	-	1.04	[160]
Isopropanol	303.15	-	1.473	[161]
Isopropanol	303.15	-	1.377	[159]
Isopropanol	303.15	-	1.322	[160]
Isopropanol	308.15	-	1.965	[161]
Isopropanol	308.15	-	1.82	[159]
Isopropanol	308.15	-	1.721	[160]
Isopropanol	313.15	-	2.55	[161]
Isopropanol	313.15	-	2.665	[159]
Isopropanol	313.15	-	2.53	[160]
Isopropanol	318.15	-	3.623	[161]
Isopropanol	318.15	-	3.815	[159]
Isopropanol	318.15	-	3.89	[160]
Isopropanol	323.15	-	5.389	[161]
Isopropanol	323.15	-	5.572	[159]
Isopropanol	323.15	-	5.837	[160]
Methanol	283.15	-	1.596	[159]
Methanol	283.15	-	1.528	[160]
Methanol	288.15	-	2.216	[161]
Methanol	288.15	-	2.116	[159]
Methanol	288.15	-	2.021	[160]
Methanol	293.15	-	2.79	[161]
Methanol	293.15	-	2.679	[159]
Methanol	293.15	-	2.56	[160]
Methanol	298.15	-	3.511	[161]
Methanol	298.15	-	3.643	[159]
Methanol	298.15	-	3.441	[160]
Methanol	303.15	-	4.406	[161]
Methanol	303.15	-	4.551	[159]
Methanol	303.15	-	4.281	[160]
Methanol	308.15	-	5.408	[161]
Methanol	308.15	-	5.716	[159]
Methanol	308.15	-	5.848	[160]
Methanol	313.15	-	7.31	[161]
Methanol	313.15	-	7.865	[159]
Methanol	313.15	-	8.285	[160]
Methanol	318.15	-	11.14	[161]
Methanol	318.15	-	12.16	[159]
Methanol	318.15	-	12.43	[160]
Methanol	323.15	-	15.4	[161]
Methanol	323.15	-	16.12	[159]
Methanol	323.15	-	16.86	[160]
Methyl acetate	283.15	-	0.8001	[160]
Methyl acetate	288.15	-	1.027	[160]
Methyl acetate	293.15	-	1.256	[160]
Methyl acetate	298.15	-	1.525	[160]
Methyl acetate	303.15	-	1.819	[160]
Methyl acetate	308.15	-	2.27	[160]
Methyl acetate	313.15	-	2.981	[160]
Methyl acetate	318.15	-	3.777	[160]
Methyl acetate	323.15	-	4.589	[160]
Methyl isobutyl ketone	283.15	-	0.7915	[160]
Methyl isobutyl ketone	288.15	-	0.9033	[160]
Methyl isobutyl ketone	293.15	-	1.091	[160]
Methyl isobutyl ketone	298.15	-	1.321	[160]
Methyl isobutyl ketone	303.15	-	1.664	[160]
Methyl isobutyl ketone	308.15	-	2.052	[160]
Methyl isobutyl ketone	313.15	-	2.528	[160]
Methyl isobutyl ketone	318.15	-	3.03	[160]
Methyl isobutyl ketone	323.15	-	3.467	[160]
Water	283.15	-	0.0023	[159]
Water	288.15	-	0.0025	[161]
Water	288.15	-	0.0024	[159]
Water	293.15	-	0.0028	[161]
Water	293.15	-	0.0029	[159]
Water	298.15	-	0.0034	[161]
Water	298.15	-	0.0035	[159]
Water	303.15	-	0.0043	[161]
Water	303.15	-	0.0045	[159]
Water	308.15	-	0.0059	[161]
Water	308.15	-	0.0063	[159]
Water	313.15	-	0.0083	[161]
Water	313.15	-	0.0088	[159]
Water	318.15	-	0.0118	[161]
Water	318.15	-	0.0123	[159]
Water	323.15	-	0.0208	[161]
Water	323.15	-	0.0212	[159]

Molecule 3D descriptors

Descriptor	Value
PMI1	3022.0165
PMI2	15616.7721
PMI3	17852.6630
NPR1	0.1693
NPR2	0.8748
RadiusOfGyration	6.0773
InertialShapeFactor	0.0003
Eccentricity	0.9856
Asphericity	0.5761
SpherocityIndex	0.0904
PBF	0.8856