Drug Details

General Information of the Drug (ID: DR5200)
Name
Glibenclamide
Synonyms
glyburide; Glibenclamide; 10238-21-8; Glybenclamide; Glynase; Micronase; Diabeta; Daonil; Euglucon; Maninil; Semi-daonil; Apo-Glibenclamide; Euglucon 5; Azuglucon; Bastiverit; Benclamin; Betanase; Duraglucon; Euglucan; Euglykon; Glibenil; Glucolon; Orabetic; Prodiabet; Renabetic; Yuglucon; Dibelet; Gilemal; Glibens; Glibil; Glimel; Glimide; Humedia; Libanil; Suraben; Tiabet; Adiab; Glybenzcyclamide; Melix; Pira; Med-Glionil; Glibenclamida; Glibenclamidum; 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide; Glibenclamidum [INN-Latin]; Glibenclamida [INN-Spanish]; HB 419; glyburide (glibenclamide); C23H28ClN3O5S; UR 606; UNII-SX6K58TVWC; 1-(p-(2-(5-Chloro-2-methoxybenzamido)ethyl)benzenesulfonyl)-3-cyclohexylurea; 1-((p-(2-(5-Chloro-o-anisamido)ethyl)phenyl)sulfonyl)-3-cyclohexylurea; Neogluconin; 5-Chloro-N-(2-(4-((((cyclohexylamino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-methoxybenzamide; U 26452; 5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxybenzamide; Gewaglucon; Glibenbeta; Glidiabet; Glucobene; Glucohexal; Glucoremed; Hexaglucon; Lederglib; Lisaglucon; Normoglucon; Praeciglucon; Calabren; Cytagon; Euclamin; Glamide; Glibesyn; Glibetic; Gliboral; Glisulin; Glitisol; Glubate; Glucomid; Glucoven; Glycomin; MFCD00056625; Miglucan; Debtan; Gliban; Gliben; Glibet; Glicem; Gluben; Glyben; Nadib; Sugril; SX6K58TVWC; CHEMBL472; Novo-Glyburide; Glibenclamid AL; Gen-Glybe; Norglicem 5; Betanese 5; N-(4-(2-(5-Chloro-2-methoxybenzamido)ethyl)phenylsulfonyl)-N'-cyclohexylurea; Glibenclamid Fabra; MLS000069721; CHEBI:5441; Glibenclamid Basics; Glibenclamid-Cophar; Glibenclamid Heumann; Semi-Euglucon; Glibenclamid Genericon; 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-; NCGC00015467-11; Abbenclamide; Diabiphage; Glibadone; SMR000058229; Semi-Gliben-Puren N; GBN 5; CAS-10238-21-8; Glibenclamid Riker M.; Glyburide (micronized); 5-Chloro-N-[4-(cyclohexylureidosulfonyl)phenethyl]-2-methoxybenzamide; Urea, 1-((p-(2-(chloro-o-anisamido)ethyl)phenyl)sulfonyl)-3-cyclohexyl-; 5-chloro-N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-2-methoxybenzamide; 5-Chloro-N-[2-[4-[[[(cyclohexylamino)carbonyl]-amino]sulfonyl]phenyl]-ethyl]-2-methoxybenzamide; DSSTox_CID_17237; DSSTox_RID_79313; DSSTox_GSID_37237; Benzamide, 5-chloro-N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-2-methoxy-; Micronized glyburide; U-26,452; 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); HB-419; 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; BRN 2230085; Amglidia; Delmide; 5-chloro-N-(4-[N-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-2-methoxybenzamide; Glibenclamide,(S); GBM; Prestwick_569; Glibenclamide B.P.; Glyburide (Diabeta); Glibenclamide [INN]; RP-1127; Spectrum_000250; Tocris-0911; Glybenzcyclamide, 99%; Glibenclamide; Glyburide; Opera_ID_801; Prestwick0_000316; Prestwick1_000316; Prestwick2_000316; Prestwick3_000316; Spectrum2_001816; Spectrum3_001327; Spectrum4_001199; Spectrum5_001631; Lopac-G-0639; ACMC-20a66i; Probes1_000431; Probes2_000378; UPCMLD-DP006; G 0639; Glibenclamide (JP17/INN); N-(4-(beta-(2-Methoxy-5-chlorbenzamido)-aethyl)-benzolsulfonyl)-N'-cyclohexyl-harnstoff; CBiol_001790; Lopac0_000499; Oprea1_764617; SCHEMBL22009; U-26452; BSPBio_000312; BSPBio_001351; BSPBio_003053; KBioGR_000071; KBioGR_001897; KBioSS_000071; KBioSS_000730; MLS001077262; BIDD:GT0239; DivK1c_000481; SPECTRUM2300229; SPBio_001831; SPBio_002531; BPBio1_000344; GTPL2414; DTXSID0037237; UPCMLD-DP006:001; HMS501I03; KBio1_000481; KBio2_000071; KBio2_000730; KBio2_002639; KBio2_003298; KBio2_005207; KBio2_005866; KBio3_000141; KBio3_000142; KBio3_002273; AOB6214; SYN3026; Glybenclamide, >=99% (HPLC); NINDS_000481; Bio1_000076; Bio1_000565; Bio1_001054; Bio2_000071; Bio2_000551; HMS1361D13; HMS1568P14; HMS1791D13; HMS1922L08; HMS1989D13; HMS2089L06; HMS2093P04; HMS2095P14; HMS3259O12; HMS3261D19; HMS3267A15; HMS3402D13; HMS3411F16; HMS3428D15; HMS3651E17; HMS3675F16; HMS3712P14; Pharmakon1600-02300229; ZINC537805; BCP05327; Tox21_110158; Tox21_300758; Tox21_500499; ANW-58936; BDBM50012957; CCG-39618; HD 419; NSC759618; SBB057426; STK362992; Glyburide - CAS 10238-21-8; AKOS001487495; N-p-[2-(5-Chloro-2-methoxybenzamido)ethyl]benzenesulfonyl-N'-cyclohexylurea; Tox21_110158_1; BCP9000729; CS-1075; DB01016; KS-5326; LP00499; MCULE-2351642942; NC00566; NSC 759618; NSC-759618; SB17414; SDCCGSBI-0050483.P004; 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; HY-15206; ST024780; SBI-0050483.P003; AB0012611; Glyburide, meets USP testing specifications; AB00051949; EU-0100499; FT-0601608; G-150; G0382; S1716; SW195828-5; A19539; C07022; D00336; J10021; W-5054; 78637-EP2270001A1; 78637-EP2270011A1; 78637-EP2272825A2; 78637-EP2272841A1; 78637-EP2275414A1; 78637-EP2287165A2; 78637-EP2287166A2; 78637-EP2292620A2; 78637-EP2298750A1; 78637-EP2298776A1; 78637-EP2298779A1; 78637-EP2301923A1; 78637-EP2301936A1; 78637-EP2305648A1; 78637-EP2308847A1; AB00051949-16; AB00051949-17; AB00051949_18; AB00051949_19; Q420626; U-26,45; SR-01000000196-2; SR-01000000196-4; SR-01000000196-5; SR-01000000196-6; SR-01000000196-8; W-108874; BRD-K36927236-001-06-0; BRD-K36927236-001-17-7; 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; 5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxybenzamide.; 5-chloro-N-[4-({[(cyclohexylamino)carbonyl]amino}sulfonyl)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-[[[(Cylcohexylamino)carbonyl]amino]sulphonyl]phenyl]ethyl]-2-methoxybenzamide; N-[(4-{2-[(5-chloro-2-methoxyphenyl)carbonylamino]ethyl}phenyl)sulfonyl](cyclo hexylamino)carboxamide
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Molecular Type
Small molecule
Disease Acute diabete complication [ICD-11: 5A2Y] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absorption AUC
The area under the plot of plasma concentration (AUC) of drug is 348 mcgh/L
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 211-315 mcg/L
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 0.9-1.0 h
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability
Bioavailability
82% of drug becomes completely available to its intended biological destination(s)
Clearance
The clearance of drug is 2.70-3.55 L/h
Elimination
50% of drug is excreted in the urine and 50% in the feces
Half-life
The concentration or amount of drug in body reduced by one-half in 4.0 - 13.4 hours
Metabolism
The drug is metabolized via the CYP3A4, followed by CYP2C9, CYP2C19, CYP3A7, and CYP3A5
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.57836 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.021%
Vd
The volume of distribution (Vd) of drug is 21.5-49.3 L
Water Solubility
The ability of drug to dissolve in water is measured as 0.004 mg/mL
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Formula
C23H28ClN3O5S
PubChem CID
3488
Canonical SMILES
COC1=C(C=C(C=C1)Cl)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCCCC3
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)
InChIKey
ZNNLBTZKUZBEKO-UHFFFAOYSA-N
CAS Number
CAS 10238-21-8
ChEBI ID
CHEBI:5441
TTD Drug ID
D05LYX
DrugBank ID
DB01016
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Metformin      Galega officinalis     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Clinical Trial
                    Experimental
                    Result(s)		 Combination of glibenclamide-metformin should be considered in patients, without renal or cardiovascular impairment, who are not controlled on monotherapy alone.
Target and Pathway
Target(s) ATP-binding cassette C8 (ABCC8)  Molecule Info  [3]
KEGG Pathway ABC transporters Click to Show/Hide
2 Insulin secretion
3 Type II diabetes mellitus
Pathwhiz Pathway Muscle/Heart Contraction Click to Show/Hide
2 Pancreas Function
Pathway Interaction Database FOXA2 and FOXA3 transcription factor networks Click to Show/Hide
Reactome ABC-family proteins mediated transport Click to Show/Hide
2 Regulation of insulin secretion
WikiPathways Potassium Channels Click to Show/Hide
2 Integration of energy metabolism
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2414).
Reference 2 Combination of glibenclamide-metformin HCl for the treatment of type 2 diabetes mellitus. Expert Opin Pharmacother. 2012 Dec;13(17):2545-54.
Reference 3 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
 Download Picture         KEGG Link