Glyburide

Details

• Internal ID: 556c5046-c8d2-4c2a-8597-e6bb296b03bd
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzenesulfonamides
• IUPAC Name: 5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxybenzamide
• SMILES (Canonical): COC1=C(C=C(C=C1)Cl)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCCCC3
• SMILES (Isomeric): COC1=C(C=C(C=C1)Cl)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCCCC3
• 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)
• InChI Key: ZNNLBTZKUZBEKO-UHFFFAOYSA-N
• Popularity: 16,388 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₈ClN₃O₅S
• Molecular Weight: 494.00 g/mol
• Exact Mass: 493.1438199 g/mol
• Topological Polar Surface Area (TPSA): 122.00 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 3.64
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

• Glibenclamide
• 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
• CHEBI:5441
• 5-chloro-N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-2-methoxybenzamide
• 5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxybenzamide
• U-26452
• U-26,452
• U-26,45
• N-(4-(beta-(2-Methoxy-5-chlorbenzamido)-aethyl)-benzolsulfonyl)-N'-cyclohexyl-harnstoff
• HB419
• 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)
• MFCD00056625
• HB-419
• UR 606
• Cirara
• 1-((p-(2-(5-Chloro-o-anisamido)ethyl)phenyl)sulfonyl)-3-cyclohexylurea
• Neogluconin
• Glibenclamide [INN]
• U 26452
• DTXSID0037237
• 5-Chloro-N-[2-[4-[[[(cyclohexylamino)carbonyl]-amino]sulfonyl]phenyl]-ethyl]-2-methoxybenzamide
• 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
• 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
• N-p-[2-(5-Chloro-2-methoxybenzamido)ethyl]benzenesulfonyl-N'-cyclohexylurea
• Urea, 1-((p-(2-(chloro-o-anisamido)ethyl)phenyl)sulfonyl)-3-cyclohexyl-
• 5-chloro-N-(2-{4-[(cyclohexylcarbamoyl)sulfamoyl]phenyl}ethyl)-2-methoxybenzamide
• 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
• 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
• 5-chloro-N-(4-[N-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-2-methoxybenzamide
• GBM
• Glyburide;5-Chloro-N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-2-methoxybenzamide
• Prestwick_569
• RP-1127
• Spectrum_000250
• Tocris-0911
• Glybenzcyclamide, 99%
• Glibenclamide; Glyburide
• 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
• 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
• BCP05327
• PXB98502
• GLIBENCLAMIDE [EP MONOGRAPH]
• Glibenclamide for peak identification
• Tox21_110158
• Tox21_300758
• Tox21_500499
• BDBM50012957
• CCG-39618
• GLUCOVANCE COMPONENT GLYBURIDE
• HD 419
• HY-15206R
• MSK7191-100M
• NSC759618
• NSC813214
• SBB057426
• STK362992
• GLIBENCLAMIDUM [WHO-IP LATIN]
• Glyburide - CAS 10238-21-8
• AKOS001487495
• MSK7191-1000M
• Tox21_110158_1
• BCP9000729
• DB01016
• FC23675
• KS-5326
• LP00499
• NC00566
• NSC 759618
• NSC-813214
• SB17414
• SDCCGSBI-0050483.P004
• 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)-phenethyl)-2-methoxybenzamide
• 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
• 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 #
• N-[(4-{2-[(5-chloro-2-methoxyphenyl)carbonylamino]ethyl}phenyl)sulfonyl](cyclo hexylamino)carboxamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9859	98.59%
Caco-2	-	0.8437	84.37%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.8857	88.57%
Subcellular localzation	Mitochondria	0.6691	66.91%
OATP2B1 inhibitior	+	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9594	95.94%
P-glycoprotein inhibitior	+	0.8301	83.01%
P-glycoprotein substrate	+	0.9343	93.43%
CYP3A4 substrate	+	0.7219	72.19%
CYP2C9 substrate	-	0.8100	81.00%
CYP2D6 substrate	-	0.8127	81.27%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	+	0.8948	89.48%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	+	0.8932	89.32%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.9818	98.18%
CYP inhibitory promiscuity	+	0.8627	86.27%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6325	63.25%
Carcinogenicity (trinary)	Non-required	0.6405	64.05%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9733	97.33%
Skin irritation	+	0.6297	62.97%
Skin corrosion	-	0.9309	93.09%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8213	82.13%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.8517	85.17%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.9224	92.24%
Acute Oral Toxicity (c)	IV	0.6192	61.92%
Estrogen receptor binding	-	0.8682	86.82%
Androgen receptor binding	+	0.6188	61.88%
Thyroid receptor binding	-	0.5325	53.25%
Glucocorticoid receptor binding	-	0.8661	86.61%
Aromatase binding	-	0.5978	59.78%
PPAR gamma	+	0.8708	87.08%
Honey bee toxicity	-	0.8989	89.89%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6733	67.33%
Fish aquatic toxicity	+	0.9946	99.46%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	18869.9 nM	Potency	via CMAUP
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	15000 nM	IC50	PMID: 21397997
CHEMBL3356	P05177	Cytochrome P450 1A2	39810.72 nM	AC50	via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	10000 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	1602 nM	IC50	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	10000 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	3981.1 nM; 3981.1 nM; 3981.1 nM; 3981.1 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	1995.3 nM; 3162.3 nM; 3162.3 nM; 1995.3 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	39810.7 nM	Potency	via CMAUP
CHEMBL235	P37231	Peroxisome proliferator-activated receptor gamma	660 nM	Ki	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	11220.2 nM	Potency	via CMAUP
CHEMBL1697668	Q9Y6L6	Solute carrier organic anion transporter family member 1B1	1400 nM; 2200 nM	IC50; IC50	PMID: 22587986; PMID: 22587986
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	125.9 nM; 125.9 nM	Potency; Potency	via CMAUP; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.49%	96.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	98.17%	96.38%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	97.34%	95.17%
CHEMBL2581	P07339	Cathepsin D	96.20%	98.95%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	94.57%	92.88%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.48%	94.45%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	93.94%	96.90%
CHEMBL4361	Q07820	Induced myeloid leukemia cell differentiation protein Mcl-1	93.52%	95.52%
CHEMBL1968	P07099	Epoxide hydrolase 1	93.34%	98.57%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.66%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.16%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	91.05%	97.14%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	90.41%	95.34%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	90.35%	93.03%
CHEMBL5203	P33316	dUTP pyrophosphatase	90.15%	99.18%
CHEMBL340	P08684	Cytochrome P450 3A4	89.29%	91.19%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.95%	94.00%
CHEMBL3085	P43003	Excitatory amino acid transporter 1	88.84%	94.67%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.25%	96.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.14%	95.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.59%	94.33%
CHEMBL2535	P11166	Glucose transporter	86.91%	98.75%
CHEMBL1795185	Q58F21	Bromodomain testis-specific protein	86.68%	89.76%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.36%	91.24%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.92%	95.89%
CHEMBL3437	Q16853	Amine oxidase, copper containing	85.44%	94.00%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	85.27%	81.11%
CHEMBL3202	P48147	Prolyl endopeptidase	84.43%	90.65%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.67%	90.71%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	83.35%	96.00%
CHEMBL1741221	Q9Y4P1	Cysteine protease ATG4B	83.21%	87.50%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.34%	89.50%
CHEMBL3401	O75469	Pregnane X receptor	82.12%	94.73%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	82.07%	94.01%
CHEMBL2664	P23526	Adenosylhomocysteinase	81.61%	86.67%
CHEMBL5255	O00206	Toll-like receptor 4	81.05%	92.50%
CHEMBL5555	O00767	Acyl-CoA desaturase	80.95%	97.50%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 3488
• NPASS: NPC208280
• ChEMBL: CHEMBL472