glibenclamide Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antihyperglycaemics 1314 10238-21-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • glyburide
  • glibenclamide
  • glicuformine
An antidiabetic sulfonylurea derivative with actions similar to those of chlorpropamide.
  • Molecular weight: 494
  • Formula: C23H28ClN3O5S
  • CLOGP: 4.24
  • LIPINSKI: 0
  • HAC: 8
  • HDO: 3
  • TPSA: 113.60
  • ALOGS: -5.38
  • ROTB: 7

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
7 mg O
10 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.00 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.58 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 82 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.08 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 0.82 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.02 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2.20 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
May 1, 1984 FDA SANOFI AVENTIS US

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Hypoglycaemia 772.39 11.29 422 22548 53927 46609165
Blood glucose increased 317.00 11.29 271 22699 71742 46591350
Lactic acidosis 158 11.29 132 22838 33777 46629315
Blood glucose decreased 123.77 11.29 90 22880 18802 46644290
Coronary artery disease 109.13 11.29 107 22863 33645 46629447
Cardiac failure congestive 107.63 11.29 175 22795 91575 46571517
Myocardial infarction 101.07 11.29 176 22794 97352 46565740
Diabetes mellitus inadequate control 100.57 11.29 69 22901 13145 46649947
Hyperglycaemia 79.36 11.29 92 22878 34979 46628113
Glycosylated haemoglobin increased 76.23 11.29 54 22916 10822 46652270
Off label use 60.22 11.29 59 22911 379782 46283310
Hypertensive emergency 58.56 11.29 24 22946 1594 46661498
Hypoglycaemic coma 50.85 11.29 25 22945 2549 46660543
Blood glucose fluctuation 39.70 11.29 25 22945 4121 46658971
Hyperkalaemia 35.92 11.29 78 22892 50631 46612461
Diabetes mellitus 35.45 11.29 77 22893 49988 46613104
Rheumatoid arthritis 32.86 11.29 42 22928 240173 46422919
Diabetic ketoacidosis 31.87 11.29 42 22928 18168 46644924
Acute kidney injury 30.80 11.29 210 22760 235645 46427447
Pancreatitis 29.64 11.29 66 22904 43561 46619531
Product use in unapproved indication 28.53 11.29 5 22965 90268 46572824
Autoimmune myositis 24.51 11.29 6 22964 70 46663022
Torsade de pointes 24.38 11.29 30 22940 12124 46650968
Carcinoid tumour of the stomach 24.20 11.29 7 22963 160 46662932
Bradyarrhythmia 24.12 11.29 14 22956 1992 46661100
Drug ineffective 23.98 11.29 216 22754 677622 45985470
Ischaemic cardiomyopathy 23.16 11.29 15 22955 2595 46660497
Blood glucose abnormal 23.14 11.29 22 22948 6650 46656442
Alopecia 22.61 11.29 28 22942 162386 46500706
Contraindicated product administered 22.08 11.29 6 22964 79941 46583151
Renal failure 20.44 11.29 110 22860 113484 46549608
Hypoglycaemic unconsciousness 20.16 11.29 9 22961 737 46662355
Enterochromaffin cell hyperplasia 20.07 11.29 5 22965 63 46663029
Obesity 19.26 11.29 29 22941 14177 46648915
Metabolic acidosis 19.24 11.29 52 22918 38728 46624364
Treatment noncompliance 19.10 11.29 44 22926 29687 46633405
Blood urea increased 19.10 11.29 40 22930 25312 46637780
Heart injury 18.59 11.29 10 22960 1229 46661863
Transient ischaemic attack 18.53 11.29 48 22922 34855 46628237
Oedema peripheral 17.81 11.29 137 22833 159569 46503523
Hypergastrinaemia 17.55 11.29 5 22965 108 46662984
Hyperhidrosis 17.10 11.29 88 22882 89220 46573872
Drug abuse 17.06 11.29 5 22965 63403 46599689
Febrile neutropenia 17.00 11.29 13 22957 94614 46568478
Cerebrovascular accident 16.94 11.29 96 22874 100943 46562149
Asthenia 16.86 11.29 230 22740 310845 46352247
Hypoglycaemic encephalopathy 16.76 11.29 6 22964 275 46662817
Pancreatitis acute 16.19 11.29 37 22933 24835 46638257
Acute myocardial infarction 16.03 11.29 43 22927 31881 46631211
Strongyloidiasis 15.90 11.29 8 22962 857 46662235
Necrotising myositis 15.72 11.29 6 22964 330 46662762
Angina pectoris 15.44 11.29 38 22932 26737 46636355
Rectal adenoma 15.17 11.29 4 22966 64 46663028
Diabetic retinopathy 15.14 11.29 11 22959 2291 46660801
Macular oedema 15.14 11.29 14 22956 4087 46659005
Hepatic artery thrombosis 15.11 11.29 4 22966 65 46663027
Mucosal erosion 14.83 11.29 9 22961 1389 46661703
Intentional product use issue 14.50 11.29 4 22966 52776 46610316
Peripheral swelling 14.08 11.29 36 22934 158035 46505057
Fatigue 14.07 11.29 213 22757 608484 46054608
Rhabdomyolysis 14.05 11.29 49 22921 41860 46621232
Neutropenia 14.04 11.29 31 22939 143173 46519919
Ketoacidosis 13.64 11.29 13 22957 3942 46659150
Drug hypersensitivity 13.42 11.29 68 22902 243757 46419335
Type 2 diabetes mellitus 13.42 11.29 30 22940 19845 46643247
Lip discolouration 13.19 11.29 6 22964 514 46662578
Myocardial ischaemia 13.16 11.29 23 22947 12726 46650366
Treatment failure 12.99 11.29 16 22954 93071 46570021
Synovitis 12.86 11.29 7 22963 61068 46602024
Anaphylactic reaction 12.84 11.29 56 22914 53056 46610036
Hepatic steatosis 12.70 11.29 33 22937 24009 46639083
Hip deformity 12.58 11.29 4 22966 127 46662965
Infusion related reaction 12.51 11.29 19 22951 101189 46561903
Pancreatic duct obstruction 12.50 11.29 3 22967 32 46663060
Oral mucosal discolouration 12.45 11.29 5 22965 315 46662777
Leukocyturia 12.43 11.29 7 22963 941 46662151
Hospitalisation 12.31 11.29 8 22962 63377 46599715
Drug interaction 12.17 11.29 153 22817 202941 46460151
Maternal exposure during pregnancy 11.97 11.29 20 22950 102529 46560563
Tobacco abuse 11.76 11.29 6 22964 662 46662430
Hyperhomocysteinaemia 11.74 11.29 4 22966 158 46662934
Hypophagia 11.37 11.29 36 22934 29270 46633822
Therapeutic product effect incomplete 11.37 11.29 13 22957 78140 46584952
Anaemia of malignant disease 11.32 11.29 5 22965 399 46662693

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Hypoglycaemia 1250.74 11.85 687 25256 50294 29876241
Blood glucose increased 222.31 11.85 270 25673 61260 29865275
Blood glucose decreased 167.94 11.85 117 25826 12936 29913599
Myocardial infarction 117.89 11.85 304 25639 125321 29801214
Coronary artery disease 115.20 11.85 176 25767 49536 29876999
Cardiac failure congestive 111.84 11.85 234 25709 84173 29842362
Lactic acidosis 110.98 11.85 136 25807 31077 29895458
Glycosylated haemoglobin increased 86.09 11.85 69 25874 9422 29917113
Hyperglycaemia 82.03 11.85 125 25818 35075 29891460
Counterfeit product administered 62.64 11.85 17 25926 166 29926369
Blood mercury abnormal 62.46 11.85 17 25926 168 29926367
5-hydroxyindolacetic acid in urine increased 60.33 11.85 17 25926 193 29926342
Off label use 55.86 11.85 81 25862 249209 29677326
Drug abuse 47.94 11.85 7 25936 82065 29844470
Cerebrovascular accident 45.28 11.85 167 25776 83310 29843225
Metabolic acidosis 42.86 11.85 98 25845 37363 29889172
Arteriosclerosis coronary artery 41.81 11.85 50 25893 11126 29915409
Product contamination 41.53 11.85 17 25926 632 29925903
Low density lipoprotein decreased 40.90 11.85 19 25924 962 29925573
Blood pressure systolic increased 40.00 11.85 57 25886 15053 29911482
Product use in unapproved indication 39.27 11.85 8 25935 73685 29852850
Pyrexia 35.75 11.85 133 25810 294356 29632179
Hyperkalaemia 34.89 11.85 131 25812 65879 29860656
Hyperoxaluria 34.32 11.85 10 25933 129 29926406
Myocardial ischaemia 34.13 11.85 57 25886 17260 29909275
Mental status changes 33.90 11.85 89 25854 36990 29889545
Platelet count normal 32.68 11.85 7 25936 21 29926514
Death 30.63 11.85 183 25760 357100 29569435
Hypoglycaemic coma 30.21 11.85 21 25922 2310 29924225
Ischaemic cardiomyopathy 30.09 11.85 32 25911 6265 29920270
Acute kidney injury 29.40 11.85 364 25579 273478 29653057
Diabetes mellitus inadequate control 29.25 11.85 45 25898 12717 29913818
Hypoglycaemic encephalopathy 29.15 11.85 10 25933 225 29926310
Blood creatinine increased 27.10 11.85 153 25790 91222 29835313
Scrotal oedema 25.59 11.85 16 25927 1473 29925062
Quadriparesis 25.30 11.85 14 25929 1027 29925508
Pancreatitis 25.02 11.85 79 25864 36411 29890124
Hepatic neoplasm 24.68 11.85 17 25926 1842 29924693
Congenital absence of bile ducts 24.21 11.85 4 25939 0 29926535
Expired product administered 24.20 11.85 20 25923 2849 29923686
Drug ineffective 22.91 11.85 187 25756 340200 29586335
Neutropenia 22.19 11.85 49 25894 128491 29798044
Oedema peripheral 22.01 11.85 162 25781 105670 29820865
Febrile neutropenia 21.60 11.85 37 25906 106656 29819879
Oliguria 21.08 11.85 29 25914 7410 29919125
Haematocrit decreased 20.62 11.85 66 25877 30633 29895902
Otitis externa 20.01 11.85 12 25931 1025 29925510
Hirsutism 19.94 11.85 7 25936 169 29926366
Neoplasm 19.90 11.85 21 25922 4075 29922460
Vascular resistance systemic decreased 19.40 11.85 6 25937 96 29926439
Nephrocalcinosis 19.07 11.85 9 25934 472 29926063
Areflexia 18.96 11.85 17 25926 2702 29923833
Emotional distress 18.86 11.85 42 25901 15723 29910812
Pneumonia 18.86 11.85 192 25751 334114 29592421
Deafness neurosensory 18.78 11.85 16 25927 2377 29924158
Blood glucose fluctuation 18.19 11.85 19 25924 3642 29922893
Shock 18.03 11.85 52 25891 22807 29903728
Pancreatitis acute 17.95 11.85 56 25887 25639 29900896
Hospitalisation 17.86 11.85 8 25935 44311 29882224
Hepatic pain 17.54 11.85 12 25931 1286 29925249
Lacunar infarction 16.81 11.85 17 25926 3138 29923397
Bladder cancer 16.67 11.85 29 25914 9073 29917462
Hyperlipidaemia 16.58 11.85 37 25906 13870 29912665
Chest pain 16.51 11.85 165 25778 117462 29809073
Treatment failure 16.08 11.85 5 25938 34674 29891861
Middle ear disorder 16.08 11.85 3 25940 3 29926532
Injury 15.78 11.85 48 25895 21683 29904852
Paratracheal lymphadenopathy 15.57 11.85 5 25938 91 29926444
Blood lactic acid increased 15.43 11.85 22 25921 5808 29920727
Diabetic neuropathy 15.28 11.85 18 25925 3941 29922594
Poor dental condition 15.24 11.85 6 25937 201 29926334
Tympanic membrane disorder 15.13 11.85 4 25939 35 29926500
Nasal neoplasm 14.60 11.85 5 25938 112 29926423
Pancreatitis chronic 14.14 11.85 12 25931 1772 29924763
Transient ischaemic attack 14.13 11.85 51 25892 25149 29901386
Cardiovascular disorder 14.04 11.85 30 25913 10922 29915613
Thrombocytopenia 14.02 11.85 66 25877 136978 29789557
Hyperlactacidaemia 13.81 11.85 14 25929 2592 29923943
Asthenia 13.62 11.85 268 25675 221022 29705513
Renal failure 13.59 11.85 171 25772 128795 29797740
Insulin C-peptide increased 13.43 11.85 4 25939 56 29926479
Blood pH decreased 13.40 11.85 13 25930 2282 29924253
Accidental exposure to product by child 13.40 11.85 11 25932 1552 29924983
Blood glucose 13.15 11.85 3 25940 13 29926522
Polyuria 13.02 11.85 23 25920 7283 29919252
Apnoea 12.87 11.85 21 25922 6237 29920298
Peripheral vascular disorder 12.81 11.85 19 25924 5200 29921335
Sensitisation 12.75 11.85 5 25938 166 29926369
Renal injury 12.65 11.85 30 25913 11699 29914836
Product complaint 12.64 11.85 20 25923 5786 29920749
Cardiac disorder 12.61 11.85 68 25875 39825 29886710
Leukocytosis 12.47 11.85 44 25899 21458 29905077
Diabetes mellitus 12.33 11.85 70 25873 41795 29884740
Diabetic retinopathy 12.32 11.85 11 25932 1739 29924796
Localised oedema 11.90 11.85 14 25929 3062 29923473

Pharmacologic Action:

SourceCodeDescription
ATC A10BB01 ALIMENTARY TRACT AND METABOLISM
DRUGS USED IN DIABETES
BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS
Sulfonylureas
FDA CS M0020795 Sulfonylurea Compounds
FDA EPC N0000175608 Sulfonylurea
CHEBI has role CHEBI:35526 hypoglycemic drug
CHEBI has role CHEBI:38070 antiarrhythmic agent
CHEBI has role CHEBI:77194 pantothenate kinase (phosphorylating) inhibitors
CHEBI has role CHEBI:131770 cystic fibrosis transmembrane conductance regulator inhibitors
MeSH PA D007004 Hypoglycemic Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Diabetes mellitus type 2 indication 44054006 DOID:9352
Alcoholism contraindication 7200002
Asthenia contraindication 13791008
Myocardial infarction contraindication 22298006 DOID:5844
Acute vomiting contraindication 23971007
Alcohol intoxication contraindication 25702006
Shock contraindication 27942005
Dehydration contraindication 34095006
Infectious disease contraindication 40733004
Hepatic porphyria contraindication 55056006 DOID:3133
Ketoacidosis contraindication 56051008
Acute nephropathy contraindication 58574008
Metabolic acidosis contraindication 59455009
Hepatic failure contraindication 59927004
Hemolytic anemia contraindication 61261009 DOID:583
Glucose-6-phosphate dehydrogenase deficiency anemia contraindication 62403005
Hypopituitarism contraindication 74728003 DOID:9406
Cardiogenic shock contraindication 89138009
Kidney disease contraindication 90708001 DOID:557
Lactic acidosis contraindication 91273001 DOID:3650
Cobalamin deficiency contraindication 190634004
Decompensated cardiac failure contraindication 195111005
Disease of liver contraindication 235856003 DOID:409
Hypoglycemic disorder contraindication 237630007
Sepsis syndrome contraindication 238150007
Primary adrenocortical insufficiency contraindication 373662000
Adrenal cortical hypofunction contraindication 386584007 DOID:10493
Fever contraindication 386661006
Surgical procedure contraindication 387713003
Severe diarrhea contraindication 409587002
Traumatic injury contraindication 417746004
Fever greater than 100.4 Fahrenheit contraindication 426000000
Radiography with IV Iodinated Contrast Agent contraindication
Severe Hypoxemia contraindication
Severe Autonomic Insufficiency contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 5.31 acidic
pKa2 12.71 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sulfonylurea receptor 1, Kir6.2 Ion channel BLOCKER Kd 9.52 SCIENTIFIC LITERATURE SCIENTIFIC LITERATURE
Cystic fibrosis transmembrane conductance regulator Ion channel BLOCKER Ki 4.66 IUPHAR
Sulfonylurea receptor 2, Kir6.2 Ion channel BLOCKER Ki 8.21 WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 4.13 CHEMBL
Bile salt export pump Transporter IC50 5.28 CHEMBL
Cytochrome P450 2C9 Enzyme INHIBITOR IC50 5.80 DRUG MATRIX
Bile salt export pump Unclassified IC50 5.55 CHEMBL
ATP-sensitive inward rectifier potassium channel 11 Unclassified BLOCKER IC50 5.70 IUPHAR

External reference:

IDSource
4018078 VUID
N0000146417 NUI
D00336 KEGG_DRUG
4018078 VANDF
C0017628 UMLSCUI
CHEBI:5441 CHEBI
GBM PDB_CHEM_ID
CHEMBL472 ChEMBL_ID
DB01016 DRUGBANK_ID
D005905 MESH_DESCRIPTOR_UI
2414 IUPHAR_LIGAND_ID
2386 INN_ID
SX6K58TVWC UNII
3488 PUBCHEM_CID
4815 RXNORM
4790 MMSL
597 MMSL
d00248 MMSL
000912 NDDF
384978002 SNOMEDCT_US
80870001 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Glynase HUMAN PRESCRIPTION DRUG LABEL 1 0009-0341 TABLET 1.50 mg ORAL NDA 26 sections
Glynase HUMAN PRESCRIPTION DRUG LABEL 1 0009-0352 TABLET 3 mg ORAL NDA 26 sections
Glynase HUMAN PRESCRIPTION DRUG LABEL 1 0009-3449 TABLET 6 mg ORAL NDA 26 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0093-8034 TABLET 1.50 mg ORAL ANDA 24 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0093-8035 TABLET 3 mg ORAL ANDA 24 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0093-8036 TABLET 6 mg ORAL ANDA 24 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0093-8342 TABLET 1.25 mg ORAL ANDA 26 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0093-8343 TABLET 2.50 mg ORAL ANDA 26 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0093-8344 TABLET 5 mg ORAL ANDA 26 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0093-9364 TABLET 5 mg ORAL NDA AUTHORIZED GENERIC 25 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0093-9433 TABLET 2.50 mg ORAL NDA AUTHORIZED GENERIC 25 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0093-9477 TABLET 1.25 mg ORAL NDA AUTHORIZED GENERIC 25 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0115-1742 TABLET 1.25 mg ORAL ANDA 22 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0115-1743 TABLET 2.50 mg ORAL ANDA 22 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0115-1744 TABLET 5 mg ORAL ANDA 22 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0121-0929 TABLET 1.25 mg ORAL ANDA 25 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0121-0930 TABLET 2.50 mg ORAL ANDA 25 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0121-0931 TABLET 5 mg ORAL ANDA 25 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0143-9918 TABLET 1.50 mg ORAL ANDA 20 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0143-9919 TABLET 3 mg ORAL ANDA 20 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0143-9920 TABLET 6 mg ORAL ANDA 20 sections
Glyburide and Metformin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0228-2751 TABLET, FILM COATED 1.25 mg ORAL ANDA 27 sections
Glyburide and Metformin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0228-2752 TABLET, FILM COATED 2.50 mg ORAL ANDA 27 sections
Glyburide and Metformin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0228-2753 TABLET, FILM COATED 5 mg ORAL ANDA 27 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 10544-232 TABLET 2.50 mg ORAL ANDA 21 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 10544-300 TABLET 5 mg ORAL ANDA 21 sections
Glyburide-Metformin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 10544-579 TABLET 5 mg ORAL ANDA 23 sections
Glyburide-Metformin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 10544-580 TABLET 2.50 mg ORAL ANDA 23 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 21695-467 TABLET 2.50 mg ORAL ANDA 22 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 21695-468 TABLET 5 mg ORAL ANDA 22 sections