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
BA (Bioavailability) 82 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
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
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 1049.52 45.20 191 495 8216 2349183
Acute kidney injury 170.06 45.20 57 629 28065 2329334
Completed suicide 160.92 45.20 51 635 20983 2336416
Lactic acidosis 139.41 45.20 34 652 5296 2352103
Drug interaction 133.10 45.20 48 638 29115 2328284
Blood glucose increased 111.27 45.20 34 652 12256 2345143
Anaphylactic reaction 105.78 45.20 31 655 9674 2347725
Toxicity to various agents 102.55 45.20 41 645 32713 2324686
Blood glucose decreased 101.71 45.20 24 662 3228 2354171
Drug intolerance 91.15 45.20 30 656 13687 2343712
Toxic epidermal necrolysis 81.74 45.20 20 666 3124 2354275
Fall 69.88 45.20 35 651 47064 2310335
Hyperkalaemia 69.29 45.20 20 666 5873 2351526
Drug hypersensitivity 67.24 45.20 34 652 46609 2310790
Treatment noncompliance 66.02 45.20 19 667 5515 2351884
Diabetes mellitus inadequate control 64.58 45.20 15 671 1872 2355527
Intentional overdose 60.28 45.20 21 665 11300 2346099
Glycosylated haemoglobin increased 59.70 45.20 14 672 1820 2355579
Hyperhidrosis 53.95 45.20 21 665 15401 2341998
Depressed level of consciousness 51.86 45.20 17 669 7587 2349812
Somnolence 51.79 45.20 23 663 23462 2333937
Brain death 50.90 45.20 10 676 560 2356839
Exposure during pregnancy 50.22 45.20 23 663 25196 2332203
Poisoning 48.91 45.20 13 673 2807 2354592
Brain oedema 46.56 45.20 12 674 2298 2355101

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 2151.30 54.43 390 522 8048 1737821
Completed suicide 246.42 54.43 80 832 16232 1729637
Lactic acidosis 235.72 54.43 60 852 5069 1740800
Blood glucose decreased 193.51 54.43 44 868 2281 1743588
Mental status changes 151.56 54.43 44 868 6031 1739838
Toxicity to various agents 136.69 54.43 61 851 29080 1716789
Acute kidney injury 132.23 54.43 63 849 34881 1710988
Intentional overdose 120.63 54.43 39 873 7631 1738238
Hyperglycaemia 105.08 54.43 32 880 5133 1740736
Unresponsive to stimuli 99.81 54.43 30 882 4599 1741270
Overdose 94.38 54.43 40 872 16661 1729208
Confusional state 81.98 54.43 39 873 21239 1724630
Blood glucose increased 79.03 54.43 31 881 10553 1735316
Hypotension 75.29 54.43 41 871 29613 1716256
Hypoglycaemic coma 71.46 54.43 15 897 525 1745344
Drug interaction 66.35 54.43 37 875 27921 1717948
Fall 64.53 54.43 36 876 27178 1718691
Medication error 61.90 54.43 21 891 4722 1741147
Hypophagia 55.69 54.43 18 894 3479 1742390
Hypoglycaemic encephalopathy 55.53 54.43 9 903 70 1745799
Otitis externa 54.81 54.43 10 902 165 1745704

Pharmacologic Action:

SourceCodeDescription
ATC A10BB01 ALIMENTARY TRACT AND METABOLISM
DRUGS USED IN DIABETES
BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS
Sulfonylureas
FDA EPC N0000175608 Sulfonylurea
FDA Chemical/Ingredient N0000008054 Sulfonylurea Compounds
MeSH PA D007004 Hypoglycemic Agents
CHEBI has role CHEBI:38070 anti-arrhythmia drug
CHEBI has role CHEBI:35526 hypoglycemic agent

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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Glynase HUMAN PRESCRIPTION DRUG LABEL 1 0009-0341 TABLET 1.50 mg ORAL NDA 12 sections
Glynase HUMAN PRESCRIPTION DRUG LABEL 1 0009-0352 TABLET 3 mg ORAL NDA 12 sections
Glynase HUMAN PRESCRIPTION DRUG LABEL 1 0009-3449 TABLET 6 mg ORAL NDA 12 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0093-8034 TABLET 1.50 mg ORAL ANDA 11 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0093-8035 TABLET 3 mg ORAL ANDA 11 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0093-8036 TABLET 6 mg ORAL ANDA 11 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0093-8342 TABLET 1.25 mg ORAL ANDA 11 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0093-8343 TABLET 2.50 mg ORAL ANDA 11 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0093-8344 TABLET 5 mg ORAL ANDA 11 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0093-9364 TABLET 5 mg ORAL NDA AUTHORIZED GENERIC 12 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0093-9433 TABLET 2.50 mg ORAL NDA AUTHORIZED GENERIC 12 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0093-9477 TABLET 1.25 mg ORAL NDA AUTHORIZED GENERIC 12 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0115-1742 TABLET 1.25 mg ORAL ANDA 11 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0115-1743 TABLET 2.50 mg ORAL ANDA 11 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0115-1744 TABLET 5 mg ORAL ANDA 11 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0143-9918 TABLET 1.50 mg ORAL ANDA 12 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0143-9919 TABLET 3 mg ORAL ANDA 12 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0143-9920 TABLET 6 mg ORAL ANDA 12 sections
Glyburide and Metformin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0228-2751 TABLET, FILM COATED 1.25 mg ORAL ANDA 14 sections
Glyburide and Metformin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0228-2752 TABLET, FILM COATED 2.50 mg ORAL ANDA 14 sections
Glyburide and Metformin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0228-2753 TABLET, FILM COATED 5 mg ORAL ANDA 14 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0615-1556 TABLET 5 mg ORAL ANDA 11 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0615-4509 TABLET 2.50 mg ORAL ANDA 11 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 10544-232 TABLET 2.50 mg ORAL ANDA 10 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 10544-300 TABLET 5 mg ORAL ANDA 10 sections
Glyburide-Metformin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 10544-579 TABLET 5 mg ORAL ANDA 11 sections
Glyburide-Metformin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 10544-580 TABLET 2.50 mg ORAL ANDA 11 sections
Glyburide and Metformin HUMAN PRESCRIPTION DRUG LABEL 2 21695-568 TABLET, FILM COATED 5 mg ORAL ANDA 12 sections
GLYBURIDE HUMAN PRESCRIPTION DRUG LABEL 1 23155-056 TABLET 1.25 mg ORAL ANDA 10 sections
GLYBURIDE HUMAN PRESCRIPTION DRUG LABEL 1 23155-057 TABLET 2.50 mg ORAL ANDA 10 sections