glibenclamide indications/contra

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

Drug dosage:

DoseUnitRoute
7 mg O
10 mg O

Approvals:

DateAgencyCompanyOrphan
May 1, 1984 FDA SANOFI AVENTIS US

FDA Adverse Event Reporting System

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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 3431.55 41.97 626 1221 13692 3370320
Blood glucose increased 371.83 41.97 112 1735 19043 3364969
Completed suicide 345.60 41.97 119 1728 30995 3353017
Blood glucose decreased 337.97 41.97 78 1769 4680 3379332
Lactic acidosis 288.07 41.97 75 1772 7425 3376587
Toxicity to various agents 239.41 41.97 102 1745 46952 3337060
Acute kidney injury 234.07 41.97 102 1745 49581 3334431
Diabetes mellitus inadequate control 190.32 41.97 45 1802 2974 3381038
Intentional overdose 178.99 41.97 61 1786 15164 3368848
Drug interaction 178.39 41.97 83 1764 46729 3337283
Mental status changes 173.41 41.97 54 1793 10093 3373919
Overdose 160.29 41.97 70 1777 33908 3350104
Medication error 145.05 41.97 49 1798 11822 3372190
Hyperglycaemia 139.13 41.97 44 1803 8624 3375388
Confusional state 131.05 41.97 63 1784 37935 3346077
Diarrhoea 128.11 41.97 88 1759 104260 3279752
Hypoglycaemic coma 118.80 41.97 25 1822 962 3383050
Metabolic acidosis 114.15 41.97 38 1809 8740 3375272
Unresponsive to stimuli 109.46 41.97 36 1811 7972 3376040
Asthenia 103.80 41.97 65 1782 65600 3318412
Blood glucose fluctuation 102.89 41.97 23 1824 1177 3382835
Dizziness 99.50 41.97 67 1780 76445 3307567
Hyperhidrosis 96.23 41.97 44 1803 23566 3360446
Loss of consciousness 91.85 41.97 45 1802 28102 3355910
Glycosylated haemoglobin increased 91.73 41.97 25 1822 2907 3381105
Coma 90.07 41.97 35 1812 12517 3371495
Suicide attempt 88.88 41.97 37 1810 15810 3368202
Fall 87.25 41.97 56 1791 58827 3325185
Hypotension 83.14 41.97 51 1796 49463 3334549
Hypophagia 81.79 41.97 27 1820 6034 3377978

Pharmacologic Action:

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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)

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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 DOID:2862
Hypopituitarism contraindication 74728003 DOID:9406
Cardiogenic shock contraindication 89138009
Kidney disease contraindication 90708001 DOID:2527
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 DOID:9993
Sepsis syndrome contraindication 238150007
Primary adrenocortical insufficiency contraindication 373662000 DOID:13774
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

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

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
1.25MG GLUCOVANCE BRISTOL MYERS SQUIBB N021178 July 31, 2000 DISCN TABLET ORAL 6303146 July 14, 2019 TREATMENT OF TYPE 2 DIABETES
2.5MG GLUCOVANCE BRISTOL MYERS SQUIBB N021178 July 31, 2000 DISCN TABLET ORAL 6303146 July 14, 2019 TREATMENT OF TYPE 2 DIABETES
5MG GLUCOVANCE BRISTOL MYERS SQUIBB N021178 July 31, 2000 DISCN TABLET ORAL 6303146 July 14, 2019 TREATMENT OF TYPE 2 DIABETES

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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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:

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IDSource
2414 IUPHAR_LIGAND_ID
4018078 VUID
N0000146417 NUI
C0017628 UMLSCUI
D00336 KEGG_DRUG
CHEMBL472 ChEMBL_ID
DB01016 DRUGBANK_ID
4815 RXNORM
80870001 SNOMEDCT_US
4790 MMSL
d00248 MMSL
4018078 VANDF
597 MMSL
384978002 SNOMEDCT_US
N0000006295 NDFRT
N0000146417 NDFRT
000912 NDDF
3488 PUBCHEM_CID
D005905 MESH_DESCRIPTOR_UI
SX6K58TVWC UNII
2386 INN_ID
CHEBI:5441 CHEBI
GBM PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
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
DiaBeta HUMAN PRESCRIPTION DRUG LABEL 1 0039-0051 TABLET 2.50 mg ORAL NDA 12 sections
DiaBeta HUMAN PRESCRIPTION DRUG LABEL 1 0039-0052 TABLET 5 mg ORAL NDA 12 sections
DiaBeta HUMAN PRESCRIPTION DRUG LABEL 1 0039-0053 TABLET 1.25 mg ORAL NDA 12 sections
GLUCOVANCE HUMAN PRESCRIPTION DRUG LABEL 2 0087-6073 TABLET, FILM COATED 2.50 mg ORAL NDA 13 sections
GLUCOVANCE HUMAN PRESCRIPTION DRUG LABEL 2 0087-6074 TABLET, FILM COATED 5 mg ORAL NDA 13 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 and Metformin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0115-1648 TABLET, FILM COATED 1.25 mg ORAL ANDA 14 sections
Glyburide and Metformin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0115-1649 TABLET, FILM COATED 2.50 mg ORAL ANDA 14 sections
Glyburide and Metformin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0115-1650 TABLET, FILM COATED 5 mg ORAL ANDA 14 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 0378-1113 TABLET 1.50 mg ORAL ANDA 11 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0378-1125 TABLET 3 mg ORAL ANDA 11 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0378-1142 TABLET 6 mg ORAL ANDA 11 sections
Glyburide HUMAN PRESCRIPTION DRUG LABEL 1 0615-1556 TABLET 5 mg ORAL ANDA 11 sections