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

Stem definition	Drug id	CAS RN
antihyperglycaemics	1314	10238-21-8

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
7	mg	O
10	mg	O

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	82 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
t_half (Half-life)	2.20 hours	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
CL (Clearance)	0.82 mL/min/kg	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	0.58 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution)	0.08 L/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.02 %	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.01 mg/mL	Bocci G, Oprea TI, Benet LZ
EoM (Fraction excreted unchanged in urine)	0 %	Benet LZ, Broccatelli F, Oprea TI

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Approvals:

Date	Agency	Company	Orphan
May 1, 1984	FDA	SANOFI AVENTIS US
May 24, 2018	EMA	Ammtek

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Hypoglycaemia	687.39	11.85	364	22527	59701	63406430
Blood glucose increased	357.34	11.85	272	22619	83484	63382647
Cardiac failure congestive	147.33	11.85	174	22717	92259	63373872
Lactic acidosis	140.70	11.85	114	22777	38173	63427958
Coronary artery disease	135.32	11.85	104	22787	32273	63433858
Myocardial infarction	134.92	11.85	173	22718	99720	63366411
Blood glucose decreased	133.30	11.85	87	22804	20865	63445266
Diabetes mellitus inadequate control	119.34	11.85	72	22819	15054	63451077
Glycosylated haemoglobin increased	97.76	11.85	59	22832	12339	63453792
Off label use	73.71	11.85	81	22810	674381	62791750

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Hypoglycaemia	1170.87	12.93	633	24584	54007	34877707
Blood glucose increased	241.28	12.93	268	24949	66450	34865264
Blood glucose decreased	183.45	12.93	116	25101	13121	34918593
Myocardial infarction	152.25	12.93	295	24922	120790	34810924
Coronary artery disease	137.83	12.93	172	25045	48133	34883581
Cardiac failure congestive	136.75	12.93	228	24989	83042	34848672
Lactic acidosis	97.84	12.93	123	25094	34649	34897065
Glycosylated haemoglobin increased	92.74	12.93	72	25145	11288	34920426
Off label use	89.42	12.93	103	25114	419421	34512293
Hyperglycaemia	81.24	12.93	120	25097	39360	34892354

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Hypoglycaemia	1754.83	11.40	903	39010	100691	79603784
Blood glucose increased	478.02	11.40	422	39491	114553	79589922
Myocardial infarction	267.35	11.40	391	39522	183738	79520737
Lactic acidosis	239.19	11.40	231	39682	70128	79634347
Coronary artery disease	237.86	11.40	223	39690	65251	79639224
Cardiac failure congestive	237.16	11.40	323	39590	142079	79562396
Blood glucose decreased	223.86	11.40	148	39765	26086	79678389
Glycosylated haemoglobin increased	162.71	11.40	108	39805	19152	79685323
Off label use	145.91	11.40	144	39769	907071	78797404
Hyperglycaemia	133.12	11.40	170	39743	70165	79634310

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FDA Adverse Event Reporting System (Pediatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Insulin resistance	24.06	8.84	3	4	3	89782

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Pharmacologic Action:

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Source	Code	Description
ATC	A10BB01	ALIMENTARY TRACT AND METABOLISM DRUGS USED IN DIABETES BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS Sulfonylureas
CHEBI has role	CHEBI:35526	antidiabetic
CHEBI has role	CHEBI:38070	antiarrhythmic agent
CHEBI has role	CHEBI:77194	ATP:pantothenate 4-phosphotransferase inhibitor
CHEBI has role	CHEBI:131770	CFTR inhibitors
FDA CS	M0020795	Sulfonylurea Compounds
FDA EPC	N0000175608	Sulfonylurea
MeSH PA	D007004	Hypoglycemic Agents

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Diabetes mellitus type 2	indication	44054006	DOID:9352
Neonatal diabetes mellitus	indication	49817004	DOID:11717
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

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (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:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Sulfonylurea receptor 1, Kir6.2	Ion channel	Q09428 Q14654	ABCC8_HUMAN KCJ11_HUMAN	BLOCKER	Kd	9.52	SCIENTIFIC LITERATURE	SCIENTIFIC LITERATURE
Bile salt export pump	Transporter	O95342	ABCBB_HUMAN		IC50	5.28	CHEMBL
Cytochrome P450 2C9	Enzyme	P11712	CP2C9_HUMAN	INHIBITOR	IC50	5.80	DRUG MATRIX
Peroxisome proliferator-activated receptor gamma	Nuclear hormone receptor	P37231	PPARG_HUMAN		Ki	6.18	CHEMBL
Cystic fibrosis transmembrane conductance regulator	Ion channel	P13569	CFTR_HUMAN	BLOCKER	Ki	4.66	IUPHAR
Sulfonylurea receptor 2, Kir6.2	Ion channel	O60706 Q14654	ABCC9_HUMAN KCJ11_HUMAN	BLOCKER	Ki	8.21	WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2	Ion channel	Q12809	KCNH2_HUMAN		IC50	4.13	CHEMBL
NACHT, LRR and PYD domains-containing protein 3	Unclassified	Q96P20	NLRP3_HUMAN		IC50	4.92	CHEMBL
CDGSH iron-sulfur domain-containing protein 1	Unclassified	Q9NZ45	CISD1_HUMAN		Ki	5.78	CHEMBL
ATP-sensitive inward rectifier potassium channel 11	Ion channel		KCJ11_MOUSE	BLOCKER	IC50	5.70	IUPHAR

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External reference:

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ID	Source
GBM	PDB_CHEM_ID
000912	NDDF
2386	INN_ID
2414	IUPHAR_LIGAND_ID
3488	PUBCHEM_CID
384978002	SNOMEDCT_US
4018078	VUID
4018078	VANDF
4790	MMSL
4815	RXNORM

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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

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