Details of the Drug

General Information of Drug (ID: DMZA5PQ)

Drug Name

Glipizide

Synonyms

Aldiab; Digrin; Dipazide; Glibenese; Glibetin; Glican; Glide; Glidiab; Glidiazinamide; Glipid; Glipizida; Glipizidum; Glucolip; Glucotrol; Glucozide; Glupitel; Glupizide; Glyde; Glydiazinamide; Glypidizine; Melizide; Metaglip; Mindiab; Minidab; Minidiab; Minodiab; Napizide; Ozidia; Semiglynase; Sucrazide; Alphapharm Brand of Glipizide; Glibenese Brand of Glipizide; Glipizide Kenfarma Brand; Glucotrol XL; Kenfarma Brand of Glipizide; Lacer Brand of Glipizide; Lilly Brand of Glipizide; CP 28720; K 4024; K4024; PfizerBrand 1 of Glipizide; Pfizer Brand 2 of Glipizide; TK 1320; CP 28,720; CP-28720; G-117; Glipizida [INN-Spanish]; Glipizide Extended-Release Tablets; Glipizidum [INN-Latin]; Gluco-Rite; Glucotrol (TN); K-4024; KS-1068; Samarium(III) ionophore I; Glipizide (USP/INN); Glipizide [USAN:BAN:INN]; Glucotrol XL, Glucotrol, Glipizide; N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-5-methylpyrazine-2-carboxamide; N-(2-{4-[(cyclohexylcarbamoyl)sulfamoyl]phenyl}ethyl)-5-methylpyrazine-2-carboxamide; N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-5-methylpyrazine-2-carboxamide; N-(4-(beta-(5-Methylpyrazine-2-carboxamido)ethyl)benzenesulphonyl)-N'-cyclohexylurea; 1-Cyclohexyl-3-((p-(2-(5-methylpyrazinecarboxamido)ethyl)phenyl)sulfonyl)urea; 1-Cyclohexyl-3-{4-[2-(5-methylpyrazine-2-carboxamido)ethyl]phenylsulfonyl}urea

Indication

Disease Entry	ICD 11	Status	REF
Diabetic complication	5A2Y	Approved	[1]
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Therapeutic Class

Hypoglycemic Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

445.5

Logarithm of the Partition Coefficient (xlogp)

1.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]
Bioavailability: The bioavailability of drug is 100% [3]
Clearance: The total body clearance of drug is 3 L/h []
Elimination: 4.5% of drug is excreted from urine in the unchanged form [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 2 - 5 hours [4]
Metabolism: The drug is metabolized via the hepatic []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.9619 micromolar/kg/day [5]
Unbound Fraction: The unbound fraction of drug in plasma is 0.02% [4]
Vd: The volume of distribution (Vd) of drug is 10 L [6]

Adverse Drug Reaction (ADR)

ADR Term	Variation	Related DOT	DOT ID	REF
Liver disorder	Not Available	SLC2A4	OTJZG0LD	[7]
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Chemical Identifiers

Formula: C21H27N5O4S
IUPAC Name: N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-5-methylpyrazine-2-carboxamide
Canonical SMILES: CC1=CN=C(C=N1)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCCCC3
InChI: InChI=1S/C21H27N5O4S/c1-15-13-24-19(14-23-15)20(27)22-12-11-16-7-9-18(10-8-16)31(29,30)26-21(28)25-17-5-3-2-4-6-17/h7-10,13-14,17H,2-6,11-12H2,1H3,(H,22,27)(H2,25,26,28)
InChIKey: ZJJXGWJIGJFDTL-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 3478
ChEBI ID: CHEBI:5384
CAS Number: 29094-61-9
DrugBank ID: DB01067
TTD ID: D0Z4SB
VARIDT ID: DR00329
INTEDE ID: DR0778
ACDINA ID: D00303

Combinatorial Drugs (CBD)

Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Inward rectifier potassium channel Kir1.2 (KCNJ10)	TTG140O	KCJ10_HUMAN	Blocker	[8]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Bile salt export pump (ABCB11)	DTJ0EW4	ABCBB_HUMAN	Substrate	[9]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[10]
Cytochrome P450 2C9 (CYP2C9)	DE5IED8	CP2C9_HUMAN	Substrate	[11]
UDP-glucuronosyltransferase 1A1 (UGT1A1)	DEYGVN4	UD11_HUMAN	Substrate	[12]
Mephenytoin 4-hydroxylase (CYP2C19)	DEGTFWK	CP2CJ_HUMAN	Substrate	[13]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Aldo-keto reductase family 1 member C1 (AKR1C1)	OTQKR4CM	AK1C1_HUMAN	Gene/Protein Processing	[14]
Aldo-keto reductase family 1 member C2 (AKR1C2)	OTQ2XMO3	AK1C2_HUMAN	Gene/Protein Processing	[14]
Aldo-keto reductase family 1 member C3 (AKR1C3)	OTU2SXBA	AK1C3_HUMAN	Gene/Protein Processing	[14]
Bile salt export pump (ABCB11)	OTRU7THO	ABCBB_HUMAN	Gene/Protein Processing	[9]
Solute carrier family 2, facilitated glucose transporter member 4 (SLC2A4)	OTJZG0LD	GLUT4_HUMAN	Drug Response	[7]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Glipizide (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Sodium bicarbonate	DMMU6BJ	Moderate	Decreased absorption of Glipizide due to altered gastric pH caused by Sodium bicarbonate.	Acidosis [5C73]	[15]
Tromethamine	DMOBLGK	Minor	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Glipizide caused by Tromethamine mediated altered urine pH.	Acidosis [5C73]	[16]
Arn-509	DMT81LZ	Moderate	Increased metabolism of Glipizide caused by Arn-509 mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[17]
Oxymetholone	DMFXUT8	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Oxymetholone.	Aplastic anaemia [3A70]	[18]
Clarithromycin	DM4M1SG	Moderate	Increased plasma concentration of Glipizide and Clarithromycin due to competitive binding of plasma proteins.	Bacterial infection [1A00-1C4Z]	[19]
Alpelisib	DMEXMYK	Moderate	Increased metabolism of Glipizide caused by Alpelisib mediated induction of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[20]
Fluoxymesterone	DMUHCF1	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Fluoxymesterone.	Breast cancer [2C60-2C6Y]	[18]
Fenofibric acid	DMGO2MC	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Fenofibric acid.	Cardiovascular disease [BA00-BE2Z]	[18]
Ardeparin	DMYRX8B	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Ardeparin.	Coronary thrombosis [BA43]	[18]
Ivacaftor	DMZC1HS	Moderate	Decreased metabolism of Glipizide caused by Ivacaftor mediated inhibition of CYP450 enzyme.	Cystic fibrosis [CA25]	[21]
MK-8228	DMOB58Q	Moderate	Increased metabolism of Glipizide caused by MK-8228 mediated induction of CYP450 enzyme.	Cytomegaloviral disease [1D82]	[22]
Sertraline	DM0FB1J	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Sertraline.	Depression [6A70-6A7Z]	[18]
Vilazodone	DM4LECQ	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Vilazodone.	Depression [6A70-6A7Z]	[18]
Vortioxetine	DM6F1PU	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Vortioxetine.	Depression [6A70-6A7Z]	[18]
Isocarboxazid	DMAF1NB	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Isocarboxazid.	Depression [6A70-6A7Z]	[18]
Escitalopram	DMFK9HG	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Escitalopram.	Depression [6A70-6A7Z]	[18]
SODIUM CITRATE	DMHPD2Y	Minor	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Glipizide caused by SODIUM CITRATE mediated altered urine pH.	Discovery agent [N.A.]	[16]
Miconazole	DMPMYE8	Major	Decreased metabolism of Glipizide caused by Miconazole mediated inhibition of CYP450 enzyme.	Fungal infection [1F29-1F2F]	[18]
Sunitinib	DMCBJSR	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Sunitinib.	Gastrointestinal stromal tumour [2B5B]	[18]
Sulfinpyrazone	DMEV954	Moderate	Decreased renal excretion of Glipizide caused by Sulfinpyrazone.	Gout [FA25]	[17]
Rifapentine	DMCHV4I	Moderate	Increased metabolism of Glipizide caused by Rifapentine mediated induction of CYP450 enzyme.	HIV-infected patients with tuberculosis [1B10-1B14]	[23]
Etravirine	DMGV8QU	Moderate	Decreased metabolism of Glipizide caused by Etravirine mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[24]
Gemfibrozil	DMD8Q3J	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Gemfibrozil.	Hyper-lipoproteinaemia [5C80]	[18]
Captopril	DM458UM	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Captopril.	Hypertension [BA00-BA04]	[18]
Sodium acetate anhydrous	DMH21E0	Minor	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Glipizide caused by Sodium acetate anhydrous mediated altered urine pH.	Hypo-osmolality/hyponatraemia [5C72]	[16]
PF-06463922	DMKM7EW	Moderate	Increased metabolism of Glipizide caused by PF-06463922 mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[25]
Hydroxychloroquine	DMSIVND	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Hydroxychloroquine.	Malaria [1F40-1F45]	[18]
Sulphadoxine	DMZI2UF	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Sulphadoxine.	Malaria [1F40-1F45]	[18]
Dabrafenib	DMX6OE3	Moderate	Increased metabolism of Glipizide caused by Dabrafenib mediated induction of CYP450 enzyme.	Melanoma [2C30]	[25]
Mecasermin	DM1O3BY	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Mecasermin.	Multiple structural anomalies syndrome [LD2F]	[18]
Rucaparib	DM9PVX8	Moderate	Decreased metabolism of Glipizide caused by Rucaparib mediated inhibition of CYP450 enzyme.	Ovarian cancer [2C73]	[26]
Safinamide	DM0YWJC	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Safinamide.	Parkinsonism [8A00]	[18]
Rasagiline	DM3WKQ4	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Rasagiline.	Parkinsonism [8A00]	[18]
Choline salicylate	DM8P137	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Choline salicylate.	Postoperative inflammation [1A00-CA43]	[18]
Enzalutamide	DMGL19D	Moderate	Increased metabolism of Glipizide caused by Enzalutamide mediated induction of CYP450 enzyme.	Prostate cancer [2C82]	[27]
Salsalate	DM13P4C	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Salsalate.	Rheumatoid arthritis [FA20]	[18]
Leflunomide	DMR8ONJ	Moderate	Decreased metabolism of Glipizide caused by Leflunomide mediated inhibition of CYP450 enzyme.	Rheumatoid arthritis [FA20]	[28]
Ifosfamide	DMCT3I8	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Ifosfamide.	Solid tumour/cancer [2A00-2F9Z]	[18]
Methyltestosterone	DMWLFGO	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Methyltestosterone.	Solid tumour/cancer [2A00-2F9Z]	[18]
Pramlintide	DM0EZ9Q	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Pramlintide.	Type-1/2 diabete [5A10-5A11]	[18]
Olsalazine	DMZW9HA	Moderate	Increased risk of hypoglycemia by the combination of Glipizide and Olsalazine.	Ulcerative colitis [DD71]	[18]
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⏷ Show the Full List of 41 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
Butylated hydroxytoluene	E00336	31404	Antioxidant
FD&C blue no. 2	E00446	2723854	Colorant
Glyceryl monostearate	E00310	24699	Emollient; Emulsifying agent; Emulsion stabilizing agent; Solubilizing agent; Surfactant; Viscosity-controlling agent
Isopropyl alcohol	E00070	3776	Antimicrobial preservative; Solvent
Sodium stearyl fumarate	E00545	23665634	lubricant
Stearic acid	E00079	5281	Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Sunset yellow FCF	E00255	17730	Colorant
Acetyltributyl citrate	E00127	6505	Plasticizing agent
Ammonia	E00007	222	Alkalizing agent
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Butyl alcohol	E00011	263	Flavoring agent; Solvent
Carmellose sodium	E00625	Not Available	Disintegrant
Eisenoxyd	E00585	56841934	Colorant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Hypromellose	E00634	Not Available	Coating agent
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Polyethylene glycol 3350	E00652	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 400	E00653	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polysorbate 80	E00665	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Sodium chloride	E00077	5234	Diluent; Tonicity agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Triacetin	E00080	5541	Humectant; Plasticizing agent; Solvent
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⏷ Show the Full List of 28 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Glipizide 2.5 mg tablet	2.5 mg	24 HR Extended Release Oral Tablet	Oral
Glipizide 5 mg tablet	5 mg	24 HR Extended Release Oral Tablet	Oral
Glipizide 10 mg tablet	10 mg	24 HR Extended Release Oral Tablet	Oral
Glipizide 10 mg tablet	10 mg	Oral Tablet	Oral
Glipizide 5 mg tablet	5 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6821).
2	BDDCS applied to over 900 drugs
3	Melander A, Wahlin-Boll E: Clinical pharmacology of glipizide. Am J Med. 1983 Nov 30;75(5B):41-5.
4	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6	Glipizide 5 mg Tablets - Summary of Product Characteristics (SmPC) - European Medicines Agency
7	ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
8	Triggering and amplification of insulin secretion by dimethyl alpha-ketoglutarate, a membrane permeable alpha-ketoglutarate analogue. Eur J Pharmacol. 2009 Apr 1;607(1-3):41-6.
9	Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43.
10	Repaglinide : a pharmacoeconomic review of its use in type 2 diabetes mellitus. Pharmacoeconomics. 2004;22(6):389-411.
11	Clinical consequences of cytochrome P450 2C9 polymorphisms. Clin Pharmacol Ther. 2005 Jan;77(1):1-16.
12	Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8.
13	Pharmacokinetics of chlorpheniramine, phenytoin, glipizide and nifedipine in an individual homozygous for the CYP2C9*3 allele. Pharmacogenetics. 1999 Feb;9(1):71-80.
14	Initro inhibition of AKR1Cs by sulphonylureas and the structural basis. Chem Biol Interact. 2015 Oct 5;240:310-5.
15	Kivisto KT, Neuvonen PJ "Effect of magnesium hydroxide on the absorption and efficacy of tolbutamide and chlorpropamide." Eur J Clin Pharmacol 42 (1992): 675-80. [PMID: 1623912]
16	Kivisto KT, Neuvonen PJ "Differential effects of sodium bicarbonate and aluminium hydroxide on the absorption and activity of glipizide." Eur J Clin Pharmacol 40 (1991): 383-6. [PMID: 1646724]
17	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
18	Abad S, Moachon L, Blanche P, Bavoux F, Sicard D, Salmon-Ceron D "Possible interaction between glicazide, fluconazole and sulfamethoxazole resulting in severe hypoglycaemia." Br J Clin Pharmacol 52 (2001): 456-7. [PMID: 11678792]
19	Bussing R, Gende A "Severe hypoglycemia from clarithromycin-sulfonylurea drug interaction." Diabetes Care 25 (2002): 1659-61. [PMID: 12196446]
20	Product Information. Piqray (alpelisib). Novartis Pharmaceuticals, East Hanover, NJ.
21	Product Information. Kalydeco (ivacaftor). Vertex Pharmaceuticals, Cambridge, MA.
22	Product Information. Prevymis (letermovir). Merck & Company Inc, Whitehouse Station, NJ.
23	Product Information. Priftin (rifapentine). Hoechst Marion-Roussel Inc, Kansas City, MO.
24	Product Information. Intelence (etravirine). Ortho Biotech Inc, Bridgewater, NJ.
25	Cerner Multum, Inc. "Australian Product Information.".
26	EMA. European Medicines Agency. European Union "EMA - List of medicines under additional monitoring.".
27	Benoist G, van Oort I, et al "Drug-drug interaction potential in men treated with enzalutamide: Mind the gap." Br J Clin Pharmacol 0 (2017): epub. [PMID: 28881501]
28	Product Information. Arava (leflunomide). Hoechst Marion-Roussel Inc, Kansas City, MO.