Details of the Drug

General Information of Drug (ID: DMIHRNA)

Drug Name
Tolazamide
Synonyms
Diabewas; Norglycin; Tolamide; Tolanase; Tolazamida; Tolazamidum; Tolazolamide; Tolinase; Pharmacia Brand of Tolazamide; T 2408; U 17835; Tolazamida [INN-Spanish]; Tolazamidum [INN-Latin]; Tolinase (TN); U-17835; Tolazamide (JP15/USP/INN); Tolazamide [USAN:INN:BAN:JAN]; N-(p-Toluenesulfonyl)-N'-hexamethyleniminourea; N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide; N-(((hexahydro-1H-azepin-1-yl)amino)carbonyl)-4-methylbenzenesulfonamide; Benzenesulfonamide, {N-[[(hexahydro-1H-azepin-1-yl)amino]carbonyl]-4-methyl-}; N-(((Hexahydro-1H-azepin-1-yl)-amino)carbonyl)-4-methylbenzenesulfonamide; 1-(((((4-Methylphenyl)sulfonyl)amino)carbonyl)amino)azepane; 1-(Hexahydro-1-azepinyl)-3-p-tolylsulfonylurea; 1-(Hexahydro-1H-azepin-1-yl)-3-(p-toluenesulfonyl)urea; 1-(Hexahydro-1H-azepin-1-yl)-3-(p-tolylsulfonyl)urea; 1-(azepan-1-yl)-3-(4-methylphenyl)sulfonylurea; 3-azepan-1-yl-1-(4-methylphenyl)sulfonyl-urea; 4-(p-Tolylsulfonyl)-1,1-hexamethylene; 4-(p-Tolylsulfonyl)-1,1-hexamethylenesemicarbazide; 59866P
Indication
Disease Entry ICD 11 Status REF
Diabetic complication 5A2Y Approved [1]
Therapeutic Class
Hypoglycemic Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 311.4
Logarithm of the Partition Coefficient (xlogp) 1.5
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 7 hours [3]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 53.62778 micromolar/kg/day [4]
Water Solubility
The ability of drug to dissolve in water is measured as 0.278 mg/mL [2]
Adverse Drug Reaction (ADR)
ADR Term Variation Related DOT DOT ID REF
Encephalopathy Not Available TKT OTT5KPUB [5]
Chemical Identifiers
Formula
C14H21N3O3S
IUPAC Name
1-(azepan-1-yl)-3-(4-methylphenyl)sulfonylurea
Canonical SMILES
CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN2CCCCCC2
InChI
InChI=1S/C14H21N3O3S/c1-12-6-8-13(9-7-12)21(19,20)16-14(18)15-17-10-4-2-3-5-11-17/h6-9H,2-5,10-11H2,1H3,(H2,15,16,18)
InChIKey
OUDSBRTVNLOZBN-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
5503
ChEBI ID
CHEBI:9613
CAS Number
1156-19-0
DrugBank ID
DB00839
TTD ID
D09FJB
INTEDE ID
DR1611
ACDINA ID
D00684

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 [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2C9 (CYP2C9)
Main DME 		DE5IED8 CP2C9_HUMAN Substrate [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Transketolase (TKT) OTT5KPUB TKT_HUMAN Drug Response [5]
Molecular Interaction Atlas (MIA) 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 Tolazamide (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Sodium bicarbonate DMMU6BJ Moderate Decreased absorption of Tolazamide due to altered gastric pH caused by Sodium bicarbonate. Acidosis [5C73] [8]
Tromethamine DMOBLGK Minor as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Tolazamide caused by Tromethamine mediated altered urine pH. Acidosis [5C73] [9]
Oxymetholone DMFXUT8 Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Oxymetholone. Aplastic anaemia [3A70] [10]
Clarithromycin DM4M1SG Moderate Increased plasma concentration of Tolazamide and Clarithromycin due to competitive binding of plasma proteins. Bacterial infection [1A00-1C4Z] [11]
Sulfamethoxazole DMB08GE Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Sulfamethoxazole. Bacterial infection [1A00-1C4Z] [10]
Alpelisib DMEXMYK Moderate Increased metabolism of Tolazamide caused by Alpelisib mediated induction of CYP450 enzyme. Breast cancer [2C60-2C6Y] [12]
Fluoxymesterone DMUHCF1 Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Fluoxymesterone. Breast cancer [2C60-2C6Y] [13]
Fenofibric acid DMGO2MC Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Fenofibric acid. Cardiovascular disease [BA00-BE2Z] [13]
Ketoprofen DMRKXPT Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Ketoprofen. Chronic pain [MG30] [13]
Ardeparin DMYRX8B Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Ardeparin. Coronary thrombosis [BA43] [13]
Ivacaftor DMZC1HS Moderate Decreased metabolism of Tolazamide caused by Ivacaftor mediated inhibition of CYP450 enzyme. Cystic fibrosis [CA25] [14]
MK-8228 DMOB58Q Moderate Increased metabolism of Tolazamide caused by MK-8228 mediated induction of CYP450 enzyme. Cytomegaloviral disease [1D82] [15]
Sertraline DM0FB1J Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Sertraline. Depression [6A70-6A7Z] [13]
Vilazodone DM4LECQ Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Vilazodone. Depression [6A70-6A7Z] [13]
Selegiline DM6034S Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Selegiline. Depression [6A70-6A7Z] [13]
Vortioxetine DM6F1PU Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Vortioxetine. Depression [6A70-6A7Z] [13]
Isocarboxazid DMAF1NB Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Isocarboxazid. Depression [6A70-6A7Z] [13]
Escitalopram DMFK9HG Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Escitalopram. Depression [6A70-6A7Z] [13]
SODIUM CITRATE DMHPD2Y Minor as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Tolazamide caused by SODIUM CITRATE mediated altered urine pH. Discovery agent [N.A.] [9]
Miconazole DMPMYE8 Major Decreased metabolism of Tolazamide caused by Miconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [13]
Sulfinpyrazone DMEV954 Moderate Decreased renal excretion of Tolazamide caused by Sulfinpyrazone. Gout [FA25] [16]
Rifampin DMA8J1G Moderate Increased metabolism of Tolazamide caused by Rifampin mediated induction of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [17]
Rifapentine DMCHV4I Moderate Increased metabolism of Tolazamide caused by Rifapentine mediated induction of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [18]
Etravirine DMGV8QU Moderate Decreased metabolism of Tolazamide caused by Etravirine mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [19]
Gemfibrozil DMD8Q3J Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Gemfibrozil. Hyper-lipoproteinaemia [5C80] [13]
Fenofibrate DMFKXDY Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Fenofibrate. Hyper-lipoproteinaemia [5C80] [13]
Captopril DM458UM Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Captopril. Hypertension [BA00-BA04] [13]
Methyldopa DM5I621 Minor Decreased metabolism of Tolazamide caused by Methyldopa. Hypertension [BA00-BA04] [20]
Quinapril DMR8H31 Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Quinapril. Hypertension [BA00-BA04] [13]
Sodium acetate anhydrous DMH21E0 Minor as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Tolazamide caused by Sodium acetate anhydrous mediated altered urine pH. Hypo-osmolality/hyponatraemia [5C72] [9]
Probenecid DMMFWOJ Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Probenecid. Inborn purine/pyrimidine/nucleotide metabolism error [5C55] [13]
Balsalazide DM7I1T9 Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Balsalazide. Indeterminate colitis [DD72] [13]
Meclofenamic acid DM05FXR Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Meclofenamic acid. Inflammatory spondyloarthritis [FA92] [10]
PF-06463922 DMKM7EW Moderate Increased metabolism of Tolazamide caused by PF-06463922 mediated induction of CYP450 enzyme. Lung cancer [2C25] [21]
Hydroxychloroquine DMSIVND Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Hydroxychloroquine. Malaria [1F40-1F45] [13]
Sulphadoxine DMZI2UF Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Sulphadoxine. Malaria [1F40-1F45] [10]
Dabrafenib DMX6OE3 Moderate Increased metabolism of Tolazamide caused by Dabrafenib mediated induction of CYP450 enzyme. Melanoma [2C30] [21]
Mecasermin DM1O3BY Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Mecasermin. Multiple structural anomalies syndrome [LD2F] [13]
Aspirin DM672AH Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Aspirin. Pain [MG30-MG3Z] [10]
Diflunisal DM7EN8I Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Diflunisal. Pain [MG30-MG3Z] [13]
Ibuprofen DM8VCBE Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Ibuprofen. Pain [MG30-MG3Z] [13]
Safinamide DM0YWJC Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Safinamide. Parkinsonism [8A00] [13]
Rasagiline DM3WKQ4 Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Rasagiline. Parkinsonism [8A00] [13]
Ranitidine DM0GUSX Moderate Decreased absorption of Tolazamide due to altered gastric pH caused by Ranitidine. Peptic ulcer [DA61] [22]
Famotidine DMRL3AB Moderate Decreased absorption of Tolazamide due to altered gastric pH caused by Famotidine. Peptic ulcer [DA61] [22]
Choline salicylate DM8P137 Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Choline salicylate. Postoperative inflammation [1A00-CA43] [10]
Bromfenac DMKB79O Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Bromfenac. Postoperative inflammation [1A00-CA43] [10]
Salsalate DM13P4C Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Salsalate. Rheumatoid arthritis [FA20] [13]
Oxaprozin DM9UB0P Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Oxaprozin. Rheumatoid arthritis [FA20] [13]
Leflunomide DMR8ONJ Moderate Decreased metabolism of Tolazamide caused by Leflunomide mediated inhibition of CYP450 enzyme. Rheumatoid arthritis [FA20] [23]
Salicyclic acid DM2F8XZ Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Salicyclic acid. Seborrhoeic dermatitis [EA81] [10]
Ifosfamide DMCT3I8 Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Ifosfamide. Solid tumour/cancer [2A00-2F9Z] [13]
Methyltestosterone DMWLFGO Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Methyltestosterone. Solid tumour/cancer [2A00-2F9Z] [13]
Pramlintide DM0EZ9Q Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Pramlintide. Type-1/2 diabete [5A10-5A11] [13]
Olsalazine DMZW9HA Moderate Increased risk of hypoglycemia by the combination of Tolazamide and Olsalazine. Ulcerative colitis [DD71] [13]
⏷ Show the Full List of 55 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
Sodium lauryl sulfate E00464 3423265 Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Carmellose sodium E00625 Not Available Disintegrant
Magnesium stearate E00208 11177 lubricant
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Tolazamide 250 mg tablet 250 mg Oral Tablet Oral
Tolazamide 500 mg tablet 500 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: 6847).
2 BDDCS applied to over 900 drugs
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 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
5 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.
6 Inhibition of ATP-activated potassium channels exerts pressor effects and improves survival in a rat model of severe hemorrhagic shock. Shock. 1996 Jun;5(6):391-4.
7 Clinically and pharmacologically relevant interactions of antidiabetic drugs. Ther Adv Endocrinol Metab. 2016 Apr;7(2):69-83.
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13 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]
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