QuickView for Tolbutamide (compound)

Summary
General Info

PubChem

PubChem Compound 5505

Name:	Tolbutamide
PubChem Compound ID:	5505
Description:	A sulphonylurea hypoglycemic agent with actions and uses similar to those of CHLORPROPAMIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290)
Molecular formula:	C₁₂H₁₈N₂O₃S
Molecular weight:	270.349 g/mol
Synonyms:	CAS-64-77-7; 1-Butyl-3-(p-tolylsulfonyl)urea; Diabetol; CBiol_001920; Spectrum3_000599; 3-(p-Tolyl-4-sulfonyl)-1-butylurea; Spectrum2_001210; Spectrum4_000358; N-(Sulfonyl-p-methylbenzene)-N'-butylurea; N-Butyl-N'-(p-tolylsulfonyl)urea. show more » CAS-64-77-7; 1-Butyl-3-(p-tolylsulfonyl)urea; Diabetol; CBiol_001920; Spectrum3_000599; 3-(p-Tolyl-4-sulfonyl)-1-butylurea; Spectrum2_001210; Spectrum4_000358; N-(Sulfonyl-p-methylbenzene)-N'-butylurea; N-Butyl-N'-(p-tolylsulfonyl)urea; NCIOpen2_009592; Mobenol; KBioGR_000795; Oterben; Urea, 1-butyl-3-(p-tolylsulfonyl)-; Benzenesulfonamide, N-[(butylamino)carbonyl]-4-methyl-; Lopac-T-0891; NSC87833; Toluvan; NCGC00022721-03; Diabuton; NINDS_000341; EINECS 200-594-3; Diasulfon; Tarasina; N-Butyl-N'-toluene-p-sulfonylurea; Bio2_000707; Tolylsulfonylbutylurea; CHEBI:27999; Bio1_001184; N-4-Methylbenzolsulfonyl-N-butylurea; CCRIS 592; Drabet; SPBio_002040; Pramidex; Tolbutamidum [INN-Latin]; DivK1c_000341; BRN 1984428; Benzenesulfonamide, N-[ (butylamino)carbonyl]-4-methyl-; Prestwick_471; KBio3_000454; Dolipol; Oralin; Diaben; Orabet; Urea, 1-butyl-3- (p-tolylsulfonyl)-; KBio3_002755; KBio2_002275; KBio2_002795; KBio3_000453; Artosin; Butamidum; Ipoglicone; Tolbutamide (JP15/USP); Tolbutamidum; Orezan; D00380; Tolbet; MLS000028399; NSC 23813; KBioSS_000227; SPBio_001000; Beglucin; NSC23813; SK-Tolbutamide; N-(4-Methylbenzenesulfonyl)-N'-butylurea; Tolumid; AIDS097016; KBio2_003495; SMR000058363; 1-Butyl-3-(p-methylphenylsulfonyl)urea; KBioGR_000227; Orinase; Arkozal; Artozin; N-Butyl-N'-p-toluenesulfonylurea; Tolbusal; 100735-34-0; Benzenesulfonamide, N-((butylamino)carbonyl)-4-methyl-; Diabetamid; Tolbutamide [BAN:INN:JAN]; HSDB 3393; Bio2_000227; KBio2_005363; Rastinon; KBio2_000927; Orinase (TN); KBioSS_000927; N-(p-Tolylsulfonyl)-N'-butylcarbamide; Tolbutone; Prestwick1_000190; KBio2_004843; 1-Butyl-3-tosylurea; KBio1_000341; Dirastan; Spectrum_000447; Bio1_000695; Diabesan; C07148; Butamid; KBio2_006063; Aglicid; N-Butyl-N'-(4-methylphenylsulfonyl)urea; U 2043; Bio1_000206; KBioGR_002275; N-[(butylamino)carbonyl]-4-methylbenzenesulfonamide; AIDS-097016; HLS 831; 64-77-7; ZINC01530703; D 860; KBioSS_002276; N-n-Butyl-N'-tosylurea; Willbutamide; N-4-(Methylbenzolsulfonyl)-n-butylurea; N-(Sulfonyl-p-methylbenzene)-N'-N-butylurea; NCGC00015999-01; Arcosal; NCGC00015999-02; Toluina; Tolbutamide; Orinaz; Tolbutamid; KBio2_000227; 1-p-Toluenesulfonyl-3-butylurea; EU-0101154; Prestwick0_000190; N-((Butylamino)carbonyl)-4-methylbenzenesulfonamide; NCI-C01763; KBio3_001578; N-(4-Methylphenylsulfonyl)-N'-butylurea; Tolbutamida [INN-Spanish]; KBio2_007411; Glyconon; 4-11-00-00396 (Beilstein Handbook Reference); Butamide show less «

DrugBank

Identification

Name:	Tolbutamide
Name (isomeric):	DB01124
Drug Type:	small molecule
Description:	A sulphonylurea hypoglycemic agent with actions and uses similar to those of CHLORPROPAMIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290)
Brand:	Apo-Tolbutamide, Toluvan, Sk-tolbutamide, Artozin, Diaben, Orabet, Diabetamid, Orinase Diagnostic, Drabet, Dolipol, Diabetol, Glyconon, Tolumid, Ipoglicone, Orinaz, Dirastan, Mobenol, Oterben, Rastinon, Diabuton, Tolbutamid, Diasulfon, Tol-Tab, Butamid, Willbutamide, Novo-Butamide, Pramidex, Orinase, Oralin, Toluina, Tolylsulfonylbutylurea, Aglicid, Orezan, Restinon, Arkozal, Tolbusal, Artosin, Butamide
Category:	Hypoglycemic Agents, Sulfonylureas
CAS number:	64-77-7

Pharmacology

Indication:	For treatment of NIDDM (non-insulin-dependent diabetes mellitus) in conjunction with diet and exercise.
Pharmacology:	Tolbutamide, a first-generation sulfonylurea antidiabetic agent, is used with diet to lower blood glucose levels in patients with diabetes mellitus type II. Tolbutamide is twice as potent as the related second-generation agent glipizide. Tolbutamide lowers blood sugar by stimulating the pancreas to secrete insulin and helping the body use insulin e... show more » Tolbutamide, a first-generation sulfonylurea antidiabetic agent, is used with diet to lower blood glucose levels in patients with diabetes mellitus type II. Tolbutamide is twice as potent as the related second-generation agent glipizide. Tolbutamide lowers blood sugar by stimulating the pancreas to secrete insulin and helping the body use insulin efficiently. The pancreas must be able to produce insulin for this drug to work. show less «
Mechanism of Action:	Sulfonylureas lower blood glucose in patients with NIDDM by directly stimulating the acute release of insulin from functioning beta cells of pancreatic islet tissue by an unknown process that involves a sulfonylurea receptor (receptor 1) on the beta cell. Sulfonylureas inhibit the ATP-potassium channels on the beta cell membrane and potassium efflu... show more » Sulfonylureas lower blood glucose in patients with NIDDM by directly stimulating the acute release of insulin from functioning beta cells of pancreatic islet tissue by an unknown process that involves a sulfonylurea receptor (receptor 1) on the beta cell. Sulfonylureas inhibit the ATP-potassium channels on the beta cell membrane and potassium efflux, which results in depolarization and calcium influx, calcium-calmodulin binding, kinase activation, and release of insulin-containing granules by exocytosis, an effect similar to that of glucose. show less «
Absorption:	Readily absorbed following oral administration. Tolbutamide is detectable in plasma 30-60 minutes following oral administration of a single dose with peak plasma concentrations occurring within 3-5 hours. Absorption is unaltered if taken with food but is increased with high pH.
Protein binding:	Approximately 95% bound to plasma proteins.
Biotransformation:	Metabolized in the liver principally via oxidation of the p-methyl group producing the carboxyl metabolite, 1-butyl-3-p-carboxyphenylsulfonylurea. May also be metabolized to hydroxytolbutamide. Tolbutamide does not undergo acetylation like antibacterial sulfonamides as it does not have a p-amino group.
Route of elimination:	Unchanged drug and metabolites are eliminated in the urine and feces. Approximately 75-85% of a single orally administered dose is excreted in the urine principally as the 1-butyl-3-p-carboxyphenylsulfonylurea within 24 hours.
Half Life:	Approximately 7 hours with interindividual variations ranging from 4-25 hours. Tolbutamide has the shortest duration of action, 6-12 hours, of the antidiabetic sulfonylureas.
Toxicity:	Oral, mouse: LD₅₀ = 2600 mg/kg
Affected organisms:	Humans and other mammals

Interactions

Drug interaction:

Piroxicam	Piroxicam, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Piroxicam is initiated, discontinued or dose changed.
Montelukast	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Montelukast. Consider alternate therapy or monitor for changes in Montelukast therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Mefenamic acid	Mefanamic acid, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Mefanamic acid is initiated, discontinued or dose changed.
Digoxin	Tolbutamide increases the effect of digoxin
Sulfisoxazole	Tolbutamide and Sulfisoxazole are strong CYP2C9 inhibitors and substrates. Decreased metabolism and clearance of both agents may occur during concomitant therapy. Consider alternate therpy or monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or dose(s) changed.

Piroxicam	Piroxicam, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Piroxicam is initiated, discontinued or dose changed.
Montelukast	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Montelukast. Consider alternate therapy or monitor for changes in Montelukast therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Mefenamic acid	Mefanamic acid, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Mefanamic acid is initiated, discontinued or dose changed.
Digoxin	Tolbutamide increases the effect of digoxin
Sulfisoxazole	Tolbutamide and Sulfisoxazole are strong CYP2C9 inhibitors and substrates. Decreased metabolism and clearance of both agents may occur during concomitant therapy. Consider alternate therpy or monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or dose(s) changed.
Gemfibrozil	Gemfibrozil, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Gemfibrozil is initiated, discontinued or dose changed.
Sulfadiazine	Tolbutamide and Sulfadiazine are strong CYP2C9 inhibitors and substrates. Decreased metabolism and clearance of both agents may occur during concomitant therapy. Consider alternate therpy or monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or dose(s) changed.
Clofibrate	Clofibrate may increase the effect of sulfonylurea, tolbutamide.
Mestranol	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Mestranol. Consider alternate therapy or monitor for changes in Mestranol therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Celecoxib	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Celecoxib. Consider alternate therapy or monitor for changes in Celecobix therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Rifampin	Rifampin may decrease the effect of sulfonylurea, tolbutamide.
Glimepiride	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Glimepiride. Consider alternate therapy or monitor for changes in Glimepiride therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Fluoxetine	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Fluoxetine. Consider alternate therapy or monitor for changes in Fluoxetine therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Warfarin	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if tolbutamide is initiated, discontinued or dose changed.
Bisoprolol	The beta-blocker, bisoprolol, may decrease symptoms of hypoglycemia.
Atenolol	The beta-blocker, atenolol, may decrease symptoms of hypoglycemia.
Losartan	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Losartan. Consider alternate therapy or monitor for changes in Losartan therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Nateglinide	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Nateglinide. Consider alternate therapy or monitor for changes in Nateglinide therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Floxuridine	Floxuridine, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Floxuridine is initiated, discontinued or dose changed.
Bosentan	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Bosentan. Consider alternate therapy or monitor for changes in Bosentan therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Paclitaxel	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Paclitaxel. Consider alternate therapy or monitor for changes in Paclitaxel therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Propranolol	The beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
Labetalol	The beta-blocker, labetalol, may decrease symptoms of hypoglycemia.
Sulfinpyrazone	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Sulfinpyrazone. Consider alternate therapy or monitor for changes in Sulfinpyrazone therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Zafirlukast	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of zafirlukast. Consider alternate therapy or monitor for changes in zafirlukast therapeutic and adverse effects if tolbutamide is initiated, discontinued or dose changed.
Glipizide	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Glipizide. Consider alternate therapy or monitor for changes in Glipizide therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Trimethoprim	The strong CYP2C9 inhibitor, Tolbutamide, may decrease the metabolism and clearance of Trimethoprim, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimethoprim if Tolbutamide is initiated, discontinued or dose changed.
Acebutolol	Acebutolol may decrease symptoms of hypoglycemia and increase the time required for the body to compensate for hypoglycemia.
Chloramphenicol	Chloramphenicol may increase the effect of sulfonylurea, tolbutamide.
Sulfamethoxazole	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Sulfamethoxazole. Consider alternate therapy or monitor for changes in Sulfamethoxazole therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Fosphenytoin	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Fosphenytoin. Consider alternate therapy or monitor for changes in Fosphenytoin therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Dapsone	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Dapsone. Consider alternate therapy or monitor for changes in Dapsone therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Ketamine	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Ketamine. Consider alternate therapy or monitor for changes in Ketamine therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Voriconazole	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Voriconazole. Consider alternate therapy or monitor for changes in Voriconazole therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Acenocoumarol	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Acenocoumarol. Consider alternate therapy or monitor for changes in Acenocoumarol therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Indomethacin	Indomethacin, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Indomethacin is initiated, discontinued or dose changed.
Oxprenolol	The beta-blocker, oxprenolol, may decrease symptoms of hypoglycemia.
Miconazole	Miconazole, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Miconazole is initiated, discontinued or dose changed.
Esmolol	The beta-blocker, esmolol, may decrease symptoms of hypoglycemia.
Somatropin recombinant	Somatropin may antagonize the hypoglycemic effect of Tolbutamide. Dose adjustments of Tolbutamide may be required.
Metoprolol	The beta-blocker, metoprolol, may decrease symptoms of hypoglycemia.
Capecitabine	Capecitabine, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Capecitabine is initiated, discontinued or dose changed.
Phenytoin	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Phenytoin. Consider alternate therapy or monitor for changes in Phenytoin therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Timolol	The beta-blocker, timolol, may decrease symptoms of hypoglycemia.
Lumiracoxib	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Lumiracoxib. Consider alternate therapy or monitor for changes in Lumiracoxib therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Zopiclone	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Zopiclone. Consider alternate therapy or monitor for changes in Zopiclone therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Pindolol	The beta-blocker, pindolol, may decrease symptoms of hypoglycemia.
Fluorouracil	Fluorouracil, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Fluorouracil is initiated, discontinued or dose changed.
Phenylbutazone	Phenylbutazone increases the effect of the hypoglycemic agent
Nadolol	The beta-blocker, nadolol, may decrease symptoms of hypoglycemia.
Delavirdine	Delavirdine, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Delavirdine is initiated, discontinued or dose changed.
Torasemide	Tolbutamide, a strong CYP2C9 inhibitor, may increase the serum concentration of Torasemide, a CYP2C9 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Torasemide if Tolbutamide is initiated, discontinued or dose changed.
Carvedilol	The beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.
Acetylsalicylic acid	Acetylsalicylic acid increases the effect of the sulfonylurea, tolbutamide.
Tamoxifen	Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tamoxifen. Consider alternate therapy or monitor for changes in Tamoxifen therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Fluconazole	Fluconazole, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Fluconazole therapeutic and adverse effects if Delavirdine is initiated, discontinued or dose changed.
Ibuprofen	Ibuprofen, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Ibuprofen is initiated, discontinued or dose changed.
Ketoconazole	Ketoconazole, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Ketoconazole is initiated, discontinued or dose changed.
Sitaxentan	Sitaxsentan, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Sitaxsentan is initiated, discontinued or dose changed.
Flurbiprofen	Flurbiprofen, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Flurbiprofen is initiated, discontinued or dose changed.
Nicardipine	Nicardipine, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Nicardipine is initiated, discontinued or dose changed.

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Targets

ATP-binding cassette transporter sub-family C member 8

ATP-sensitive inward rectifier potassium channel 1

Enzymes

Transporters

Oligopeptide transporter, small intestine isoform

Solute carrier organic anion transporter family member 1A2

Solute carrier family 22 member 6

Oligopeptide transporter, kidney isoform

Solute carrier organic anion transporter family member 2B1