Structure via PubChem · Public domain (PubChem)
tolbutamide
Sign in to saveAlso known as Orinase®, tolbutamide sodium, N-n-Butyl-N'-tosylurea, N-Butyl-N'-(p-tolylsulfonyl)urea, N-Butyl-N'-(4-methylphenylsulfonyl)urea, N-(4-Methylphenylsulfonyl)-N'-butylurea, 1-Butyl-3-tosylurea, 1-Butyl-3-(p-tolylsulfonyl)urea
Tolbutamide is a first-generation potassium channel blocker, sulfonylurea oral hypoglycemic medication. This drug may be used in the management of type 2 diabetes if diet alone is not effective. Tolbutamide stimulates the secretion of insulin by the pancreas.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 470611441
- Drug.IUPAC_name
- N-[(Butylamino)carbonyl]-4-methylbenzenesulfonamide
- Drug.image
- Tolbutamide.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 250
- Drug.tradename
- Orinase
- Drug.MedlinePlus
- a682481
- Drug.licence_US
- Tolbutamide
- Drug.pregnancy_AU
- C
- Drug.pregnancy_US
- C
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
- Drug.routes_of_administration
- Oral (tablet)
- Drug.protein_bound
- 96%
- Drug.metabolism
- Hepatic (CYP2C19-mediated)
- Drug.elimination_half life
- 4.5 to 6.5 hours
- Drug.excretion
- Renal
via Wikipedia infobox
Chemical data
- Formula
- C12H18N2O3S
- Molecular weight
- 270.35 g/mol
- IUPAC name
- 1-butyl-3-(4-methylphenyl)sulfonylurea
- SMILES
- CCCCNC(=O)NS(=O)(=O)C1=CC=C(C=C1)C
- InChIKey
- JLRGJRBPOGGCBT-UHFFFAOYSA-N
- XLogP
- 2.3
- Polar surface area
- 83.7 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
6,862 papers- Tolbutamide and diabetes.Canadian Medical Association journal · 1971
- Tolbutamide-induced hemolytic anemia.Diabetes · 1977
- Tolbutamide photosensitivity.Journal of the Indian Medical Association · 1984
- Tolbutamide-associated hyponatremia.JAMA · 1978
- Tolbutamide: teratogenic effects.Indian pediatrics · 1991
via PubMed
Wikidata facts
- Mass
- 270.104
Show 8 more facts
- chemical formula
- C₁₂H₁₈N₂O₃S
- defined daily dose
- 1.5
- isomeric SMILES
- CCCC/N=C(/NS(=O)(=O)C1=CC=C(C=C1)C)\O
- canonical SMILES
- CCCCNC(=O)NS(=O)(=O)C1=CC=C(C=C1)C
- World Health Organisation international non-proprietary name
- tolbutamide
- melting point
- 129
- Commons category
- Tolbutamide
- stylized name
- TOLBUTamide
Sources (7)
via Wikidata · CC0
~9 min read
Article
5 sectionsContents
- Side effects
- History
- Historical consequences
- See also
- References
Tolbutamide is a first-generation potassium channel blocker, sulfonylurea oral hypoglycemic medication. This drug may be used in the management of type 2 diabetes if diet alone is not effective. Tolbutamide stimulates the secretion of insulin by the pancreas.
It is not routinely used due to a higher incidence of adverse effects compared to newer, second-generation sulfonylureas, such as Glibenclamide. It generally has a short duration of action due to its rapid metabolism, so is safe for use in older people.