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Tolbutamide information


Not to be confused with topilutamide.
Tolbutamide
Clinical data
Trade namesOrinase
AHFS/Drugs.comMonograph
MedlinePlusa682481
License data
  • US FDA: Tolbutamide
Pregnancy
category
  • AU: C
Routes of
administration		Oral (tablet)
ATC code
  • A10BB03 (WHO) V04CA01 (WHO)
Legal status
Legal status
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic data
Protein binding96%
MetabolismHepatic (CYP2C19-mediated)
Elimination half-life4.5 to 6.5 hours
ExcretionRenal
Identifiers
IUPAC name
  • N-[(Butylamino)carbonyl]-4-methylbenzenesulfonamide
CAS Number
  • 64-77-7 checkY
PubChem CID
  • 5505
IUPHAR/BPS
  • 6848
DrugBank
  • DB01124 checkY
ChemSpider
  • 5304 checkY
UNII
  • 982XCM1FOI
KEGG
  • D00380 checkY
ChEBI
  • CHEBI:27999 checkY
ChEMBL
  • ChEMBL782 checkY
CompTox Dashboard (EPA)
  • DTXSID8021359 Edit this at Wikidata
ECHA InfoCard100.000.541 Edit this at Wikidata
Chemical and physical data
FormulaC12H18N2O3S
Molar mass270.35 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point128.5 to 129.5 °C (263.3 to 265.1 °F)
SMILES
  • O=S(=O)(c1ccc(cc1)C)NC(=O)NCCCC
InChI
  • InChI=1S/C12H18N2O3S/c1-3-4-9-13-12(15)14-18(16,17)11-7-5-10(2)6-8-11/h5-8H,3-4,9H2,1-2H3,(H2,13,14,15) checkY
  • Key:JLRGJRBPOGGCBT-UHFFFAOYSA-N checkY
  (verify)

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.

It was discovered in 1956.[1]

  1. ^ Walker SR (2012). Trends and Changes in Drug Research and Development. Springer Science & Business Media. p. 109. ISBN 978-94-009-2659-2.

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ATC code A10

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