Tolbutamide

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Tolbutamide

Clinical data
Trade names	Orinase
AHFS/Drugs.com	Monograph
MedlinePlus	a682481
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 binding	96%
Metabolism	Hepatic (CYP2C19-mediated)
Elimination half-life	4.5 to 6.5 hours
Excretion	Renal
Identifiers
IUPAC name N-[(Butylamino)carbonyl]-4-methylbenzenesulfonamide
CAS Number	64-77-7 Y
PubChem CID	5505
IUPHAR/BPS	6848
DrugBank	DB01124 Y
ChemSpider	5304 Y
UNII	982XCM1FOI
KEGG	D00380 Y
ChEBI	CHEBI:27999 Y
ChEMBL	ChEMBL782 Y
CompTox Dashboard (EPA)	DTXSID8021359
ECHA InfoCard	100.000.541
Chemical and physical data
Formula	C12H18N2O3S
Molar mass	270.35 g·mol−1
3D model (JSmol)	Interactive image
Melting point	128.5 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) Y Key:JLRGJRBPOGGCBT-UHFFFAOYSA-N Y
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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]