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Substance Name: Tolbutamide [USP:INN:BAN:JAN]
RN: 64-77-7
UNII: 982XCM1FOI
InChIKey: JLRGJRBPOGGCBT-UHFFFAOYSA-N

Note

  • A sulphonylurea hypoglycemic agent with actions and uses similar to those of CHLORPROPAMIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290)

Molecular Formula

  • C12-H18-N2-O3-S

Molecular Weight

  • 270.3512
 

Classification Codes

  • Antidiabetic
  • Drug / Therapeutic Agent
  • Human Data
  • Hypoglycemic Agents
  • Mutation Data
  • Reproductive Effect
  • Tumor Data

Names and Synonyms

Name of Substance

  • Tolbutamide
  • Tolbutamide [USP:INN:BAN:JAN]

MeSH Heading

  • Tolbutamide

Synonyms

  • 1-Butyl-3-(p-methylphenylsulfonyl)urea
  • 1-Butyl-3-(p-tolylsulfonyl)urea
  • 1-Butyl-3-tosylurea
  • 1-p-Toluenesulfonyl-3-butylurea
  • 3-(p-Tolyl-4-sulfonyl)-1-butylurea
  • 4-11-00-00396 (Beilstein Handbook Reference)
  • Aglicid
  • Arcosal
  • Arkozal
  • Artosin
  • Artozin
  • Beglucin
  • Benzenesulfonamide, N-((butylamino)carbonyl)-4-methyl-
  • BRN 1984428
  • Butamid
  • Butamide
  • Butamidum
  • CCRIS 592
  • D 860
  • Diaben
  • Diabesan
  • Diabetamid
  • Diabetol
  • Diabuton
  • Diasulfon
  • Dirastan
  • Dolipol
  • Drabet
  • EINECS 200-594-3
  • Glyconon
  • HLS 831
  • HSDB 3393
  • Ipoglicone
  • Mobenol
  • N-((Butylamino)carbonyl)-4-methylbenzenesulfonamide
  • N-(4-Methylbenzenesulfonyl)-N'-butylurea
  • N-(4-Methylphenylsulfonyl)-N'-butylurea
  • N-(p-Tolylsulfonyl)-N'-butylcarbamide
  • N-(Sulfonyl-p-methylbenzene)-N'-butylurea
  • N-(Sulfonyl-p-methylbenzene)-N'-N-butylurea
  • N-4-(Methylbenzolsulfonyl)-n-butylurea
  • N-4-Methylbenzolsulfonyl-N-butylurea
  • N-Butyl-N'-(4-methylphenylsulfonyl)urea
  • N-Butyl-N'-(p-tolylsulfonyl)urea
  • N-Butyl-N'-p-toluenesulfonylurea
  • N-n-Butyl-N'-tosylurea
  • NCI-C01763
  • NSC 23813
  • Orabet
  • Oralin
  • Orezan
  • Orinase
  • Orinaz
  • Oterben
  • Pramidex
  • Rastinon
  • SK-Tolbutamide
  • Tarasina
  • Tolbet
  • Tolbusal
  • Tolbutamid
  • Tolbutamida
  • Tolbutamida [INN-Spanish]
  • Tolbutamide
  • Tolbutamidum
  • Tolbutamidum [INN-Latin]
  • Tolbutone
  • Toluina
  • Tolumid
  • Toluvan
  • Tolylsulfonylbutylurea
  • U 2043
  • UNII-982XCM1FOI
  • Urea, 1-butyl-3-(p-tolylsulfonyl)-
  • Willbutamide

Systematic Names

  • Benzenesulfonamide, N-((butylamino)carbonyl)-4-methyl-
  • Tolbutamide
  • Urea, 1-butyl-3-(p-tolylsulfonyl)-

Superlist Name

  • Tolbutamide

Registry Numbers

CAS Registry Number

  • 64-77-7

FDA UNII

  • 982XCM1FOI

Other Registry Number

  • 100735-34-0

System Generated Number

  • 0000064777

Structure Descriptors

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)

InChIKey

JLRGJRBPOGGCBT-UHFFFAOYSA-N

Smiles

CCCCNC(=O)NS(=O)(=O)c1ccc(cc1)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 intraperitoneal 750mg/kg (750mg/kg)   Farmatsevtichnii Zhurnal Vol. (1), Pg. 51, 1985.
mouse LD50 intraperitoneal 650mg/kg (650mg/kg) BEHAVIORAL: ATAXIA

ENDOCRINE: HYPOGLYCEMIA
Toxicology and Applied Pharmacology. Vol. 4, Pg. 631, 1962.
mouse LD50 intravenous 770mg/kg (770mg/kg)   Progress in Medical Chemistry. Vol. 1, Pg. 187, 1961.
mouse LD50 oral 490mg/kg (490mg/kg)   International Journal of Crude Drug Research. Vol. 26, Pg. 81, 1988.
mouse LD50 subcutaneous 980mg/kg (980mg/kg)   Nature. Vol. 193, Pg. 891, 1962.
mouse LD50 unreported 700mg/kg (700mg/kg)   Farmatsevtichnii Zhurnal Vol. (5), Pg. 26, 1983.
rat LD50 intraperitoneal 860mg/kg (860mg/kg)   Farmaco, Edizione Scientifica. Vol. 12, Pg. 268, 1957.
rat LD50 intravenous 700mg/kg (700mg/kg)   Progress in Medical Chemistry. Vol. 1, Pg. 187, 1961.
rat LD50 oral 2490mg/kg (2490mg/kg)   Progress in Medical Chemistry. Vol. 1, Pg. 187, 1961.
women LDLo oral 1gm/kg (1000mg/kg) ENDOCRINE: HYPOGLYCEMIA

GASTROINTESTINAL: NAUSEA OR VOMITING
Archiv fuer Toxikologie. Vol. 23, Pg. 153, 1968.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 128.5 deg C   EXP
pKa Dissociation Constant 5.16 (none)   EXP
log P (octanol-water) 2.34 (none)   EXP
Water Solubility 109 mg/L 37 EXP
Vapor Pressure 2.74E-08 mm Hg 25 EST
Henry's Law Constant 2.53E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.07E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.