Carbutamide

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Structural formula
Structural formula of carbutamide
General
Non-proprietary name Carbutamide
other names

1-butyl-3-sulfanilylurea

Molecular formula C 11 H 17 N 3 O 3 S
External identifiers / databases
CAS number 339-43-5
EC number 206-424-4
ECHA InfoCard 100.005.841
PubChem 9564
Wikidata Q5038107
Drug information
ATC code

A10 BB06

properties
Molar mass 271.33 g · mol -1
Physical state

firmly

Melting point

144-145 ° C

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Carbutamide is a chemical compound from the group of the sulfonylureas and sulfonamides , which in 1959 as the first oral antidiabetic agent from Boehringer Mannheim was patented. Carbutamide came onto the market in Germany in 1956 as Oranil or Nadisan . It was developed by Erich Haack (Klinische Tests Hellmuth Kleinsorge ). The preparation was licensed in France to Servier , who sold it for several years.

pharmacology

Like many sulfonamides, carbutamide has a pronounced bacteriostatic effect. By substituting the amino group on the phenyl ring with a methyl group ( tolbutamide ), this undesirable effect was eliminated without losing the blood sugar-lowering property. Carbutamide is therefore no longer used today.

The blood sugar-lowering effect comes about through the release of insulin from the islets of Langerhans in the pancreas (pancreas). It is rapidly absorbed in the body and almost exclusively excreted renally . Hypoglycemia caused by carbutamide can be avoided by combining it with an injection of alcohol .

Individual evidence

  1. ↑ a b c d Entry on carbutamide. In: Römpp Online . Georg Thieme Verlag, accessed on May 7, 2014.
  2. ↑ a b Data sheet 1-Butyl-3-sulfanilylurea from Sigma-Aldrich , accessed on May 7, 2014 ( PDF ).
  3. ↑ Pharmaceutical Newspaper No. 11, 1966, p. 391.
  4. ^ Burkhardt Röper: Competition in the pharmaceutical industry . Duncker & Humblot , 1980, pp. 143 ( limited preview in Google Book search).
  5. ^ W. Creutzfeldt et al. a .: The effect of N1-sulfanilyl-N2-butylcarbamide (carbutamide) on the metabolism of the isolated perfused liver of normal and alloxandiabetic ketotic rats In: Diabetologia . 1967 , Volume 3, pp. 9-19.
  6. ↑ Ernst Mutschler, Monika Schäfer-Korting a. a .: Textbook of pharmacology and toxicology . 8th, completely revised and expanded edition. Wissenschaftliche Verlagsgesellschaft Stuttgart 2001. ISBN 3-8047-1763-2 , p. 415ff.
  7. ↑ Gabriel Pogátsa, Anton Káldor, Elisabeth Bellus, Endre Somogyi: On the effect of insulin, carbutamide and 2-deoxy-d-glucose in acute ethyl alcohol poisoning in rats . In: Klinische Wochenschrift 1965 Volume 48; P. 612.