Sulfanilamide

Structural formula
General
Non-proprietary name	Sulfanilamide
other names	4-aminobenzenesulfonamide ( IUPAC ); p -aminobenzenesulfonamide; Sulfanilylamine; 1662 Fourneau ; Prontosil album; Septoplix;
Molecular formula	C 6 H 8 N 2 O 2 S
Brief description	white solid
External identifiers / databases
EC number	200-563-4
ECHA InfoCard	100,000,513
PubChem	5333
ChemSpider	5142
DrugBank	DB00259
Wikidata	Q423423
Drug information
ATC code	J01 EB06 ; D06 BA05 ;
Drug class	Sulfonamides
properties
Molar mass	172.21 g mol −1
Physical state	firmly
density	1.08 g cm −3
Melting point	165-166 ° C
pK s value	10.58
solubility	poorly soluble in water (7.5 g · l −1 at 25 ° C), well in hot water; soluble in acetone , dilute mineral acids and alkalis; very bad in chloroform and diethyl ether ;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	3900 mg kg −1 ( LD 50 , rat , oral ) ; 1400 mg kg −1 ( LD 50 , rat , iv ) ; 3000 mg kg −1 ( LD 50 , mouse , oral ) ; 500 mg kg −1 ( LD 50 , mouse , iv ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Sulfanilamide is a drug from the sulfonamide group that was used as an antibiotic .

history

Elixir sulfanilamide

Sulphanilamide was the first representative of the sulphonamides to be synthesized in 1908 by Paul Gelmo , but it was not until Gerhard Domagk who published his publication in 1935 that he recognized the chemotherapeutic benefits of sulphonamides ( sulfamidochrysoidin , Prontosil ). Sulphanilamide was used therapeutically from 1935, but has been replaced by other sulphonamides.

In 1937, the sulfanilamide disaster in the United States, in which more than a hundred people were killed by sulfanilamide syrup made with diethylene glycol, resulted in the passage of the Federal Food, Drug, and Cosmetic Act , the core of United States drug law .

Extraction and presentation

The three-stage synthesis of the compound starts with acetanilide , which is reacted with chlorosulfonic acid. The target compound is then obtained by converting the acid chloride to the acid amide using ammonia and subsequent saponification of the acetamide function.

Chemical properties

Sulfanilamide belongs to the group of sulfonamides. These consist of a benzene nucleus with an amino and a sulfonamide group. They are all weak organic acids and mostly poorly soluble in water (the sodium salts of the sulfonamides are usually highly soluble in water).

use

Sulfanilamide is mainly used as an antibiotic. It is used in the synthesis of folic acid instead of para-amino benzoic acid incorporated into the folic acid, which thereby becomes ineffective. This does not cause any damage to organisms that have to ingest folic acid through food, such as humans.

It is also the starting material for the production of other derivatives.

safety instructions

Sulfanilamide is a breakdown product of the herbicide asulam .

Web links

Entry on sulfanilamide at Vetpharm, accessed on November 21, 2011.

Individual evidence

↑ ^a ^b ^c ^d ^e Entry on sulfanilamide in the GESTIS substance database of the IFA , accessed on December 14, 2012 (JavaScript required)
↑ ^a ^b Entry on sulfanilamide in the ChemIDplus database of the United States National Library of Medicine (NLM)
↑ ^a ^b ^c Entry on sulfanilamide. In: Römpp Online . Georg Thieme Verlag, accessed on May 6, 2014.
↑ ^a ^b ^c ^d A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th edition (2000), Thieme-Verlag Stuttgart, ISBN 978-1-58890-031 -9
↑ LF Fieser, M. Fieser In: Textbook of organic chemistry. 3. Edition. Verlag Chemie, Weinheim ad Bergstrasse 1957, p. 1193.
^ Domagk: Contribution to the chemotherapy of bacterial infections , German. Med. Wochenschrift, Volume 61, February 15, 1935, pp. 250-253,
Domagk: Chemotherapy of bacterial infections , Angewandte Chemie , Volume 46, 1935, pp. 657-667
↑ Julius Hirsch : The mechanism of action of sulfanilamide therapy. In: İstanbul Seririyatı. No. 5/6, 1942.

[GESTIS-1] Entry on sulfanilamide in the GESTIS substance database of the IFA , accessed on December 14, 2012 (JavaScript required)

[ChemIDplus-2] Entry on sulfanilamide in the ChemIDplus database of the United States National Library of Medicine (NLM)

[roempp-3] Entry on sulfanilamide. In: Römpp Online . Georg Thieme Verlag, accessed on May 6, 2014.

[Kleemann-4] A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th edition (2000), Thieme-Verlag Stuttgart, ISBN 978-1-58890-031 -9

[5] LF Fieser, M. Fieser In: Textbook of organic chemistry. 3. Edition. Verlag Chemie, Weinheim ad Bergstrasse 1957, p. 1193.

[6] Domagk: Contribution to the chemotherapy of bacterial infections , German. Med. Wochenschrift, Volume 61, February 15, 1935, pp. 250-253,
Domagk: Chemotherapy of bacterial infections , Angewandte Chemie , Volume 46, 1935, pp. 657-667

[7] Julius Hirsch : The mechanism of action of sulfanilamide therapy. In: İstanbul Seririyatı. No. 5/6, 1942.