Sulfadimidine

Structural formula
General
Surname	Sulfadimidine
other names	Sulfamethazine; 4-Amino- N - (4,6-dimethylpyrimidin-2-yl) benzene sulfonamide ( IUPAC ); N 1 - (4,6-dimethylpyrimidin-2-yl) sulfanilamide; 2-sulfa-4,6-dimethylpyrimidine;
Molecular formula	C 12 H 14 N 4 O 2 S
Brief description	White dust
External identifiers / databases
EC number	200-346-4
ECHA InfoCard	100,000,315
PubChem	5327
ChemSpider	5136
DrugBank	DB01582
Wikidata	Q3976823
Drug information
ATC code	J01 EB03
properties
Molar mass	278.3 g mol −1
Melting point	197-200 ° C
pK s value	pK s 1 = 7.4; pK s 2 = 2.65;
solubility	sparingly soluble in water and ether ; easily soluble in acetone ; Easily soluble in dilute mineral acids and aqueous alkalis;
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	1.6 g kg −1 ( LD 50 , mouse , ip )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Sulfadimidine (also sulfamethazine ) is an antibiotic from the group of sulfonamides , which is used as a sodium salt in veterinary medicine for the treatment of bacterial and parasitic infectious diseases (for example coccidiosis or diphtheroid diseases). In contrast to other sulfonamides, the medium-acting drug is used therapeutically as a single substance.

history

Sulfadimidine was discovered by Ward Blenkinsop in 1942 , by ICI in 1943, by Sharp & Dohme in 1946, and by Ist in 1964. Chemioterap. Ital. patented. The patent protection has now expired. The substance was brought onto the market as a diazil by the company Cilag (see also Bracco (company) ).

Extraction and presentation

Sulfadimidine can be obtained by reaction of 4-acetylaminobenzenesulfonyl chloride with 2-amino-4,6-dimethylpyrimidine and subsequent hydrolysis of the acetylamino group is synthesized. For this, the 2-amino-4,6-dimethylpyrimidine is in turn produced by condensation of acetylacetone with guanidine . It can also be prepared directly by reacting sulfanilylguanidine with acetylacetone.

Clinic and Pharmacology

Sulfadimidine competitively inhibits an enzyme in the metabolic pathway of folic acid synthesis, which catalyzes the formation of dihydropteroic acid. The toxicity of the antibiotic is low. Some chickens are an exception , as toxic effects can occur even in the therapeutic dose range. After use, sulfadimidine lowers the laying performance.

Trivia

Sulfadimidine is not a poison for certain soil-dwelling bacteria, but rather a welcome source of food. The compound that is used in animal husbandry reaches fields and the soil via the manure. The bacteria, which belong to the genus Microbacterium , use the nitrogen and carbon from the chemical compound specifically for their metabolism.

Individual evidence

↑ ^a ^b ^c data sheet sulfamethazine from Sigma-Aldrich , accessed on June 3, 2017 ( PDF ).
↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on sulfadimidine. In: Römpp Online . Georg Thieme Verlag, accessed on July 26, 2014.
↑ Prof. Dr. Michael Fehr, Dr. Lutz Sassenburg, Prof. Dr. Peernel Zwart: Diseases of pets . Schlütersche, 2014, ISBN 978-3-8426-8593-2 , p. 235 ( limited preview in Google Book Search).
↑ Gerrit Dirksen: Internal medicine and surgery of the cattle . Georg Thieme Verlag, 2006, ISBN 978-3-8304-4169-4 , p. 290 ( limited preview in Google Book Search).
^ Joint FAO / WHO Expert Committee on Food Additives: Residues of Some Veterinary Drugs in Animals and Foods Monographs Prepared by the Thirty-Fourth Meeting of the Joint FAO / WHO Expert Committee on Food Additives, Geneva, 30 January-8 February 1989 . Food & Agriculture Org., 1990, ISBN 978-92-5102933-6 , pp. 101 ( limited preview in Google Book search).
↑ Karl Wurm, AM Walter: Infectious Diseases. In: Ludwig Heilmeyer (ed.): Textbook of internal medicine. Springer-Verlag, Berlin / Göttingen / Heidelberg 1955; 2nd edition, ibid. 1961, pp. 9-223, here: pp. 43-45.
^ Ruben Vardanyan, Victor Hruby: Synthesis of Essential Drugs . Elsevier, 2006, ISBN 978-0-08-046212-7 , pp. 503 ( limited preview in Google Book search).
^ Profiles of Drug Substances, Excipients and Related Methodology . Academic Press, 1978, ISBN 978-0-08-086102-9 , pp. 413 ( limited preview in Google Book search).
^ IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, International Agency for Research on Cancer, World Health Organization: Some Thyrotropic Agents . World Health Organization, 2001, ISBN 978-92-832-1279-9 , pp. 341 ( limited preview in Google Book search).
↑ H. Frey, W. Löscher u. a .: Textbook of pharmacology and toxicology for veterinary medicine . 3. Edition. Enke, 2009, ISBN 978-3-8304-1079-9 , pp. 452ff.
↑ Reinhard Röder: Veterinary Medicines in the Environment . Oldenbourg Industrieverlag, 2007, ISBN 978-3-8356-3135-9 , p. 98 ( limited preview in Google Book search).
↑ Bild der Wissenschaft: Antibiotic becomes bacterial feed - Bild der Wissenschaft , accessed on July 1, 2017.
↑ Edward Topp, Ralph Chapman, Marion Devers-Lamrani, Alain Hartmann, Romain Marti, Fabrice Martin-Laurent, Lyne Sabourin, Andrew Scott, Mark Sumarah: Accelerated Biodegradation of Veterinary Antibiotics in Agricultural Soil following Long-Term Exposure, and Isolation of a Sulfamethazine-degrading sp. In: Journal of Environment Quality. 42, 2013, p. 173, doi : 10.2134 / jeq2012.0162 .

[Sigma-1] ta sheet sulfamethazine from Sigma-Aldrich , accessed on June 3, 2017 ( PDF ).

[RömppOnline-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on sulfadimidine. In: Römpp Online . Georg Thieme Verlag, accessed on July 26, 2014.

[Prof._Dr._Michael_Fehr,_Dr._Lutz_Sassenburg,_Prof._Dr._Peernel_Zwart-3] Prof. Dr. Michael Fehr, Dr. Lutz Sassenburg, Prof. Dr. Peernel Zwart: Diseases of pets . Schlütersche, 2014, ISBN 978-3-8426-8593-2 , p. 235 ( limited preview in Google Book Search).

[Gerrit_Dirksen-4] Gerrit Dirksen: Internal medicine and surgery of the cattle . Georg Thieme Verlag, 2006, ISBN 978-3-8304-4169-4 , p. 290 ( limited preview in Google Book Search).

[Joint_FAO/WHO_Expert_Committee_on_Food_Additives-5] Joint FAO / WHO Expert Committee on Food Additives: Residues of Some Veterinary Drugs in Animals and Foods Monographs Prepared by the Thirty-Fourth Meeting of the Joint FAO / WHO Expert Committee on Food Additives, Geneva, 30 January-8 February 1989 . Food & Agriculture Org., 1990, ISBN 978-92-5102933-6 , pp. 101 ( limited preview in Google Book search).

[6] Karl Wurm, AM Walter: Infectious Diseases. In: Ludwig Heilmeyer (ed.): Textbook of internal medicine. Springer-Verlag, Berlin / Göttingen / Heidelberg 1955; 2nd edition, ibid. 1961, pp. 9-223, here: pp. 43-45.

[Ruben_Vardanyan,_Victor_Hruby-7] Ruben Vardanyan, Victor Hruby: Synthesis of Essential Drugs . Elsevier, 2006, ISBN 978-0-08-046212-7 , pp. 503 ( limited preview in Google Book search).

[8] Profiles of Drug Substances, Excipients and Related Methodology . Academic Press, 1978, ISBN 978-0-08-086102-9 , pp. 413 ( limited preview in Google Book search).

[IARC_Working_Group_on_the_Evaluation_of_Carcinogenic_Risks_to_Humans,_International_Agency_for_Research_on_Cancer,_World_Health_Organization-9] IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, International Agency for Research on Cancer, World Health Organization: Some Thyrotropic Agents . World Health Organization, 2001, ISBN 978-92-832-1279-9 , pp. 341 ( limited preview in Google Book search).

[Frey-10] H. Frey, W. Löscher u. a .: Textbook of pharmacology and toxicology for veterinary medicine . 3. Edition. Enke, 2009, ISBN 978-3-8304-1079-9 , pp. 452ff.

[Reinhard_Röder-11] Reinhard Röder: Veterinary Medicines in the Environment . Oldenbourg Industrieverlag, 2007, ISBN 978-3-8356-3135-9 , p. 98 ( limited preview in Google Book search).

[bild_der_wissenschaft-12] Bild der Wissenschaft: Antibiotic becomes bacterial feed - Bild der Wissenschaft , accessed on July 1, 2017.

[DOI10.2134/jeq2012.0162-13] Edward Topp, Ralph Chapman, Marion Devers-Lamrani, Alain Hartmann, Romain Marti, Fabrice Martin-Laurent, Lyne Sabourin, Andrew Scott, Mark Sumarah: Accelerated Biodegradation of Veterinary Antibiotics in Agricultural Soil following Long-Term Exposure, and Isolation of a Sulfamethazine-degrading sp. In: Journal of Environment Quality. 42, 2013, p. 173, doi : 10.2134 / jeq2012.0162 .