Sulfamerazine

Structural formula
General
Non-proprietary name	Sulfamerazine
other names	4-Amino- N - (4-methylpyrimidin-2-yl) benzenesulfonamide ( IUPAC ); 2-sulfa-4-methylpyrimidine;
Molecular formula	C 11 H 12 N 4 O 2 S
Brief description	yellow-white or pink-white crystalline powder or crystals
External identifiers / databases
EC number	204-866-2
ECHA InfoCard	100.004.425
PubChem	5325
ChemSpider	5134
DrugBank	DB01581
Wikidata	Q415196
Drug information
ATC code	J01 ED07 ; D06 BA06 ;
Drug class	Sulfonamides
properties
Molar mass	264,30 g · mol -1
Physical state	firmly
Melting point	235 ° C (decomposition)
pK s value	7.1 (25 ° C)
solubility	poor in water (350 mg l −1 at 37 ° C and pH 5.5; 1.7 g l −1 at pH 7.5); little in acetone , bad in ethanol , very bad in diethyl ether and chloroform ; quickly soluble in dilute mineral acids and sodium, potassium and ammonium hydroxide solutions;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
Toxicological data	10,000 mg kg −1 ( LD 50 , mouse , oral ) ; 14,000 mg kg −1 ( LD 50 , rat , oral ) ; 1400 mg kg −1 ( LD 50 , mouse , ip ) ; 1190 mg kg −1 ( LD 50 , mouse , sc ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Sulfamerazine (trade names including Trimetox vet. - manufacturer Veyx) is a chemotherapeutic agent in the sulfonamide group , which is indicated as an antibiotic primarily for infections of the respiratory system, urinary tract and ENT area .

To cover a broader spectrum of activity, oral preparation forms are available in combination with trimethoprim .

Clinical information

Application areas (indications)

A combination preparation with trimethoprim is used for infections of the respiratory system, urinary tract and ENT area.

Sulfamerazine is used in veterinary medicine.

Drug interactions

The nephrotoxic effect of cyclosporine A can be increased.

Adverse effects (side effects)

The undesirable effects are essentially the same as those of sulfadiazine and sulfamethoxazole .

Pharmacological properties

Mechanism of action (pharmacodynamics)

The effect is based on the competitive enzyme inhibition in the bacteria during the formation of dihydro folic acid . Sulfamerazine acts as a p -Aminobenzoesäuree - antagonist and thus acts bacteriostatic .

Physical Properties

The compound occurs in two polymorphic crystal forms. Polymorph I melts at 237 ° C. Polymorph II converts to polymorph I in a solid phase transition at 175 ° C. Both forms are enantiotropic to one another.

Residue check

Residues of sulfamerazine in food ( e.g. chicken eggs) from treated animals can be found up to ten days after treatment.

synthesis

Sulfamerazine is made by the condensation of 2-amino-4-methylpyrimidine with acetylsulfanilyl chloride , followed by hydrolysis of the acetyl group :

Synthesis step 1

Synthesis step 2: hydrolysis of the acyl group

Purity testing

The purity test for related substances is carried out with the help of thin layer chromatography (TLC). According to the European Pharmacopoeia , the detection is carried out with fluorescent plates under the UV lamp ( λ = 254 nm), wherein in the case an erasure (dark spot) caused by the UV - absorption of Sulfamerazin- chromophores , can be seen. It is also possible to make the substance stains visible with DMAB (Ehrlich's reagent), which produces a yellow reaction product after heat treatment:

Sulfamerazine reacts with DMABA (Ehrlich's reagent)

storage

Sulfamerazine should be stored away from light.

Trade names

Monotherapy is not recommended.

Trade names of some combination preparations of sulfamerazine are:

Decotox ( vet. ) - Manufacturer Ascor (IT)
Trimetox ( vet. ) - Manufacturer Veyx (DE)
Berlocombin - manufacturer Berlin-Chemie

preparations

Berlocombin 100 suspension and Berlocombin 200 tablets

Individual evidence

↑ European Pharmacopoeia 6.8.
↑ European Pharmacopoeia, Deutscher Apotheker Verlag Stuttgart, 6th edition, 2008, pp. 4033-4034, ISBN 978-3-7692-3962-1 .
↑ ^a ^b ^c ^d ^e ^f DrugBase: Hager's Encyclopedia .
↑ ^a ^b ^c ^d The Merck Index 11 (December 1989). Merck Publications, ISBN 0-911910-28-X .
↑ ^a ^b data sheet Sulfamerazine from Sigma-Aldrich , accessed on April 23, 2011 ( PDF ).
↑ ^a ^b Safety data sheet from Caelo ( Memento from January 17, 2016 in the Internet Archive ).
↑ ^a ^b Entry on sulfamerazine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ ^a ^b ^c Index Nominum: International Drug Directory / Internationales Arzneimittel- und Arzneimittelverzeichnis 2007. Wissenschaftliche Verlagsgesellschaft / Medipharm, ISBN 3-8047-5042-7 .
^ Roche Lexicon Medicine .
↑ Entry on sulfamerazine at Vetpharm, accessed on December 3, 2011.
↑ Zhang, GGZ; Gu, C .; Zell, MT; Burkhardt, RT; Munson, EJ: Crystallization and Transition of Sulfamerazine Polymorphs in J. Pharm. Sci. 91 (2002) 1089-1100.

[1] European Pharmacopoeia 6.8.

[EuropäischesArzneibuch-2] European Pharmacopoeia, Deutscher Apotheker Verlag Stuttgart, 6th edition, 2008, pp. 4033-4034, ISBN 978-3-7692-3962-1 .

[HagersEnzyklop-3] ↑ ^a ^b ^c ^d ^e ^f DrugBase: Hager's Encyclopedia .

[MerckIndexElf-4] The Merck Index 11 (December 1989). Merck Publications, ISBN 0-911910-28-X .

[Sigma-5] ta sheet Sulfamerazine from Sigma-Aldrich , accessed on April 23, 2011 ( PDF ).

[SulfamerazinCealo-6] Safety data sheet from Caelo ( Memento from January 17, 2016 in the Internet Archive ).

[ChemIDplus-7] Entry on sulfamerazine in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[IndexNominum-8] Index Nominum: International Drug Directory / Internationales Arzneimittel- und Arzneimittelverzeichnis 2007. Wissenschaftliche Verlagsgesellschaft / Medipharm, ISBN 3-8047-5042-7 .

[9] Roche Lexicon Medicine .

[10] Entry on sulfamerazine at Vetpharm, accessed on December 3, 2011.

[11] Zhang, GGZ; Gu, C .; Zell, MT; Burkhardt, RT; Munson, EJ: Crystallization and Transition of Sulfamerazine Polymorphs in J. Pharm. Sci. 91 (2002) 1089-1100.