SULFISOMIDINE Property

Melting point:

245°C

Boiling point:

294°C (rough estimate)

Density 

1.2997 (rough estimate)

refractive index 

1.6440 (estimate)

storage temp. 

0-6°C

solubility 

Acetonitrile (Slightly), DMSO (Slightly)

pka

pKa 7.25 (Uncertain)

color 

White to Off-White

Water Solubility 

1.382g/L(25 ºC)

Merck 

8951

BRN 

261305

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36-26

RIDADR 

3249

WGK Germany 

2

RTECS 

WO9270000

HazardClass 

6.1(b)

PackingGroup 

III

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

SULFISOMIDINE Chemical Properties,Usage,Production

Originator

Elkosin,Ciba,US,1951

Uses

Sulfisomidine is a sulfanilamide antibacterial agent.

Definition

ChEBI: A sulfonamide consisting of pyrimidine having methyl substituents at the 2- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position.

Manufacturing Process

This starting material can be prepared as follows. 123 parts of finely powdered 6-amino-2,4-dimethylpyrimidine are suspended in 250 parts of dry pyridine and 222 parts of p-nitrobenzenesulfonyl chloride added at 50°C to 55°C. The whole is then warmed for 2 hours to 55°C. Water is added to the crystalline aggregate obtained, the precipitated bis-N-(pnitrobenzenesulfonyl)- 6-amino-2,4-dimethylpyrimidine filtered off by suction and washed with water. It is purified by recrystallizing from methyl ethyl ketone. On slowly heating it decomposes; on rapidly heating it melts at about 210°C to 215°C with decomposition.
49.3 parts of bis-N-(p-nitrobenzenesulfonyl)-6-amino-2,4-dimethylpyrimidine are heated to boiling for one hour with 12.3 parts of 6-amino-2,4- dimethylpyrimidine in 50 parts of dry pyridine. After cooling, the 6-(pnitrobenzenesulfonamido)- 2,4-dimethylpyrimidine formed is precipitated with water and filtered off by suction. It is purified by dissolving in dilute caustic soda and precipitating with acid. On recrystallization from dilute alcohol it melts (with decomposition) at 188°C to 189°C.
On reaction, for example, with iron and hydrochloric acid, 6-(paminobenzenesulfonamido)- 2,4-dimethylpyrimidine, melting point 236°C is obtained.

brand name

Isosulf;Oestro-gynedron;Poly-gynedron;Sulfamethine;Tricho-gynedron.

Therapeutic Function

Antibacterial

World Health Organization (WHO)

Sulfisomide, a sulfonamide anti-infective agent, was introduced several decades ago for the treatment of bacterial infections. The importance of sulfonamides has subsequently decreased as a result of increasing resistance and their replacement by antibiotics which are generally more active and less toxic. The sulfonamides are known to cause serious adverse effects such as renal toxicity, sometimes fatal exfoliative dermatitis and erythema multiforma and dangerous adverse reactions affecting blood formation such as agranulocytosis and haemolytic or aplastic anaemia. Sulfisomide is still used topically in some countries for vaginal infection.

Pharmaceutical Applications

6-Sulfanilamido-2,4-dimethylpyrimidine (syn: sulphasomidine). A highly soluble sulfonamide with a plasma half-life of 6–8 h. Protein binding is about 90%. Activity is similar to that of sulfadiazine. It is less extensively metabolized than most other sulfonamides and is largely excreted unchanged in the urine.