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.
Originator
Elkosin,Ciba,US,1951
Uses
Sulfisomidine is a sulfanilamide antibacterial agent.
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.
