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SULFISOMIDINE

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SULFISOMIDINE Basic information

Product Name:
SULFISOMIDINE
Synonyms:
  • (p-aminobenzolsulfonyl)-4-amino-2,6-dimethylpyrimidin
  • (p-Aminobenzolsulfonyl)-4-amino-2,6-dimethylpyrimidine
  • 2,4-Dimethyl-6-sulfanilamidopyrimidine
  • 2,6-Dimethyl-4-sulfanilamidopyrimidine
  • 4-amino-n-(2,6-dimethyl-4-pyrimidinyl)-benzenesulfonamid
  • 4-Sulfa-2,6-dimethylpyrimidine
  • 4-Sulfanilamido-2,6-dimethylpyrimidine
  • 6-(4-Aminobenzenesulfonamido)-2,4-dimethylpyrimidine
CAS:
515-64-0
MF:
C12H14N4O2S
MW:
278.33
EINECS:
208-204-3
Mol File:
515-64-0.mol
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SULFISOMIDINE Chemical Properties

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)
form 
Solid
color 
White to Off-White
Water Solubility 
1.382g/L(25 ºC)
Merck 
8951
BRN 
261305
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Safety Information

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
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SULFISOMIDINE Usage And Synthesis

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.

SULFISOMIDINESupplier

J & K SCIENTIFIC LTD.
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