Uses
Sulfacytine is a soluble short-acting sulfonamide. Sulfacytine is used as an oral antibiotic.
Definition
ChEBI: Sulfacytine is a member of benzenes and a sulfonamide.
brand name
Renoquid (Glenwood).
Antimicrobial activity
This drug is effective for infections caused by streptococci, gonococci, pneumococci, staphylococci, and also colon bacillus. Sulfacytine is used for pneumonia, cerebral meningitis,
staphylococcal and streptococcal sepsis, and other infectious diseases. A synonym of this
drug is renoquid.
Synthesis
Sulfacytine, N1-(1-ethyl-1,2-dihydro-2-oxo-4-pyrimidinyl)-sulfanilamide
(33.1.5), is synthesized by reacting 4-acetylaminobenzenesulfonyl chloride with 1-ethyl-cytosine (33.1.3) followed by reductive deacylation of the acetanilide part of the molecule (33.1.4)
using a system of zinc ¨C sodium hydroxide, which gives the desired sulfacytine.
1-Ethylcytosine (33.1.3) is in turn synthesized from 3-ethylaminopropionitrile, which is
reacted with cyanic acid (potassium cyanate¨Chydrochloric acid) in the first stage of synthesis
to give 1-(2-cyanoethyl)-1-ethylurea (33.1.1). This easily cyclizes to 1-ethyl-5,6-dihydrocytosine in the presence of sodium methoxide, and is isolated in the form of a hydrobromide
(33.1.2) for subsequent oxidation of the ordinary C5¨CC6 bond. Bromine turns out to be the
optimal oxidant for this purpose, and using nitrobenzene as the solvent gives a heteroaromatic amine, 1-ethylcytosine (33.1.3), which was transformed to the desired sulfacytine in
the aforementioned manner?a by reacting it with 4-acetylaminobenzenesulfonyl chloride and
subsequent removal of the protecting acetyl group from the amine part of the molecule.
