Sulfacytine Chemical Properties

pka

6.9(at 25℃)

Sulfacytine Usage And Synthesis

Uses

Antibacterial.

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.

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