Sulphonamide. 1. Sulfonamide (Sulpha Drugs) S.SEETARAM SWAMY, M.Pharm., Asst. Professor, Dept. Fashion popcorn cindy sherman for machine.

Of Pharmaceutical Chemistry, E-mail:seetaram.443@gmail.com. Building on Ehrlich’s early work, Gerhard Domagk, a medical doctor employed by a German dye manufacturer made a breakthrough discovery by finding that a dye known as prontosil, dosed orally, was effective in curing life threatening streptococci infections in humans.

He made the discovery in a desperate, but successful attempt to save his daughter who was dying of a streptococci infection. PRONTOSIL SH2N O O NH2 SN O O NH2N NH2 H2N NH2 H2N NH2 Prontosil Sulfanilamide Metabolisim In-Vivo German bacteriologist and pathologist who was awarded the 1939 Nobel Prize for Physiology or Medicine for his discovery (announced in 1932) of the antibacterial effects of Prontosil, the first of the sulfonamide drugs. Recognized since 1932. In clinical usage since 1935.

First compounds found to be effective antibacterial agents in safe dose ranges. Chemically, it is a molecule containing the sulfonamido (sulfanilamide, SO2NH2) functional group attached to an aniline. Structurally related to p-amino benzoic acid (PABA). This group is also present in other non-antibacterial compounds like -Sulphonureas -Benzothiazids -Furosemide -Acetazolamide They act as antimicrobial agents by inhibiting bacterial growth and activity and commonly called sulfa drugs. Chemistry of Sulfonamide.

Sulfonamide molecular structure is similar to p-Amino benzoic acid (PABA) which is needed in bacteria organisms as a substrate of the enzyme dihydro pteroate synthetase for the synthesis of Tetra Hydro Folic acid (THF). Folic acid - synthesized from PABA, pteridine and glutamate. All sulfonamides are analogs of PABA.

All sulfa drugs are bacteriostatic. Mechanism of Sulfonamide. SH2N O O NH R 4 3 2 1 p-Amino group Aromatic ring Sulfanilamide group N1 -Substitution group The amino & Sulphonyl groups on the benzene ring are essential & should be in 1,4-position Replacement of Aromatic ring by other ring systems or the introduction of additional substituents on it decreases or abolish activity. Exchange of the -SO2NH group by –CO-NH reduce the activity. Substitution of Aromatic Heterocyclic nuclei at N1 - yields highly potent compounds. N1 –Di substitution in general leads to inactive.

Sulfonamides Ppt Presentations

SulfonamidesPHRM 304: Antibiotics and chemotherapeutic agents No relation with any natural product Not properly termed as antibiotic For example: SulfonamidesSynthetic Antimicrobial AgentsAntibacterial agents which act against cell metabolism (antimetabolites)The best examples of antibacterial agents acting as antimetabolites are the sulfonamides (also known as sulfa drugs).Sulfonamides:History The sulfonamide story began in 1935 when it was discovered that a red dye called prontosil had antibacterial properties in vivo (in animals). Strangely enough, no antibacterial effect was observed in vitro (in petri dish).

Sulfonamides Presentation

This remained a mystery until it was discovered that prontosil was not in fact the antibacterial agent.It was found that the dye was metabolized by bacteria present in the small intestine, and broken down to give a product called sulfanilamide. It was this compound which was the true antibacterial agent. Thus, prontosil was the first example of a prodrug. Sulfanilamide was synthesized in the laboratory and became the first synthetic antibacterial agent active against a wide range of infections.Fig. In vivo metabolism of prontosilFurther developments led to a range of sulfonamides which proved effective against Grampositive organisms, especially pneumococci and meningococci. Despite their undoubted benefits, sulfa drugs have proved ineffective against infections such as Salmonella (Gram-negative)- the organism responsible for typhoid.

Sulfonamides Presentation

Other problems have resulted from the way these drugs are metabolized, since toxic products are frequently obtained.