KIMIA ORGANIK 3 Prodi Farmasi
Fakultas Farmasi dan Sains
Pertemuan 12
Sintesa Senyawa Obat Turunan Sulfonamida
• Sulfonamida (atau sering juga disebut obat sulfa) merupakan golongan obat-obatan yang memiliki gugus fungsi sulfonamide
• Golongan obat ini ada yang memiliki sifat antimikroba dan ada juga yang tidak.
• Obat sulfa yang tidak memiliki aktivitas antibakteri misalnya sultiam yang digunakan sebagai antikonvulsan, juga sulfonilurea dan diuretik tiazid.
• Sulfonamid digunakan untuk mengobati alergi dan batuk, serta fungsi antijamur dan antimalaria.
• Golongan obat ini juga terdapat dalam obat lain yang bukan
antimikroba, termasuk diuretik tiazid (termasuk hidroklorotiazid, metolazon, dan indapamide), diuretik loop (termasuk furosemid, bumetanid, dan torsemid), asetazolamid, sulfonilurea (termasuk
glipizid, gliburid atau glibenklamid), dan beberapa penghambat COX-2 (misalnya selekosib).
• Sulfasalazin, selain digunakan sebagai antibiotik, juga digunakan dalam pengobatan penyakit radang usus.
• Obat sulfonamida pertama bermerek dagang Prontosil.
• Penelitian mengenai protonsil ini dimulai pada 1932 pada laboratorium Bayer AG.
• Sulfanilamide (also spelled sulphanilamide) is a sulfonamide antibacterial drug.
• Chemically, it is an organic compound consisting of an aniline derivatized with a sulfonamide group
• Powdered sulfanilamide was used by the Allies in World War II to reduce infection rates and contributed to a dramatic reduction in mortality rates compared to previous wars.
• Modern antibiotics have supplanted sulfanilamide on the battlefield;
however, sulfanilamide remains in use today, primarily for treatment of vaginal yeast infections.
• Sulfanilamide was first prepared in 1908 by the Austrian chemist Paul Josef Jakob Gelmo (1879–1961)
• as part of his dissertation for a doctoral degree from the Technische Hochschule of Vienna. It was patented in 1909.
• Gerhard Domagk, who directed the testing of the prodrug Prontosil in 1935, and Jacques and Thérèse Tréfouël, who along with Federico
Nitti and Daniel Bovet in the laboratory of Ernest Fourneau at the Pasteur Institute, determined sulfanilamide as the active form, are generally credited with the discovery of sulfanilamide as a
chemotherapeutic agent. Domagk was awarded the Nobel Prize for his work.
• In 1937 Elixir sulfanilamide, a medicine where the sulfanilamide was synthesized using diethylene glycol as a solvent, poisoned and killed more than 100 people as a result of acute kidney failure, prompting new US regulation for drug testing. In 1938, the Food, Drug and
Cosmetic Act was passed.
• Sulfathiazole is an organosulfur compound used as a short-acting
sulfa drug. Formerly, it was a common oral and topical antimicrobial, until less toxic alternatives were discovered.
• Sulfathiazole exists in various forms (polymorphs). The imine
tautomer is dominant, at least in the solid state. In this tautomer, the proton resides on the ring nitrogen.
• Sulfadiazine is an antibiotic.Used together with pyrimethamine, it is the treatment of choice for toxoplasmosis. It is a second-line
treatment for otitis media, prevention of rheumatic fever, chancroid, chlamydia, and infections by Haemophilus influenzae. It is taken by mouth.
• Common side effects include nausea, diarrhea, headache, fever, rash, depression, and pancreatitis. It should not be used in people who
have severe liver problems, kidney problems, or porphyria.
• If used during pregnancy, it may increase the risk of kernicterus in the baby. While the company that makes it does not recommend use
during breastfeeding, use is believed to be safe if the baby is otherwise healthy. It is in the sulfonamide class of medications.
• Sulfadiazine was approved for medical use in the United States in 1941. It is on the World Health Organization's List of Essential
Medicines. Sulfadiazine is available as a generic medication.
