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Sulphonamide drugs and their mechanism
Submitted by: Hassan khalid 3216
Submitted to: Dr. Afzal qamar
• Gerhard Domagk (1895–1964) discovered
• sulfa drugs in 1935.
• Mietzsch and Klarer for Domagk to test
were some related to the azo dyes. They
had the characteristic -N=N- coupling of azo dyes, but
one of the hydrogens attached to nitrogen had been
replaced by a sulfonamide group.
• In 1931 the two chemists presented a compound (KL 695)
that, although it proved inactive in vitro, was weakly active
in laboratory mice infected with streptococcus.
History
• The chemists made substitutions in the structure
of this molecule and, several months and
35 compounds later, produced KL 730, which
showed incredible antibacterial effects on diseased
laboratory mice. It was named prontosil rubrum and
patented as Prontosil.
• Among the early patients was Domagk’s own six-year-old
daughter, Hildegard, who had contracted a severe
streptococcal infection from an unsterilized needle.
Prontosil-the first sulfonamide drug
• Sulfonamides (sulphonamides) are a group of
man-made (synthetic) medicines that contain the
sulfonamide chemical group. They may also be
called sulfa drugs.
or
• The sulfa-related group of antibiotics, which are
used to treat bacterial infection and some fungal
infections.
What are sulfonamides
Brands of Sulphamethoxazole
(sulphonamide)
• Aksotran tablets (Rs:260 )
Sulphamethoxazole : 800 mg/5ml
Trimethoprin : 160mg/5ml
• Bactrim tablets (Rs:280)
Sulphamethoxazole : 200mg/5ml
Trimethoprin : 40mg/5ml
• Dosatran suspension (Rs:400/400ml)
Sulphamethoxazole : 400mg/5ml
Trimethoprin : 80mg/5ml
• Fedran tablets (Rs: 260)
Sulphamethoxazole : 400mg/5ml
Trimethoprin : 80mg/5ml
 Molecular formula: C10H11N3O3S
 Molar mass: 253.279 g/mol
 Elimination half-life: 10 hours
 Metabolism: Hepatic acetylation and glucuronidat
ion
 Excretion: Renal
 Protein binding: 70%
Chemical properties of Sulfamethoxazole
 Formula: C14H18N4O3
 Metabolism: hepatic
 Elimination half-life: 8–12 hours
 Protein binding: 44%
 Bioavailability: 90–100%
 Excretion: Urine (50–60%), faeces (4%)
Chemical properties of Trimethoprim
Structural Formulas of Trimethoprim and
sulfamethoxazole
Sulfonamides structurally resemble p-
aminobenzoic acid (PABA), a precursor in
bacterial DHF synthesis. As false substrates,
sulfonamides competitively inhibit utilization of
PABA, and hence DHF synthesis. Because most
bacteria cannot take up exogenous folate, they are
depleted of DHF.
Mechanism of Action
Biosynthesis of bacterial dihydrofolic acid
Dihydropterote synthase use of sulfametaxazol
Instead of p-aminobenzoic acid
Side Effects
Common Side effects
 Dizziness
 Lethargy
 Diarrhea
 Anorexia
 Nausea
 Vomiting
 rash
Other Side effects
• liver damage,
• low white blood cell count,
• low platelet
count (thrombocytopenia),
and
• anemia.
Sulfa drugs and mechanism of action

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Sulfa drugs and mechanism of action

  • 1. Sulphonamide drugs and their mechanism Submitted by: Hassan khalid 3216 Submitted to: Dr. Afzal qamar
  • 2. • Gerhard Domagk (1895–1964) discovered • sulfa drugs in 1935. • Mietzsch and Klarer for Domagk to test were some related to the azo dyes. They had the characteristic -N=N- coupling of azo dyes, but one of the hydrogens attached to nitrogen had been replaced by a sulfonamide group. • In 1931 the two chemists presented a compound (KL 695) that, although it proved inactive in vitro, was weakly active in laboratory mice infected with streptococcus. History
  • 3. • The chemists made substitutions in the structure of this molecule and, several months and 35 compounds later, produced KL 730, which showed incredible antibacterial effects on diseased laboratory mice. It was named prontosil rubrum and patented as Prontosil. • Among the early patients was Domagk’s own six-year-old daughter, Hildegard, who had contracted a severe streptococcal infection from an unsterilized needle. Prontosil-the first sulfonamide drug
  • 4. • Sulfonamides (sulphonamides) are a group of man-made (synthetic) medicines that contain the sulfonamide chemical group. They may also be called sulfa drugs. or • The sulfa-related group of antibiotics, which are used to treat bacterial infection and some fungal infections. What are sulfonamides
  • 5. Brands of Sulphamethoxazole (sulphonamide) • Aksotran tablets (Rs:260 ) Sulphamethoxazole : 800 mg/5ml Trimethoprin : 160mg/5ml • Bactrim tablets (Rs:280) Sulphamethoxazole : 200mg/5ml Trimethoprin : 40mg/5ml • Dosatran suspension (Rs:400/400ml) Sulphamethoxazole : 400mg/5ml Trimethoprin : 80mg/5ml • Fedran tablets (Rs: 260) Sulphamethoxazole : 400mg/5ml Trimethoprin : 80mg/5ml
  • 6.  Molecular formula: C10H11N3O3S  Molar mass: 253.279 g/mol  Elimination half-life: 10 hours  Metabolism: Hepatic acetylation and glucuronidat ion  Excretion: Renal  Protein binding: 70% Chemical properties of Sulfamethoxazole
  • 7.  Formula: C14H18N4O3  Metabolism: hepatic  Elimination half-life: 8–12 hours  Protein binding: 44%  Bioavailability: 90–100%  Excretion: Urine (50–60%), faeces (4%) Chemical properties of Trimethoprim
  • 8. Structural Formulas of Trimethoprim and sulfamethoxazole
  • 9. Sulfonamides structurally resemble p- aminobenzoic acid (PABA), a precursor in bacterial DHF synthesis. As false substrates, sulfonamides competitively inhibit utilization of PABA, and hence DHF synthesis. Because most bacteria cannot take up exogenous folate, they are depleted of DHF. Mechanism of Action
  • 10. Biosynthesis of bacterial dihydrofolic acid
  • 11. Dihydropterote synthase use of sulfametaxazol Instead of p-aminobenzoic acid
  • 12. Side Effects Common Side effects  Dizziness  Lethargy  Diarrhea  Anorexia  Nausea  Vomiting  rash Other Side effects • liver damage, • low white blood cell count, • low platelet count (thrombocytopenia), and • anemia.