Overview of Antibacterial Sulfonamides in Pharmaceutical Chemistry

 
Assist . Prof . Karima F. Ali
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Antibacterial sulfonamides
The sulfonamide antimicrobial drugs were the first
effective chemotherapeutic agents that could be used
systemically for the cure of bacterial infections in
humans. Their introduction led to a sharp decline in the
morbidity and mortality of infectious diseases.
The rapid development of widespread resistance to the
sulfonamides soon after their introduction and the
increasing use of the broader-spectrum penicillins in the
treatment of infectious disease diminished the usefulness
of sulfonamides.
 
Today, there are a few sulfonamides and especially
sulfonamide-trimethoprim combinations that are used
extensively for opportunistic infections in patients with
AIDS
The sulfonamides are drugs of choice for a few other types
of infections, but their use is quite limited in modern
antimicrobial chemotherapy.
The sulfonamides can be grouped into three classes on
the basis of their use: oral absorbable agents, designed to
give systemic distribution; oral non absorbable agents such
as sulfasalazine; and topical agents such as sodium
sulfacetamide ophthalmic drops
.
 
Nomenclature of the Sulfonamides
Sulfonamide is a generic term that denotes three different
cases:
1. Antibacterials that are 
aniline-substituted sulfonamides
(the “sulfanilamides”).
 
 
2. 
Prodrugs
 that react to generate active sulfanilamides
(i.e., sulfasalazine).
3. 
Non aniline sulfonamides 
(i.e., mafenide acetate).
 
There are also other commonly used drugs that are
sulfonamides or sulfanilamides. Among these are the oral
hypoglycemic drug tolbutamide, the diuretic furosemide,
and the diuretic chlorthalidone.
 
Spectrum of Action of theSulfonamides
Sulfonamides inhibit Gram-positive and Gram-negative
bacteria, nocardia, Chlamydia trachomatis, and some
protozoa.
Some enteric bacteria, such as E. coli and Klebsiella,
Salmonella, Shigella, and Enterobacter spp. are
inhibited.
 Sulfonamides today used as combination
 Trimethoprim (Cotrimoxazole) as antibacterial
Pyrimethamine (Cotrimazine) as anti-Malarial.
 
 
 
Topical Sulfonamides
 
Sulfacetamide Sodium
 
 
The sodium salt is highly soluble at the physiological
pH of 7.4, it is especially suited, as a solution, for
repeated topical applications in the local management
of ophthalmic infections susceptible to sulfonamide
therapy.
 
 
 
 
 
                      
Sulfacetamide Sodium
 
Non absorbable sulfonamides
Topical sulfonamides for burn therapy
 
 
Mafenide Acetate
4-(Amino methyl) benzene sulfonamide acetate
(Sulfamylon) is a homologue of the sulfanilamide molecule.
It is not a true sulfanilamide-type compound, as it is not
inhibited by PABA. Its antibacterial action involves a
mechanism that differs from that of true sulfanilamide-type
compounds.
 
Sulfonamides for Intestinal Infections,
Ulcerative Colitis, or Reduction of Bowel Flora
sulfasalazine
 
 
 
 
Each of the sulfonamides in this group is 
a prodrug
, which is
designed to be poorly absorbable, though usually, in practice, a
little is absorbed. Therefore, usual precautions with
sulfonamide therapy should be observed. In the large intestine,
the N4-protecting groups are cleaved, releasing the free
sulfonamide antibacterial agent. Today, only one example is
used clinically, sulfasalazine.
Sulfasalazine is broken down in the body to meta- amino
salicylic acid and sulfapyridine.
 
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Trisulfapyrimidines, Oral Suspension
The oral suspension of trisulfapyrimidines contains equal
weights of sulfadiazine, USP; sulfamerazine, USP; and
sulfamethazine, USP, either with or without an agent to raise
the pH of the urine.
Trisulfapyrimidines, Tablets
Trisulfapyrimidine tablets contain essentially equal
quantities of sulfadiazine, sulfamerazine, and
sulfamethazine.
 
Trimethoprim
 
 
 
 
Trimethoprim (5-[(3,4,5-trimethoxyphenyl)methyl]-2,4-
pyrimidinediamine or 2,4-diamino-5-(3,4,5
trimethoxybenzyl) pyrimidine) is closely related to several
antimalarial but does not have good antimalarial activity by
itself; it is, however, a potent antibacterial. Originally
introduced in combination with sulfamethoxazole, it is now
available as a single agent
.
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Antibacterial sulfonamides were the first effective chemotherapeutic agents used systemically to cure bacterial infections in humans, leading to a decline in infectious disease morbidity. Despite rapid resistance development, they still find use in opportunistic infections, with limited applications due to broader-spectrum antibiotics. Classified into absorbable, non-absorbable, and topical agents, sulfonamides inhibit various pathogens and continue to be used in combination therapies.


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  1. Pharmaceutical chemistry Antibacterial Antibiotics Assist . Prof . Karima F. Ali AL-Mustansiriyah university College of pharmacy

  2. Antibacterial sulfonamides The sulfonamide antimicrobial drugs were the first effective chemotherapeutic agents that could be used systemically for the cure of bacterial infections in humans. Their introduction led to a sharp decline in the morbidity and mortality of infectious diseases. The rapid development of widespread resistance to the sulfonamides soon after their introduction and the increasing use of the broader-spectrum penicillins in the treatment of infectious disease diminished the usefulness of sulfonamides.

  3. Today, there are a few sulfonamides and especially sulfonamide-trimethoprim combinations extensively for opportunistic infections in patients with AIDS The sulfonamides are drugs of choice for a few other types of infections, but their use is quite limited in modern antimicrobial chemotherapy. The sulfonamides can be grouped into three classes on the basis of their use: oral absorbable agents, designed to give systemic distribution; oral non absorbable agents such as sulfasalazine; and topical agents such as sodium sulfacetamide ophthalmic drops. that are used

  4. Nomenclature of the Sulfonamides Sulfonamide is a generic term that denotes three different cases: 1. Antibacterials that are aniline-substituted sulfonamides (the sulfanilamides ). 2. Prodrugs that react to generate active sulfanilamides (i.e., sulfasalazine). 3. Non aniline sulfonamides (i.e., mafenide acetate).

  5. There are also other commonly used drugs that are sulfonamides or sulfanilamides. Among these are the oral hypoglycemic drug tolbutamide, the diuretic furosemide, and the diuretic chlorthalidone.

  6. Spectrum of Action of theSulfonamides Sulfonamides inhibit Gram-positive and Gram-negative bacteria, nocardia, Chlamydia trachomatis, and some protozoa. Some enteric bacteria, such as E. coli and Klebsiella, Salmonella, Shigella, and inhibited. Sulfonamides today used as combination Trimethoprim (Cotrimoxazole) as antibacterial Pyrimethamine (Cotrimazine) as anti-Malarial. Enterobacter spp. are

  7. Topical Sulfonamides Sulfacetamide Sodium Sulfacetamide Sodium The sodium salt is highly soluble at the physiological pH of 7.4, it is especially suited, as a solution, for repeated topical applications in the local management of ophthalmic infections susceptible to sulfonamide therapy.

  8. Non absorbable sulfonamides Topical sulfonamides for burn therapy Mafenide Acetate 4-(Amino methyl) benzene sulfonamide acetate (Sulfamylon) is a homologue of the sulfanilamide molecule. It is not a true sulfanilamide-type compound, as it is not inhibited by PABA. Its antibacterial action involves a mechanism that differs from that of true sulfanilamide-type compounds.

  9. Sulfonamides for Intestinal Infections, Ulcerative Colitis, or Reduction of Bowel Flora sulfasalazine Each of the sulfonamides in this group is a prodrug, which is designed to be poorly absorbable, though usually, in practice, a little is absorbed. Therefore, usual precautions with sulfonamide therapy should be observed. In the large intestine, the N4-protecting groups are cleaved, releasing the free sulfonamide antibacterial agent. Today, only one example is used clinically, sulfasalazine. Sulfasalazine is broken down in the body to meta- amino salicylic acid and sulfapyridine.

  10. Mixed Sulfonamides Trisulfapyrimidines, Oral Suspension The oral suspension of trisulfapyrimidines contains equal weights of sulfadiazine, USP; sulfamerazine, USP; and sulfamethazine, USP, either with or without an agent to raise the pH of the urine. Trisulfapyrimidines, Tablets Trisulfapyrimidine tablets contain essentially equal quantities of sulfadiazine, sulfamerazine, and sulfamethazine.

  11. Trimethoprim Trimethoprim (5-[(3,4,5-trimethoxyphenyl)methyl]-2,4- pyrimidinediamine or 2,4-diamino-5-(3,4,5 trimethoxybenzyl) pyrimidine) is closely related to several antimalarial but does not have good antimalarial activity by itself; it is, however, a potent antibacterial. Originally introduced in combination with sulfamethoxazole, it is now available as a single agent.

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