SULFONAMIDES and

Fluroquinolones
By. Dr. Smita singh
 SULFONAMIDES
• In 1937,Domagk cured an infant of staphylo-
coccal septicaemia (which was 100% fatal at
that time) with Prontosil Red which released
Sulfanilamide

• All Sulfonamides are derivatives of p-

aminobenzene.
 Classification
• 1. Short acting (4-8 hr): Sulfadiazine

• 2. Intermediate acting (8-12 hr): Sulfamethoxazole

• 3. Long acting (-7 days): Sulfadoxine

• 4. Special purpose sulfonamides: Sulfacetamide

sod., Sulfasalazine, Silver sulfadiazine
 Mechanism of action

Bacteria synthesize their folic acid of which PABA is a constituent.

Sulfonamides being structural analogue of PABA(p-aminobenzoic acid)

compete for the enzyme folate synthase and forms non –functional folic
acid/ FA is not formed .

- Bacteriostatic
 Uses
• Sulfadoxine is combined with pyrimethamine, and used
for malaria.

• Ocular Sulfacetamide trachoma/ inclusion

conjunctivitis.

• Topical Silver sulfadiazine or Mafenide are used for

preventing infection on burn surfaces

• Sulfasalazine is used in Ulcerative Colitis.

 ADVERSE EFFECTS
• Nausea, vomiting and epigastric pain

• Crystalluria

• Hypersensitivity, Photosensitization

• Hepatitis

• Haemolysis in G-6-PD deficiency(idiosyncrasy)

• Kernicterus in premature infants(displacement of bilirubin)

 COTRIMOXAZOLE
• Fixed dose combination of Sulfamethoxazole
and Trimethoprim (5:1) is called Cotrimoxazole

• Sulfamethoxazole was selected for

combination with Trimethoprim because both
of them have nearly same half life ( nearly 10
hrs)
 Uses
• Pneumocystis jiroveci causes severe pneumonia in
neutropenic and AIDS patients. Prophylactic as well as
therapeutic Value.

• Respiratory tract infections

• Uncomplicated Urinary tract infections

• Typhoid
• Bacterial diarrhoeas and dysentery
 Adverse effects
• All adverse effect of sulfonamide
• Folate deficiency (megaloblastic anaemia)
• Contraindicated in pregnancy
 Preparation
• Trimethoprim + Sulfamethoxazole
- 80 mg + 400 mg tab
- 160 mg+ 800 mg tab
 QUINOLONES
• Active primarily against gram-negative
bacteria.

• Nalidixic acid has limited usefulness to

urinary and g.i. tract infections.
A breakthrough was achieved
by fluorination of the
quinolone structure at
position 6 and introduction of
a piperazine substitution at
position 7 resulting in
Fluoroquinolones
Fluoroquinolones have
- high potency
- expanded spectrum
- slow development of resistance,
- better tissue penetration and good tolerability
 Mechanism of action
• The FQs inhibit the enzyme bacterial DNA gyrase (primarily active
in gram negative bacteria), which nicks double stranded DNA,
introduces negative supercoils and then reseals the nicked ends

• In gram-positive bacteria, it inhibits topoisomerase IV .

• Greater affinity for topoisomerase IV may confer higher activity

against gram-positive bacteria

• Bactericidal action probably results from digestion of DNA by

exonucleases whose production is signalled by damaged DNA
 Ciprofloxacin
• It is the most potent first generation FQ active
against a broad range of bacteria, the most
susceptible ones are the aerobic gram-
negative bacilli, especially the
Enterobacteriaceae and Neisseria
 Adverse effects

1. Gastrointestinal: nausea, vomiting, bad taste, anorexia

2. CNS: dizziness, headache, restlessness , anxiety, insomnia, impairment

of concentration , Tremor and seizure.

3. Skin/hypersensitivity: rash, pruritus, photosensitivity, urticaria,

swelling of lips, etc

4. Tendinitis and tendon rupture

5. Cartilage damage in weight bearing joints

 Uses

• Urinary tract infections

• Gonorrhoea
• Chancroid
• Bacterial gastroenteritis
• Typhoid
• Bone, soft tissue, gynaecological and wound infections
• Tuberculosis
• Meningitis
• Gram-negative septicaemias
• Conjunctivitis: by gram-negative bacteria: topical therapy is
effective
 Levofloxacin
• levo(s) isomer of Ofloxacin

• Good activity against Strep. pneumoniae and some

other gram-positive and gram-negative bacteria

• The primary indication is community acquired

pneumonia and exacerbations of chronic bronchitis

• Sinusitis, pyelonephritis, prostatitis , UTI, as well as

skin/soft tissue infections
 Moxifloxacin
• - A long-acting 2nd generation FQ having high
activity against Str. pneumoniae other gram-
positive bacteria including β Iactam, macrolide
resistant ones and some anaerobes

• It is the most potent FQ against M.

tuberculosis
 s/e of 2 genrn
nd

• Phototoxicity
• Qt –interval prolonged

• Banned drug:- Sparfloxacin, Gatifloxacin

• Thank U