Chemistry · MU Pleven

Derivatives of benzene as drugs.

Covers benzene's toxicity and its industrial role, then benzoic acid as a preservative and its metabolism to hippuric acid. Moves through PABA and its anaesthetic esters such as anesthesin and procaine, explaining the three-part structure of procaine. Sulfanilic acid and sulfonamides follow, with their bacteriostatic mechanism via folic acid, and the note ends with salicylic acid, aspirin, paracetamol, p-aminosalicylic acid and gallic acid.

Inside: 7 sections · 15 labelled pictures · 15 flashcards · 11 min

Topic 33 of 47 in the MU Pleven syllabus for Chemistry (Medicine, Year 1). The free AceMed note covers it in 7 sections, about 1,584 words (11 min of reading), with 15 flashcards.

In this note

  1. DERIVATIVES OF BENZENE AS DRUGS
  2. Benzene
  3. Benzoic acid (C6H5COOH).
  4. p-Aminobenzoic acid (4-aminobenzoic acid, PABA)
  5. Derivatives of p-aminobenzoic acid:
  6. Sulfanilic acid and its derivatives
  7. Salicylic acid and its derivatives

Benzene

Benzene (C6H6) is a colorless, volatile liquid with a rather pleasant odor.

Benzene is toxic when it gains access to the body by any route. Poisoning commonly occurs, however, as a result of the inhalation of the vapors. Notwithstanding its insidious toxicity, benzene continues to be extensively used in the petroleum, explosive, plastics, pesticide, and other industries. It has no therapeutic uses.

Benzoic acid (C6H5COOH).

Benzoic acid has been widely used as a food preservative. In a concentration of 0.1% it prevents bacterial and fungal growth if the medium is slightly acidic. Benzoic acid is relatively nontoxic and almost tasteless and for these reasons it can be added to food.

After ingestion, the benzoic acid is conjugated with glycine and excreted in the urine as hippuric acid (C6H5CONH-CH2-COOH).

Sodium benzoate (C6H5COONa) is used as a drug for cough.

p-Aminobenzoic acid (4-aminobenzoic acid, PABA)

Para-aminobenzoic acid has the interesting property of neutralizing the bacteriostatic action of sulfonamide drugs. PABA has been included as a member of the vitamin B complex.

PABA is a vitamin-like substance and a growth factor required by several types of microorganisms. In bacteria, PABA is used in the synthesis of the vitamin folic acid. Although a structural unit of folic acid, PABA is not considered a vitamin.

The mammalian organismisincapable of converting PABA to folic acid and the folic requirements of mammals must thereforebemet with performed folic acid. Thus, there is no evidence that PABA is a dietary essential in man.

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