Thioamide

Thioamide is a functional group in organic chemistry. This group is characterized by the presence of a sulfur atom connected to an amide. Thioamides are found in a number of clinically important drugs, most notably those used in the treatment of hyperthyroidism.

Structure and Properties

Thioamides are characterized by the presence of a sulfur atom, which replaces the oxygen atom in amides. This substitution results in a molecule with a similar structure to an amide, but with different chemical properties. The sulfur atom in thioamides is more electronegative than the nitrogen atom in amides, which results in a stronger bond and a lower reactivity.

Medical Uses

Thioamides are primarily used in the treatment of hyperthyroidism, a condition characterized by an overactive thyroid gland. The two most commonly used thioamide drugs are methimazole and propylthiouracil. These drugs work by inhibiting the enzyme thyroid peroxidase, which is involved in the production of thyroid hormones.

Methimazole is generally preferred over propylthiouracil due to its longer half-life and lower incidence of side effects. However, propylthiouracil is often used in pregnant women and individuals with severe hyperthyroidism due to its ability to inhibit the peripheral conversion of thyroxine to triiodothyronine.

Side Effects and Risks

While thioamides are generally well-tolerated, they can cause a number of side effects. The most common side effects include skin rash, nausea, and a metallic taste in the mouth. More serious side effects, such as liver damage and a decrease in white blood cell count, can also occur.

Thioamides can also cause a rare but serious condition known as agranulocytosis, which is characterized by a severe decrease in white blood cell count. This condition can lead to serious infections and requires immediate medical attention.

See Also

• Hyperthyroidism
• Methimazole
• Propylthiouracil
• Thyroid peroxidase

References

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  Thioamide

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  Tolrestat synthesis

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  Thionamide synthesis

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  Reaction of imidoyl chloride and hydrogen sulfide