Amides in Medicine: Amytal, Valium And Polycillin

This study explored use of amides in medicine and to inform about the medicinal value of amides. Amytal, amobarbital, valium and polycillin are medicinal drugs that contain amides and are the focus of this project. These drugs are mostly found in antibiotics, barbiturates, tranquilizers and Insomnia Treatments. Most of the information gathered was from secondary sources. Drugs containing amides are usually ones that attack the nervous system or brain. Therefore, amides are more widely used due its stability and ability to efficiently bond with other molecules.

Amides are essential to life; they are proteins that consist of amino acid building blocks and amide bonds that link different amino acids together to make different proteins in all living organisms. This research project will look at the physical and chemical structure of amides and the reactions they undergo. This research will also focus on three specific amide compounds used in medicinal practice – Amytal, Valium and Polycillin.

Amides are derived from carboxylic acids. A carboxylic acid contains the -COOH group, and in an amide the -OH part of that group is replaced by an -NH2 group.

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Amides contain the chemical group -CONH2. As with amines, the nomenclature used for an amide depends on the number of carbons attached to the nitrogen. A primary (1°) amide has nitrogen attached to a single carbon; a secondary (2°) amide has the nitrogen attached to two carbons; a tertiary (3°) amide has the nitrogen attached to three carbons. Amides are widespread in biologically active compounds with a broad range of applications in medicine.

Some important medications made with amides include antibiotics, barbiturates, tranquilizers and Insomnia Treatments. Amytal also known as sodium amytal is generically known as Amobarbital. According to the website Net Doctor, Amobarbital belongs to the group of medicines known as barbiturates. Barbiturates work by enhancing the action of a neurotransmitter called GABA in the brain. GABA is a neurotransmitter that acts as a natural ‘nerve-calming’ agent. Amobarbital increases the activity of GABA in the brain, which results in depressed sensory cortex, decrease motor activity, altered cerebellar function, drowsiness, sedation, and hypnosis. Other than its use to treat insomnia, Amytal is used to produce preanesthetic sedation, to produce sedation during labour or as a treatment of epileptic seizures (anticonvulsant effect). Amobarbital is also referred to as a ‘truth serum’. In psychiatric emergency settings amytal is used in clinical application known as an ‘Amytal Interview’. Amytal interviews have a valid role in the assessment and initial management of catatonia, hysterical stupor, and unexplained muteness as well as in distinguishing between depressive, schizophrenic, and organic stuporous states. Valid therapeutic indications include the abreaction of traumatic neurosis, recovery of memory in amnesic and fugue states, and recovery of function in conversion disorders. There are certain warnings/ precautions to be considered when taking Amytal. Amytal may be prescribed by a doctor or bought over the counter, whichever way the drug is acquired, certain precautions and warnings must be taken into consideration. Amobarbital sodium may be habit forming. Tolerance, psychological and physical dependence may occur with continued use. Too rapid administration may cause respiratory depression, apnea, laryngo- spasm, or vasodilation with fall in blood pressure. Caution should be exercised when barbiturates are administered to patients with acute or chronic pain because paradoxical excitement could be induced, or important symptoms could be masked. Barbiturates can also cause foetal damage when administered to a pregnant woman.

Valium is another medical drug containing amides. It is generically known as Diazepam. Diazepam acts on central nervous system by stimulating GABA (gamma amino butyric acid) which inhibits the excitatory stimulation in the brain. It suppresses the activity of brain and suppresses the convulsions. It potentiates the inhibitory neurotransmitters in the limbic system and there by decreases the emotions and anxiety. Diazepam (Valium) is therefore used following the conditions insomnia, anxiety, epilepsy, alcohol withdrawal syndrome, headache, night tremors, muscular spasm, somnambulism and is also used as a premedication before anaesthesia and surgery. Valium is not recommended in the treatment of psychotic patients and should not be employed instead of appropriate treatment. Since Valium has a central nervous system depressant effect, patients should be advised against the simultaneous ingestion of alcohol and other CNS-depressant drugs during Valium therapy. As with other agents that have anticonvulsant activity, when Valium is used as an adjunct in treating convulsive disorders, the possibility of an increase in the frequency and/or severity of grand mal seizures may require an increase in the dosage of standard anticonvulsant medication. Abrupt withdrawal of Valium in such cases may also be associated with a temporary increase in the frequency and/or severity of seizures. There is also an increased risk of congenital malformations and other developmental abnormalities associated with the use of benzodiazepine.

Polycillin (Ampicillin) is described as a semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic. Ampicillin is used to treat a wide variety of bacterial infections. It is a penicillin-type antibiotic and works by stopping the growth of bacteria. This antibiotic treat only bacterial infections. It will not work for viral infections (such as common cold, flu). Using any antibiotic when it is not needed can cause it to not work for future infections. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Ampicillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that Ampicillin interferes with an autolysin inhibitor.

There are certain precautions to consider when taking ampicillin. Prolonged use of antibiotics may promote the overgrowth of nonsusceptible organisms, including fungi. Should superinfection occur, appropriate measures should be taken. Patients with gonorrhea and who also have syphilis should be given additional appropriate parenteral penicillin treatment. Treatment with ampicillin does not preclude the need for surgical procedures, particularly in staphylococcal infections.

What is an Amide?

An amide is a functional group containing a carbonyl group linked to a nitrogen atom or any compound containing the amide functional group. Amides are derived from carboxylic acid and an amine. Amide is also the name for the inorganic anion NH2. It is the conjugate base of ammonia (NH3). Amides are formed by the addition of ammonia (NH3) to a carboxylic acid forms an amide, but the reaction is very slow in the laboratory at room temperature. Water molecules are split out, and a bond is formed between the nitrogen atom and the carbonyl carbon atom.

In living cells, amide formation is catalyzed by enzymes. Proteins are polyamides; they are formed by joining amino acids into long chains. In proteins, the amide functional group is called a peptide bond. The amides generally have high boiling points and melting points. These characteristics and their solubility in water result from the polar nature of the amide group and hydrogen bonding. Examples of amides include carboxamides, sulfonamides, and phosphoramides. Nylon is a polyamide. Several drugs are amides, including LCD, penicillin, and paracetamol.

Structure of Amides

Amides have a resonance structure that is because the lone pair on the nitrogen can be delocalized which destroys most of the electrophilic nature of the carbonyl hence the reason for not being able to react with nucleophiles (do not usually undergo addition of nucleophiles to the carbonyl carbon).

Classification of Amides

Amides are commonly grouped based on the number of hydrogen atoms the nitrogen has attached to it. A primary (1°) amide has nitrogen attached to a single carbon; a secondary (2°) amide has the nitrogen attached to two carbons; a tertiary (3°) amide has the nitrogen attached to three carbons.

Synthesis of Amides

One popular method of making Amide is undergo hydrolysis in the presence of aqueous acid, that is carboxylic acid and convert it to an acid chloride by using Thionyl Chloride (SOCL2). The acid chloride tends to be very reactive and it is essential in the formation of amides. However, this reaction is usual very sluggish and requires high temperatures to reacted. Another way of synthesizing Amides undergo is hydrolysis in the presence of alkaline solution such as sodium hydroxide to give carboxylate salt and ammonia. Amides can be hydrolyzed in hot alkali as well as in strong acidic conditions. Acidic conditions yield the carboxylic acid and the ammonium ion while basic hydrolysis yields the carboxylate ion and ammonia. Acid hydrolysis of amides involves the formation of protonated carbonyl group which is electrophilic enough to be attacked by water. Then, protonation of the nitrogen atom to be good leaving group.

Reduction of Amides

This reaction is where amides is reduced to amines by using a very strong reducing agent called lithium aluminum hydride. The carbon to oxygen bond is broken and replaced by two carbons to hydrogen bonds to forms an amine product.

Summary

Amides are the chemical ties that bind amino acids together to form peptides and proteins. Amides also turn up in a variety of other small molecules that nature makes. So, it’s not surprising that amides are frequently found in pharmaceutical drugs.

For a drug to be effective orally, it generally must be reasonably soluble in water so that it can be transported through the blood. Since amines are weak bases, they are often reacted to be converted to salts with some acid and therefore may oral drugs have amine salts as part of their structure. One reason for their presence is that they confer some water solubility to the drug.

Safety and efficacy of pharmaceuticals are two fundamental issues of importance in drug therapy. Instability of pharmaceuticals can cause changes in the physical, chemical, pharmacological, and toxicological properties of the active pharmaceutical ingredients. Pharmacists should therefore take various parameters into consideration, for example drug stability, possible degradation products, and potential interactions with excipients used in the formulation, to ensure successful therapy. To assess stability of drug product, methods are used which enable precise and accurate quantification of the drug, its degradation products, and interaction products, if any. As mentioned before, amides can be hydrolyzed in acidic or basic conditions into degradation products which may be with no pharmacological activity. Thus, stability indicating methods are required to afford the selective determination of a drug substance in presence of its decomposition and reaction products.