Dicyclomine Hydrochloride: Structure , Synthesis , SAR , Mechanism , Uses

Dicyclomine Hydrochloride

  • it  is a medication used to treat symptoms of irritable bowel syndrome (IBS), including abdominal cramping, pain, bloating, and discomfort. It is also sometimes used to treat other gastrointestinal disorders.
  • Dicyclomine hydrochloride works by relaxing the muscles in the intestines and reducing spasms in the digestive system. It belongs to a class of drugs called antispasmodics.
  • This medication is usually taken orally, either as a tablet or a capsule, with or without food. The usual recommended dose is 20 milligrams (mg) taken four times per day, although the specific dose and frequency may vary depending on individual needs and medical history.
  • Common side effects of dicyclomine hydrochloride include dry mouth, dizziness, blurred vision, drowsiness, and constipation. It may also cause more serious side effects in some individuals, such as difficulty urinating or an allergic reaction.
  • It is important to talk to a healthcare provider before taking dicyclomine hydrochloride, as it may interact with other medications or health conditions. Pregnant or breastfeeding individuals should also consult a healthcare provider before using this medication.

Structure –

The chemical name for it is (±)-cis-1-benzyl-3,4-dimethyl-2,2-dioxido-1,2,3,4,5,6-hexahydro- azocin-5-yl]-3-hydroxy-1,1-dimethylpiperidinium chloride.

Its molecular formula is C19H35NO2.ClH, and its molecular weight is 345.95 g/mol.

The structural formula of Dicyclomine Hydrochloride is:

Dicyclomine Hydrochloride

This structure consists of a piperidine ring with a benzyl group and two methyl groups attached, as well as a hydroxyl group and a quaternary ammonium group. The hydrochloride salt is formed by adding one molecule of hydrochloric acid to one molecule of dicyclomine.

Synthesis –

The synthesis of it can be achieved through several different routes. Here’s one possible synthetic pathway:

  1. The reaction of 1-methylpiperidine with acrolein in the presence of a Lewis acid catalyst (such as aluminum trichloride) yields 1-benzyl-3,4-dimethyl-2,2-dioxido-1,2,3,4,5,6-hexahydroazocine.
  2. The resulting azocine compound is then reacted with methyl iodide and a strong base (such as sodium hydride) to form the quaternary ammonium salt 1-benzyl-3,4-dimethyl-1,1-dimethylpiperidinium iodide.
  3. The piperidinium iodide is then reacted with sodium hydroxide to generate the hydroxyl group and convert the iodide to chloride.
  4. The final step involves the reaction of the piperidinium hydroxide with hydrochloric acid to form Dicyclomine Hydrochloride.

Dicyclomine Hydrochloride

Overall, the synthesis of Dicyclomine Hydrochloride involves several chemical reactions, including condensation, alkylation, base-induced hydrolysis, and acid-base neutralization. The resulting compound has a complex molecular structure that is important for its therapeutic activity in treating irritable bowel syndrome.

SAR –

The structure-activity relationship (SAR) of Dicyclomine Hydrochloride involves the interaction between its molecular structure and its pharmacological activity.

Dicyclomine Hydrochloride is a muscarinic receptor antagonist that works by blocking the action of the neurotransmitter acetylcholine at the muscarinic receptors in the smooth muscles of the gastrointestinal tract. The SAR of Dicyclomine Hydrochloride suggests that the following structural features are essential for its pharmacological activity:

  1. Quaternary ammonium group: Dicyclomine Hydrochloride has a quaternary ammonium group that is positively charged, which allows it to interact with the negatively charged site on the muscarinic receptor.
  2. Aromatic ring: Dicyclomine Hydrochloride has an aromatic ring that contributes to its binding affinity to the muscarinic receptor.
  3. Carbonyl group: Dicyclomine Hydrochloride has a carbonyl group that is involved in hydrogen bonding with the muscarinic receptor.
  4. Cyclohexyl ring: Dicyclomine Hydrochloride has a cyclohexyl ring that contributes to its hydrophobic interactions with the muscarinic receptor.

By incorporating these structural features, Dicyclomine Hydrochloride is able to selectively block the muscarinic receptors in the smooth muscles of the gastrointestinal tract, leading to its therapeutic effect in the treatment of gastrointestinal disorders.

Mechanism –

Dicyclomine Hydrochloride is a medication that is used to treat gastrointestinal disorders such as irritable bowel syndrome (IBS) and functional bowel disorders. It works by relaxing the smooth muscles of the gastrointestinal tract and thereby reducing the frequency and intensity of muscle spasms.

Dicyclomine Hydrochloride belongs to a class of drugs known as antispasmodics. It acts by blocking the action of acetylcholine, a neurotransmitter that stimulates the muscles of the gastrointestinal tract. By inhibiting acetylcholine, dicyclomine reduces the muscle contractions and spasm in the gastrointestinal tract, resulting in relief from the symptoms of IBS and other gastrointestinal disorders.

Dicyclomine Hydrochloride is rapidly absorbed from the gastrointestinal tract and reaches peak plasma concentrations within one to two hours after oral administration. It is metabolized in the liver and excreted in the urine.

It is important to note that Dicyclomine Hydrochloride should be used only as directed by a healthcare professional and should not be taken for an extended period of time without medical supervision.

Uses –

Dicyclomine Hydrochloride is a medication that is primarily used for the treatment of gastrointestinal disorders such as irritable bowel syndrome (IBS) and functional bowel disorders. It works by relaxing the smooth muscles of the gastrointestinal tract, thereby reducing the frequency and intensity of muscle spasms.

Some of the common uses of Dicyclomine Hydrochloride include:

  1. Irritable bowel syndrome (IBS): It is used to treat the symptoms of IBS, such as abdominal pain, bloating, and diarrhea.
  2. Functional bowel disorders: It is used to treat other functional bowel disorders, such as functional dyspepsia, that cause abdominal pain, bloating, and other digestive symptoms.
  3. Gastrointestinal spasms: It is used to relieve gastrointestinal spasms that can occur due to various medical conditions, such as peptic ulcer disease, diverticulitis, and inflammatory bowel disease.
  4. Gallbladder spasms: It is used to relieve spasms of the gallbladder, which can occur after gallbladder surgery or due to other medical conditions.

Dicyclomine Hydrochloride is a prescription medication and should be taken only as directed by a healthcare professional. It is important to discuss any potential side effects and drug interactions with your healthcare provider before taking this medication.

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