Alvimopan dihydrate
[CAS# 170098-38-1]

Identification

• Classification: API >> Digestive system medication
• Name: Alvimopan dihydrate
• Synonyms: N-[(2S)-2-[[(3R,4R)-4-(3-Hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl]-1-oxo-3-phenylpropyl]glycine dihydrate
• Molecular Formula: C₂₅H₃₂N₂O₄^.2(H₂O)
• Molecular Weight: 460.57
• CAS Registry Number: 170098-38-1
• EC Number: 814-137-6
• SMILES: C[C@H]1CN(CC[C@@]1(C)C2=CC(=CC=C2)O)C[C@H](CC3=CC=CC=C3)C(=O)NCC(=O)O.O.O

Properties

• Solubility: 60 mg/mL (DMSO), <1 mg/mL (water) (Expl.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

Alvimopan dihydrate is a pharmaceutical compound primarily used as a medication to manage postoperative ileus (a condition where the bowel does not function normally following surgery). It belongs to a class of drugs known as peripheral opioid receptor antagonists. Alvimopan works by selectively blocking the effects of opioids on the gastrointestinal tract, which helps to accelerate the recovery of bowel function following surgery. Its discovery and development were driven by the need for a safe and effective solution to combat the side effects of opioid analgesics, particularly constipation and delayed bowel recovery after surgeries such as abdominal operations.

The discovery of alvimopan was motivated by the recognition that while opioids are effective pain relievers, their use often results in opioid-induced constipation and delayed gastrointestinal recovery. Opioids exert their analgesic effects by binding to opioid receptors in the central nervous system. However, these receptors are also present in the gastrointestinal tract, where their activation can lead to a reduction in motility and the development of constipation. As a result, scientists focused on designing a drug that could block the opioid receptors in the gastrointestinal tract without affecting the pain-relieving effects of opioids in the brain.

Alvimopan is designed to act selectively on the peripheral opioid receptors in the gut, specifically the μ-opioid receptors. By blocking these receptors in the gastrointestinal tract, alvimopan helps to restore normal bowel movement and function, thereby alleviating symptoms of constipation caused by opioid use. Unlike other opioid antagonists that can cross the blood-brain barrier and potentially reverse opioid-induced analgesia, alvimopan does not significantly affect opioid receptors in the brain. This selectivity allows patients to benefit from opioid pain relief while minimizing the adverse effects on bowel motility.

One of the most significant applications of alvimopan is in the treatment of postoperative ileus, a common complication following abdominal surgeries such as bowel resections, colectomies, and pelvic surgeries. Postoperative ileus can result in delayed recovery, prolonged hospital stays, and increased healthcare costs. Alvimopan has been shown to accelerate the recovery of bowel function in patients who have undergone such surgeries, leading to faster hospital discharge and a reduction in the need for additional medical interventions related to gastrointestinal complications.

Alvimopan is administered orally, typically as a capsule, and is used in the hospital setting to manage patients recovering from surgery. It is typically used in conjunction with standard postoperative care protocols, including early mobilization, adequate hydration, and nutritional support. It is important to note that alvimopan is typically only administered for short periods, and its use is carefully monitored due to its potential side effects and contraindications.

Beyond its use in postoperative ileus, research into alvimopan's potential applications in other gastrointestinal disorders has been ongoing. Some studies have explored its use in conditions such as chronic constipation and opioid-induced bowel dysfunction, although its approval and widespread use outside of postoperative care remain limited.

Alvimopan's discovery and development represent a significant advancement in the management of opioid-related side effects. By targeting peripheral opioid receptors in the gastrointestinal system, it provides a solution to a major challenge in postoperative care, helping to improve patient outcomes and reduce the burdens of opioid-induced constipation.