Structure via PubChem · Public domain (PubChem)
alvimopan
Sign in to saveAlso known as ADL 8-2698, Entereg®, alvimopan anhydrous, Alvimopan anhydrous, Anhydrous alvimopan
Alvimopan (trade name Entereg) is a drug which behaves as a peripherally acting μ-opioid receptor antagonist. With the limited ability to cross the blood–brain barrier and reach the μ-opioid receptors of the central nervous system, the clinically undesirable effects of centrally acting opioid antagonists (like reversal of opioid-mediated analgesia) are avoided without affecting the intended blockade of μ-opioid receptors in the gastrointestinal tract. It is currently only Food and Drug Administration approved for the treatment of postoperative ileus which it received in May 2008.
Chemical data
- Formula
- C25H32N2O4
- Molecular weight
- 424.5 g/mol
- IUPAC name
- 2-[[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanoyl]amino]acetic acid
- 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
- InChIKey
- UPNUIXSCZBYVBB-JVFUWBCBSA-N
- XLogP
- 1.7
- Polar surface area
- 89.9 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2008
- Admin. routes
- oral
- Indications
- Constipation, urinary bladder cancer, peritoneum cancer, fallopian tube cancer
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 424.236
- Has use
- medication
Show 5 more facts
- chemical formula
- C₂₅H₃₂N₂O₄
- isomeric 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
- canonical SMILES
- CC1CN(CCC1(C)C2=CC(=CC=C2)O)CC(CC3=CC=CC=C3)C(=O)NCC(=O)O
- Commons category
- Alvimopan
- legal status (medicine)
- boxed warning
via Wikidata · CC0
~5 min read
Encyclopedic overview
14 sectionsContents
- Medical uses
- Adverse effects
- Contraindications
- Interactions
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- Absorption
- Distribution
- Metabolism
- Elimination
- Dosing and administration
- See also
- References
Alvimopan (trade name Entereg) is a drug which behaves as a peripherally acting μ-opioid receptor antagonist. With the limited ability to cross the blood–brain barrier and reach the μ-opioid receptors of the central nervous system, the clinically undesirable effects of centrally acting opioid antagonists (like reversal of opioid-mediated analgesia) are avoided without affecting the intended blockade of μ-opioid receptors in the gastrointestinal tract. It is currently only Food and Drug Administration approved for the treatment of postoperative ileus which it received in May 2008.
== Medical uses == Alvimopan is indicated in people to avoid postoperative ileus following partial large or small bowel resection with primary anastomosis. Alvimopan accelerates the gastrointestinal recovery period as defined by time to first bowel movement or flatus.
Excerpted from Wikipedia’s “alvimopan” article, available under the CC BY-SA 4.0 licence.