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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyAlvimopan
Identification
- Name
- Alvimopan
- Accession Number
- DB06274
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Description
Alvimopan is a peripherally acting μ opioid antagonist. It is used to avoid postoperative ileus following small or large bowel resection and accelerates the gastrointestinal recovery period.
- Structure
Structure for Alvimopan (DB06274)
- Synonyms
- Alvimopan
- Alvimopan anhydrous
- Anhydrous alvimopan
- Product Ingredients
Ingredient UNII CAS InChI Key Alvimopan dihydrate 677C126AET 170098-38-1 USPVLEIQIUNQGE-DBFLIVQGSA-N - Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataEntereg Capsule 12 mg/1 Oral Merck Sharp & Dohme Corp. 2012-04-16 Not applicable US 
Entereg Capsule 12 mg/1 Oral Adolor Corporation 2008-05-20 2014-11-30 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Categories
- UNII
- Q153V49P3Z
- CAS number
- 156053-89-3
- Weight
- Average: 424.5326
Monoisotopic: 424.236207522 - Chemical Formula
- C25H32N2O4
- InChI Key
- UPNUIXSCZBYVBB-JVFUWBCBSA-N
- InChI
- InChI=1S/C25H32N2O4/c1-18-16-27(12-11-25(18,2)21-9-6-10-22(28)14-21)17-20(24(31)26-15-23(29)30)13-19-7-4-3-5-8-19/h3-10,14,18,20,28H,11-13,15-17H2,1-2H3,(H,26,31)(H,29,30)/t18-,20-,25+/m0/s1
- IUPAC Name
- 2-[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanamido]acetic acid
- SMILES
- C[C@H]1CN(C[C@H](CC2=CC=CC=C2)C(=O)NCC(O)=O)CC[C@@]1(C)C1=CC(O)=CC=C1
Pharmacology
- Indication
Used to accelerate the time to upper and lower gastrointestinal recovery following partial large or small bowel resection surgery with primary anastomosis. Also investigated for use in the treatment of pain (acute or chronic).
- Associated Therapies
- Pharmacodynamics
- Not Available
- Mechanism of action
Alvimopan competitively binds to mu-opioid receptor in the gastrointestinal tract but, unlike methylnaltrexone which relies upon it ionic charge, alvimopan owes its selectivity for peripheral receptors to its pharmacokinetics. Alvimopan binds to peripheral mu-receptors with a Ki of 0.2 ng/mL.
Target Actions Organism AMu-type opioid receptor antagonistHumans UKappa-type opioid receptor antagonistHumans UDelta-type opioid receptor antagonistHumans - Absorption
Alvimopan's high affinity for the peripheral mu-receptor leads to slower absorption dependent on dissociation from the receptor and subsequently low oral bioavailability of less than 7%.
- Volume of distribution
- 30±10 L
- Protein binding
80% to 90% bound in after entering systemic circulation.
- Metabolism
Alvimopan is primarily metabolized by intestinal flora to an active metabolite although it has no clinically significant contribution to the effects of the drug.
- Route of elimination
Biliary secretion was considered the primary pathway for alvimopan elimination. Unabsorbed drug and unchanged alvimopan resulting from biliary excretion were then hydrolyzed to its ‘metabolite’ by gut microflora. Feces (via biliary excretion) & urine (35%)
- Half life
10 to 17 hours (gut metabolite: 10 to 18 hours)
- Clearance
- 402 ± 89 mL/min
- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
Pathway Category Alvimopan Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Unlock Additional Data
Additional Data Available
Adverse Effects
Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.
Learn more Additional Data Available
Contraindications
Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.
Learn more Additional Data Available
Blackbox Warnings
Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.
Learn moreInteractions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAlfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Alvimopan. Alphacetylmethadol The risk or severity of adverse effects can be increased when Alphacetylmethadol is combined with Alvimopan. Alphaprodine The risk or severity of adverse effects can be increased when Alphaprodine is combined with Alvimopan. Benzhydrocodone The risk or severity of adverse effects can be increased when Benzhydrocodone is combined with Alvimopan. Bezitramide The risk or severity of adverse effects can be increased when Bezitramide is combined with Alvimopan. Buprenorphine The risk or severity of adverse effects can be increased when Buprenorphine is combined with Alvimopan. Butorphanol The risk or severity of adverse effects can be increased when Butorphanol is combined with Alvimopan. Carfentanil The risk or severity of adverse effects can be increased when Carfentanil is combined with Alvimopan. Carfentanil, C-11 The risk or severity of adverse effects can be increased when Carfentanil, C-11 is combined with Alvimopan. Codeine The risk or severity of adverse effects can be increased when Codeine is combined with Alvimopan. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- Food Interactions
- Take with or without food. High-fat meals may reduce the Cmax and AUC by 38% and 21%, respectively; however, the clinical significance of this is unknown.
References
- General References
- Wang S, Shah N, Philip J, Caraccio T, Feuerman M, Malone B: Role of alvimopan (entereg) in gastrointestinal recovery and hospital length of stay after bowel resection. P T. 2012 Sep;37(9):518-25. [PubMed:23066346]
- Buchler MW, Seiler CM, Monson JR, Flamant Y, Thompson-Fawcett MW, Byrne MM, Mortensen ER, Altman JF, Williamson R: Clinical trial: alvimopan for the management of post-operative ileus after abdominal surgery: results of an international randomized, double-blind, multicentre, placebo-controlled clinical study. Aliment Pharmacol Ther. 2008 Aug 1;28(3):312-25. [PubMed:19086236]
- Link [Link]
- External Links
- Human Metabolome Database
- HMDB0015631
- KEGG Drug
- D02878
- PubChem Compound
- 5488548
- PubChem Substance
- 99443242
- ChemSpider
- 4589864
- BindingDB
- 50088381
- RxNav
- 480639
- ChEBI
- 135686
- ChEMBL
- CHEMBL270190
- ZINC
- ZINC000003802417
- Therapeutic Targets Database
- DAP001140
- PharmGKB
- PA164754864
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Alvimopan
- ATC Codes
- A06AH02 — Alvimopan
- FDA label
- Download (149 KB)
- MSDS
- Download (127 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Completed Treatment Bowel Dysfunction / Constipation 1 2 Completed Treatment Bowel Dysfunction / Malignancies 1 2 Completed Treatment Laparoscopic Colonic Resection 1 2 Terminated Treatment Constipation / Malignancies 1 2 Terminated Treatment Ileus 1 3 Completed Prevention Fallopian Tube Cancer / Malignant Peritoneal Neoplasm / Ovarian Cancer / Primary Peritoneal Cancer 1 3 Completed Treatment Bowel Dysfunction / Constipation 3 3 Completed Treatment Ileus 4 3 Not Yet Recruiting Treatment Ileus / Surgery, Colorectal 1 3 Recruiting Treatment Cancer, Bladder 1 4 Completed Treatment Postoperative paralytic ileus 1 4 Recruiting Treatment Constipation 1 4 Terminated Prevention Post Operative Ileus 1 4 Withdrawn Treatment Pain, Acute / Postoperative pain / Surgery, Colorectal 1 Not Available Completed Not Available Ileus 1 Not Available Completed Treatment Fusion of Spine (Disease) / Ileus 1 Not Available Completed Treatment Ileus 1 Not Available Terminated Treatment Ventral Hernias 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Adolor Corp.
- GlaxoSmithKline Inc.
- Pharmaceutics International Inc.
- Dosage forms
Form Route Strength Capsule Oral 12 mg/1 - Prices
Unit description Cost Unit Entereg 12 mg capsule 79.5USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Unlock Additional DataUS5250542 No 1993-10-05 2016-03-29 US US6469030 No 2002-10-22 2020-11-29 US US8645160 No 2014-02-04 2029-06-18 US US8112290 No 2012-02-07 2030-07-31 US US8946262 No 2015-02-03 2030-02-12 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility <0.1 mg/mL FDA Label - Predicted Properties
Property Value Source Water Solubility 0.00834 mg/mL ALOGPS logP 3.25 ALOGPS logP 0.82 ChemAxon logS -4.7 ALOGPS pKa (Strongest Acidic) 3.71 ChemAxon pKa (Strongest Basic) 10.66 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 89.87 Å2 ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 120.56 m3·mol-1 ChemAxon Polarizability 46.77 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9103 Blood Brain Barrier - 0.96 Caco-2 permeable - 0.6875 P-glycoprotein substrate Substrate 0.8627 P-glycoprotein inhibitor I Non-inhibitor 0.6845 P-glycoprotein inhibitor II Non-inhibitor 0.6478 Renal organic cation transporter Non-inhibitor 0.8596 CYP450 2C9 substrate Non-substrate 0.7966 CYP450 2D6 substrate Non-substrate 0.7292 CYP450 3A4 substrate Substrate 0.5908 CYP450 1A2 substrate Non-inhibitor 0.9362 CYP450 2C9 inhibitor Non-inhibitor 0.9109 CYP450 2D6 inhibitor Non-inhibitor 0.7964 CYP450 2C19 inhibitor Non-inhibitor 0.8729 CYP450 3A4 inhibitor Non-inhibitor 0.8447 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9803 Ames test Non AMES toxic 0.8684 Carcinogenicity Non-carcinogens 0.8594 Biodegradation Not ready biodegradable 0.9694 Rat acute toxicity 2.6978 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9599 hERG inhibition (predictor II) Non-inhibitor 0.7208
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Peptidomimetics
- Sub Class
- Hybrid peptides
- Direct Parent
- Hybrid peptides
- Alternative Parents
- N-acyl-alpha amino acids / Phenylpiperidines / Beta amino acids and derivatives / 1-hydroxy-2-unsubstituted benzenoids / 1-hydroxy-4-unsubstituted benzenoids / Aralkylamines / Fatty amides / Benzene and substituted derivatives / Trialkylamines / Secondary carboxylic acid amides show 8 more
- Substituents
- Hybrid peptide / N-acyl-alpha amino acid or derivatives / N-acyl-alpha-amino acid / Phenylpiperidine / Beta amino acid or derivatives / Alpha-amino acid or derivatives / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Aralkylamine show 26 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Voltage-gated calcium channel activity
- Specific Function
- Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
- Gene Name
- OPRM1
- Uniprot ID
- P35372
- Uniprot Name
- Mu-type opioid receptor
- Molecular Weight
- 44778.855 Da
References
- Kraft MD: Emerging pharmacologic options for treating postoperative ileus. Am J Health Syst Pharm. 2007 Oct 15;64(20 Suppl 13):S13-20. [PubMed:17909271]
- Buchler MW, Seiler CM, Monson JR, Flamant Y, Thompson-Fawcett MW, Byrne MM, Mortensen ER, Altman JF, Williamson R: Clinical trial: alvimopan for the management of post-operative ileus after abdominal surgery: results of an international randomized, double-blind, multicentre, placebo-controlled clinical study. Aliment Pharmacol Ther. 2008 Aug 1;28(3):312-25. [PubMed:19086236]
- Saufl NM, Strzyzewski N: Nurses are everywhere: a practical perspective on the surgical team in managing postoperative ileus. J Perianesth Nurs. 2006 Apr;21(2A Suppl):S24-9. [PubMed:16597533]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Neary P, Delaney CP: Alvimopan. Expert Opin Investig Drugs. 2005 Apr;14(4):479-88. [PubMed:15882122]
- Schmidt WK: Alvimopan* (ADL 8-2698) is a novel peripheral opioid antagonist. Am J Surg. 2001 Nov;182(5A Suppl):27S-38S. [PubMed:11755894]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Opioid receptor activity
- Specific Function
- G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
- Gene Name
- OPRK1
- Uniprot ID
- P41145
- Uniprot Name
- Kappa-type opioid receptor
- Molecular Weight
- 42644.665 Da
References
- Beattie DT, Cheruvu M, Mai N, O'Keefe M, Johnson-Rabidoux S, Peterson C, Kaufman E, Vickery R: The in vitro pharmacology of the peripherally restricted opioid receptor antagonists, alvimopan, ADL 08-0011 and methylnaltrexone. Naunyn Schmiedebergs Arch Pharmacol. 2007 May;375(3):205-20. Epub 2007 Mar 6. [PubMed:17340127]
- Neary P, Delaney CP: Alvimopan. Expert Opin Investig Drugs. 2005 Apr;14(4):479-88. [PubMed:15882122]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Opioid receptor activity
- Specific Function
- G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
- Gene Name
- OPRD1
- Uniprot ID
- P41143
- Uniprot Name
- Delta-type opioid receptor
- Molecular Weight
- 40368.235 Da
References
- Neary P, Delaney CP: Alvimopan. Expert Opin Investig Drugs. 2005 Apr;14(4):479-88. [PubMed:15882122]
- Beattie DT, Cheruvu M, Mai N, O'Keefe M, Johnson-Rabidoux S, Peterson C, Kaufman E, Vickery R: The in vitro pharmacology of the peripherally restricted opioid receptor antagonists, alvimopan, ADL 08-0011 and methylnaltrexone. Naunyn Schmiedebergs Arch Pharmacol. 2007 May;375(3):205-20. Epub 2007 Mar 6. [PubMed:17340127]
Drug created on March 19, 2008 10:20 / Updated on June 12, 2020 10:52
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