U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C25H32N2O4
Molecular Weight 424.5326
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALVIMOPAN ANHYDROUS

SMILES

C[C@H]1CN(C[C@H](CC2=CC=CC=C2)C(=O)NCC(O)=O)CC[C@@]1(C)C3=CC=CC(O)=C3

InChI

InChIKey=UPNUIXSCZBYVBB-JVFUWBCBSA-N
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

HIDE SMILES / InChI
Molecular Formula C25H32N2O4
Molecular Weight 424.5326
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/8057274 | http://adisinsight.springer.com/drugs/800003539

Alvimopan (LY246736, ADL 8-2698, trade name Entereg) is a potent, peripherally selective mu-opioid receptor antagonist. Alvimopan was developed by Adolor Corporation (now Cubist Pharmaceuticals) and GlaxoSmithKline for the treatment of postoperative ileus. Postoperative ileus is the impairment of gastrointestinal motility after intra-abdominal surgery or other non-abdominal surgeries. This may potentially delay gastrointestinal recovery and hospital discharge until its resolution. Morphine and other mu-opioid receptor agonists are universally used for the treatment of acute postsurgical pain; however, they are known to have an inhibitory effect on gastrointestinal motility and may prolong the duration of postoperative ileus. Following oral administration, alvimopan antagonizes the peripheral effects of opioids on gastrointestinal motility and secretion by competitively binding to gastrointestinal tract mu-opioid receptors.

CNS Activity

Originator

Eli Lilly
239
Curator's Comment: # Eli Lilly

Approval Year

2008
174
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 0.77 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8583
ENTEREG

Approved Use

ENTEREG is a peripherally acting μ-opioid receptor antagonist indicated to accelerate the time to upper and lower gastrointestinal recovery following partial large or small bowel resection surgery with primary anastomosis.

Launch Date

2008
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
10.98 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021775lbl.pdf
12 mg 2 times / day multiple, oral
dose: 12 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ALVIMOPAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
40.2 ng × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021775lbl.pdf
12 mg 2 times / day multiple, oral
dose: 12 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ALVIMOPAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
13.5 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021775lbl.pdf
12 mg 2 times / day multiple, oral
dose: 12 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ALVIMOPAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
20%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021775lbl.pdf
12 mg 2 times / day multiple, oral
dose: 12 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ALVIMOPAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
120 mg single, oral
Highest studied dose
Dose: 120 mg
Route: oral
Route: single
Dose: 120 mg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021775lbl.pdf
healthy, adult
Health Status: healthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021775lbl.pdf
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021775lbl.pdf
48 mg 1 times / day multiple, oral
Highest studied dose
Dose: 48 mg, 1 times / day
Route: oral
Route: multiple
Dose: 48 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021775lbl.pdf
healthy, adult
Health Status: healthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021775lbl.pdf
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021775lbl.pdf
12 mg 2 times / day multiple, oral
Recommended
Dose: 12 mg, 2 times / day
Route: oral
Route: multiple
Dose: 12 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021775lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021775lbl.pdf
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021775lbl.pdf
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Other AEs: Ascites, Ileus...
Other AEs:
Ascites (serious, 1 patient)
Ileus (serious, 1 patient)
Electrolyte imbalance (serious, 1 patient)
Failure to thrive (serious, 1 patient)
Syncope (serious, 1 patient)
Wound infection (serious, 2 patients)
Wound complication (serious, 1 patient)
Mania (serious, 1 patient)
Hypertension (below serious, 3 patients)
Constipation (below serious, 18 patients)
Diarrhea (below serious, 6 patients)
Dyspepsia (below serious, 1 patient)
Nausea (below serious, 20 patients)
Vomiting (below serious, 9 patients)
Anorexia (below serious, 4 patients)
Esophagitis (below serious, 1 patient)
Gastroparesis (below serious, 1 patient)
Weight loss (below serious, 3 patients)
Leukocytosis (below serious, 4 patients)
International normalized ratio increased (below serious, 1 patient)
Electrolyte imbalance (below serious, 8 patients)
Hypomagnesemia (below serious, 2 patients)
Elevated liver enzymes (below serious, 2 patients)
Delirium (below serious, 3 patients)
Insomnia (below serious, 1 patient)
Sensory neuropathy (below serious, 3 patients)
Cystostomy (below serious, 1 patient)
Pelvic abscess (below serious, 1 patient)
Urinary tract obstruction (below serious, 1 patient)
Allergic reaction to chemotherapy (below serious, 1 patient)
Pneumonitis (below serious, 2 patients)
Pneumothorax (below serious, 2 patients)
Wound infection (below serious, 7 patients)
Skin infection (below serious, 2 patients)
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
AEs

AEs

AESignificanceDosePopulation
Allergic reaction to chemotherapy below serious, 1 patient
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Cystostomy below serious, 1 patient
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Dyspepsia below serious, 1 patient
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Esophagitis below serious, 1 patient
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Gastroparesis below serious, 1 patient
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Insomnia below serious, 1 patient
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
International normalized ratio increased below serious, 1 patient
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Pelvic abscess below serious, 1 patient
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Urinary tract obstruction below serious, 1 patient
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Constipation below serious, 18 patients
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Elevated liver enzymes below serious, 2 patients
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Hypomagnesemia below serious, 2 patients
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Pneumonitis below serious, 2 patients
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Pneumothorax below serious, 2 patients
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Skin infection below serious, 2 patients
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Nausea below serious, 20 patients
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Delirium below serious, 3 patients
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Hypertension below serious, 3 patients
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Sensory neuropathy below serious, 3 patients
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Weight loss below serious, 3 patients
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Anorexia below serious, 4 patients
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Leukocytosis below serious, 4 patients
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Diarrhea below serious, 6 patients
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Wound infection below serious, 7 patients
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Electrolyte imbalance below serious, 8 patients
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Vomiting below serious, 9 patients
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Ascites serious, 1 patient
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Electrolyte imbalance serious, 1 patient
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Failure to thrive serious, 1 patient
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Ileus serious, 1 patient
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Mania serious, 1 patient
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Syncope serious, 1 patient
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Wound complication serious, 1 patient
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Wound infection serious, 2 patients
12 mg 2 times / day steady, oral
Dose: 12 mg, 2 times / day
Route: oral
Route: steady
Dose: 12 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
unhealthy
Health Status: unhealthy
Sources:
https://clinicaltrials.gov/ct2/show/NCT01704651
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252
inhibitor
2438

inducer
440
inhibitor
2507
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
2153

CYP2A6
879

CYP2B6
926

CYP2C8
1057

CYP2C19
2057

CYP2E1
1060

P-gp
1741
CYP
303

P-gp
2052
CYP1A2
832

CYP2B6
669

CYP2C19
329

CYP3A4/5
133
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
2333
 no [IC50 >50 uM]
CYP2A6
911
 no [IC50 >50 uM]
CYP2B6
1160
 no [IC50 >50 uM]
CYP2C19
2141
 no [IC50 >50 uM]
CYP2C8
1117
 no [IC50 >50 uM]
CYP2C9
2497
 no [IC50 >50 uM]
CYP2D6
2546
 no [IC50 >50 uM]
CYP2E1
1146
 no [IC50 >50 uM]
CYP3A4
2633
 no [IC50 >50 uM]
CYP1A2
2333
 no
CYP2B6
1160
 no
CYP2C19
2141
 no
CYP2C9
2497
 no
CYP3A4/5
357
 no
P-gp
1932
 no
no (co-administration study)
Comment: based on study using MDCKII cells, digoxin transport not affected
Page: 66, 67
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
303
 no
P-gp
2052
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
PubMed

PubMed

TitleDatePubMed
The effects of a short course of antibiotics on alvimopan and metabolite pharmacokinetics.
2010-03
Gastrointestinal recovery after laparoscopic colectomy: results of a prospective, observational, multicenter study.
2010-03
Alvimopan (entereg) for the management of postoperative ileus in patients undergoing bowel resection.
2010-01
Intensive Care Unit-acquired infection as a side effect of sedation.
2010
New drugs 09, part 1.
2009-12-24
Peripheral opioid antagonism.
2009-12
Comment on alvimopan guidelines.
2009-09
Pharmacologic options to prevent postoperative ileus.
2009-09
Economic analysis of alvimopan in North American Phase III efficacy trials.
2009-08-01
Alvimopan for postoperative ileus: only one piece of the puzzle.
2009-07-15
Alvimopan for postoperative ileus.
2009-07-15
An overview of constipation and newer therapies.
2009-06-18
Opioid receptors in the gastrointestinal tract.
2009-06-05
Preventing paralytic ileus: can the anesthesiologist help.
2009-06
Peripherally acting mu-opioid receptor antagonists and postoperative ileus: mechanisms of action and clinical applicability.
2009-06
Novel opioid antagonists for opioid-induced bowel dysfunction and postoperative ileus.
2009-04-04
Pharmacological management of postoperative ileus.
2009-04
Pathogenesis and management of postoperative ileus.
2009-02
Alvimopan (Entereg) for postoperative ileus.
2008-12-01
Gastrointestinal tract recovery in patients undergoing bowel resection: results of a randomized trial of alvimopan and placebo with a standardized accelerated postoperative care pathway.
2008-11
New drugs: methylnaltrexone bromide, alvimopan, and rilonacept.
2008-10-02
Alvimopan (Entereg), a Peripherally Acting mu-Opioid Receptor Antagonist For Postoperative Ileus.
2008-10
Management of postoperative ileus: focus on alvimopan.
2008-10
Postoperative ileus: strategies for reduction.
2008-10
Development of peripheral opioid antagonists' new insights into opioid effects.
2008-10
Alvimopan.
2008-09
Efficacy and safety of mu-opioid antagonists in the treatment of opioid-induced bowel dysfunction: systematic review and meta-analysis of randomized controlled trials.
2008-09
[News from the cochrane library: mu opioid antagonists for opioid-induced bowel dysfunction].
2008-09
Methylnaltrexone, a new peripherally acting mu-opioid receptor antagonist being evaluated for the treatment of postoperative ileus.
2008-09
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.
2008-08-01
New approaches to the treatment of opioid-induced constipation.
2008-08
Alvimopan, a peripherally acting mu-opioid receptor (PAM-OR) antagonist for the treatment of opioid-induced bowel dysfunction: results from a randomized, double-blind, placebo-controlled, dose-finding study in subjects taking opioids for chronic non-cancer pain.
2008-07-15
New drug to restore bowel function approved under new FDA rules.
2008-07-01
Alvimopan hastens recovery from abdominal surgery.
2008-07
Alvimopan and COX-2 inhibition reverse opioid and inflammatory components of postoperative ileus.
2008-06
Mu-opioid antagonists for opioid-induced bowel dysfunction.
2008-04-16
Novel trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as mu opioid receptor antagonists with improved opioid receptor selectivity profiles.
2008-03-15
New therapies in the treatment of postoperative ileus after gastrointestinal surgery.
2008-01-29
Systemic prokinetic pharmacologic treatment for postoperative adynamic ileus following abdominal surgery in adults.
2008-01-23
The involvement of the mu-opioid receptor in gastrointestinal pathophysiology: therapeutic opportunities for antagonism at this receptor.
2008-01
Opioid-induced bowel dysfunction.
2008-01
Alvimopan.
2008
Opioid-induced constipation in intensive care patients: relief in sight?
2008
Mu opioid receptor antagonists: recent developments.
2007-11
Peripherally acting opioid antagonists in the treatment of opiate-related constipation: a systematic review.
2007-11
Emerging pharmacologic options for treating postoperative ileus.
2007-10-15
Alvimopan accelerates gastrointestinal recovery after bowel resection regardless of age, gender, race, or concomitant medication use.
2007-10
Alvimopan: a peripherally acting mu-opioid receptor antagonist.
2007-09
Novel opioid antagonists for opioid-induced bowel dysfunction and postoperative ileus.
2007
Methylnaltrexone and alvimopan: economic management of opioid-induced bowel dysfunction.
2004-04
Patents

Patents

JP4343948B2
9
WO2007047935A1
3
WO2011161646A2
3
WO2013080221A2
3

Sample Use Guides

In Vivo Use Guide
12 mg administered 30 minutes to 5 hours prior to surgery followed by 12 mg twice daily for up to 7 days for a maximum of 15 doses
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: In morphine-naive guinea pig ileum alvimopan increased, the amplitude of electrically evoked contractions and spontaneous mechanical activity.
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:25:14 GMT 2025
Edited
by admin
on Mon Mar 31 18:25:14 GMT 2025
Record UNII
Q153V49P3Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALVIMOPAN ANHYDROUS
Common Name English
ANHYDROUS ALVIMOPAN
MART.  
Preferred Name English
Alvimopan [WHO-DD]
Common Name English
ALVIMOPAN [MI]
Common Name English
N-((2S)-2-(((3R,4R)-4-(3-HYDROXYPHENYL)-3,4-DIMETHYL-1-PIPERIDINYL)METHYL)-1-OXO-3-PHENYLPROPYL)GLYCINE
Systematic Name English
ALVIMOPAN [MART.]
Common Name English
GLYCINE, N-(2-((4-(3-HYDROXYPHENYL)-3,4-DIMETHYL-1-PIPERIDINYL)METHYL)-1-OXO-3-PHENYLPROPYL)-, (3R-((S*),3.ALPHA.,4.ALPHA.))-
Common Name English
alvimopan [INN]
Common Name English
ANHYDROUS ALVIMOPAN [MART.]
Common Name English
((2(S)-((4(R)-(3-HYDROXYPHENYL)-3(R),4-DIMETHYL-1-PIPERIDINYL)METHYL)-1-OXO-3-PHENYLPROPYL)AMINO)ACETIC ACID
Systematic Name English
(((2S)-2-(((3R,4R)-4-(3-HYDROXYPHENYL)-3,4-DIMETHYLPIPERIDIN-1-YL)METHYL)-3-PHENYLPROPANOYL)AMINO)ACETIC ACID
Systematic Name English
Classification Tree Code System Code
NDF-RT N0000000154
Created by admin on Mon Mar 31 18:25:14 GMT 2025 , Edited by admin on Mon Mar 31 18:25:14 GMT 2025
WHO-ATC A06AH02
Created by admin on Mon Mar 31 18:25:14 GMT 2025 , Edited by admin on Mon Mar 31 18:25:14 GMT 2025
NCI_THESAURUS C681
Created by admin on Mon Mar 31 18:25:14 GMT 2025 , Edited by admin on Mon Mar 31 18:25:14 GMT 2025
NDF-RT N0000175691
Created by admin on Mon Mar 31 18:25:14 GMT 2025 , Edited by admin on Mon Mar 31 18:25:14 GMT 2025
Code System Code Type Description
MERCK INDEX
m1636
Created by admin on Mon Mar 31 18:25:14 GMT 2025 , Edited by admin on Mon Mar 31 18:25:14 GMT 2025
PRIMARY Merck Index
CAS
156053-89-3
Created by admin on Mon Mar 31 18:25:14 GMT 2025 , Edited by admin on Mon Mar 31 18:25:14 GMT 2025
PRIMARY
EVMPD
SUB20585
Created by admin on Mon Mar 31 18:25:14 GMT 2025 , Edited by admin on Mon Mar 31 18:25:14 GMT 2025
PRIMARY
INN
8245
Created by admin on Mon Mar 31 18:25:14 GMT 2025 , Edited by admin on Mon Mar 31 18:25:14 GMT 2025
PRIMARY
SMS_ID
100000085983
Created by admin on Mon Mar 31 18:25:14 GMT 2025 , Edited by admin on Mon Mar 31 18:25:14 GMT 2025
PRIMARY
DAILYMED
Q153V49P3Z
Created by admin on Mon Mar 31 18:25:14 GMT 2025 , Edited by admin on Mon Mar 31 18:25:14 GMT 2025
PRIMARY
FDA UNII
Q153V49P3Z
Created by admin on Mon Mar 31 18:25:14 GMT 2025 , Edited by admin on Mon Mar 31 18:25:14 GMT 2025
PRIMARY
NCI_THESAURUS
C77377
Created by admin on Mon Mar 31 18:25:14 GMT 2025 , Edited by admin on Mon Mar 31 18:25:14 GMT 2025
PRIMARY
EPA CompTox
DTXSID60166035
Created by admin on Mon Mar 31 18:25:14 GMT 2025 , Edited by admin on Mon Mar 31 18:25:14 GMT 2025
PRIMARY
HSDB
7704
Created by admin on Mon Mar 31 18:25:14 GMT 2025 , Edited by admin on Mon Mar 31 18:25:14 GMT 2025
PRIMARY
PUBCHEM
5488548
Created by admin on Mon Mar 31 18:25:14 GMT 2025 , Edited by admin on Mon Mar 31 18:25:14 GMT 2025
PRIMARY
RXCUI
1516803
Created by admin on Mon Mar 31 18:25:14 GMT 2025 , Edited by admin on Mon Mar 31 18:25:14 GMT 2025
PRIMARY RxNorm
Related Record Type Details
Structure of ALVIMOPAN MONOHYDRATE
SOLVATE->ANHYDROUS
Structure of ALVIMOPAN ANHYDROUS
EXCRETED UNCHANGED
AMOUNT EXCRETED
URINE
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
Plasma protein binding of alvimopan was independent of concentration over ranges observed clinically and averaged 80% .
BINDING
Structure of ALVIMOPAN ANHYDROUS
EXCRETED UNCHANGED
AMOUNT EXCRETED
FECAL
MU-TYPE OPIOID RECEPTOR
TARGET -> INHIBITOR
Ki
Structure of ALVIMOPAN
SOLVATE->ANHYDROUS
Structure of ALVIMOPAN MONOHYDRATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of ADL-08-0011
METABOLITE -> PARENT
demonstrated in vitro to be equipotent to alvimopan
MAJOR
URINE
Structure of (2S,3S,4S,5R,6S)-6-(3-((3R,4R)-1-((2S)-2-BENZYL-3-HYDROXY-3-OXO-PROPYL)-3,4-DIMETHYL-4-PIPERIDYL)PHENOXY)-3,4,5-TRIHYDROXY-TETRAHYDROPYRAN-2-CARBOXYLIC ACID
METABOLITE -> PARENT
URINE
Related Record Type Details
Structure of ALVIMOPAN ANHYDROUS
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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