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156053-89-3 | Glycine, N-[(2S)-2-[[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl]-1-oxo-3-phenylpropyl]-
CAS No: 156053-89-3 Catalog No: AG001OGS MDL No:MFCD09838268
Product Description
Catalog Number:
AG001OGS
Chemical Name:
Glycine, N-[(2S)-2-[[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl]-1-oxo-3-phenylpropyl]-
CAS Number:
156053-89-3
Molecular Formula:
C25H32N2O4
Molecular Weight:
424.5326
MDL Number:
MFCD09838268
IUPAC Name:
2-[[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanoyl]amino]acetic acid
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
InChI Key:
UPNUIXSCZBYVBB-JVFUWBCBSA-N
SMILES:
OC(=O)CNC(=O)[C@@H](Cc1ccccc1)CN1CC[C@@]([C@H](C1)C)(C)c1cccc(c1)O
UNII:
Q153V49P3Z
Properties
Complexity:
606
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
3
Defined Bond Stereocenter Count:
0
Exact Mass:
424.236g/mol
Formal Charge:
0
Heavy Atom Count:
31
Hydrogen Bond Acceptor Count:
5
Hydrogen Bond Donor Count:
3
Isotope Atom Count:
0
Molecular Weight:
424.541g/mol
Monoisotopic Mass:
424.236g/mol
Rotatable Bond Count:
8
Topological Polar Surface Area:
89.9A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.7
Literature
| Title | Journal |
|---|---|
| Role of alvimopan (entereg) in gastrointestinal recovery and hospital length of stay after bowel resection. | P & T : a peer-reviewed journal for formulary management 20120901 |
| Alvimopan provides rapid gastrointestinal recovery without nasogastric tube decompression after radical cystectomy and urinary diversion. | The Canadian journal of urology 20120601 |
| Re: Alvimopan provides rapid gastrointestinal recovery without nasogastric tube decompression after radical cystectomy and urinary diversion. | The Canadian journal of urology 20120601 |
| A meta-analysis of the effectiveness of the opioid receptor antagonist alvimopan in reducing hospital length of stay and time to GI recovery in patients enrolled in a standardized accelerated recovery program after abdominal surgery. | Diseases of the colon and rectum 20120501 |
| Evaluation of clinical outcomes with alvimopan in clinical practice: a national matched-cohort study in patients undergoing bowel resection. | Annals of surgery 20120401 |
| Pathogenesis and clinical and economic consequences of postoperative ileus. | The Surgical clinics of North America 20120401 |
| Real world efficacy of alvimopan on elective bowel resection patients: an analysis of statistical versus clinical significance. | American journal of surgery 20120301 |
| Alternatives to prokinetics to move the pylorus and colon. | Current opinion in clinical nutrition and metabolic care 20120301 |
| Management of postoperative ileus. | Orthopedics 20120301 |
| The effect of erythromycin on gastrointestinal motility in subtotal gastrectomized patients. | Journal of the Korean Surgical Society 20120301 |
| Economic analysis of alvimopan for prevention and management of postoperative ileus. | Pharmacotherapy 20120201 |
| Ghrelin agonist TZP-101/ulimorelin accelerates gastrointestinal recovery independently of opioid use and surgery type: covariate analysis of phase 2 data. | World journal of surgery 20120101 |
| Role of gum chewing on the duration of postoperative ileus following ileostomy closure done for typhoid ileal perforation: a prospective randomized trial. | Saudi journal of gastroenterology : official journal of the Saudi Gastroenterology Association 20120101 |
| Drug management of visceral pain: concepts from basic research. | Pain research and treatment 20120101 |
| Alvimopan for acceleration of GI recovery after bowel resection. | Medsurg nursing : official journal of the Academy of Medical-Surgical Nurses 20120101 |
| Introduction of alvimopan into an enhanced recovery protocol for colectomy offers benefit in open but not laparoscopic colectomy. | Journal of laparoendoscopic & advanced surgical techniques. Part A 20111201 |
| Does alvimopan enhance return of bowel function in laparoscopic right colectomy? | The American surgeon 20111101 |
| Perioperative bowel management for gynecologic surgery. | American journal of obstetrics and gynecology 20111001 |
| Risk factors for postoperative ileus. | Journal of the Korean Surgical Society 20111001 |
| Diagnosis and treatment of chronic constipation--a European perspective. | Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20110801 |
| Novel opioid antagonists for opioid-induced bowel dysfunction. | Expert opinion on investigational drugs 20110801 |
| An update on analgesics. | British journal of anaesthesia 20110701 |
| The effect of alvimopan on recovery after laparoscopic segmental colectomy. | Diseases of the colon and rectum 20110601 |
| Opioid-induced constipation: challenges and therapeutic opportunities. | The American journal of gastroenterology 20110501 |
| Impact of alvimopan (entereg) on hospital costs after bowel resection: results from a large inpatient database. | P & T : a peer-reviewed journal for formulary management 20110401 |
| A randomized, placebo-controlled phase 3 trial (Study SB-767905/013) of alvimopan for opioid-induced bowel dysfunction in patients with non-cancer pain. | The journal of pain : official journal of the American Pain Society 20110201 |
| A randomized, placebo-controlled phase 3 trial (Study SB-767905/012) of alvimopan for opioid-induced bowel dysfunction in patients with non-cancer pain. | The journal of pain : official journal of the American Pain Society 20110201 |
| Effects of casoxin 4 on morphine inhibition of small animal intestinal contractility and gut transit in the mouse. | Clinical and experimental gastroenterology 20110101 |
| Current concepts in the management of opioid-induced constipation: a perfect review with an imperfect concept. | Journal of opioid management 20110101 |
| Opioid-induced constipation in advanced illness: safety and efficacy of methylnaltrexone bromide. | Clinical Medicine Insights. Oncology 20110101 |
| Anesthetic Routines: The Anesthesiologist's Role in GI Recovery and Postoperative Ileus. | Advances in preventive medicine 20110101 |
| Alvimopan addition to a standard perioperative recovery pathway. | JSLS : Journal of the Society of Laparoendoscopic Surgeons 20110101 |
| Alvimopan use in laparoscopic and open bowel resections: clinical results in a large community hospital system. | The Annals of pharmacotherapy 20101101 |
| Efficacy and safety of prucalopride in patients with chronic noncancer pain suffering from opioid-induced constipation. | Digestive diseases and sciences 20101001 |
| Opioid antagonists for prevention and treatment of opioid-induced gastrointestinal effects. | Current opinion in anaesthesiology 20101001 |
| Alvimopan for the management of postoperative ileus after bowel resection: characterization of clinical benefit by pooled responder analysis. | World journal of surgery 20100901 |
| Neuropathy, retinopathy, and glucose-lowering treatments. | Diabetes care 20100601 |
| Gastrointestinal recovery after laparoscopic colectomy: results of a prospective, observational, multicenter study. | Surgical endoscopy 20100301 |
| The effects of a short course of antibiotics on alvimopan and metabolite pharmacokinetics. | Journal of clinical pharmacology 20100301 |
| Alvimopan (entereg) for the management of postoperative ileus in patients undergoing bowel resection. | P & T : a peer-reviewed journal for formulary management 20100101 |
| Intensive Care Unit-acquired infection as a side effect of sedation. | Critical care (London, England) 20100101 |
| Managing opioid-induced constipation in advanced illness: focus on methylnaltrexone bromide. | Therapeutics and clinical risk management 20100101 |
| Update on the management of constipation in the elderly: new treatment options. | Clinical interventions in aging 20100101 |
| Pathogenesis and clinical and economic consequences of postoperative ileus. | Clinical and experimental gastroenterology 20100101 |
| Comment: update on the management of constipation in the elderly: new treatment options. | Clinical interventions in aging 20100101 |
| Peripheral opioid antagonism. | Anaesthesia 20091201 |
| Pharmacologic options to prevent postoperative ileus. | The Annals of pharmacotherapy 20090901 |
| Comment on alvimopan guidelines. | Critical care medicine 20090901 |
| Economic analysis of alvimopan in North American Phase III efficacy trials. | American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20090801 |
| Alvimopan for postoperative ileus. | American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20090715 |
| Alvimopan for postoperative ileus: only one piece of the puzzle. | American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20090715 |
| Opioid receptors in the gastrointestinal tract. | Regulatory peptides 20090605 |
| Peripherally acting mu-opioid receptor antagonists and postoperative ileus: mechanisms of action and clinical applicability. | Anesthesia and analgesia 20090601 |
| Preventing paralytic ileus: can the anesthesiologist help. | Middle East journal of anaesthesiology 20090601 |
| Novel opioid antagonists for opioid-induced bowel dysfunction and postoperative ileus. | Lancet (London, England) 20090404 |
| Pharmacological management of postoperative ileus. | Canadian journal of surgery. Journal canadien de chirurgie 20090401 |
| Pathogenesis and management of postoperative ileus. | Clinics in colon and rectal surgery 20090201 |
| An overview of constipation and newer therapies. | The American journal of hospice & palliative care 20090101 |
| New drugs 09, part 1. | Plastic surgical nursing : official journal of the American Society of Plastic and Reconstructive Surgical Nurses 20090101 |
| Methylnaltrexone: the evidence for its use in the management of opioid-induced constipation. | Core evidence 20090101 |
| Recent advances in the use of opioids for cancer pain. | Journal of pain research 20090101 |
| Alvimopan (Entereg) for postoperative ileus. | The Medical letter on drugs and therapeutics 20081201 |
| Gastrointestinal tract recovery in patients undergoing bowel resection: results of a randomized trial of alvimopan and placebo with a standardized accelerated postoperative care pathway. | Archives of surgery (Chicago, Ill. : 1960) 20081101 |
| Development of peripheral opioid antagonists' new insights into opioid effects. | Mayo Clinic proceedings 20081001 |
| Postoperative ileus: strategies for reduction. | Therapeutics and clinical risk management 20081001 |
| Management of postoperative ileus: focus on alvimopan. | Therapeutics and clinical risk management 20081001 |
| Alvimopan (Entereg), a Peripherally Acting mu-Opioid Receptor Antagonist For Postoperative Ileus. | P & T : a peer-reviewed journal for formulary management 20081001 |
| Methylnaltrexone, a new peripherally acting mu-opioid receptor antagonist being evaluated for the treatment of postoperative ileus. | Expert opinion on investigational drugs 20080901 |
| [News from the cochrane library: mu opioid antagonists for opioid-induced bowel dysfunction]. | Zeitschrift fur Gastroenterologie 20080901 |
| Efficacy and safety of mu-opioid antagonists in the treatment of opioid-induced bowel dysfunction: systematic review and meta-analysis of randomized controlled trials. | Pain medicine (Malden, Mass.) 20080901 |
| Alvimopan. | Nature reviews. Drug discovery 20080901 |
| New approaches to the treatment of opioid-induced constipation. | European review for medical and pharmacological sciences 20080801 |
| 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. | Alimentary pharmacology & therapeutics 20080801 |
| 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. | Pain 20080715 |
| New drug to restore bowel function approved under new FDA rules. | American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20080701 |
| Alvimopan hastens recovery from abdominal surgery. | Managed care (Langhorne, Pa.) 20080701 |
| Alvimopan and COX-2 inhibition reverse opioid and inflammatory components of postoperative ileus. | Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20080601 |
| Pharmacokinetics of alvimopan and its metabolite in healthy volunteers and patients in postoperative ileus trials. | Clinical pharmacology and therapeutics 20080501 |
| Mu-opioid antagonists for opioid-induced bowel dysfunction. | The Cochrane database of systematic reviews 20080416 |
| Novel trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as mu opioid receptor antagonists with improved opioid receptor selectivity profiles. | Bioorganic & medicinal chemistry letters 20080315 |
| Opioid-induced bowel dysfunction. | Current treatment options in gastroenterology 20080201 |
| Systemic prokinetic pharmacologic treatment for postoperative adynamic ileus following abdominal surgery in adults. | The Cochrane database of systematic reviews 20080123 |
| Opioid-induced bowel dysfunction. | Journal of pain and symptom management 20080101 |
| The involvement of the mu-opioid receptor in gastrointestinal pathophysiology: therapeutic opportunities for antagonism at this receptor. | Pharmacology & therapeutics 20080101 |
| New therapies in the treatment of postoperative ileus after gastrointestinal surgery. | American journal of therapeutics 20080101 |
| Opioid-induced constipation in intensive care patients: relief in sight? | Critical care (London, England) 20080101 |
| Alvimopan. | Drugs 20080101 |
| New drugs: methylnaltrexone bromide, alvimopan, and rilonacept. | Journal of the American Pharmacists Association : JAPhA 20080101 |
| Methylnaltrexone in the treatment of opioid-induced constipation. | Clinical and experimental gastroenterology 20080101 |
| Peripherally acting opioid antagonists in the treatment of opiate-related constipation: a systematic review. | Journal of pain and symptom management 20071101 |
| Mu opioid receptor antagonists: recent developments. | ChemMedChem 20071101 |
| Emerging pharmacologic options for treating postoperative ileus. | American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20071015 |
| Alvimopan accelerates gastrointestinal recovery after bowel resection regardless of age, gender, race, or concomitant medication use. | Surgery 20071001 |
| Is alvimopan a safe and effective treatment for postoperative ileus? | Nature clinical practice. Gastroenterology & hepatology 20070901 |
| Alvimopan: a peripherally acting mu-opioid receptor antagonist. | Drugs of today (Barcelona, Spain : 1998) 20070901 |
| Cancer-related constipation. | Current oncology reports 20070701 |
| Patterns of gastrointestinal recovery after bowel resection and total abdominal hysterectomy: pooled results from the placebo arms of alvimopan phase III North American clinical trials. | Journal of the American College of Surgeons 20070701 |
| Novel and alternative therapies for childhood constipation. | Current gastroenterology reports 20070601 |
| Moving ahead or falling behind? | Nature clinical practice. Gastroenterology & hepatology 20070601 |
| The in vitro pharmacology of the peripherally restricted opioid receptor antagonists, alvimopan, ADL 08-0011 and methylnaltrexone. | Naunyn-Schmiedeberg's archives of pharmacology 20070501 |
| Postoperative ileus-related morbidity profile in patients treated with alvimopan after bowel resection. | Journal of the American College of Surgeons 20070401 |
| Alvimopan, for postoperative ileus following bowel resection: a pooled analysis of phase III studies. | Annals of surgery 20070301 |
| Pharmacologic management of postoperative ileus: the next chapter in GI surgery. | Annals of surgery 20070301 |
| Treatment of opioid-induced gut dysfunction. | Expert opinion on investigational drugs 20070201 |
| Meta-analysis: Alvimopan vs. placebo in the treatment of post-operative ileus. | Alimentary pharmacology & therapeutics 20070101 |
| Bench-to-bedside review: Routine postoperative use of the nasogastric tube - utility or futility? | Critical care (London, England) 20070101 |
| Novel opioid antagonists for opioid-induced bowel dysfunction and postoperative ileus. | Journal of pain & palliative care pharmacotherapy 20070101 |
| Pain management research goes beyond the obvious. | American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20061201 |
| The selective mu opioid receptor antagonist, alvimopan, improves delayed GI transit of postoperative ileus in rats. | Brain research 20060802 |
| A double-blind, randomized, placebo-controlled phase III study of the safety of alvimopan in patients who undergo simple total abdominal hysterectomy. | American journal of obstetrics and gynecology 20060801 |
| Use of novel prokinetic agents to facilitate return of gastrointestinal motility in adult critically ill patients. | Current opinion in critical care 20060801 |
| Current gut-directed therapies for irritable bowel syndrome. | Current treatment options in gastroenterology 20060701 |
| Optimizing perioperative management of patients undergoing colorectal surgery: what is new? | Current opinion in critical care 20060401 |
| Peripherally acting mu-opioid-receptor antagonists and the connection between postoperative ileus and pain management: The anesthesiologist's view and beyond. | Journal of perianesthesia nursing : official journal of the American Society of PeriAnesthesia Nurses 20060401 |
| The surgical team and outcomes management: focus on postoperative ileus. | Journal of perianesthesia nursing : official journal of the American Society of PeriAnesthesia Nurses 20060401 |
| Nurses are everywhere: a practical perspective on the surgical team in managing postoperative ileus. | Journal of perianesthesia nursing : official journal of the American Society of PeriAnesthesia Nurses 20060401 |
| Current choices--good or bad--for the proactive management of postoperative ileus: A surgeon's view. | Journal of perianesthesia nursing : official journal of the American Society of PeriAnesthesia Nurses 20060401 |
| Postoperative upper and lower gastrointestinal recovery and gastrointestinal morbidity in patients undergoing bowel resection: pooled analysis of placebo data from 3 randomized controlled trials. | American journal of surgery 20060301 |
| Alvimopan, a peripherally acting mu-opioid receptor antagonist, compared with placebo in postoperative ileus after major abdominal surgery: results of a randomized, double-blind, controlled study. | Surgical endoscopy 20060101 |
| Peripheral opioids for functional GI disease: a reappraisal. | Digestive diseases (Basel, Switzerland) 20060101 |
| Alvimopan: ADL 8-2698, ADL 82698, Entrareg, LY 246736. | Drugs in R&D 20060101 |
| Basic and clinical pharmacology of new motility promoting agents. | Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20051001 |
| [(3)H]Alvimopan binding to the micro opioid receptor: comparative binding kinetics of opioid antagonists. | European journal of pharmacology 20050927 |
| Alvimopan for the management of postoperative ileus. | The Annals of pharmacotherapy 20050901 |
| Effect of alvimopan and codeine on gastrointestinal transit: a randomized controlled study. | Clinical gastroenterology and hepatology : the official clinical practice journal of the American Gastroenterological Association 20050801 |
| Phase III trial of alvimopan, a novel, peripherally acting, mu opioid antagonist, for postoperative ileus after major abdominal surgery. | Diseases of the colon and rectum 20050601 |
| Molecule of the month. Alvimopan hydrate. | Drug news & perspectives 20050601 |
| Alvimopan, a selective peripherally acting mu-opioid antagonist. | Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20050401 |
| Alvimopan. | Expert opinion on investigational drugs 20050401 |
| Alvimopan: an oral, peripherally acting, mu-opioid receptor antagonist for the treatment of opioid-induced bowel dysfunction--a 21-day treatment-randomized clinical trial. | The journal of pain : official journal of the American Pain Society 20050301 |
| Peripheral opiate action on afferent fibres supplying the rat intestine. | Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20041001 |
| Preclinical studies of opioids and opioid antagonists on gastrointestinal function. | Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20041001 |
| Alvimopan, a novel, peripherally acting mu opioid antagonist: results of a multicenter, randomized, double-blind, placebo-controlled, phase III trial of major abdominal surgery and postoperative ileus. | Annals of surgery 20041001 |
| Opioids and opioid receptors in the enteric nervous system: from a problem in opioid analgesia to a possible new prokinetic therapy in humans. | Neuroscience letters 20040506 |
| Emerging techniques for postoperative analgesia in orthopedic surgery. | American journal of orthopedics (Belle Mead, N.J.) 20040501 |
| Methylnaltrexone and alvimopan: economic management of opioid-induced bowel dysfunction. | Expert review of pharmacoeconomics & outcomes research 20040401 |
| Postoperative ileus: etiologies and interventions. | Clinical gastroenterology and hepatology : the official clinical practice journal of the American Gastroenterological Association 20030301 |
| Opioid-induced bowel dysfunction: pathophysiology and potential new therapies. | Drugs 20030101 |
| Alvimopan (Adolor/GlaxoSmithKline). | Current opinion in investigational drugs (London, England : 2000) 20021001 |
| Awakening the sleeping postsurgical abdomen. | Gastroenterology 20020401 |
| Use of selective opiate receptor inhibitors to prevent postoperative ileus. | Minerva anestesiologica 20020401 |
| Alvimopan* (ADL 8-2698) is a novel peripheral opioid antagonist. | American journal of surgery 20011101 |
| Selective postoperative inhibition of gastrointestinal opioid receptors. | The New England journal of medicine 20010927 |
| An opioid antagonist for postoperative ileus. | The New England journal of medicine 20010927 |
| ADL 8-2698, a trans-3,4-dimethyl-4-(3-hydroxyphenyl) piperidine, prevents gastrointestinal effects of intravenous morphine without affecting analgesia. | Clinical pharmacology and therapeutics 20010101 |
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