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
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
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 |
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/8057274 | http://adisinsight.springer.com/drugs/800003539
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
Sources: http://adisinsight.springer.com/drugs/800003539
Curator's Comment: # Eli Lilly
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8057274 |
0.77 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | ENTEREG Approved UseENTEREG 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 Date1.21124159E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.98 ng/mL |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
40.2 ng × h/mL |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
13.5 h |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
20% |
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
Dose | Population | Adverse events |
---|---|---|
120 mg single, oral Highest studied dose Dose: 120 mg Route: oral Route: single Dose: 120 mg Sources: |
healthy, adult Health Status: healthy Age Group: adult Sources: |
|
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: |
healthy, adult Health Status: healthy Age Group: adult Sources: |
|
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: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
|
12 mg 2 times / day steady, oral Dose: 12 mg, 2 times / day Route: oral Route: steady Dose: 12 mg, 2 times / day Sources: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
Other AEs: Ascites, Ileus... Other AEs: Ascites (serious, 1 patient) Sources: 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) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
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: |
unhealthy n = 66 Health Status: unhealthy Condition: ovarian cancer Population Size: 66 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/021775_ENTEREG_CAPSULES_BIOPHARMR.pdf Page: 94.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/021775_ENTEREG_CAPSULES_BIOPHARMR.pdf Page: 67, 97 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/021775_ENTEREG_CAPSULES_PHARMR.pdf Page: 99, 108 |
PubMed
Title | Date | PubMed |
---|---|---|
Selective postoperative inhibition of gastrointestinal opioid receptors. | 2001 Sep 27 |
|
Postoperative ileus: etiologies and interventions. | 2003 Mar |
|
Alvimopan, a selective peripherally acting mu-opioid antagonist. | 2005 Apr |
|
Alvimopan: an oral, peripherally acting, mu-opioid receptor antagonist for the treatment of opioid-induced bowel dysfunction--a 21-day treatment-randomized clinical trial. | 2005 Mar |
|
Basic and clinical pharmacology of new motility promoting agents. | 2005 Oct |
|
Alvimopan: ADL 8-2698, ADL 82698, Entrareg, LY 246736. | 2006 |
|
The surgical team and outcomes management: focus on postoperative ileus. | 2006 Apr |
|
Peripherally acting mu-opioid-receptor antagonists and the connection between postoperative ileus and pain management: The anesthesiologist's view and beyond. | 2006 Apr |
|
Bench-to-bedside review: Routine postoperative use of the nasogastric tube - utility or futility? | 2007 |
|
Treatment of opioid-induced gut dysfunction. | 2007 Feb |
|
Emerging pharmacologic options for treating postoperative ileus. | 2007 Oct 15 |
|
New approaches to the treatment of opioid-induced constipation. | 2008 Aug |
|
The involvement of the mu-opioid receptor in gastrointestinal pathophysiology: therapeutic opportunities for antagonism at this receptor. | 2008 Jan |
|
Pharmacokinetics of alvimopan and its metabolite in healthy volunteers and patients in postoperative ileus trials. | 2008 May |
|
Postoperative ileus: strategies for reduction. | 2008 Oct |
|
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 Sep |
|
[News from the cochrane library: mu opioid antagonists for opioid-induced bowel dysfunction]. | 2008 Sep |
|
New drugs: methylnaltrexone bromide, alvimopan, and rilonacept. | 2008 Sep-Oct |
|
Novel opioid antagonists for opioid-induced bowel dysfunction and postoperative ileus. | 2009 Apr 4 |
|
Alvimopan for postoperative ileus. | 2009 Jul 15 |
|
Gastrointestinal recovery after laparoscopic colectomy: results of a prospective, observational, multicenter study. | 2010 Mar |
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17340127
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
Edited
Fri Dec 15 16:19:53 UTC 2023
by
admin
on
Fri Dec 15 16:19:53 UTC 2023
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Record UNII |
Q153V49P3Z
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000000154
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WHO-ATC |
A06AH02
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NCI_THESAURUS |
C681
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NDF-RT |
N0000175691
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m1636
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156053-89-3
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SUB20585
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100000085983
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Q153V49P3Z
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PRIMARY | RxNorm |
Related Record | Type | Details | ||
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SOLVATE->ANHYDROUS | |||
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EXCRETED UNCHANGED |
AMOUNT EXCRETED
URINE
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BINDER->LIGAND |
Plasma protein binding of alvimopan was independent of concentration over ranges observed clinically and averaged 80% .
BINDING
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EXCRETED UNCHANGED |
AMOUNT EXCRETED
FECAL
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TARGET -> INHIBITOR |
Ki
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SOLVATE->ANHYDROUS | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
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METABOLITE -> PARENT |
demonstrated in vitro to be equipotent to alvimopan
MAJOR
URINE
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METABOLITE -> PARENT |
URINE
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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