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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

Description

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

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.77 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
ENTEREG

Cmax

ValueDoseCo-administeredAnalytePopulation
10.98 ng/mL
12 mg 2 times / day multiple, oral
ALVIMOPAN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
40.2 ng × h/mL
12 mg 2 times / day multiple, oral
ALVIMOPAN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
13.5 h
12 mg 2 times / day multiple, oral
ALVIMOPAN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
20%
12 mg 2 times / day multiple, oral
ALVIMOPAN plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

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
Unknown