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Compound Detail

CHEMBL270190

ALVIMOPAN
💊 Approved Drug
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💊 Approved Drug
C[C@H]1CN(C[C@H](Cc2ccccc2)C(=O)NCC(=O)O)CC[C@@]1(C)c1cccc(O)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL270190
Name ALVIMOPAN
Phase Approved
Structure Type MOL
InChI Key UPNUIXSCZBYVBB-JVFUWBCBSA-N
Therapeutic ✓ Yes

Known Names

ADL 8-2698 ADL-8-2698 Alvimopan Alvimopan anhydrous Alvimopan dihydrate Anhydrous alvimopan Entereg LY-246736 LY-246736 DIHYDRATE LY246736
6
Targets
15
Activities
2
Assay Types
3
PK Parameters
20
Publications
10
Known Names
6
Indications
1
Mechanisms

Molecular Properties

424.5
MW (Da)
3.05
ALogP
4
HBA
3
HBD
89.9
PSA (Ų)
0.61
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2008
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Year 2002

Extended Properties

Molecular Formula C25H32N2O4
MW 424.54
Aromatic Rings 2
Heavy Atoms 31
NP-Likeness 0.32

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Mu opioid receptor antagonist ANTAGONIST Mu-type opioid receptor ✓ ✓

Indications

Constipation Fallopian Tube Neoplasms Ileus Ovarian Neoplasms Peritoneal Neoplasms Urinary Bladder Neoplasms

ATC Classification

A06AH02
alvimopan
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS FOR CONSTIPATION

Drug Warnings

Black Box Warning
cardiotoxicity
Country: United States
Black Box Warning
psychiatric toxicity
Country: United States

Activity Summary

IC50 8 meas. best 8.77
Ki 7 meas. best 9.5

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL233
 Ki 9.5 9.3133 0.3 3
Mu-type opioid receptor
CHEMBL233
 IC50 8.77 8.5967 1.7 3
Delta-type opioid receptor
CHEMBL236
 Ki 8.3 8.11 5.0 2
Kappa-type opioid receptor
CHEMBL3952
 Ki 8.3 8.3 5.0 1
Kappa-type opioid receptor
CHEMBL237
 Ki 7.0 7.0 100.0 1
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL1940
 IC50 5.3 5.3 5011.9 1
Voltage-gated potassium channel, IKs; KCNQ1(Kv7.1)/KCNE1(MinK)
CHEMBL2221347
 IC50 4.3 4.3 50118.7 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 1.5 hr Rattus norvegicus
T1/2 1.5 hr Canis lupus familiaris
T1/2 1.5 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor Ki = 0.3162 nM 9.5 Displacement of [3H]DPN from recombinant human mu opioid receptor expressed in C... 28499731
Mu-type opioid receptor Ki = 0.47 nM 9.33 Displacement of [3H]diprenorphine from human cloned mu opioid receptor 18313920
Mu-type opioid receptor Ki = 0.77 nM 9.11 Displacement of [3H]DAMGO from human cloned mu-opioid receptor by radioligand bi... 30243589
Mu-type opioid receptor IC50 = 1.7 nM 8.77 Antagonist activity at human cloned mu opioid receptor assessed as inhibition of... 18313920
Mu-type opioid receptor IC50 = 3.0 nM 8.52 Antagonist activity at recombinant human MOR expressed in HEK293T cells assessed... 28726402
Mu-type opioid receptor IC50 = 3.162 nM 8.5 Antagonist activity at recombinant human MOR expressed in HEK293T cells assessed... 28726402
Delta-type opioid receptor Ki = 5.012 nM 8.3 Displacement of [3H]DPN from recombinant human delta opioid receptor expressed i... 28499731
Kappa-type opioid receptor Ki = 5.012 nM 8.3 Displacement of [3H]DPN from guinea pig kappa opioid receptor expressed in CHOK1... 28499731
Delta-type opioid receptor Ki = 12.0 nM 7.92 Displacement of [3H]diprenorphine from human cloned delta opioid receptor 18313920
Kappa-type opioid receptor Ki = 100.0 nM 7.0 Displacement of [3H]diprenorphine from human cloned kappa opioid receptor 18313920
Voltage-dependent L-type calcium channel subunit alpha-1C IC50 = 5011.87 nM 5.3 Inhibition of long-lasting type calcium current (hICa) in Chinese Hamster Ovary ... 25087753
Voltage-gated potassium channel, IKs; KCNQ1(Kv7.1)/KCNE1(MinK) IC50 = 50118.72 nM 4.3 Inhibition of slow delayed inward rectifying potassium current (Iks) in Chinese ... 25087753

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5058564 HEK-293T 9
- 10.6019/CHEMBL5058564 U2OS 6
28726402 10.1021/acs.jmedchem.7b00643 Mu-type opioid receptor 3
28499731 10.1016/j.bmcl.2017.04.092 Liver 3
- 10.6019/CHEMBL5209801 G-protein coupled receptor 35 2
28726402 10.1021/acs.jmedchem.7b00643 Kappa-type opioid receptor 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
28726402 10.1021/acs.jmedchem.7b00643 Delta-type opioid receptor 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 2
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 2
28499731 10.1016/j.bmcl.2017.04.092 Mu-type opioid receptor 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 2
- 10.6019/CHEMBL5209801 Apelin receptor 2
25087753 10.1016/j.vascn.2014.07.002 Voltage-gated inwardly rectifying potassium channel KCNH2 2
23116124 10.1021/jm301247n Unchecked 2
18313920 10.1016/j.bmcl.2008.01.106 Unchecked 2
- 10.6019/CHEMBL5058564 Fibroblast 2
18313920 10.1016/j.bmcl.2008.01.106 Mu-type opioid receptor 2

Data from ChEMBL 36 via Core Engine