General
Preferred name
NALDEMEDINE
Synonyms
Symproic ()
NALDEMEDINE TOSYLATE ()
S-297995 ()
Naldemedine (tosylate) ()
S-297995 (tosylate) ()
Naldemedina ()
Naldemedine ()
Rizmoic ()
Naldemedine tosilate ()
P&D ID
PD046720
CAS
1345728-04-2
916072-89-4
Tags
available
drug
Approved by
FDA
EMA
First approval
2017
Drug indication
Constipation
Opioid-induced constipation
Opioid dependence
Drug Status
approved
investigational
Max Phase
4.0
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION
Naldemedine is a μ opioid receptor antagonist, designed to act peripherally (peripherally acting mu-opioid receptor antagonist or PAMORA). It is being investigated for its ability to counteract opioid agonist-induced adverse effects such as constipation, nausea, and vomiting. Naldemedine is being developed by Shionogi Inc. It is the compound claimed in patent WO2013172297 with formula IA (17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3,6,14-trihydroxy-N-[2-(3-phenyl-1,2,4-oxadiazol-5-yl)propan-2-yl]morphinan-7-carboxamide 4-methylbenzenesulfonic acid) .
DESCRIPTION
Naldemedine (S-297995) is a dual μ/δ opioid receptor antagonist, designed to act peripherally (peripherally acting mu-opioid receptor antagonist or PAMORA) . It is used clinically for its ability to counteract opioid agonist-induced adverse effects such as constipation, nausea, and vomiting. Naldemedine was developed by Shionogi Inc. It is the compound claimed in patent WO2013172297 with formula IA (17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3,6,14-trihydroxy-N-[2-(3-phenyl-1,2,4-oxadiazol-5-yl)propan-2-yl]morphinan-7-carboxamide 4-methylbenzenesulfonic acid) .
(GtoPdb)
DESCRIPTION
Naldemedine (S-297995) tosylate is an orally active ¦Ì-opioid receptor antagonist (PAMORA)[1]. Naldemedine tosylate shows potent binding affinities (Ki=0.34, 0.43, 0.94 nM, respectively) and antagonist activities (IC50=25.57, 7.09, 16.1 nM, respectively) for recombinant human ¦Ì-, ¦Ä-, and ¦Ê- opioid receptors[2]. Naldemedine can be used in opioid-induced constipation (OIC) research[2]. Naldemedine tosylate is predicted to bind to 3CLpro encoded by SARS-CoV2 genome[3].
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Compound Sets
13
ChEMBL Approved Drugs
ChEMBL Drugs
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP Approved Drugs
Guide to Pharmacology
MedChem Express Bioactive Compound Library
Natural product-based probes and drugs
NCATS Inxight Approved Drugs
ReFrame library
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
40
Molecular Weight
570.25
Hydrogen Bond Acceptors
9
Hydrogen Bond Donors
4
Rotatable Bonds
6
Ring Count
8
Aromatic Ring Count
3
cLogP
3.48
TPSA
141.18
Fraction CSP3
0.47
Chiral centers
4.0
Largest ring
6.0
QED
0.35
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Biosynthetic Origin
Alkaloid
Therapeutic Indication
Opioid Induced Constipation
Therapeutic Class
CNS & PNS
Target
Opioid Receptor
Pathway
GPCR/G protein
Neuronal Signaling
Source data
