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Details

Stereochemistry ABSOLUTE
Molecular Formula C28H28N2O5
Molecular Weight 472.5323
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NALTALIMIDE

SMILES

OC1=CC=C2C[C@H]3N(CC4CC4)CC[C@@]56[C@@H](OC1=C25)[C@@H](CC[C@@]36O)N7C(=O)C8=C(C=CC=C8)C7=O

InChI

InChIKey=DHAITNWJDOSRBU-IBHWKQIPSA-N
InChI=1S/C28H28N2O5/c31-20-8-7-16-13-21-28(34)10-9-19(30-25(32)17-3-1-2-4-18(17)26(30)33)24-27(28,22(16)23(20)35-24)11-12-29(21)14-15-5-6-15/h1-4,7-8,15,19,21,24,31,34H,5-6,9-14H2/t19-,21-,24+,27+,28-/m1/s1

HIDE SMILES / InChI

Molecular Formula C28H28N2O5
Molecular Weight 472.5323
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Naltalimide (TRK-130), a mu opioid receptor partial agonist, is being developed by Toray Industries for the treatment of overactive bladder. A phase IIb trial is underway in Japan. In radioligand-binding assays with cells expressing human µ-opioid receptors (MORs), δ-opioid receptors (DORs), or κ-opioid receptors (KORs), TRK-130 showed high selectivity for MORs (Ki for MORs, DORs, and KORs = 0.268, 121, and 8.97 nM, respectively). TRK-130 is a potent and selective human MOR partial agonist without undesirable opioid adverse effects such as constipation and enhances the storage function by suppressing the afferent limb of the micturition reflex pathway.

Approval Year

PubMed

PubMed

TitleDatePubMed
Characteristics of TRK-130 (Naltalimide), a novel opioid ligand, as a new therapeutic agent for overactive bladder.
2014 Sep
Mechanisms of inhibitory action of TRK-130 (Naltalimide), a μ-opioid receptor partial agonist, on the micturition reflex.
2017 Apr
Re: Mechanisms of Inhibitory Action of TRK-130 (Naltalimide), a μ-Opioid Receptor Partial Agonist, on the Micturition Reflex.
2019 Apr
Patents

Sample Use Guides

Rats: Naltalimide (0.001-0.01 mg/kg, iv) dose-dependently inhibited RBCs, which was dose-dependently antagonized by naloxone; however, the antagonism susceptibility was different from morphine (1 mg/kg, iv). The minimum effective dose (0.003 mg/kg) of Naltalimide remained similar in spinal cord-transected animals. Naltalimide (0.0025 mg/kg, iv) increased bladder capacity without changing the voiding efficiency, maximum flow rate, and intravesical pressure at the maximum flow rate, whereas oxybutynin (1 mg/kg, iv) increased the bladder capacity but affected the other parameters. Naltalimide (0.005 mg/kg, iv) did not produce significant changes on the bladder contractions induced by peripheral stimulation of the pelvic nerve, while oxybutynin (1 mg/kg, iv) significantly suppressed the bladder contractions.
Route of Administration: Intravenous
In radioligand-binding assays with cells expressing human µ-opioid receptors (MORs), δ-opioid receptors (DORs), or κ-opioid receptors (KORs), TRK-130 showed high selectivity for MORs (Ki for MORs, DORs, and KORs = 0.268, 121, and 8.97 nM, respectively). In a functional assay (cAMP accumulation) with cells expressing each human opioid receptor subtype, TRK-130 showed potent but partial agonistic activity for MORs [EC50 (Emax) for MORs, DORs, and KORs = 2.39 nM (66.1%), 26.1 nM (71.0%), and 9.51 nM (62.6%), respectively].
Substance Class Chemical
Created
by admin
on Thu Jul 06 07:50:09 UTC 2023
Edited
by admin
on Thu Jul 06 07:50:09 UTC 2023
Record UNII
PUO0LMS4NX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NALTALIMIDE
INN  
INN  
Official Name English
naltalimide [INN]
Common Name English
TAK-363
Code English
2-(17-(CYCLOPROPYLMETHYL)-4,5.ALPHA.-EPOXY-3,14-DIHYDROXYMORPHINAN-6.BETA.-YL)ISOINDOLE-1,3-DIONE
Systematic Name English
Code System Code Type Description
FDA UNII
PUO0LMS4NX
Created by admin on Thu Jul 06 07:50:09 UTC 2023 , Edited by admin on Thu Jul 06 07:50:09 UTC 2023
PRIMARY
EPA CompTox
DTXSID10166868
Created by admin on Thu Jul 06 07:50:09 UTC 2023 , Edited by admin on Thu Jul 06 07:50:09 UTC 2023
PRIMARY
ChEMBL
CHEMBL3545408
Created by admin on Thu Jul 06 07:50:09 UTC 2023 , Edited by admin on Thu Jul 06 07:50:09 UTC 2023
PRIMARY
CAS
160359-68-2
Created by admin on Thu Jul 06 07:50:09 UTC 2023 , Edited by admin on Thu Jul 06 07:50:09 UTC 2023
PRIMARY
WIKIPEDIA
Naltalimide
Created by admin on Thu Jul 06 07:50:09 UTC 2023 , Edited by admin on Thu Jul 06 07:50:09 UTC 2023
PRIMARY
NCI_THESAURUS
C174856
Created by admin on Thu Jul 06 07:50:09 UTC 2023 , Edited by admin on Thu Jul 06 07:50:09 UTC 2023
PRIMARY
SMS_ID
300000034307
Created by admin on Thu Jul 06 07:50:09 UTC 2023 , Edited by admin on Thu Jul 06 07:50:09 UTC 2023
PRIMARY
INN
9548
Created by admin on Thu Jul 06 07:50:09 UTC 2023 , Edited by admin on Thu Jul 06 07:50:09 UTC 2023
PRIMARY
PUBCHEM
16066809
Created by admin on Thu Jul 06 07:50:09 UTC 2023 , Edited by admin on Thu Jul 06 07:50:09 UTC 2023
PRIMARY
Related Record Type Details
TARGET->PARTIAL AGONIST
Related Record Type Details
ACTIVE MOIETY