Trends in LIMS

Naltalimide

Clinical data
ATC code	None
Identifiers
IUPAC name 2-[(5α,6β)-17-(Cyclopropylmethyl)-3,14-dihydroxy-4,5-epoxymorphinan-6-yl]-1H-isoindole-1,3(2H)-dione
CAS Number	160359-68-2
PubChem CID	16066809
ChemSpider	17226389
UNII	PUO0LMS4NX
CompTox Dashboard (EPA)	DTXSID10166868
Chemical and physical data
Formula	C28H28N2O5
Molar mass	472.541 g·mol−1
3D model (JSmol)	Interactive image
SMILES c1ccc2c(c1)C(=O)N(C2=O)[C@@H]3CC[C@]4([C@H]5Cc6ccc(c7c6[C@]4([C@H]3O7)CCN5CC8CC8)O)O
InChI 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 Key:DHAITNWJDOSRBU-IBHWKQIPSA-N

Naltalimide (INN) (code name TRK-130, formerly TAK 363) is a novel, centrally-acting opioid drug which is under development by Takeda and Toray for the treatment of overactive bladder/urinary incontinence.^[1][2] It acts as a potent and selective partial agonist of the μ-opioid receptor (K_i = 0.268 nM, EC₅₀ = 2.39 nM, E_max = 66.1%) over the δ-opioid (K_i = 121 nM, EC₅₀ = 26.1 nM, E_max = 71.0%) and κ-opioid receptors (K_i = 8.97 nM, EC₅₀ = 9.51 nM, E_max = 62.6%).^[1] Notably, naltalimide somehow appears to lack certain undesirable side effects such as constipation seen with other μ-opioid receptor agonists such as morphine.^[1] It enhances bladder storage via suppression of the afferent limb of the micturition reflex pathway.^[1]