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Naltalimide

From Wikipedia, the free encyclopedia

Naltalimide
Clinical data
ATC code
  • None
Identifiers
  • 2-[(5α,6β)-17-(Cyclopropylmethyl)-3,14-dihydroxy-4,5-epoxymorphinan-6-yl]-1H-isoindole-1,3(2H)-dione
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC28H28N2O5
Molar mass472.541 g·mol−1
3D model (JSmol)
  • 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=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 (Ki = 0.268 nM, EC50 = 2.39 nM, Emax = 66.1%) over the δ-opioid (Ki = 121 nM, EC50 = 26.1 nM, Emax = 71.0%) and κ-opioid receptors (Ki = 8.97 nM, EC50 = 9.51 nM, Emax = 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]

References

  1. ^ a b c d Fujimura M, Izumimoto N, Momen S, Yoshikawa S, Kobayashi R, Kanie S, et al. (September 2014). "Characteristics of TRK-130 (Naltalimide), a novel opioid ligand, as a new therapeutic agent for overactive bladder". The Journal of Pharmacology and Experimental Therapeutics. 350 (3): 543–51. doi:10.1124/jpet.114.214031. PMID 24928951. S2CID 2238176.
  2. ^ "TRK 130 Takeda Toray licensing agreement". HighBeam. Archived from the original on 2016-03-09.
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This page was last edited on 20 December 2023, at 20:12
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