Naldemedine

Naldemedine
Clinical data
Trade namesSymproic, Rizmoic
Other namesS-297,995
AHFS/Drugs.comMonograph
MedlinePlusa617031
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding93–94%
Metabolismprimarily CYP3A4
Elimination half-life11 hrs
ExcretionUrine, feces
Identifiers
  • 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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC32H34N4O6
Molar mass570.646 g·mol−1
3D model (JSmol)
  • CC(C)(c1nc(no1)c2ccccc2)NC(=O)C3=C([C@H]4[C@@]56CCN([C@@H]([C@@]5(C3)O)Cc7c6c(c(cc7)O)O4)CC8CC8)O
  • InChI=1S/C32H34N4O6/c1-30(2,29-33-27(35-42-29)18-6-4-3-5-7-18)34-28(39)20-15-32(40)22-14-19-10-11-21(37)25-23(19)31(32,26(41-25)24(20)38)12-13-36(22)16-17-8-9-17/h3-7,10-11,17,22,26,37-38,40H,8-9,12-16H2,1-2H3,(H,34,39)/t22-,26+,31+,32-/m1/s1
  • Key:AXQACEQYCPKDMV-RZAWKFBISA-N

Naldemedine, sold under the brand name Symproic in the US and Rizmoic in the European Union, is a medication that is used for the treatment of opioid-induced constipation in adults who have previously been treated with a laxative in the European Union, or to treat opioid induced constipation in adults with chronic non-cancer pain in the US. It is a peripherally acting μ-opioid receptor antagonist and was developed by Shionogi.[3] Clinical studies have found it to possess statistically significant effectiveness for these indications and to be generally well tolerated, with predominantly mild to moderate gastrointestinal side effects.[4] Effects indicative of central opioid withdrawal or impact on the analgesic or miotic effects of co-administered opioids have only been observed in a small number of patients.[1]

  1. ^ a b "Symproic- naldemedine tablet". DailyMed. 23 December 2022. Retrieved 13 June 2024.
  2. ^ "Rizmoic EPAR". European Medicines Agency. 18 February 2019. Retrieved 13 June 2024.
  3. ^ "Summary of product information from European Medicines Agency (EMA)" (PDF). EMA. 30 April 2024. Retrieved 30 April 2024.
  4. ^ Shionogi (27 March 2009). "Research and Development at Shionogi (as of March 2009)" (PDF). Archived from the original (PDF) on 22 May 2013. Retrieved 12 May 2012.