Naldemedine

Naldemedine
Clinical data
Trade names	Symproic, Rizmoic
Other names	S-297,995
AHFS/Drugs.com	Monograph
MedlinePlus	a617031
License data	US DailyMed: Naldemedine;
Routes of; administration	By mouth
ATC code	A06AH05 (WHO) ;
Legal status
Legal status	US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Protein binding	93–94%
Metabolism	primarily CYP3A4
Elimination half-life	11 hrs
Excretion	Urine, feces
Identifiers
	IUPAC name 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	916072-89-4 ; 1345728-04-2 (tosylate);
PubChem CID	54732242;
DrugBank	DB11691;
ChemSpider	28530803;
UNII	03KSI6WLXH;
KEGG	D10188; as salt: D10478;
Chemical and physical data
Formula	C32H34N4O6
Molar mass	570.646 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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. 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. 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.