Apadoline

Apadoline
Clinical data
Other names	RP-60180; RP60180; RP-60,180; RP-60180A
Drug class	κ-Opioid receptor agonist
ATC code	None;
Identifiers
	IUPAC name N-propyl-10-[(2R)-1-pyrrolidin-1-ylpropan-2-yl]phenothiazine-2-carboxamide;
CAS Number	135003-30-4;
PubChem CID	179334;
DrugBank	DB20043;
ChemSpider	156101;
UNII	5Q36UVB8YA;
ChEMBL	ChEMBL442174;
CompTox Dashboard (EPA)	DTXSID101350883 ;
Chemical and physical data
Formula	C23H29N3OS
Molar mass	395.57 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCNC(=O)C1=CC2=C(C=C1)SC3=CC=CC=C3N2[C@H](C)CN4CCCC4;
	InChI InChI=1S/C23H29N3OS/c1-3-12-24-23(27)18-10-11-22-20(15-18)26(17(2)16-25-13-6-7-14-25)19-8-4-5-9-21(19)28-22/h4-5,8-11,15,17H,3,6-7,12-14,16H2,1-2H3,(H,24,27)/t17-/m1/s1; Key:KXMAIWXPZGQNCR-QGZVFWFLSA-N;

Apadoline (INNTooltip International Nonproprietary Name; developmental code name RP-60180) is a κ-opioid receptor agonist and experimental analgesic which was under development for the treatment of cancer pain but was never marketed.^[1]^[2]^[3]^[4] It produces effects and adverse effects in humans including analgesia, drowsiness, and headache, among others.^[3]^[5] Its affinities (K_i) for the opioid receptors are 0.55 nM for the κ-opioid receptor, 11.4 nM for the δ-opioid receptor, and 57 nM for the μ-opioid receptor.^[5] Apadoline was first described in the scientific literature by 1990.^[6]^[7]^[8]^[9]^[10] It was under development by Rhône-Poulenc in the 1990s and reached phase 2 clinical trials prior to the discontinuation of its development.^[1]^[2] An analogue with greater potency, RP-61127, has also been described.^[4]^[3]