Wikipedia

Apadoline

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 (Ki) 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]

Apadoline
Clinical data
Other namesRP-60180; RP60180; RP-60,180; RP-60180A
Drug classκ-Opioid receptor agonist
ATC code
  • None
Identifiers
  • N-propyl-10-[(2R)-1-pyrrolidin-1-ylpropan-2-yl]phenothiazine-2-carboxamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H29N3OS
Molar mass395.57 g·mol−1
3D model (JSmol)
  • CCCNC(=O)C1=CC2=C(C=C1)SC3=CC=CC=C3N2[C@H](C)CN4CCCC4
  • 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

See also

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References

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  1. 1 2 "Apadoline". AdisInsight. 9 October 2001. Retrieved 15 May 2026.
  2. 1 2 "Delving into the Latest Updates on Apadoline with Synapse". Synapse. 21 March 2026. Retrieved 15 May 2026.
  3. 1 2 3 Barber A, Gottschlich R (October 1997). "Novel developments with selective, non-peptidic kappa-opioid receptor agonists". Expert Opinion on Investigational Drugs. 6 (10): 1351–1368. doi:10.1517/13543784.6.10.1351. PMID 15989506.
  4. 1 2 Szmuszkovicz J (1999). "U-50,488 and the к receptor Part II: 1991–1998". Progress in Drug Research. Basel: Birkhäuser Basel. pp. 1–51. doi:10.1007/978-3-0348-8735-9_1. ISBN 978-3-0348-9749-5.
  5. 1 2 Lötsch J, Ditterich W, Hummel T, Kobal G (June 1997). "Antinociceptive effects of the kappa-opioid receptor agonist RP 60180 compared with pentazocine in an experimental human pain model". Clinical Neuropharmacology. 20 (3): 224–233. doi:10.1097/00002826-199706000-00006. PMID 9197945.
  6. ↑ Fardin V, Plau B, Carruette A, Guyon C, Bardon T, Taurand G, et al. (1990). "RP 60180: A novel phenothiazine with high affinity for kappa binding sites and with antinociceptive effects in rodents". Pain. 41: S192. doi:10.1016/0304-3959(90)92520-Z.
  7. ↑ Fardin V, Jolly A, Flamand O, Carruette A, Laduron PM, Garret C (1990). "RP 60180, a new phenothiazine with high affinity for opiate kappa binding sites in animal and human brain". European Journal of Pharmacology. 183 (6): 2332. doi:10.1016/0014-2999(90)93890-3.
  8. ↑ Raghubir R, Patnaik GK, Sharma SD, Mathur KB, Dhawan BN (1990). "A parentrally active highly potent analgesic peptide with reduced abuse potential". Pain. 41: S192. doi:10.1016/0304-3959(90)92521-Q.
  9. ↑ Reibaud, M., Stutzmann, J. M., Böhme, G. A., Lafforgue, J., Garret, C., & Laduron, P. M. (1990). Electrocorticograpnic profile and discriminative stimulus properties of RP 60180, a new kappa agonist. European Journal of Pharmacology, 183(6), 2331. https://scholar.google.com/scholar?cluster=6360720396979939973
  10. ↑ Boireau A, Dubedat P, Laduron P, Blanchard JC, Doble A, Garret C (1990). "Effects of RP 60180, a kappa-receptor agonist, on dopamine metabolism and utilization in rat and guinea-pig brain". European Journal of Pharmacology. 183 (6): 2330. doi:10.1016/0014-2999(90)93888-W.
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