Nalfurafine

Nalfurafine
Clinical data
Other namesTRK-820, AC-820, MT-9938
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Intravenous[1]
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life14 hours (acute);[2]
25–28 hours (chronic)[2]
Identifiers
  • (2E)-N-[(5α,6β)-17-(Cyclopropylmethyl)-3,14-dihydroxy-4,5-epoxymorphinan-6-yl]-3-(3-furyl)-N-methylacrylamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC28H32N2O5
Molar mass476.573 g·mol−1
3D model (JSmol)
  • CN([C@@H]1CC[C@]2([C@H]3CC4=C5[C@]2([C@H]1OC5=C(C=C4)O)CCN3CC6CC6)O)C(=O)/C=C/C7=COC=C7
  • InChI=1S/C28H32N2O5/c1-29(23(32)7-4-18-9-13-34-16-18)20-8-10-28(33)22-14-19-5-6-21(31)25-24(19)27(28,26(20)35-25)11-12-30(22)15-17-2-3-17/h4-7,9,13,16-17,20,22,26,31,33H,2-3,8,10-12,14-15H2,1H3/b7-4+/t20-,22-,26+,27+,28-/m1/s1 ☒N
  • Key:XGZZHZMWIXFATA-UEZBDDGYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Nalfurafine (INN, USAN)[3] (brand name Remitch; former developmental code names TRK-820, AC-820, MT-9938) is an antipruritic (anti-itch drug) that is marketed in Japan for the treatment of uremic pruritus in individuals with chronic kidney disease undergoing hemodialysis.[2][4] It activates the κ-opioid receptor (KOR)[5] and is potent, selective, and centrally active.[6] It was the first selective KOR agonist approved for clinical use.[7][8] It has also been dubiously referred to as the "first non-narcotic opioid drug" in history.[8]

  1. ^ Nunley JR, Lerma EV (3 July 2015). Dermatological Manifestations of Kidney Disease. Springer. pp. 85–. ISBN 978-1-4939-2395-3.
  2. ^ a b c Inui S (2015). "Nalfurafine hydrochloride to treat pruritus: a review". Clinical, Cosmetic and Investigational Dermatology. 8: 249–255. doi:10.2147/CCID.S55942. PMC 4433050. PMID 26005355.
  3. ^ Statement on a Nonproprietary Name adopted by the USAN Council
  4. ^ Cowan A, Yosipovitch G (10 April 2015). Pharmacology of Itch. Springer. pp. 304–305. ISBN 978-3-662-44605-8.
  5. ^ El Daibani A, Paggi JM, Kim K, Laloudakis YD, Popov P, Bernhard SM, et al. (March 2023). "Molecular mechanism of biased signaling at the kappa opioid receptor". Nature Communications. 14 (1): 1338. Bibcode:2023NatCo..14.1338E. doi:10.1038/s41467-023-37041-7. PMC 10008561. PMID 36906681.
  6. ^ Cite error: The named reference RapakaSadée2008 was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference Patrick2013 was invoked but never defined (see the help page).
  8. ^ a b Nagase H (21 January 2011). Chemistry of Opioids. Springer. pp. 34, 48, 57–60. ISBN 978-3-642-18107-8.