Nalfurafine HCl
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MedKoo CAT#: 326666

CAS#: 152658-17-8 (HCl)

Description: Nalfurafine, also known as 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. It acts as a potent, selective, centrally-penetrant κ-opioid receptor (KOR) agonist, and is the first and currently the only selective KOR agonist to have been approved for clinical use. It has also been referred to as the "first non-narcotic opioid drug" in history.


Price and Availability

Size
Price

100mg
USD 1450
1g
USD 3950
Size
Price

200mg
USD 2650
2g
USD 5450
Size
Price

500mg
USD 3150
5g
USD 9450

Nalfurafine HCl, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: from $30.00 (USA); from $45.00 (Canada); from $70.00 (international).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 326666
Name: Nalfurafine HCl
CAS#: 152658-17-8 (HCl)
Chemical Formula: C28H33ClN2O5
Exact Mass:
Molecular Weight: 513.031
Elemental Analysis: C, 65.55; H, 6.48; Cl, 6.91; N, 5.46; O, 15.59


Related CAS #: 152658-17-8 (HCl)   152657-84-6 (free base)    

Synonym: TRK-820; TRK820; TRK 820; AC-820; AC 820; AC820; MT-9938; MT 9938; MT9938; Nalfurafine HCl, brand name Remitch.

IUPAC/Chemical Name: (E)-N-(17-(Cyclopropylmethyl)-4,5alpha-epoxy-3,14-dihydroxymorphinan-6beta-yl)-3-(furan-3-yl)-N-methylprop-2-enamide monohydrochloride

InChi Key: DJSFYNINGIMKAG-DFRGBLIASA-N

InChi Code: InChI=1S/C28H32N2O5.ClH/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;1H/b7-4+;/t20-,22+,26+,27-,28+;/m0./s1

SMILES Code: O=C(N([C@@H]1[C@@H]2[C@]34C5=C(O2)C(O)=CC=C5C[C@@H](N(CC6CC6)CC4)[C@]3(O)CC1)C)/C=C/C7=COC=C7.[H]Cl


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

Related CAS#
152658-17-8 (HCl); 152657-84-6 (free base).


References

1: Nakao K, Hirakata M, Miyamoto Y, Kainoh M, Wakasa Y, Yanagita T. Nalfurafine hydrochloride, a selective κ opioid receptor agonist, has no reinforcing effect on intravenous self-administration in rhesus monkeys. J Pharmacol Sci. 2016 Jan;130(1):8-14. doi: 10.1016/j.jphs.2015.11.008. Epub 2015 Dec 2. PubMed PMID: 26786553.

2: Ando A, Sasago S, Ohzone Y, Miyamoto Y. Drug-Drug Interactions of a Novel κ-Opioid Receptor Agonist, Nalfurafine Hydrochloride, Involving the P-Glycoprotein. Eur J Drug Metab Pharmacokinet. 2015 Jun 10. [Epub ahead of print] PubMed PMID: 26058994.

3: Inui S. Nalfurafine hydrochloride to treat pruritus: a review. Clin Cosmet Investig Dermatol. 2015 May 11;8:249-55. doi: 10.2147/CCID.S55942. eCollection 2015. Review. PubMed PMID: 26005355; PubMed Central PMCID: PMC4433050.

4: Akiyama T, Carstens MI, Piecha D, Steppan S, Carstens E. Nalfurafine suppresses pruritogen- and touch-evoked scratching behavior in models of acute and chronic itch in mice. Acta Derm Venereol. 2015 Feb;95(2):147-50. doi: 10.2340/00015555-1879. PubMed PMID: 24890341.

5: Ueno Y, Mori A, Yanagita T. One year long-term study on abuse liability of nalfurafine in hemodialysis patients. Int J Clin Pharmacol Ther. 2013 Nov;51(11):823-31. doi: 10.5414/CP201852. PubMed PMID: 24040851.

6: Nagase H, Fujii H. Essential structure of the κ opioid receptor agonist nalfurafine for binding to the κ receptor. Curr Pharm Des. 2013;19(42):7400-14. PubMed PMID: 23448474.

7: Nemoto T, Yamamoto N, Wada N, Harada Y, Tomatsu M, Ishihara M, Hirayama S, Iwai T, Fujii H, Nagase H. The effect of 17-N substituents on the activity of the opioid κ receptor in nalfurafine derivatives. Bioorg Med Chem Lett. 2013 Jan 1;23(1):268-72. doi: 10.1016/j.bmcl.2012.10.100. Epub 2012 Oct 30. PubMed PMID: 23200250.

8: Fujii H, Imaide S, Hirayama S, Nemoto T, Gouda H, Hirono S, Nagase H. Essential structure of opioid κ receptor agonist nalfurafine for binding to the κ receptor 3: synthesis of decahydro(iminoethano)phenanthrene derivatives with an oxygen functionality at the 3-position and their pharmacologies. Bioorg Med Chem Lett. 2012 Dec 15;22(24):7711-4. doi: 10.1016/j.bmcl.2012.09.101. Epub 2012 Oct 5. PubMed PMID: 23103094.

9: Nakao K, Togashi Y, Honda T, Momen S, Umeuchi H, Sakakibara S, Tanaka T, Okano K, Mochizuki H. In vitro and in vivo pharmacological characterization of the main metabolites of nalfurafine hydrochloride. Eur J Pharmacol. 2012 Nov 15;695(1-3):57-61. doi: 10.1016/j.ejphar.2012.08.017. Epub 2012 Sep 4. PubMed PMID: 22981641.

10: Nagase H, Imaide S, Yamada T, Hirayama S, Nemoto T, Yamaotsu N, Hirono S, Fujii H. Essential structure of opioid κ receptor agonist nalfurafine for binding to κ receptor 1: synthesis of decahydroisoquinoline derivatives and their pharmacologies. Chem Pharm Bull (Tokyo). 2012;60(8):945-8. PubMed PMID: 22863695.

11: Nagase H, Imaide S, Hirayama S, Nemoto T, Fujii H. Essential structure of opioid κ receptor agonist nalfurafine for binding to the κ receptor 2: synthesis of decahydro(iminoethano)phenanthrene derivatives and their pharmacologies. Bioorg Med Chem Lett. 2012 Aug 1;22(15):5071-4. doi: 10.1016/j.bmcl.2012.05.122. Epub 2012 Jun 7. PubMed PMID: 22742909.

12: Inui S. Nalfurafine hydrochloride for the treatment of pruritus. Expert Opin Pharmacother. 2012 Jul;13(10):1507-13. doi: 10.1517/14656566.2012.693164. Epub 2012 Jun 5. Review. PubMed PMID: 22663138.

13: Ando A, Oshida K, Fukuyama S, Watanabe A, Hashimoto H, Miyamoto Y. Identification of human cytochrome P450 enzymes involved in the metabolism of a novel к-opioid receptor agonist, nalfurafine hydrochloride. Biopharm Drug Dispos. 2012 Jul;33(5):257-64. doi: 10.1002/bdd.1793. Epub 2012 May 29. PubMed PMID: 22581509.

14: Inui S, Shirakawa Y, Itami S. Effect of nalfurafine hydrochloride on pruritus and anxiety level in hemodialysis patients. J Dermatol. 2012 Oct;39(10):886-7. doi: 10.1111/j.1346-8138.2011.01442.x. Epub 2011 Dec 5. PubMed PMID: 22142516.

15: Nakao K, Hasebe K, Yoshikawa S, Ikeda K, Hirakata M, Miyamoto Y, Mochizuki H. [Pharmacological effects of nalfurafine hydrochloride, a kappa-opioid receptor agonist]. Nihon Shinkei Seishin Yakurigaku Zasshi. 2010 Nov;30(5-6):185-91. Review. Japanese. PubMed PMID: 21226314.

16: Nakao K, Ando A, Hirakata M, Ando N, Takeshita K, Miyamoto Y, Mochizuki H. [Pharmacological and clinical profiles of nalfurafine hydrochloride (Remitch) capsules 2.5 microg) , a new therapeutic agent for the treatment of uremic pruritus in hemodialysis patients]. Nihon Yakurigaku Zasshi. 2010 May;135(5):205-14. Review. Japanese. PubMed PMID: 20467170.

17: Molecule of the Month. Nalfurafine hydrochloride. Drug News Perspect. 2009 Dec;22(10):619. PubMed PMID: 20140281.

18: Kumagai H, Ebata T, Takamori K, Muramatsu T, Nakamoto H, Suzuki H. Effect of a novel kappa-receptor agonist, nalfurafine hydrochloride, on severe itch in 337 haemodialysis patients: a Phase III, randomized, double-blind, placebo-controlled study. Nephrol Dial Transplant. 2010 Apr;25(4):1251-7. doi: 10.1093/ndt/gfp588. Epub 2009 Nov 19. PubMed PMID: 19926718.

19: Nakao K, Mochizuki H. Nalfurafine hydrochloride: a new drug for the treatment of uremic pruritus in hemodialysis patients. Drugs Today (Barc). 2009 May;45(5):323-9. doi: 10.1358/dot.2009.45.5.1362067. Review. PubMed PMID: 19584962.

20: Inan S, Dun NJ, Cowan A. Nalfurafine prevents 5'-guanidinonaltrindole- and compound 48/80-induced spinal c-fos expression and attenuates 5'-guanidinonaltrindole-elicited scratching behavior in mice. Neuroscience. 2009 Sep 29;163(1):23-33. doi: 10.1016/j.neuroscience.2009.06.016. Epub 2009 Jun 10. PubMed PMID: 19524022; PubMed Central PMCID: PMC2735087.