(2E)-N-[(1S,5R,13R,14R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-yl]-3-(furan-3-yl)-N-methylprop-2-enamide hydrochloride

• ChemBase ID: 174920
• Molecular Formular: C28H33ClN2O5
• Molecular Mass: 513.02502
• Monoisotopic Mass: 512.20779985
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H]([C@@H](CC4)N(C(=O)/C=C/c3ccoc3)C)O2)CCN1CC1CC1)O)O.Cl
• Canonical SMILES: CN([C@@H]1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)CC2CC2)ccc1O)O)C(=O)/C=C/c1ccoc1.Cl
• InChI: 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-;/m1./s1
• InChIKey: DJSFYNINGIMKAG-FQJQBBMWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-N-[(1S,5R,13R,14R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10-trien-14-yl]-3-(furan-3-yl)-N-methylprop-2-enamide hydrochloride
• IUPAC Traditional name: (2E)-N-[(1S,5R,13R,14R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10-trien-14-yl]-3-(furan-3-yl)-N-methylprop-2-enamide hydrochloride
• Synonyms: (2E)-N-[(5α,6β)-17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-yl]-3-(3-furanyl)-N-methyl-2-propenamide Hydrochloride; (-)-17-(Cyclopropylmethyl)-3,14β-dihydroxy-4,5α-epoxy-6β-[N-methyl-trans-3-(3-furyl)acrylamido]morphinan Hydrochloride; Remitch; TRK 820; Nalfurafine Hydrochloride

Database IDs

• CAS Number: 152658-17-8
• PubChem SID: 164230830
• PubChem CID: 6918287

CALCULATED PROPERTIES

• Acid pKa: 10.292829
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.7288464
• LogD (pH = 7.4): 0.4166298
• Log P: 2.2386599
• Molar Refractivity: 131.3265 cm^3
• Polarizability: 50.691563 Å^3
• Polar Surface Area: 86.38 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

DETAILS

Toronto Research Chemicals - N255600

Nalfurafine hydrochloride was launched on March of 2009 in Japan as the first in class non-narcotic opioid drug for intractable itch caused by hemodialysis. It showed significant opioid κ-agonist activity and induced neither aversion nor preference in rat

REFERENCES

• Fujii, H., et al.: Bioorg. Med. Chem., 12, 4133 (2004)
• Mori, T., et al.: Life Sci., 75, 2433 (2004)
• Fujii, H., et al.: Curr. Med. Chem., 13, 1109 (2004)
• Nagase, H., et al.: Bioorg. Med. Chem. Lett., 20, 6302 (2004)