sodium (1S,5R,13R,17S)-17-hydroxy-14-oxo-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-10-yl sulfate

• ChemBase ID: 174939
• Molecular Formular: C19H20NNaO7S
• Molecular Mass: 429.41937
• Monoisotopic Mass: 429.08581727
• SMILES: c12[C@]34[C@@]5([C@@H](Cc1ccc(c2O[C@H]3C(=O)CC5)OS(=O)(=O)[O-])N(CC=C)CC4)O.[Na+]
• Canonical SMILES: C=CCN1CC[C@@]23[C@@]4([C@H]1Cc1c3c(O[C@H]2C(=O)CC4)c(cc1)OS(=O)(=O)[O-])O.[Na+]
• InChI: InChI=1S/C19H21NO7S.Na/c1-2-8-20-9-7-18-15-11-3-4-13(27-28(23,24)25)16(15)26-17(18)12(21)5-6-19(18,22)14(20)10-11;/h2-4,14,17,22H,1,5-10H2,(H,23,24,25);/q;+1/p-1/t14-,17+,18+,19-;/m1./s1
• InChIKey: NAWJXCVVOVUEKA-STHHAXOLSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (1S,5R,13R,17S)-17-hydroxy-14-oxo-4-(prop-2-en-1-yl)-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-10-yl sulfate
• IUPAC Traditional name: sodium (1S,5R,13R,17S)-17-hydroxy-14-oxo-4-(prop-2-en-1-yl)-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-10-yl sulfate
• Synonyms: (5α)-4,5-Epoxy-14-hydroxy-17-(2-propenyl)-3-(sulfooxy)morphinan-6-one Monosodium Salt; Naloxone-3-sulfate Sodium Salt

Database IDs

• CAS Number: 156047-22-2
• PubChem SID: 164230849
• PubChem CID: 71750918

CALCULATED PROPERTIES

• Acid pKa: -2.0644424
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): -0.33495277
• LogD (pH = 7.4): -0.46634138
• Log P: -0.33289462
• Molar Refractivity: 97.5923 cm^3
• Polarizability: 39.232895 Å^3
• Polar Surface Area: 116.2 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N285025

A prodrug of the two opiate antagonists Naloxone (N285000) and Naltrexone (N285750).

REFERENCES

• Lazar, S., et al.: Eur. J. Med. Chem., 29, 45 (1994)