1-[(2S,4S,5S,7S,11S,13S,14R,15S)-5,14-bis(acetyloxy)-2,15-dimethyl-4-(piperidin-1-yl)tetracyclo[8.7.0.02,7.011,15]heptadecan-13-yl]-1-methylpiperidin-1-ium bromide

• ChemBase ID: 179721
• Molecular Formular: C34H57BrN2O4
• Molecular Mass: 637.73138
• Monoisotopic Mass: 636.35017031
• SMILES: [C@@]12([C@H](C3C([C@]4(C[C@@H]([C@H](C[C@@H]4CC3)OC(=O)C)N3CCCCC3)C)CC2)C[C@@H]([C@@H]1OC(=O)C)[N+]1(C)CCCCC1)C.[Br-]
• Canonical SMILES: CC(=O)O[C@H]1C[C@@H]2CCC3C([C@]2(C[C@@H]1N1CCCCC1)C)CC[C@]1([C@H]3C[C@@H]([C@@H]1OC(=O)C)[N+]1(C)CCCCC1)C.[Br-]
• InChI: InChI=1S/C34H57N2O4.BrH/c1-23(37)39-31-20-25-12-13-26-27(34(25,4)22-29(31)35-16-8-6-9-17-35)14-15-33(3)28(26)21-30(32(33)40-24(2)38)36(5)18-10-7-11-19-36;/h25-32H,6-22H2,1-5H3;1H/q+1;/p-1/t25-,26?,27?,28-,29-,30-,31-,32-,33-,34-;/m0./s1
• InChIKey: VEPSYABRBFXYIB-KTKQGDNRSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2S,4S,5S,7S,11S,13S,14R,15S)-5,14-bis(acetyloxy)-2,15-dimethyl-4-(piperidin-1-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-13-yl]-1-methylpiperidin-1-ium bromide
• IUPAC Traditional name: 1-[(2S,4S,5S,7S,11S,13S,14R,15S)-5,14-bis(acetyloxy)-2,15-dimethyl-4-(piperidin-1-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-13-yl]-1-methylpiperidin-1-ium bromide
• Synonyms: Norcuron; Vecuronium Bromide

Database IDs

• CAS Number: 50700-72-6
• PubChem SID: 164235631
• PubChem CID: 51052079

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -2.5210478
• LogD (pH = 7.4): -1.3351427
• Log P: 0.8920891
• Molar Refractivity: 169.3084 cm^3
• Polarizability: 63.49572 Å^3
• Polar Surface Area: 55.84 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Non depolarising neuromuscular blocking agent

Product Information

• Salt Data: Br-
• Application(s): Competitive neuromuscular blocker; Used as a skeletal muscle relaxant during surgery

REFERENCES

• Buckett, W.R. et al., J. Med. Chem., 1973, 16, 1116, (synth, tox, pharmacol)
• Hilgenberg, J.C., Anesth. Analg. (N.Y.), 1983, 62, 524, (rev)
• Baird, W.L.M. et al., Clin. Anaesthesiol., 1985, 3, 347, (rev)
• Reilly, C.S. et al., Drugs, 1987, 34, 98, (rev)
• Agoston, S. et al., Monogr. Anaesthesiol., 1990, 19, 12, (book)
• Kooijman, H. et al., J.C.S. Perkin 2, 1991, 1581, (cryst struct)
• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 1531
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, VGU075