1-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-5-(acetyloxy)-2,15-dimethyl-4-(piperidin-1-yl)-14-(propanoyloxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl]-1-(prop-2-en-1-yl)piperidin-1-ium bromide

• ChemBase ID: 4378
• Molecular Formular: C37H61BrN2O4
• Molecular Mass: 677.79524
• Monoisotopic Mass: 676.38147044
• SMILES: [Br-].O([C@@H]1[C@@]2([C@H]([C@H]3[C@@H]([C@@]4([C@@H](CC3)C[C@H](OC(=O)C)[C@@H](N3CCCCC3)C4)C)CC2)C[C@@H]1[N+]1(CCCCC1)CC=C)C)C(=O)CC
• Canonical SMILES: C=CC[N+]1(CCCCC1)[C@H]1C[C@@H]2[C@]([C@H]1OC(=O)CC)(C)CC[C@H]1[C@H]2CC[C@@H]2[C@]1(C)C[C@@H]([C@H](C2)OC(=O)C)N1CCCCC1.[Br-]
• InChI: InChI=1S/C37H61N2O4.BrH/c1-6-20-39(21-12-9-13-22-39)32-24-30-28-15-14-27-23-33(42-26(3)40)31(38-18-10-8-11-19-38)25-37(27,5)29(28)16-17-36(30,4)35(32)43-34(41)7-2;/h6,27-33,35H,1,7-25H2,2-5H3;1H/q+1;/p-1/t27-,28+,29-,30-,31-,32-,33-,35-,36-,37-;/m0./s1
• InChIKey: LVQTUXZKLGXYIU-GWSNJHLMSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-5-(acetyloxy)-2,15-dimethyl-4-(piperidin-1-yl)-14-(propanoyloxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl]-1-(prop-2-en-1-yl)piperidin-1-ium bromide
• IUPAC Traditional name: 1-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-5-(acetyloxy)-2,15-dimethyl-4-(piperidin-1-yl)-14-(propanoyloxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl]-1-(prop-2-en-1-yl)piperidin-1-ium bromide
• Brand Name: Raplon
• Synonyms: Rapacuronium bromide; Rapacuronium

Database IDs

• CAS Number: 156137-99-4
• PubChem SID: 46506932; 160967810
• PubChem CID: 5311398

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -1.0892621
• LogD (pH = 7.4): 0.09664296
• Log P: 2.3238747
• Molar Refractivity: 183.098 cm^3
• Polarizability: 68.781715 Å^3
• Polar Surface Area: 55.84 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.45
• LOG S: -7.57
• Solubility (Water): 1.82e-05 g/l

DETAILS

DrugBank - DB04834

• Drug Groups: withdrawn
• Description: Rapacuronium was withdrawn in 2001 in many countries due to risk of fatal bronchospasm.
• Indication: Used in anaesthesia, to aid and enable endotracheal intubation.
• Pharmacology: Rapacuronium is a rapidly acting, non-depolarizing neuromuscular blocker.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hydrolyzed to active metabolites (Cytochrome P450 system is not involved).
• Half Life: 141 minutes (mean)
• Protein Binding: Variable. Plasma protein binding of rapacuronium was studied in vitro for human plasma by equilibrium dialysis. The protein binding was variable and ranged between 50% and 88%, which was at least partly due to hydrolysis of rapacuronium bromide to its 3-hydroxy metabolite. The specific plasma protein to which rapacuronium binds is unknown. Plasma protein binding of the 3-hydroxy metabolite was not determined.
• External Links: Wikipedia; RxList