1-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-14-(acetyloxy)-5-hydroxy-2,15-dimethyl-4-(morpholin-4-yl)tetracyclo[8.7.0.02,7.011,15]heptadecan-13-yl]-1-(prop-2-en-1-yl)pyrrolidin-1-ium bromide

• ChemBase ID: 72660
• Molecular Formular: C32H53BrN2O4
• Molecular Mass: 609.67822
• Monoisotopic Mass: 608.31887019
• SMILES: [C@H]1([C@H](C[C@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H]([C@H](C2)[N+]1(CCCC1)CC=C)OC(=O)C)C)C)O)N1CCOCC1.[Br-]
• Canonical SMILES: C=CC[N+]1(CCCC1)[C@H]1C[C@@H]2[C@]([C@H]1OC(=O)C)(C)CC[C@H]1[C@H]2CC[C@@H]2[C@]1(C)C[C@@H]([C@H](C2)O)N1CCOCC1.[Br-]
• InChI: InChI=1S/C32H53N2O4.BrH/c1-5-14-34(15-6-7-16-34)28-20-26-24-9-8-23-19-29(36)27(33-12-17-37-18-13-33)21-32(23,4)25(24)10-11-31(26,3)30(28)38-22(2)35;/h5,23-30,36H,1,6-21H2,2-4H3;1H/q+1;/p-1/t23-,24+,25-,26-,27-,28-,29-,30-,31-,32-;/m0./s1
• InChIKey: OYTJKRAYGYRUJK-FMCCZJBLSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-14-(acetyloxy)-5-hydroxy-2,15-dimethyl-4-(morpholin-4-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-13-yl]-1-(prop-2-en-1-yl)pyrrolidin-1-ium bromide; 1-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-14-(acetyloxy)-5-hydroxy-2,15-dimethyl-4-(morpholin-4-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl]-1-(prop-2-en-1-yl)pyrrolidin-1-ium bromide
• IUPAC Traditional name: rocuronium bromide
• Synonyms: Rocuronium bromide; Zemuron; Esmeron; Rocuronium bromide; 1-[(2β,3α,5α,16β,17β)-17-(Acetyloxy)-3-hydroxy-2-(4-morpholinyl)androstan-16-yl]-1-(2-propenyl)pyrrolidinium Bromide; Org-9426

Database IDs

• CAS Number: 119302-91-9
• MDL Number: MFCD00867768
• PubChem SID: 162037585
• PubChem CID: 441351

CALCULATED PROPERTIES

• Acid pKa: 14.585371
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -2.7576323
• LogD (pH = 7.4): -0.99869245
• Log P: -0.33122167
• Molar Refractivity: 161.6511 cm^3
• Polarizability: 60.11785 Å^3
• Polar Surface Area: 59.0 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; H2O: soluble100 mg/mL, clear, light yellow
• Apperance: Off-white to Pale Yellow Solid
• Melting Point: 162-164°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (perchloric acid titration)
• Salt Data: Bromide
• Empirical Formula (Hill Notation): C32H53BrN2O4

DETAILS

Selleck Chemicals - S1397

Research Area: Neurological Disease
Biological Activity:
Rocuronium is an aminosteroid non-depolarizing neuromuscular blocker or muscle relaxant used in modern anaesthesia, to facilitate endotracheal intubation and to provide skeletal muscle relaxation during surgery or mechanical ventilation. [1]

Sigma Aldrich - R5155

Biochem/physiol Actions
Aminosteroid; neuromuscular blocker for anaesthesia

Toronto Research Chemicals - R639500

Aminosteroid, competitive neuromuscular blocker.

REFERENCES

• http://en.wikipedia.org/wiki/Rocuronium_bromide
• Magorian, T., et al.: Anesthesiology, 79, 913 (1993)
• Wicks, T.C., et al.: J. Am. Assoc. Nurse Anesth., 62, 33 (1994)