Rocuronium bromide
[CAS# 119302-91-9]

Identification

• Classification: API >> Anesthetic agents >> Skeletal muscle relaxant
• Name: Rocuronium bromide
• Synonyms: [3-Hydroxy-10,13-dimethyl-2-morpholin-4-yl-16-(1-prop-2-enyl-2,3,4,5-tetrahydropyrrol-1-yl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate bromide
• Molecular Formula: C₃₂H₅₃N₂O₄.Br
• Molecular Weight: 609.69
• CAS Registry Number: 119302-91-9
• EC Number: 601-597-6
• SMILES: CC(=O)O[C@H]1[C@H](C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(C[C@@H]([C@H](C4)O)N5CCOCC5)C)C)[N+]6(CCCC6)CC=C.[Br-]

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Risk Statements: H302-H312-H331
• Safety Statements: P261-P264-P270-P271-P280-P301+P317-P302+P352-P304+P340-P316-P317-P321-P330-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	1	H330
Acute toxicity	Acute Tox.	1	H310
Acute toxicity	Acute Tox.	1	H300
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Acute toxicity	Acute Tox.	2	H330

Discovery and Applications

Rocuronium bromide, a non-depolarizing neuromuscular blocking agent, was developed in the late 1980s by Organon International (now part of Merck & Co., Inc.). It belongs to the aminosteroid class of neuromuscular blockers and was synthesized through modifications of the steroid molecule. Rocuronium bromide has several important applications in clinical medicine.

One of the primary applications of rocuronium bromide is as a muscle relaxant during surgical procedures. It acts by competitively binding to nicotinic acetylcholine receptors at the neuromuscular junction, thereby blocking the action of acetylcholine and preventing muscle contraction. This induces skeletal muscle relaxation, facilitating endotracheal intubation, improving surgical access, and minimizing movement during procedures. Rocuronium bromide is commonly used to facilitate tracheal intubation during general anesthesia induction. By inducing skeletal muscle relaxation, it enables easier insertion of the endotracheal tube into the trachea, ensuring adequate ventilation and oxygenation during surgery. In addition to its role in facilitating tracheal intubation, rocuronium bromide may be used to maintain muscle relaxation throughout surgery. Its intermediate duration of action allows for titration of neuromuscular blockade levels based on the requirements of the surgical procedure, with effects typically lasting 30 to 60 minutes. While rocuronium bromide itself does not possess reversal properties, its effects can be reversed with acetylcholinesterase inhibitors such as neostigmine and sugammadex. These agents antagonize the action of rocuronium by increasing the concentration of acetylcholine at the neuromuscular junction, facilitating the restoration of neuromuscular function following surgery.

References

1994. Pharmacokinetics and Pharmacodynamics of Rocuronium in Patients with Cirrhosis. Anesthesiology.
DOI: 10.1097/00000542-199406000-00011

2007. Early Reversal of Profound Rocuronium-induced Neuromuscular Blockade by Sugammadex in a Randomized Multicenter Study: Efficacy, Safety, and Pharmacokinetics. Anesthesiology.
DOI: 10.1097/01.anes.0000265152.78943.74

2008. Adenosine and adenosine uptake inhibitors potentiate the neuromuscular blocking action of rocuronium mediated by adenosine A1 receptors in isolated rat diaphragms. Acta Anaesthesiologica Scandinavica.
DOI: 10.1111/j.1399-6576.2008.01714.x