Rocuronium

Identification

Summary

Rocuronium is a vecuronium analog used to facilitate tracheal intubation and to relax skeletal muscles during surgery.

Generic Name
Rocuronium
DrugBank Accession Number
DB00728
Background

Rocuronium (rapid onset-curonium) is a desacetoxy analogue of vecuronium with a more rapid onset of action. It 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. Introduced in 1994, rocuronium has rapid onset, and intermediate duration of action. It is commonly marketed under the trade names Zemuron and Esmeron. The drug is associated with the risk of developing allergic reactions in some high-risk patients, such as those with asthma. However, there was a similar incidence of allergic reactions associated with other non-depolarizing neuromuscular blocking agents. Sugammadex is a γ-cyclodextrin derivative that has been introduced as a novel agent to reverse the action of rocuronium.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 529.7742
Monoisotopic: 529.400533194
Chemical Formula
C32H53N2O4
Synonyms
  • Rocuronio
  • Rocuronium
External IDs
  • ORG 9426

Pharmacology

Indication

For inpatients and outpatients as an adjunct to general anesthesia to facilitate both rapid sequence and routine tracheal intubation, and to provide skeletal muscle relaxation during surgery or mechanical ventilation.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Prophylaxis ofMuscle fasciculation caused by succinylcholine••• •••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Neuromuscular blocking agents are drugs that cause skeletal muscle relaxation primarily by causing a decreased response to the neurotransmitter acetylcholine (ACh) at the myoneural (neuromuscular) junction of skeletal muscle. At that site, ACh normally produces electrical depolarization of the postjunctional membrane of motor end-plate, which leads to conduction of muscle action potential and subsequently induces skeletal muscle contraction. Neuromuscular agents are classified as depolarizing or nondepolarizing. Rocuronium is a nondepolarizing neuromuscular blocking agent with a rapid to intermediate onset depending on dose and intermediate duration. Rocuronium, like vecuronium is longer acting in infants than in children. However, unlike vecuronium, rocuronium retains the characteristics of an intermediate-acting NMBD in infants.

Mechanism of action

Rocuronium acts by competing for cholinergic receptors at the motor end-plate. This action is antagonized by acetylcholinesterase inhibitors, such as neostigmine and edrophonium. Rocuronium acts by competitively binding to nicotinic cholinergic receptors. The binding of vecuronium decreases the opportunity for acetylcholine to bind to the nicotinic receptor at the postjunctional membrane of the myoneural junction. As a result, depolarization is prevented, calcium ions are not released and muscle contraction does not occur. Evidence also suggests that nondepolarizing agents can affect ACh release. It has been hypothesized that nondepolarzing agents bind to postjunctional ("curare") receptors and may therefore interfere with the sodium and potassium flux, which is responsible for depolarization and repolarization of the membranes involved in muscle contraction.

TargetActionsOrganism
ANeuronal acetylcholine receptor subunit alpha-2
antagonist
Humans
AMuscarinic acetylcholine receptor M2
antagonist
Humans
U5-hydroxytryptamine receptor 3A
antagonist
Humans
Absorption

Poorly absorbed from the GI tract.

Volume of distribution
  • 0.3 L/kg [3 to <12 mos]
  • 0.26 L/kg [1 to <3 yrs]
  • 0.21 L/kg [3 to <8 yrs]
Protein binding

Approximately 30% bound to human plasma proteins.

Metabolism

Rocuronium is metabolized to a less active metabolite, 17-desacetyl-rocuronium, and is eliminated primarily by the liver.

Hover over products below to view reaction partners

Route of elimination

Studies of distribution, metabolism, and excretion in cats and dogs indicate that rocuronium is eliminated primarily by the liver.

Half-life

The rapid distribution half-life is 1-2 minutes and the slower distribution half-life is 14-18 minutes. Renal impairment has no net effect on half-life, however, half-life is almost doubled in patients with impaired liver function.

Clearance
  • 0.25 L/kg/hr [Adults (Ages 27 to 58 years)]
  • 0.21 L/kg/hr [Geriatrics (>=65 yrs)]
  • 0.16 L/kg/hr [Normal ewnal and hepatice function]
  • 0.13 L/kg/hr [Renal transplant patients]
  • 0.13 L/kg/hr [Hepatic dysfunction patients]
  • 0.35 +/- 0.08 L/kg/hr [Pediatric Patients 3 to <12 mos]
  • 0.32 +/- 0.07 L/kg/hr [Pediatric Patients 1 to 3 yrs]
  • 0.44 +/- 0.16 L/kg/hr [Pediatric Patients 3 to 8 yrs]
Adverse Effects
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Toxicity

No cases of significant accidental or intentional overdose have been reported. Overdosage with neuromuscular blocking agents may result in neuromuscular block beyond the time needed for surgery and anesthesia.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Rocuronium is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of CNS depression can be increased when Rocuronium is combined with Acetazolamide.
AcetophenazineThe risk or severity of CNS depression can be increased when Rocuronium is combined with Acetophenazine.
AcetylcholineThe risk or severity of adverse effects can be increased when Rocuronium is combined with Acetylcholine.
AcetyldigitoxinThe risk or severity of Cardiac Arrhythmia can be increased when Rocuronium is combined with Acetyldigitoxin.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Rocuronium bromideI65MW4OFHZ119302-91-9OYTJKRAYGYRUJK-FMCCZJBLSA-M
International/Other Brands
Esmeron
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Injectable Rocuronium BromideSolution10 mg / mLIntravenousOmega Laboratories LimitedNot applicableNot applicableCanada flag
Rocuronium BromideInjection, solution10 mg/1mLIntravenousCantrell Drug Company2015-01-292017-12-06US flag
Rocuronium Bromide InjectionSolution10 mg / mLIntravenousSterimax IncNot applicableNot applicableCanada flag
Rocuronium Bromide InjectionSolution10 mg / mLIntravenousSandoz Canada Incorporated2008-10-24Not applicableCanada flag
Rocuronium Bromide InjectionSolution10 mg / mLIntravenousHikma Canada Limited2023-09-29Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
RocuroniumInjection, solution10 mg/1mLIntravenousPhlow Corporation2022-02-08Not applicableUS flag
RocuroniumInjection, solution10 mg/1mLIntravenousThe Medicines Company2009-12-132015-03-31US flag
RocuroniumInjection, solution50 mg/5mLIntravenousbryant ranch prepack2020-07-20Not applicableUS flag
RocuroniumInjection, solution50 mg/5mLIntravenousPiramal Critical Care Inc2020-07-20Not applicableUS flag
RocuroniumInjection, solution100 mg/10mLIntravenousPiramal Critical Care Inc2020-07-20Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Rocuronium BromideRocuronium bromide (10 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2015-01-292017-12-06US flag

Categories

ATC Codes
M03AC09 — Rocuronium bromide
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as steroid esters. These are compounds containing a steroid moiety which bears a carboxylic acid ester group.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroid esters
Direct Parent
Steroid esters
Alternative Parents
Androgens and derivatives / 3-alpha-hydroxysteroids / N-alkylpyrrolidines / Morpholines / Tetraalkylammonium salts / Trialkylamines / Secondary alcohols / 1,2-aminoalcohols / Amino acids and derivatives / Cyclic alcohols and derivatives
show 11 more
Substituents
1,2-aminoalcohol / 3-alpha-hydroxysteroid / 3-hydroxysteroid / Alcohol / Aliphatic heteropolycyclic compound / Amine / Amino acid or derivatives / Androgen-skeleton / Androstane-skeleton / Azacycle
show 29 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
quaternary ammonium ion, androstane, 3alpha-hydroxy steroid (CHEBI:8884)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
WRE554RFEZ
CAS number
143558-00-3
InChI Key
YXRDKMPIGHSVRX-OOJCLDBCSA-N
InChI
InChI=1S/C32H53N2O4/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/q+1/t23-,24+,25-,26-,27-,28-,29-,30-,31-,32-/m0/s1
IUPAC Name
1-[(1R,2S,3aS,3bR,5aS,7S,8S,9aS,9bS,11aS)-1-(acetyloxy)-7-hydroxy-9a,11a-dimethyl-8-(morpholin-4-yl)-hexadecahydro-1H-cyclopenta[a]phenanthren-2-yl]-1-(prop-2-en-1-yl)pyrrolidin-1-ium
SMILES
[H][C@@]12C[C@@H]([C@H](OC(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)[C@H](C[C@]12C)N1CCOCC1)[N+]1(CC=C)CCCC1

References

Synthesis Reference

Eliezer Adar, David Sondack, Oded Friedman, Iosef Manascu, Tamir Fizitzki, Boris Freger, Oded Arad, Alexander Weisman, Joseph Kaspi, "Processes for the preparation of rocuronium bromide and intermediates thereof." U.S. Patent US20050159398, issued July 21, 2005.

US20050159398
General References
  1. Agoston S, Vandenbrom RH, Wierda JM: Clinical pharmacokinetics of neuromuscular blocking drugs. Clin Pharmacokinet. 1992 Feb;22(2):94-115. [Article]
  2. Khuenl-Brady KS, Sparr H: Clinical pharmacokinetics of rocuronium bromide. Clin Pharmacokinet. 1996 Sep;31(3):174-83. [Article]
  3. Alvarez-Gomez JA: [Rocuronium]. Rev Esp Anestesiol Reanim. 1997 Oct;44(8):310-4. [Article]
  4. Wicks TC: The pharmacology of rocuronium bromide (ORG 9426). AANA J. 1994 Feb;62(1):33-8. [Article]
  5. Sparr HJ, Beaufort TM, Fuchs-Buder T: Newer neuromuscular blocking agents: how do they compare with established agents? Drugs. 2001;61(7):919-42. [Article]
  6. Hemmerling TM, Russo G, Bracco D: Neuromuscular blockade in cardiac surgery: an update for clinicians. Ann Card Anaesth. 2008 Jul-Dec;11(2):80-90. [Article]
  7. FDA Approved Drug Products: ZEMURON (rocuronium bromide) injection [Link]
Human Metabolome Database
HMDB0014866
KEGG Drug
D00765
KEGG Compound
C07556
PubChem Compound
441290
PubChem Substance
46506855
ChemSpider
390053
RxNav
68139
ChEBI
8884
ChEMBL
CHEMBL1201244
ZINC
ZINC000053229445
Therapeutic Targets Database
DAP000349
PharmGKB
PA164754992
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
RBR
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Rocuronium_bromide
PDB Entries
8esk / 8f2s
MSDS
Download (46.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableLaparoscopy / Neuromuscular Blockade / Pneumoperitoneum / Rating Scales / Surgical Conditions1
4CompletedBasic ScienceBladder Cancer1
4CompletedHealth Services ResearchObesity, Morbid1
4CompletedOtherNeuromuscular Blockade1
4CompletedPreventionC.Delivery; Surgery (Previous), Gynecological1

Pharmacoeconomics

Manufacturers
  • App pharmaceuticals llc
  • Bioniche pharma usa llc
  • Hospira inc
  • Sagent pharmaceuticals inc
  • Sandoz canada inc
  • Teva parenteral medicines inc
  • Schering corp
Packagers
  • Baxter International Inc.
  • Generamedix Inc.
  • Gland Pharma Ltd.
  • Hospira Inc.
  • Organon Pharmaceuticals
  • Sandoz
  • Teva Pharmaceutical Industries Ltd.
Dosage Forms
FormRouteStrength
SolutionIntravenous25 mg
SolutionIntravenous10 mg
SolutionIntravenous50 mg
Solution50.000 mg
SolutionParenteral50.00 mg
SolutionParenteral50.000 mg
InjectionIntravenous50 mg
Injection, solutionIntravenous100 mg
Injection, solutionIntravenous50 mg
SolutionParenteral250 mg
SolutionIntravenous50 mg/5ml
InjectionIntravenous10 mg/ml
Injection, solutionIntravenous bolus
Injection, solutionIntravenous bolus50 MG/5ML
Injection, solution
SolutionIntravenous50.000 mg
InjectionIntravenous
Injection, solution50 mg/5ml
SolutionIntravenous100 mg
Injection, solutionParenteral10 MG/ML
Injection, solutionIntravenous bolus; Intravenous drip10 MG/ML
SolutionParenteral50 mg
InjectionIntravenous10 mg/1mL
InjectionIntravenous100 mg/10mL
InjectionIntravenous50 mg/5mL
Injection, solutionIntravenous10 mg/1mL
Injection, solutionIntravenous100 mg/10mL
Injection, solutionIntravenous50 mg/5mL
SolutionIntravenous10 mg/1mL
SolutionIntravenous10 mg / mL
Solution10 mg/1ml
Injection, solutionIntravenous
Injection, solutionIntravenous10 mg/ml
SolutionIntravenous10 mg/ml
InjectionParenteral10 mg/ml
Injection, solution10 mg/1ml
SolutionIntravenous25.000 mg
Prices
Unit descriptionCostUnit
Zemuron 10 mg/ml vial4.62USD ml
Rocuronium 100 mg/10 ml vial2.66USD ml
Rocuronium 50 mg/5 ml vial1.08USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilityCompleteNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.84e-05 mg/mLALOGPS
logP2.71ALOGPS
logP-0.33Chemaxon
logS-7.3ALOGPS
pKa (Strongest Acidic)14.59Chemaxon
pKa (Strongest Basic)7.96Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area59 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity161.65 m3·mol-1Chemaxon
Polarizability62.78 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9444
Blood Brain Barrier+0.8569
Caco-2 permeable-0.5336
P-glycoprotein substrateSubstrate0.8559
P-glycoprotein inhibitor IInhibitor0.7889
P-glycoprotein inhibitor IIInhibitor0.9009
Renal organic cation transporterNon-inhibitor0.7222
CYP450 2C9 substrateNon-substrate0.8008
CYP450 2D6 substrateNon-substrate0.7534
CYP450 3A4 substrateSubstrate0.7272
CYP450 1A2 substrateNon-inhibitor0.9103
CYP450 2C9 inhibitorNon-inhibitor0.8856
CYP450 2D6 inhibitorNon-inhibitor0.8763
CYP450 2C19 inhibitorNon-inhibitor0.8423
CYP450 3A4 inhibitorNon-inhibitor0.8582
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9119
Ames testNon AMES toxic0.7601
CarcinogenicityNon-carcinogens0.9353
BiodegradationNot ready biodegradable0.946
Rat acute toxicity2.9310 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8607
hERG inhibition (predictor II)Non-inhibitor0.8146
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-001i-1439520000-efed63eab6ab3907f152
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-228.90265
predicted
DeepCCS 1.0 (2019)
[M+H]+230.79805
predicted
DeepCCS 1.0 (2019)
[M+Na]+236.5675
predicted
DeepCCS 1.0 (2019)

Targets

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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Drug binding
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name
CHRNA2
Uniprot ID
Q15822
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-2
Molecular Weight
59764.82 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Jonsson Fagerlund M, Dabrowski M, Eriksson LI: Pharmacological characteristics of the inhibition of nondepolarizing neuromuscular blocking agents at human adult muscle nicotinic acetylcholine receptor. Anesthesiology. 2009 Jun;110(6):1244-52. doi: 10.1097/ALN.0b013e31819fade3. [Article]
  4. Jonsson M, Gurley D, Dabrowski M, Larsson O, Johnson EC, Eriksson LI: Distinct pharmacologic properties of neuromuscular blocking agents on human neuronal nicotinic acetylcholine receptors: a possible explanation for the train-of-four fade. Anesthesiology. 2006 Sep;105(3):521-33. [Article]
  5. Liu M, Dilger JP: Synergy between pairs of competitive antagonists at adult human muscle acetylcholine receptors. Anesth Analg. 2008 Aug;107(2):525-33. doi: 10.1213/ane.0b013e31817b4469. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
G-protein coupled acetylcholine receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
Molecular Weight
51714.605 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Milchert M, Spassov A, Meissner K, Nedeljkov V, Lehmann C, Wendt M, Loster BW, Mazurkiewicz-Janik M, Gedrange T, Pavlovic D: Skeletal muscle relaxants inhibit rat tracheal smooth muscle tone in vitro. J Physiol Pharmacol. 2009 Dec;60 Suppl 8:5-11. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Voltage-gated potassium channel activity
Specific Function
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gate...
Gene Name
HTR3A
Uniprot ID
P46098
Uniprot Name
5-hydroxytryptamine receptor 3A
Molecular Weight
55279.835 Da
References
  1. Min KT, Wu CL, Yang J: Nondepolarizing neuromuscular blockers inhibit the serotonin-type 3A receptor expressed in Xenopus oocytes. Anesth Analg. 2000 Feb;90(2):476-81. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. van Montfoort JE, Muller M, Groothuis GM, Meijer DK, Koepsell H, Meier PJ: Comparison of "type I" and "type II" organic cation transport by organic cation transporters and organic anion-transporting polypeptides. J Pharmacol Exp Ther. 2001 Jul;298(1):110-5. [Article]
  2. Lozano E, Herraez E, Briz O, Robledo VS, Hernandez-Iglesias J, Gonzalez-Hernandez A, Marin JJ: Role of the plasma membrane transporter of organic cations OCT1 and its genetic variants in modern liver pharmacology. Biomed Res Int. 2013;2013:692071. doi: 10.1155/2013/692071. Epub 2013 Jul 31. [Article]
  3. Wagner DJ, Hu T, Wang J: Polyspecific organic cation transporters and their impact on drug intracellular levels and pharmacodynamics. Pharmacol Res. 2016 Sep;111:237-246. doi: 10.1016/j.phrs.2016.06.002. Epub 2016 Jun 16. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
References
  1. van Montfoort JE, Hagenbuch B, Fattinger KE, Muller M, Groothuis GM, Meijer DK, Meier PJ: Polyspecific organic anion transporting polypeptides mediate hepatic uptake of amphipathic type II organic cations. J Pharmacol Exp Ther. 1999 Oct;291(1):147-52. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48