ROCURONIUM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H53N2O4
Molecular Weight	529.7742
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@@H]([C@H](OC(C)=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])C[C@H](O)[C@H](C[C@]34C)N5CCOCC5)[N+]6(CC=C)CCCC6

InChI

InChIKey=YXRDKMPIGHSVRX-OOJCLDBCSA-N

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

HIDE SMILES / InChI

Molecular Formula	C32H52N2O4
Molecular Weight	528.7663
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020214s036lbl.pdf
Curator's Comment: description was created based on several sources, including http://reference.medscape.com/drug/zemuron-rocuronium-343109 | https://www.drugs.com/pro/rocuronium-bromide-injection.html | https://www.drugbank.ca/drugs/DB00728 | https://www.ncbi.nlm.nih.gov/pubmed/2573387 | https://www.ncbi.nlm.nih.gov/pubmed/21568994

Rocuronium (brand names Zemuron, Esmeron) is an aminosteroid non-depolarizing neuromuscular blocker or muscle relaxant used in modern anesthesia to facilitate endotracheal intubation by providing skeletal muscle relaxation, most commonly required for surgery or mechanical ventilation. Rocuronium bromide is a nondepolarizing neuromuscular blocking agent with a rapid to intermediate onset depending on dose and intermediate duration. It acts by competing for cholinergic receptors at the motor end-plate. This action is antagonized by acetylcholinesterase inhibitors, such as neostigmine and edrophonium. Most common adverse reactions are transient hypotension and hypertension.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscle-type nicotinic acetylcholine receptor 65 Target ID: CHEMBL2362997 Sources: http://en.cnki.com.cn/Article_en/CJFDTotal-ZHMZ200505017.htm	Antagonist 2760		8.6 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 608 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020214s036lbl.pdf	Primary		Approved 8360	ZEMURON Approved Use Rocuronium bromide injection is indicated 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. Rocuronium bromide is a nondepolarizing neuromuscular blocking agent indicated 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. (1) Launch Date 7.6386238E11

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020214Orig1s038lbl.pdf	0.6 mg/kg single, intravenous dose: 0.6 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		ROCURONIUM unknown	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
0.9 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020214Orig1s038lbl.pdf	0.45 mg/kg single, intravenous dose: 0.45 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		ROCURONIUM unknown	Homo sapiens population: UNHEALTHY age: NEWBORN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
70% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020214Orig1s038lbl.pdf	0.6 mg/kg single, intravenous dose: 0.6 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		ROCURONIUM unknown	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
0.15 mg/kg single, intravenous Recommended Dose: 0.15 mg/kg Route: intravenous Route: single Dose: 0.15 mg/kg Co-administed with:: sevoflurane(2-2.5 MAC) Sources: https://www.fda.gov/media/71700/download	unhealthy, 0-17 n = 64 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 64 Sources: https://www.fda.gov/media/71700/download	Other AEs: Procedural pain, Vomiting... Other AEs: Procedural pain (14%) Vomiting (3%) Sources: https://www.fda.gov/media/71700/download
0.45 mg/kg single, intravenous Recommended Dose: 0.45 mg/kg Route: intravenous Route: single Dose: 0.45 mg/kg Co-administed with:: sevoflurane(2-2.5 MAC) Sources: https://www.fda.gov/media/71700/download	unhealthy, 0-17 n = 63 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 63 Sources: https://www.fda.gov/media/71700/download	Other AEs: Procedural pain, Vomiting... Other AEs: Procedural pain (14%) Vomiting (6%) Procedural hypotension (5%) Sources: https://www.fda.gov/media/71700/download
0.6 mg/kg single, intravenous Recommended Dose: 0.6 mg/kg Route: intravenous Route: single Dose: 0.6 mg/kg Co-administed with:: sevoflurane(2-2.5 MAC) Sources: https://www.fda.gov/media/71700/download	unhealthy, 0-17 n = 66 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 66 Sources: https://www.fda.gov/media/71700/download	Other AEs: Procedural pain, Vomiting... Other AEs: Procedural pain (17%) Vomiting (8%) Procedural hypotension (5%) Nausea (5%) Sources: https://www.fda.gov/media/71700/download
1 mg/kg single, intravenous Recommended Dose: 1 mg/kg Route: intravenous Route: single Dose: 1 mg/kg Co-administed with:: sevoflurane(2-2.5 MAC) Sources: https://www.fda.gov/media/71700/download	unhealthy, 0-17 n = 56 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 56 Sources: https://www.fda.gov/media/71700/download	Other AEs: Procedural pain, Vomiting... Other AEs: Procedural pain (18%) Vomiting (12%) Procedural hypotension (4%) Nausea (4%) Sources: https://www.fda.gov/media/71700/download
10 ug/kg/min single, intravenous Recommended Dose: 10 ug/kg/min Route: intravenous Route: single Dose: 10 ug/kg/min Co-administed with:: sevoflurane(2-2.5 MAC) Sources: https://www.fda.gov/media/71700/download	unhealthy, 0-17 n = 73 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 73 Sources: https://www.fda.gov/media/71700/download	Other AEs: Procedural pain, Hypercapnia... Other AEs: Procedural pain (12%) Hypercapnia (3%) Nausea (3%) Sources: https://www.fda.gov/media/71700/download
0.6 mg/kg single, intravenous Recommended Dose: 0.6 mg/kg Route: intravenous Route: single Dose: 0.6 mg/kg Co-administed with:: midazolam(1-2 mg) propofol(1.8 mg/kg) alfentanil(9 ug/kg) Sources: https://pubmed.ncbi.nlm.nih.gov/9836032/	unhealthy, 33.1 n = 20 Health Status: unhealthy Condition: surgical procedures Age Group: 33.1 Sex: F Population Size: 20 Sources: https://pubmed.ncbi.nlm.nih.gov/9836032/	Other AEs: Nausea and vomiting... Other AEs: Nausea and vomiting (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/9836032/

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1709	substrate 1010	substrate 1193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 506 BSEP 401 MRP2 367 MRP3 157 MRP4 203	OATP1A2 61 CYP1A2 1032 CYP2A6 523 CYP2B6 660 CYP2C8 688 CYP2C19 985 CYP2E1 648 OCT1 322

Drug as perpetrator

Target	Modality	Activity
BSEP 402	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP2 459	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 208	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 237	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
OCT1 523	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/11408531/	yes

Drug as victim

Target	Modality	Activity
OCT1 322	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/11408531/	likely
CYP1A2 1032	substrate 3326 Sources: https://www.pmda.go.jp/drugs/2007/P200700034/53018500_21900AMY00035_A101_1.pdf#page=1, https://www.pmda.go.jp/drugs/2007/P200700034/53018500_21900AMY00035_K101_1.pdf#page=13 Page: (PMDA_A101) 1, (PMDA_K101) 13	unlikely
CYP2A6 523	substrate 3326 Sources: https://www.pmda.go.jp/drugs/2007/P200700034/53018500_21900AMY00035_A101_1.pdf#page=1, https://www.pmda.go.jp/drugs/2007/P200700034/53018500_21900AMY00035_K101_1.pdf#page=13 Page: (PMDA_A101) 1, (PMDA_K101) 13	unlikely
CYP2B6 660	substrate 3326 Sources: https://www.pmda.go.jp/drugs/2007/P200700034/53018500_21900AMY00035_A101_1.pdf#page=1, https://www.pmda.go.jp/drugs/2007/P200700034/53018500_21900AMY00035_K101_1.pdf#page=13 Page: (PMDA_A101) 1, (PMDA_K101) 13	unlikely
CYP2C19 985	substrate 3326 Sources: https://www.pmda.go.jp/drugs/2007/P200700034/53018500_21900AMY00035_A101_1.pdf#page=1, https://www.pmda.go.jp/drugs/2007/P200700034/53018500_21900AMY00035_K101_1.pdf#page=13 Page: (PMDA_A101) 1, (PMDA_K101) 13	unlikely
CYP2C8 688	substrate 3326 Sources: https://www.pmda.go.jp/drugs/2007/P200700034/53018500_21900AMY00035_A101_1.pdf#page=1, https://www.pmda.go.jp/drugs/2007/P200700034/53018500_21900AMY00035_K101_1.pdf#page=13 Page: (PMDA_A101) 1, (PMDA_K101) 13	unlikely
CYP2C9 1010	substrate 3326 Sources: https://www.pmda.go.jp/drugs/2007/P200700034/53018500_21900AMY00035_A101_1.pdf#page=1, https://www.pmda.go.jp/drugs/2007/P200700034/53018500_21900AMY00035_K101_1.pdf#page=13 Page: (PMDA_A101) 1, (PMDA_K101) 13	unlikely
CYP2D6 1193	substrate 3326 Sources: https://www.pmda.go.jp/drugs/2007/P200700034/53018500_21900AMY00035_A101_1.pdf#page=1, https://www.pmda.go.jp/drugs/2007/P200700034/53018500_21900AMY00035_K101_1.pdf#page=13 Page: (PMDA_A101) 1, (PMDA_K101) 13	unlikely
CYP2E1 648	substrate 3326 Sources: https://www.pmda.go.jp/drugs/2007/P200700034/53018500_21900AMY00035_A101_1.pdf#page=1, https://www.pmda.go.jp/drugs/2007/P200700034/53018500_21900AMY00035_K101_1.pdf#page=13 Page: (PMDA_A101) 1, (PMDA_K101) 13	unlikely
CYP3A4 1709	substrate 3326 Sources: https://www.pmda.go.jp/drugs/2007/P200700034/53018500_21900AMY00035_A101_1.pdf#page=1, https://www.pmda.go.jp/drugs/2007/P200700034/53018500_21900AMY00035_K101_1.pdf#page=13 Page: (PMDA_A101) 1, (PMDA_K101) 13	unlikely
OATP1A2 61	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/10490898/, https://www.pmda.go.jp/drugs/2007/P200700034/53018500_21900AMY00035_A100_1.pdf#page=18 Page: (PMDA_A100) 18	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:8884	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8884
MolPort	MolPort-006-167-617	https://www.molport.com/shop/molecule-link/MolPort-006-167-617
ZINC	ZINC000053229445	http://zinc15.docking.org/substances/ZINC000053229445
eMolecules	32452457	https://www.emolecules.com/cgi-bin/more?vid=32452457

PubMed

Title	Date	PubMed
Choice of the muscle relaxant for rapid-sequence induction.	2001	11766251
Choice of the hypnotic and the opioid for rapid-sequence induction.	2001	11766250
Comparison of the influence of desflurane nitrous oxide anesthesia to propofol nitrous oxide anesthesia on rocuronium bromide induced neuromuscular block.	2001	11732388
Comparative study of the TOF-ratio measured by the ParaGraph versus the TOF-Guard, with and without thumb repositioning.	2001	11732387
Anaesthetic management of an adolescent for scoliosis surgery with a Fontan circulation.	2001	11696127
Recent advances in myorelaxant therapy.	2001	11696115
Target controlled infusion of remifentanil and propofol for cesarean section in a patient with multivalvular disease and severe pulmonary hypertension.	2001	11534314
Use of remifentanil in combination with desflurane or propofol for ambulatory oral surgery.	2001	11534310
Increased sensitivity to depolarization and nondepolarizing neuromuscular blocking agents in young rat hemidiaphragms.	2001 Aug	11506123
Transcranial Doppler ultrasonography with induction of anesthesia and neuromuscular blockade in surgical patients.	2001 Aug	11498313
A double-blind, randomized comparison of low-dose rocuronium and atracurium in a desflurane anesthetic.	2001 Aug	11498311
Safety and efficacy of rocuronium for controlled intubation with paralytics in the pediatric emergency department.	2001 Aug	11493818
The pharmacoeconomics of neuromuscular blocking drugs: a perioperative cost-minimization strategy in children.	2001 Aug	11473856
The influence of fentanyl vs. s-ketamine on intubating conditions during induction of anaesthesia with etomidate and rocuronium.	2001 Aug	11473558
[Anesthesia in Prader-Willi syndrome for major surgery for kyphoscoliosis].	2001 Aug-Sep	11591286
[New muscle relaxants].	2001 Dec	11871089
Why do we still use suxamethonium for caesarean section?	2001 Dec	11810746
[Sevoflurane augments the degree and speeds the onset of rocuronium evoked neuromuscular blockade in children].	2001 Dec	11743672
The effect of rocuronium on intraocular pressure: a comparison with succinylcholine.	2001 Dec	11737185
Comparison of effects of remifentanil and alfentanil on cardiovascular response to tracheal intubation in hypertensive patients.	2001 Jan	11575417
[Prophylaxis of nausea and vomiting after thyroid surgery: comparison of oral and intravenous dolasetron with intravenous droperidol and placebo].	2001 Jul	11496617
The corrugator supercilii, not the orbicularis oculi, reflects rocuronium neuromuscular blockade at the laryngeal adductor muscles.	2001 Jul	11465590
Intubating conditions after three different doses of rocuronium in the elderly.	2001 Jun	11529339
Rocuronium: high risk for anaphylaxis?	2001 May	11575345
Rocuronium and anaphylaxis--a statistical challenge.	2001 Nov	11736669
Allergic reactions during anaesthesia - increased attention to the problem in Denmark and Norway.	2001 Nov	11736666
Precurarization and priming: a theoretical analysis of safety and timing.	2001 Nov	11682407
Is succinylcholine appropriate or obsolete in the intensive care unit?	2001 Oct	11737897
Huntington's chorea: use of rocuronium.	2001 Oct	11576133
Reexamined: the recommended endotracheal intubating dose for nondepolarizing neuromuscular blockers of rapid onset.	2001 Oct	11574363
Probability of acceptable intubation conditions with low dose rocuronium during light sevoflurane anaesthesia in children.	2001 Sep	11576058
Spontaneous movements, local reactions and pain on injection of rocuronium. A comparison between female and male patients.	2001 Sep	11576052
Different patterns of mast cell activation by muscle relaxants in human skin.	2001 Sep	11575539
Incidence of UK reactions involving rocuronium may simply reflect market use.	2001 Sep	11556293
Effect of ondansetron pretreatment on pain after rocuronium and propofol injection: a randomised, double-blind controlled comparison with lidocaine.	2001 Sep	11531681
Protocol for rapid sequence intubation in pediatric patients -- a four-year study.	2002 Apr	11951062
Rocuronium pharmacokinetic-pharmacodynamic relationship under stable propofol or isoflurane anesthesia.	2002 Apr	11927473
Neuromuscular pharmacology of TAAC3, a new nondepolarizing muscle relaxant with rapid onset and ultrashort duration of action.	2002 Apr	11916790
Postoperative muscle paralysis after rocuronium: less residual block when acceleromyography is used.	2002 Feb	11942873
Resistance to rocuronium in a child with Schwartz-Jampel syndrome type 1 B.	2002 Feb	11930277
Comparison of rocuronium and suxamethonium for rapid tracheal intubation in children.	2002 Feb	11882225
2-O-substituted cyclodextrins as reversal agents for the neuromuscular blocker rocuronium bromide.	2002 Jun	11937340
Presynaptic inhibitory effects of rocuronium and SZ1677 on [3H]acetylcholine release from the mouse hemidiaphragm preparation.	2002 Jun	11900861
Impact of shorter-acting neuromuscular blocking agents on fast-track recovery of the cardiac surgical patient.	2002 Mar	11873034
The Laryngeal Mask Airway ProSeal(TM) as a temporary ventilatory device in grossly and morbidly obese patients before laryngoscope-guided tracheal intubation.	2002 Mar	11867408
Prolonged neuromuscular block after rocuronium in postpartum patients.	2002 Mar	11867398
The potency of new muscle relaxants on recombinant muscle-type acetylcholine receptors.	2002 Mar	11867382
The neuromuscular transmission module versus the relaxometer mechanomyograph for neuromuscular block monitoring.	2002 Mar	11867381
Pretreatment before succinylcholine for outpatient anesthesia?	2002 Mar	11867378
The hemodynamic effects of rapacuronium in patients with coronary artery disease: succinylcholine and vecuronium compared.	2002 May	11973169

Patents

Sample Use Guides

In Vivo Use Guide

0.45-0.6 mg/kg IV Maintenance: 0.1-0.2 mg/kg IV repeat PRN OR Continuous infusion: 0.01-0.012 mg/kg/min IV

Route of Administration: Intravenous

In Vitro Use Guide

Aliquots of 100 mkl whole heparinized blood of rocuronium-allergic patients (positive basophil activation test and skin test) were challenged at 37 C with buffer as a negative control, anti-IgE (Pharmingen,BDBioscience, Erembodegem, Belgium) as a positive control, serial dilutions of rocuronium (Esmeron, Organon, Brussels, Belgium, 0.2–2.0 x 10^3 mkg/ml), serial dilutions of sugammadex (Bridion; Merck Sharp & Dohme, Oss, The Netherlands) 0.2–2.0 x 10^3 mkg/ml and with a mixture of different concentrations of rocuronium and sugammadex. Flow cytometric analysis of basophils was performed using triple labelling with CD123-PE, HLA-DR-PerCP, CD63-FITC (BD Biosciences) and using monoclonal antihuman IgE (clone GE-1; Sigma-Aldrich Chemic GmBH, Steinheim, Germany), labelled with AlexaFluor 488 (Molecular Probes, Invitrogen, Paisley, UK). Samples were analysed on a flow cytometer (FACsCanto BD; Immunocytometry Systems, San Jose, CA, USA) and expressed as CD63-positive basophils. Samples were regarded as positive when CD63-reactive basophils were higher than 4%

Substance Class	Chemical Created by `admin` on `Wed Jul 05 23:13:02 UTC 2023` Edited by `admin` on `Wed Jul 05 23:13:02 UTC 2023`
Record UNII	WRE554RFEZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ROCURONIUM

Common Name

English

ROCURONIUM ION

Common Name

English

ROCURONIUM [MI]

Common Name

English

Rocuronium [WHO-DD]

Common Name

English

PYRROLIDINIUM, 1-((2.BETA.,3.ALPHA.,5.ALPHA.,16.BETA.,17.BETA.)-17-(ACETYLOXY)-3-HYDROXY-2-(4-MORPHOLINYL)ANDROSTAN-16-YL)-1-(2-PROPENYL)-

Systematic Name

English

ROCURONIUM CATION

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66886