ROCURONIUM BROMIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H53N2O4.Br
Molecular Weight	609.678
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Br-].[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=OYTJKRAYGYRUJK-FMCCZJBLSA-M

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

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

Molecular Formula	BrH
Molecular Weight	80.912
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 2737		8.6 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 607 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020214s036lbl.pdf	Primary		Approved 8307	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 1670	substrate 985	substrate 1168

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 498 BSEP 392 MRP2 363 MRP3 156 MRP4 202	OATP1A2 59 CYP1A2 1013 CYP2A6 510 CYP2B6 648 CYP2C8 670 CYP2C19 955 CYP2E1 633 OCT1 317

Drug as perpetrator

Target	Modality	Activity
BSEP 393	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP2 452	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 206	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 235	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
OCT1 513	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/11408531/	yes

Drug as victim

Target	Modality	Activity
OCT1 317	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/11408531/	likely
CYP1A2 1013	substrate 3264 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 510	substrate 3264 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 648	substrate 3264 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 955	substrate 3264 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 670	substrate 3264 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 985	substrate 3264 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 1168	substrate 3264 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 633	substrate 3264 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 1670	substrate 3264 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 59	substrate 3264 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
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
Recovery of neuromuscular block in morbidly obese patients following an infusion of rocuronium.	2001	11732386
Anaesthetic management of an adolescent for scoliosis surgery with a Fontan circulation.	2001	11696127
Recent advances in myorelaxant therapy.	2001	11696115
Newer neuromuscular blocking agents: how do they compare with established agents?	2001	11434449
Rocuronium-induced neuromuscular blockade is affected by chronic phenytoin therapy.	2001 Apr	11294462
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
Why do we still use suxamethonium for caesarean section?	2001 Dec	11810746
Propofol anaesthesia via target controlled infusion or manually controlled infusion: effects on the bispectral index as a measure of anaesthetic depth.	2001 Dec	11771598
The effect of rocuronium on intraocular pressure: a comparison with succinylcholine.	2001 Dec	11737185
Quantitative determination of rocuronium in human plasma by liquid chromatography-electrospray ionization mass spectrometry.	2001 Feb 23	11263576
Multicenter trial of prolonged infusions of rocuronium bromide in critically ill patients: effects of multiple organ failure.	2001 Jan	11213940
Muscle relaxant choices for rapid sequence induction.	2001 Jan-Feb	11182700
[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
Anaesthetic considerations for a child with combined Prader-Willi syndrome and mitochondrial myopathy.	2001 Jul	11442870
Intubating conditions after three different doses of rocuronium in the elderly.	2001 Jun	11529339
The effects of remifentanil on haemodynamic stability during rigid bronchoscopy.	2001 Jun	11412167
Gas chromatographic-mass spectrometric assay for rocuronium with potential for quantifying its metabolite, 17-desacetylrocuronium, in human plasma.	2001 Jun 15	11417864
Pediatric renal transplantation: anesthesia and perioperative complications.	2001 Mar	11315282
Induction with propofol target-concentration infusion vs. 8% sevoflurane inhalation and alfentanil in hypertensive patients.	2001 Mar	11251433
The prone position is associated with a decrease in respiratory system compliance in healthy anaesthetized infants.	2001 May	11359586
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
Rapid sequence induction: a national survey of practice.	2001 Nov	11703243
Precurarization and priming: a theoretical analysis of safety and timing.	2001 Nov	11682407
Anaphylaxis during anaesthesia. Results of a two-year survey in France.	2001 Oct	11878723
Is succinylcholine appropriate or obsolete in the intensive care unit?	2001 Oct	11737897
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
Different patterns of mast cell activation by muscle relaxants in human skin.	2001 Sep	11575539
Effect of ondansetron pretreatment on pain after rocuronium and propofol injection: a randomised, double-blind controlled comparison with lidocaine.	2001 Sep	11531681
An isolated, antegrade, perfused, peroneal nerve anterior tibialis muscle model in the rat: a novel model developed to study the factors governing the time course of action of neuromuscular blocking agents.	2002 Apr	11964606
Protocol for rapid sequence intubation in pediatric patients -- a four-year study.	2002 Apr	11951062
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
Effect of 17 beta-estradiol-D-17 beta-glucuronide on the rat organic anion transporting polypeptide 2-mediated transport differs depending on substrates.	2002 Feb	11792694
Population pharmacodynamic modeling without plasma concentrations of rocuronium in children.	2002 Jan	11808822
Prehospital tracheal intubating conditions during rapid sequence intubation: rocuronium versus vecuronium.	2002 Jan-Feb	11805764
2-O-substituted cyclodextrins as reversal agents for the neuromuscular blocker rocuronium bromide.	2002 Jun	11937340
The neuropathologic effects in rats and neurometabolic effects in humans of large-dose remifentanil.	2002 May	11973195
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 `Fri Dec 16 18:09:11 UTC 2022` Edited by `admin` on `Fri Dec 16 18:09:11 UTC 2022`
Record UNII	I65MW4OFHZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ROCURONIUM BROMIDE

Official Name

English

ROCURONIUM BROMIDE [JAN]

Common Name

English

ROCURONIUM BROMIDE [MI]

Common Name

English

ROCURONIUM BROMIDE [VANDF]

Common Name

English

(+)-ROCURONIUM BROMIDE

Common Name

English

ROCURONIUM BROMIDE [EP MONOGRAPH]

Common Name

English

rocuronium bromide [INN]

Common Name

English

ZEMURON

Brand Name

English

ROCURONIUM BROMIDE [USAN]

Common Name

English

ORG 9426

Code

English

1-Allyl-1-(3?,17?-dihydroxy-2?-morpholino-5?-androstan-16?-yl)pyrrolidinium bromide, 17-acetate

Common Name

English

ESMERON

Brand Name

English

ROCURONIUM BROMIDE [USP-RS]

Common Name

English

ROCURONIUM BROMIDE [MART.]

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)-, BROMIDE

Common Name

English

ROCURONIUM BROMIDE [USP MONOGRAPH]

Common Name

English

ROCURONIUM BROMIDE [ORANGE BOOK]

Common Name

English

ORG-9426

Code

English

Rocuronium bromide [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QM03AC09