ROCURONIUM BROMIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H53N2O4.Br
Molecular Weight	609.678
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Br-].CC(=O)O[C@H]1[C@H](C[C@H]2[C@@H]3CC[C@H]4C[C@H](O)[C@H](C[C@]4(C)[C@H]3CC[C@]12C)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	BrH
Molecular Weight	80.912
Charge	0
Count

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

Molecular Formula	C32H52N2O4
Molecular Weight	528.7663
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	10 / 11
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 2849		8.6 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020214s036lbl.pdf	Primary		Approved 8583	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 1994

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 plasma	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 plasma	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 plasma	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 Sources: https://www.fda.gov/media/71700/download	unhealthy, 0-17 Health Status: unhealthy Age Group: 0-17 Sex: M+F 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 Sources: https://www.fda.gov/media/71700/download	unhealthy, 0-17 Health Status: unhealthy Age Group: 0-17 Sex: M+F 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 Sources: https://www.fda.gov/media/71700/download	unhealthy, 0-17 Health Status: unhealthy Age Group: 0-17 Sex: M+F 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 Sources: https://www.fda.gov/media/71700/download	unhealthy, 0-17 Health Status: unhealthy Age Group: 0-17 Sex: M+F 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 Sources: https://www.fda.gov/media/71700/download	unhealthy, 0-17 Health Status: unhealthy Age Group: 0-17 Sex: M+F 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 Sources: https://pubmed.ncbi.nlm.nih.gov/9836032/	unhealthy, 33.1 Health Status: unhealthy Age Group: 33.1 Sex: F 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 1946	substrate 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 620 BSEP 550 MRP2 499 MRP3 246 MRP4 290	OATP1A2 67 CYP1A2 1197 CYP2A6 626 CYP2B6 776 CYP2C8 810 CYP2C19 1119 CYP2E1 729 OCT1 393

Drug as perpetrator

Target	Modality	Activity
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 326	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 345	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
OCT1 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11408531/	yes

Drug as victim

Target	Modality	Activity
OCT1 393	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11408531/	likely
CYP1A2 1197	substrate 4014 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 626	substrate 4014 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 776	substrate 4014 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 1119	substrate 4014 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 810	substrate 4014 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 1193	substrate 4014 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 1388	substrate 4014 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 729	substrate 4014 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 1946	substrate 4014 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 67	substrate 4014 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
eMolecules	32452457	https://www.emolecules.com/cgi-bin/more?vid=32452457
MolPort	MolPort-006-167-617	https://www.molport.com/shop/molecule-link/MolPort-006-167-617
ZINC	ZINC000053229445	http://zinc15.docking.org/substances/ZINC000053229445

PubMed

Title	Date	PubMed
2-O-substituted cyclodextrins as reversal agents for the neuromuscular blocker rocuronium bromide.	2002-06	11937340
Presynaptic inhibitory effects of rocuronium and SZ1677 on [3H]acetylcholine release from the mouse hemidiaphragm preparation.	2002-06	11900861
Mild core hypothermia and anesthetic requirement for loss of responsiveness during propofol anesthesia for craniotomy.	2002-05	11973207
The neuropathologic effects in rats and neurometabolic effects in humans of large-dose remifentanil.	2002-05	11973195
The hemodynamic effects of rapacuronium in patients with coronary artery disease: succinylcholine and vecuronium compared.	2002-05	11973169
Cyclodextrin-derived host molecules as reversal agents for the neuromuscular blocker rocuronium bromide: synthesis and structure-activity relationships.	2002-04-25	11960492
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.	2002-04	11964606
Protocol for rapid sequence intubation in pediatric patients -- a four-year study.	2002-04	11951062
Rocuronium pharmacokinetic-pharmacodynamic relationship under stable propofol or isoflurane anesthesia.	2002-04	11927473
Neuromuscular pharmacology of TAAC3, a new nondepolarizing muscle relaxant with rapid onset and ultrashort duration of action.	2002-04	11916790
The detection and identification of quaternary nitrogen muscle relaxants in biological fluids and tissues by ion-trap LC-ESI-MS.	2002-03-14	11890177
Effects of remifentanil and alfentanil on the cardiovascular responses to induction of anaesthesia and tracheal intubation in the elderly.	2002-03	11990278
[Anaphylaxis after rocuronium: advantage of blood tests for early diagnosis].	2002-03	11963386
The influence of induction technique on intubating conditions 1 min after rocuronium administration: a comparison of a propofol-ephedrine combination and propofol.	2002-03	11879210
Impact of shorter-acting neuromuscular blocking agents on fast-track recovery of the cardiac surgical patient.	2002-03	11873034
The Laryngeal Mask Airway ProSeal(TM) as a temporary ventilatory device in grossly and morbidly obese patients before laryngoscope-guided tracheal intubation.	2002-03	11867408
Prolonged neuromuscular block after rocuronium in postpartum patients.	2002-03	11867398
The potency of new muscle relaxants on recombinant muscle-type acetylcholine receptors.	2002-03	11867382
The neuromuscular transmission module versus the relaxometer mechanomyograph for neuromuscular block monitoring.	2002-03	11867381
Pretreatment before succinylcholine for outpatient anesthesia?	2002-03	11867378
Postoperative muscle paralysis after rocuronium: less residual block when acceleromyography is used.	2002-02	11942873
Resistance to rocuronium in a child with Schwartz-Jampel syndrome type 1 B.	2002-02	11930277
Effects of rocuronium pretreatment on muscle enzyme levels following suxamethonium.	2002-02	11882227
Comparison of rocuronium and suxamethonium for rapid tracheal intubation in children.	2002-02	11882225
Effect of 17 beta-estradiol-D-17 beta-glucuronide on the rat organic anion transporting polypeptide 2-mediated transport differs depending on substrates.	2002-02	11792694
Prehospital tracheal intubating conditions during rapid sequence intubation: rocuronium versus vecuronium.	2002-01-24	11805764
Population pharmacodynamic modeling without plasma concentrations of rocuronium in children.	2002-01	11808822
Target controlled infusion of rocuronium: selection of a pharmacokinetic model.	2002	11975424
The new neuromuscular blocking agents: do they offer any advantages?	2001-12	11878696
[New muscle relaxants].	2001-12	11871089
Why do we still use suxamethonium for caesarean section?	2001-12	11810746
Propofol anaesthesia via target controlled infusion or manually controlled infusion: effects on the bispectral index as a measure of anaesthetic depth.	2001-12	11771598
Equi-lasting doses of rocuronium, compared to mivacurium, result in improved neuromuscular blockade in patients undergoing gynecological laparoscopy : [Des doses de durée équivalente de rocuronium, comparé au mivacurium, améliorent la curarisation chez des patientes qui subissent une laparoscopie gynécologique].	2001-12	11744584
[Sevoflurane augments the degree and speeds the onset of rocuronium evoked neuromuscular blockade in children].	2001-12	11743672
The effect of rocuronium on intraocular pressure: a comparison with succinylcholine.	2001-12	11737185
Rocuronium: high risk for anaphylaxis?	2001-11	11878544
Rocuronium and anaphylaxis--a statistical challenge.	2001-11	11736669
Allergic reactions during anaesthesia - increased attention to the problem in Denmark and Norway.	2001-11	11736666
Rapid sequence induction: a national survey of practice.	2001-11	11703243
Anaphylaxis during anaesthesia. Results of a two-year survey in France.	2001-10	11878723
Is succinylcholine appropriate or obsolete in the intensive care unit?	2001-10	11737897
Choice of the muscle relaxant for rapid-sequence induction.	2001	11766251
Choice of the hypnotic and the opioid for rapid-sequence induction.	2001	11766250
Muscle relaxants in paediatric day case surgery.	2001	11766247
Muscle relaxants suitable for day case surgery.	2001	11766246
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

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 `Mon Mar 31 18:08:23 GMT 2025` Edited by `admin` on `Mon Mar 31 18:08:23 GMT 2025`
Record UNII	I65MW4OFHZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ZEMURON

Preferred Name

English

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

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