ROCURONIUM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H53N2O4
Molecular Weight	529.7754
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

C=CC[N+]1(CCCC1)[C@@]2([H])C[C@@]3([H])[C@]4([H])CC[C@@]5([H])C[C@@]([H])([C@]([H])(C[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]2([H])OC(=O)C)N6CCOCC6)O

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	528.7675
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 64 Target ID: CHEMBL2362997 Sources: http://en.cnki.com.cn/Article_en/CJFDTotal-ZHMZ200505017.htm	Antagonist 2575		8.6 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 580 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020214s036lbl.pdf	Primary		Approved 8043	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 1601	substrate 936	substrate 1118

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 480 BSEP 376 MRP2 346 MRP3 150 MRP4 194	OATP1A2 57 CYP1A2 972 CYP2A6 485 CYP2B6 616 CYP2C8 634 CYP2C19 910 CYP2E1 606 OCT1 302

Drug as perpetrator

Target	Modality	Activity
BSEP 377	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP2 434	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 200	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 226	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
OCT1 495	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/11408531/	yes

Drug as victim

Target	Modality	Activity
OCT1 302	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/11408531/	likely
CYP1A2 972	substrate 3113 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 485	substrate 3113 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 616	substrate 3113 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 910	substrate 3113 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 634	substrate 3113 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 936	substrate 3113 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 1118	substrate 3113 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 606	substrate 3113 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 1601	substrate 3113 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 57	substrate 3113 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
Effects of pretreatment with cisatracurium, rocuronium, and d-tubocurarine on succinylcholine-induced fasciculations and myalgia: a comparison with placebo.	1999 Dec	10680105
Choice of the muscle relaxant for rapid-sequence induction.	2001	11766251
Recovery of neuromuscular block in morbidly obese patients following an infusion of rocuronium.	2001	11732386
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
[Rocuronium or vecuronium for intubation for short operations in the preschool age? Effects on time in the operating room and postoperative phase].	2001	11455866
Newer neuromuscular blocking agents: how do they compare with established agents?	2001	11434449
[Total intravenous anesthesia using remifentanil and propofol with midazolam co-induction in laparoscopic surgery of the gallbladder].	2001	11432253
Anesthesia for Cesarean section and posterior fossa craniotomy in a patient with von Hippel-Lindau disease.	2001 Apr	11339783
Neostigmine antagonism of rocuronium block during anesthesia with sevoflurane, isoflurane or propofol.	2001 Apr	11339776
Rocuronium-induced neuromuscular blockade is affected by chronic phenytoin therapy.	2001 Apr	11294462
Postoperative residual block after intermediate-acting neuromuscular blocking drugs.	2001 Apr	11284816
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 new neuromuscular blocking agents: do they offer any advantages?	2001 Dec	11878696
[New muscle relaxants].	2001 Dec	11871089
Why do we still use suxamethonium for caesarean section?	2001 Dec	11810746
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 Dec	11744584
[Sevoflurane augments the degree and speeds the onset of rocuronium evoked neuromuscular blockade in children].	2001 Dec	11743672
Reversal of rocuronium with edrophonium during propofol versus sevoflurane anesthesia.	2001 Feb	11167172
Comparison of effects of remifentanil and alfentanil on cardiovascular response to tracheal intubation in hypertensive patients.	2001 Jan	11575417
The influence of halothane, isoflurane and sevoflurane on rocuronium infusion in children.	2001 Jan	11152037
No substitute for the intravenous route.	2001 Jan	11135714
The effects of remifentanil on haemodynamic stability during rigid bronchoscopy.	2001 Jun	11412167
Rocuronium: high risk for anaphylaxis?	2001 May	11575345
Onset and duration of action of rocuronium--from tracheal intubation, through intense block to complete recovery.	2001 May	11309014
Rocuronium and anaphylaxis--a statistical challenge.	2001 Nov	11736669
Rapid sequence induction: a national survey of practice.	2001 Nov	11703243
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
Spontaneous movements, local reactions and pain on injection of rocuronium. A comparison between female and male patients.	2001 Sep	11576052
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
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
Neuromuscular pharmacology of TAAC3, a new nondepolarizing muscle relaxant with rapid onset and ultrashort duration of action.	2002 Apr	11916790
Cyclodextrin-derived host molecules as reversal agents for the neuromuscular blocker rocuronium bromide: synthesis and structure-activity relationships.	2002 Apr 25	11960492
Comparison of rocuronium and suxamethonium for rapid tracheal intubation in children.	2002 Feb	11882225
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
Effects of remifentanil and alfentanil on the cardiovascular responses to induction of anaesthesia and tracheal intubation in the elderly.	2002 Mar	11990278
The influence of induction technique on intubating conditions 1 min after rocuronium administration: a comparison of a propofol-ephedrine combination and propofol.	2002 Mar	11879210
The neuropathologic effects in rats and neurometabolic effects in humans of large-dose remifentanil.	2002 May	11973195

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 Jun 25 23:07:23 UTC 2021` Edited by `admin` on `Fri Jun 25 23:07:23 UTC 2021`
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 [WHO-DD]

Common Name

English

ROCURONIUM [MI]

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