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 2778		8.6 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020214s036lbl.pdf	Primary		Approved 8429	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 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 1737	substrate 1037	substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 512 BSEP 402 MRP2 383 MRP3 157 MRP4 204	OATP1A2 62 CYP1A2 1054 CYP2A6 543 CYP2B6 664 CYP2C8 693 CYP2C19 991 CYP2E1 667 OCT1 327

Drug as perpetrator

Target	Modality	Activity
BSEP 403	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP2 475	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 207	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 238	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
OCT1 543	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11408531/	yes

Drug as victim

Target	Modality	Activity
OCT1 327	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11408531/	likely
CYP1A2 1054	substrate 3367 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 543	substrate 3367 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 664	substrate 3367 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 991	substrate 3367 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 693	substrate 3367 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 1037	substrate 3367 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 1217	substrate 3367 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 667	substrate 3367 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 1737	substrate 3367 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 62	substrate 3367 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
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
[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
Propofol anaesthesia via target controlled infusion or manually controlled infusion: effects on the bispectral index as a measure of anaesthetic depth.	2001 Dec	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 Dec	11744584
[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
Rocuronium: high risk for anaphylaxis?	2001 Nov	11878544
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
Is succinylcholine appropriate or obsolete in the intensive care unit?	2001 Oct	11737897
Huntington's chorea: use of rocuronium.	2001 Oct	11576133
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
Target controlled infusion of rocuronium: selection of a pharmacokinetic model.	2002	11975424
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
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
Cyclodextrin-derived host molecules as reversal agents for the neuromuscular blocker rocuronium bromide: synthesis and structure-activity relationships.	2002 Apr 25	11960492
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
The detection and identification of quaternary nitrogen muscle relaxants in biological fluids and tissues by ion-trap LC-ESI-MS.	2002 Jan-Feb	11890177
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
Presynaptic inhibitory effects of rocuronium and SZ1677 on [3H]acetylcholine release from the mouse hemidiaphragm preparation.	2002 Jun	11900861
Effects of remifentanil and alfentanil on the cardiovascular responses to induction of anaesthesia and tracheal intubation in the elderly.	2002 Mar	11990278
[Anaphylaxis after rocuronium: advantage of blood tests for early diagnosis].	2002 Mar	11963386
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
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
Mild core hypothermia and anesthetic requirement for loss of responsiveness during propofol anesthesia for craniotomy.	2002 May	11973207
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 15 15:44:19 GMT 2023` Edited by `admin` on `Fri Dec 15 15:44:19 GMT 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