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
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
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 |
DescriptionCurator'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
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 |
---|---|---|---|
Target ID: CHEMBL2362997 |
8.6 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ZEMURON Approved UseRocuronium 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 Date7.6386238E11 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.4 h |
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 |
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 |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
70% |
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: |
unhealthy, 0-17 n = 64 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 64 Sources: |
Other AEs: Procedural pain, Vomiting... |
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: |
unhealthy, 0-17 n = 63 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 63 Sources: |
Other AEs: Procedural pain, Vomiting... Other AEs: Procedural pain (14%) Sources: Vomiting (6%) Procedural hypotension (5%) |
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: |
unhealthy, 0-17 n = 66 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 66 Sources: |
Other AEs: Procedural pain, Vomiting... Other AEs: Procedural pain (17%) Sources: Vomiting (8%) Procedural hypotension (5%) Nausea (5%) |
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: |
unhealthy, 0-17 n = 56 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 56 Sources: |
Other AEs: Procedural pain, Vomiting... Other AEs: Procedural pain (18%) Sources: Vomiting (12%) Procedural hypotension (4%) Nausea (4%) |
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: |
unhealthy, 0-17 n = 73 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 73 Sources: |
Other AEs: Procedural pain, Hypercapnia... Other AEs: Procedural pain (12%) Sources: Hypercapnia (3%) Nausea (3%) |
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) Sources: propofol(1.8 mg/kg) alfentanil(9 ug/kg) |
unhealthy, 33.1 n = 20 Health Status: unhealthy Condition: surgical procedures Age Group: 33.1 Sex: F Population Size: 20 Sources: |
Other AEs: Nausea and vomiting... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Procedural pain | 14% | 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: |
unhealthy, 0-17 n = 64 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 64 Sources: |
Vomiting | 3% | 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: |
unhealthy, 0-17 n = 64 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 64 Sources: |
Procedural pain | 14% | 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: |
unhealthy, 0-17 n = 63 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 63 Sources: |
Procedural hypotension | 5% | 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: |
unhealthy, 0-17 n = 63 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 63 Sources: |
Vomiting | 6% | 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: |
unhealthy, 0-17 n = 63 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 63 Sources: |
Procedural pain | 17% | 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: |
unhealthy, 0-17 n = 66 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 66 Sources: |
Nausea | 5% | 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: |
unhealthy, 0-17 n = 66 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 66 Sources: |
Procedural hypotension | 5% | 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: |
unhealthy, 0-17 n = 66 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 66 Sources: |
Vomiting | 8% | 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: |
unhealthy, 0-17 n = 66 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 66 Sources: |
Vomiting | 12% | 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: |
unhealthy, 0-17 n = 56 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 56 Sources: |
Procedural pain | 18% | 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: |
unhealthy, 0-17 n = 56 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 56 Sources: |
Nausea | 4% | 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: |
unhealthy, 0-17 n = 56 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 56 Sources: |
Procedural hypotension | 4% | 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: |
unhealthy, 0-17 n = 56 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 56 Sources: |
Procedural pain | 12% | 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: |
unhealthy, 0-17 n = 73 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 73 Sources: |
Hypercapnia | 3% | 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: |
unhealthy, 0-17 n = 73 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 73 Sources: |
Nausea | 3% | 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: |
unhealthy, 0-17 n = 73 Health Status: unhealthy Condition: surgical procedures Age Group: 0-17 Sex: M+F Population Size: 73 Sources: |
Nausea and vomiting | 2 patients | 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) Sources: propofol(1.8 mg/kg) alfentanil(9 ug/kg) |
unhealthy, 33.1 n = 20 Health Status: unhealthy Condition: surgical procedures Age Group: 33.1 Sex: F Population Size: 20 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely | ||||
Page: (PMDA_A101) 1, (PMDA_K101) 13 |
unlikely | |||
Page: (PMDA_A101) 1, (PMDA_K101) 13 |
unlikely | |||
Page: (PMDA_A101) 1, (PMDA_K101) 13 |
unlikely | |||
Page: (PMDA_A101) 1, (PMDA_K101) 13 |
unlikely | |||
Page: (PMDA_A101) 1, (PMDA_K101) 13 |
unlikely | |||
Page: (PMDA_A101) 1, (PMDA_K101) 13 |
unlikely | |||
Page: (PMDA_A101) 1, (PMDA_K101) 13 |
unlikely | |||
Page: (PMDA_A101) 1, (PMDA_K101) 13 |
unlikely | |||
Page: (PMDA_A101) 1, (PMDA_K101) 13 |
unlikely | |||
Page: (PMDA_A100) 18 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Choice of the muscle relaxant for rapid-sequence induction. | 2001 |
|
Choice of the hypnotic and the opioid for rapid-sequence induction. | 2001 |
|
Comparison of the influence of desflurane nitrous oxide anesthesia to propofol nitrous oxide anesthesia on rocuronium bromide induced neuromuscular block. | 2001 |
|
Comparative study of the TOF-ratio measured by the ParaGraph versus the TOF-Guard, with and without thumb repositioning. | 2001 |
|
Anaesthetic management of an adolescent for scoliosis surgery with a Fontan circulation. | 2001 |
|
Recent advances in myorelaxant therapy. | 2001 |
|
Target controlled infusion of remifentanil and propofol for cesarean section in a patient with multivalvular disease and severe pulmonary hypertension. | 2001 |
|
Use of remifentanil in combination with desflurane or propofol for ambulatory oral surgery. | 2001 |
|
Increased sensitivity to depolarization and nondepolarizing neuromuscular blocking agents in young rat hemidiaphragms. | 2001 Aug |
|
Transcranial Doppler ultrasonography with induction of anesthesia and neuromuscular blockade in surgical patients. | 2001 Aug |
|
A double-blind, randomized comparison of low-dose rocuronium and atracurium in a desflurane anesthetic. | 2001 Aug |
|
Safety and efficacy of rocuronium for controlled intubation with paralytics in the pediatric emergency department. | 2001 Aug |
|
The pharmacoeconomics of neuromuscular blocking drugs: a perioperative cost-minimization strategy in children. | 2001 Aug |
|
The influence of fentanyl vs. s-ketamine on intubating conditions during induction of anaesthesia with etomidate and rocuronium. | 2001 Aug |
|
[Anesthesia in Prader-Willi syndrome for major surgery for kyphoscoliosis]. | 2001 Aug-Sep |
|
[New muscle relaxants]. | 2001 Dec |
|
Why do we still use suxamethonium for caesarean section? | 2001 Dec |
|
[Sevoflurane augments the degree and speeds the onset of rocuronium evoked neuromuscular blockade in children]. | 2001 Dec |
|
The effect of rocuronium on intraocular pressure: a comparison with succinylcholine. | 2001 Dec |
|
Comparison of effects of remifentanil and alfentanil on cardiovascular response to tracheal intubation in hypertensive patients. | 2001 Jan |
|
[Prophylaxis of nausea and vomiting after thyroid surgery: comparison of oral and intravenous dolasetron with intravenous droperidol and placebo]. | 2001 Jul |
|
The corrugator supercilii, not the orbicularis oculi, reflects rocuronium neuromuscular blockade at the laryngeal adductor muscles. | 2001 Jul |
|
Intubating conditions after three different doses of rocuronium in the elderly. | 2001 Jun |
|
Rocuronium: high risk for anaphylaxis? | 2001 May |
|
Rocuronium and anaphylaxis--a statistical challenge. | 2001 Nov |
|
Allergic reactions during anaesthesia - increased attention to the problem in Denmark and Norway. | 2001 Nov |
|
Precurarization and priming: a theoretical analysis of safety and timing. | 2001 Nov |
|
Is succinylcholine appropriate or obsolete in the intensive care unit? | 2001 Oct |
|
Huntington's chorea: use of rocuronium. | 2001 Oct |
|
Reexamined: the recommended endotracheal intubating dose for nondepolarizing neuromuscular blockers of rapid onset. | 2001 Oct |
|
Probability of acceptable intubation conditions with low dose rocuronium during light sevoflurane anaesthesia in children. | 2001 Sep |
|
Spontaneous movements, local reactions and pain on injection of rocuronium. A comparison between female and male patients. | 2001 Sep |
|
Different patterns of mast cell activation by muscle relaxants in human skin. | 2001 Sep |
|
Incidence of UK reactions involving rocuronium may simply reflect market use. | 2001 Sep |
|
Effect of ondansetron pretreatment on pain after rocuronium and propofol injection: a randomised, double-blind controlled comparison with lidocaine. | 2001 Sep |
|
Protocol for rapid sequence intubation in pediatric patients -- a four-year study. | 2002 Apr |
|
Rocuronium pharmacokinetic-pharmacodynamic relationship under stable propofol or isoflurane anesthesia. | 2002 Apr |
|
Neuromuscular pharmacology of TAAC3, a new nondepolarizing muscle relaxant with rapid onset and ultrashort duration of action. | 2002 Apr |
|
Postoperative muscle paralysis after rocuronium: less residual block when acceleromyography is used. | 2002 Feb |
|
Resistance to rocuronium in a child with Schwartz-Jampel syndrome type 1 B. | 2002 Feb |
|
Comparison of rocuronium and suxamethonium for rapid tracheal intubation in children. | 2002 Feb |
|
2-O-substituted cyclodextrins as reversal agents for the neuromuscular blocker rocuronium bromide. | 2002 Jun |
|
Presynaptic inhibitory effects of rocuronium and SZ1677 on [3H]acetylcholine release from the mouse hemidiaphragm preparation. | 2002 Jun |
|
Impact of shorter-acting neuromuscular blocking agents on fast-track recovery of the cardiac surgical patient. | 2002 Mar |
|
The Laryngeal Mask Airway ProSeal(TM) as a temporary ventilatory device in grossly and morbidly obese patients before laryngoscope-guided tracheal intubation. | 2002 Mar |
|
Prolonged neuromuscular block after rocuronium in postpartum patients. | 2002 Mar |
|
The potency of new muscle relaxants on recombinant muscle-type acetylcholine receptors. | 2002 Mar |
|
The neuromuscular transmission module versus the relaxometer mechanomyograph for neuromuscular block monitoring. | 2002 Mar |
|
Pretreatment before succinylcholine for outpatient anesthesia? | 2002 Mar |
|
The hemodynamic effects of rapacuronium in patients with coronary artery disease: succinylcholine and vecuronium compared. | 2002 May |
Patents
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21568994
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
Edited
Wed Jul 05 23:13:02 UTC 2023
by
admin
on
Wed Jul 05 23:13:02 UTC 2023
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Record UNII |
WRE554RFEZ
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C66886
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NDF-RT |
N0000175732
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NDF-RT |
N0000175720
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WHO-ATC |
M03AC09
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100000084941
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C80999
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441290
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Rocuronium
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DB00728
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WRE554RFEZ
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68139
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Rocuronium
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2396
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SUB04260MIG
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C061870
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143558-00-3
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M9645
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4003
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DTXSID6048339
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WRE554RFEZ
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR | |||
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BINDER->LIGAND |
BINDING
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METABOLITE -> PARENT |
17-desacetyl-rocuronium has been found in negligible amounts
MINOR
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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