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
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
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 |
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 |
---|---|---|
Effects of pretreatment with cisatracurium, rocuronium, and d-tubocurarine on succinylcholine-induced fasciculations and myalgia: a comparison with placebo. | 1999 Dec |
|
Choice of the muscle relaxant for rapid-sequence induction. | 2001 |
|
Recovery of neuromuscular block in morbidly obese patients following an infusion of rocuronium. | 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 |
|
[Rocuronium or vecuronium for intubation for short operations in the preschool age? Effects on time in the operating room and postoperative phase]. | 2001 |
|
Newer neuromuscular blocking agents: how do they compare with established agents? | 2001 |
|
[Total intravenous anesthesia using remifentanil and propofol with midazolam co-induction in laparoscopic surgery of the gallbladder]. | 2001 |
|
Anesthesia for Cesarean section and posterior fossa craniotomy in a patient with von Hippel-Lindau disease. | 2001 Apr |
|
Neostigmine antagonism of rocuronium block during anesthesia with sevoflurane, isoflurane or propofol. | 2001 Apr |
|
Rocuronium-induced neuromuscular blockade is affected by chronic phenytoin therapy. | 2001 Apr |
|
Postoperative residual block after intermediate-acting neuromuscular blocking drugs. | 2001 Apr |
|
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 new neuromuscular blocking agents: do they offer any advantages? | 2001 Dec |
|
[New muscle relaxants]. | 2001 Dec |
|
Why do we still use suxamethonium for caesarean section? | 2001 Dec |
|
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 |
|
[Sevoflurane augments the degree and speeds the onset of rocuronium evoked neuromuscular blockade in children]. | 2001 Dec |
|
Reversal of rocuronium with edrophonium during propofol versus sevoflurane anesthesia. | 2001 Feb |
|
Comparison of effects of remifentanil and alfentanil on cardiovascular response to tracheal intubation in hypertensive patients. | 2001 Jan |
|
The influence of halothane, isoflurane and sevoflurane on rocuronium infusion in children. | 2001 Jan |
|
No substitute for the intravenous route. | 2001 Jan |
|
The effects of remifentanil on haemodynamic stability during rigid bronchoscopy. | 2001 Jun |
|
Rocuronium: high risk for anaphylaxis? | 2001 May |
|
Onset and duration of action of rocuronium--from tracheal intubation, through intense block to complete recovery. | 2001 May |
|
Rocuronium and anaphylaxis--a statistical challenge. | 2001 Nov |
|
Rapid sequence induction: a national survey of practice. | 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 |
|
Spontaneous movements, local reactions and pain on injection of rocuronium. A comparison between female and male patients. | 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 |
|
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 |
|
Neuromuscular pharmacology of TAAC3, a new nondepolarizing muscle relaxant with rapid onset and ultrashort duration of action. | 2002 Apr |
|
Cyclodextrin-derived host molecules as reversal agents for the neuromuscular blocker rocuronium bromide: synthesis and structure-activity relationships. | 2002 Apr 25 |
|
Comparison of rocuronium and suxamethonium for rapid tracheal intubation in children. | 2002 Feb |
|
Prehospital tracheal intubating conditions during rapid sequence intubation: rocuronium versus vecuronium. | 2002 Jan-Feb |
|
2-O-substituted cyclodextrins as reversal agents for the neuromuscular blocker rocuronium bromide. | 2002 Jun |
|
Effects of remifentanil and alfentanil on the cardiovascular responses to induction of anaesthesia and tracheal intubation in the elderly. | 2002 Mar |
|
The influence of induction technique on intubating conditions 1 min after rocuronium administration: a comparison of a propofol-ephedrine combination and propofol. | 2002 Mar |
|
The neuropathologic effects in rats and neurometabolic effects in humans of large-dose remifentanil. | 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
Fri Jun 25 23:07:23 UTC 2021
by
admin
on
Fri Jun 25 23:07:23 UTC 2021
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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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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C66886
Created by
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NDF-RT |
N0000175732
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NDF-RT |
N0000175720
Created by
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WHO-ATC |
M03AC09
Created by
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Code System | Code | Type | Description | ||
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C80999
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PRIMARY | |||
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441290
Created by
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PRIMARY | |||
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Rocuronium
Created by
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PRIMARY | |||
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DB00728
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PRIMARY | |||
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68139
Created by
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PRIMARY | RxNorm | ||
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Rocuronium
Created by
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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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PRIMARY | |||
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M9645
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PRIMARY | Merck Index | ||
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4003
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143558-00-3
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WRE554RFEZ
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TARGET -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR | |||
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
17-desacetyl-rocuronium has been found in negligible amounts
MINOR
URINE
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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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