Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C35H62N4O4.2Br |
| Molecular Weight | 762.699 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Br-].[Br-].[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](OC(C)=O)[C@H](C[C@]34C)N5CC[N+](C)(C)CC5)N6CC[N+](C)(C)CC6
InChI
InChIKey=TXWBOBJCRVVBJF-YTGGZNJNSA-L
InChI=1S/C35H62N4O4.2BrH/c1-24(40)42-32-21-26-9-10-27-28(35(26,4)23-31(32)37-15-19-39(7,8)20-16-37)11-12-34(3)29(27)22-30(33(34)43-25(2)41)36-13-17-38(5,6)18-14-36;;/h26-33H,9-23H2,1-8H3;2*1H/q+2;;/p-2/t26-,27+,28-,29-,30-,31-,32-,33-,34-,35-;;/m0../s1
| 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 | C35H62N4O4 |
| Molecular Weight | 602.8912 |
| Charge | 2 |
| Count |
|
| Stereochemistry | MIXED |
| Additional Stereochemistry | No |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Pipecuronium is a piperazinyl androstane derivative, which is a non-depolarizing neuromuscular blocking agent, which was approved under brand name arduan for injection. It is a long-acting neuromuscular blocking agent, indicated as an adjunct to general anesthesia, to provide skeletal muscle relaxation during surgery. Arduan can also be used to provide skeletal muscle relaxation for endotracheal intubation. Pipecuronium undergoes very little metabolism and is excreted by the kidney and the liver. Owing to its relatively long duration of action and to the residual postoperative neuromuscular block (RPONB), the use of pipecuronium was discontinued in the United States and in several European countries. Because of its excellent safety profile, the use of pipecuronium has been maintained in several countries including China, Russia, Brazil, and Hungary, among others. Its safe use, however, is dependent on the availability of a reliable reversal drug. Although widely used, there are concerns with the use of neostigmine for reversal. Arduan is a powerful competitive antagonist of acetylcholine, since it can bind pre- and postsynaptic (N1) receptors of the transmitters.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2362997 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | ARDUAN Approved UseARDUAN® (pipecuronium bromide) for injection is a long-acting neuromuscular blocking agent, indicated as an adjunct to general anesthesia, to provide skeletal muscle relaxation during surgery. ARDUAN® can also be used to provide skeletal muscle relaxation for endotracheal intubation Launch Date1990 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8751042 |
120 μg/kg single, intravenous dose: 120 μg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PIPECURONIUM plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
4.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8751042 |
140 μg/kg single, intravenous dose: 140 μg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PIPECURONIUM plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
|
3.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8751042 |
100 μg/kg single, intravenous dose: 100 μg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PIPECURONIUM plasma | Homo sapiens population: UNHEALTHY age: NEWBORN sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
50.6 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8751042 |
120 μg/kg single, intravenous dose: 120 μg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PIPECURONIUM plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
95.85 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8751042 |
140 μg/kg single, intravenous dose: 140 μg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PIPECURONIUM plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
|
106.7 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8751042 |
100 μg/kg single, intravenous dose: 100 μg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PIPECURONIUM plasma | Homo sapiens population: UNHEALTHY age: NEWBORN sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5.8 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8751042 |
120 μg/kg single, intravenous dose: 120 μg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PIPECURONIUM plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8751042 |
140 μg/kg single, intravenous dose: 140 μg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PIPECURONIUM plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
|
2.5 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8751042 |
100 μg/kg single, intravenous dose: 100 μg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PIPECURONIUM plasma | Homo sapiens population: UNHEALTHY age: NEWBORN sex: UNKNOWN food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Interaction of neuromuscular blocking drugs with recombinant human m1-m5 muscarinic receptors expressed in Chinese hamster ovary cells. | 1998 Nov |
|
| [Experience in administration of prolonged anesthesia in children]. | 2001 Jan-Feb |
|
| [Correction of cardiorespiratory disorders in laparoscopic cholecystectomy]. | 2001 Mar-Apr |
|
| [Magnesium sulfate usage for patients during cardiopulmonary bypass]. | 2002 |
|
| [Investigation of neuromuscular blocking agents at Richter Ltd]. | 2002 |
|
| Synthesis and structure-activity relationships of neuromuscular blocking agents. | 2002 Aug |
|
| Synthesis and neuromuscular blocking activity of 16beta-N-methylpiperazino steroidal derivatives. | 2002 Nov |
|
| Effect of priming in shortening onset of pipecuronium, a new nondepolarizing neuromuscular blocker. | 2005 Aug |
|
| Acute effects of lobectomy on right ventricular ejection fraction and mixed venous oxygen saturation. | 2005 Nov-Dec |
|
| Determination of pipecuronium bromide and its impurities in pharmaceutical preparation by high-performance liquid chromatography with coulometric electrode array detection. | 2008 Aug 8 |
|
| [Use of nondepolarizing myorelaxants in neonates]. | 2008 Jan-Feb |
|
| Effect of magnesium sulphate on urinary catecholamine excretion in severe tetanus. | 2008 Jul |
|
| Is time to peak effect of neuromuscular blocking agents dependent on dose? Testing the concept of buffered diffusion. | 2008 Jul |
|
| An overview of the articles published in the Indian Journal of Pharmacology during the year 2007. | 2008 Nov |
|
| [Remifentanil preconditioning lowers cardiac troponin I levels in patients undergoing off-pump coronary artery bypass graft surgery]. | 2009 Aug |
|
| Low-dose ketamine combined with pentobarbital in a miniature porcine model for a cardiopulmonary bypass procedure: a randomized controlled study. | 2009 May |
|
| Pre-hospital cooling of patients following cardiac arrest is effective using even low volumes of cold saline. | 2010 |
|
| Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
|
| [Accuracy of perioperative cardiac preload monitoring by global end-diastolic volume and intrathoracic blood volume in orthotopic liver transplantation]. | 2010 Jul |
|
| Drug interaction: focusing on response surface models. | 2010 May |
|
| [Isoflurance-based intravenous and inhalation combined anesthesia versus low-dose-ketamine-based total intravenous anesthesia for valvuloplasty in minipigs]. | 2010 Sep |
|
| Reversal of profound vecuronium-induced neuromuscular block under sevoflurane anesthesia: sugammadex versus neostigmine. | 2010 Sep 1 |
Patents
Sample Use Guides
The recommended initial dose of ARDUAN (pipecuronium bromide) for injection under balanced anesthesia, halothane, isoflurane, or enflurane anesthesia in patients with normal renal function who were not obese is 0.07–0.085 mg/kg (70–85 µg/kg). Good to excellent intubating conditions are generally provided within 2.5 to 3 minutes. Maximum blockade, usually > 95%, is achieved in approximately 5 minutes. Doses in this range provide approximately 1–2 hours of clinical relaxation under balanced anesthesia (range 47–124 minutes). Under halothane, isoflurane and enflurane anesthesia, extension of the period of clinical relaxation should be expected
Route of Administration:
Intravenous
In Vitro Use Guide
Curator's Comment: The effects of pipecuronium bromide on prejunctional and postjunctional muscarinic receptors were studied in 96 isolated human bronchial rings from 12 patients. Contractile isometric responses to electric field stimulation of pilocarpine-stimulated and nonstimulated M2 muscarinic receptors were compared before and after incubation with the muscle relaxant. The effect on postjunctional muscarinic receptors was studied by comparing acetylcholine concentration-response curves before and after incubation with the muscle relaxant. Pipecuronium bromide inhibited pilocarpine-stimulated prejunctional M2 muscarinic receptors, but it didn’t have significant inhibitory effect on nonstimulated M2 muscarinic receptors and on postjunctional M3 muscarinic receptors.
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 14:57:40 GMT 2023
by
admin
on
Fri Dec 15 14:57:40 GMT 2023
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| Record UNII |
R6ZTY81RE1
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| Record Status |
Validated (UNII)
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| Record Version |
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WHO-ATC |
M03AC06
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WHO-VATC |
QM03AC06
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NCI_THESAURUS |
C29696
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| Code System | Code | Type | Description | ||
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Pipecuronium bromide
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SUB14880MIG
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Y-86
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DTXSID8023478
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66983
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DBSALT000367
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R6ZTY81RE1
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4645
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65332
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C66393
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257-740-4
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m8841
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CHEMBL1201206
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100000079451
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52212-02-9
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SOLVATE->ANHYDROUS | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |