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
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 |
|---|---|---|
| [Magnesium sulfate usage for patients during cardiopulmonary bypass]. | 2002 |
|
| [Investigation of neuromuscular blocking agents at Richter Ltd]. | 2002 |
|
| Synthesis and neuromuscular blocking activity of 16beta-N-methylpiperazino steroidal derivatives. | 2002 Nov |
|
| [Carboxyperitoneum and clinical efficacy of nondepolarizing relaxants with different types of metabolism]. | 2002 Sep-Oct |
|
| [Acute normovolaemic haemodilution in children]. | 2003 |
|
| Chemical and analytical characterization of related organic impurities in drugs. | 2003 Nov |
|
| [Effect of carboxyperitoneum on duration of the action of some non-depolarizing muscle relaxants]. | 2004 Mar-Apr |
|
| Development of bronchoconstriction after administration of muscle relaxants in rabbits with normal or hyperreactive airways. | 2006 Jul |
|
| Magnesium sulphate for treatment of severe tetanus: a randomised controlled trial. | 2006 Oct 21 |
|
| Influence of dextran-70 on systemic inflammatory response and myocardial ischaemia-reperfusion following cardiac operations. | 2007 |
|
| Single transpulmonary thermodilution in off-pump coronary artery bypass grafting: haemodynamic changes and effects of different anaesthetic techniques. | 2007 Apr |
|
| [Use of nondepolarizing myorelaxants in neonates]. | 2008 Jan-Feb |
|
| An overview of the articles published in the Indian Journal of Pharmacology during the year 2007. | 2008 Nov |
|
| Low-dose ketamine combined with pentobarbital in a miniature porcine model for a cardiopulmonary bypass procedure: a randomized controlled study. | 2009 May |
|
| [Accuracy of perioperative cardiac preload monitoring by global end-diastolic volume and intrathoracic blood volume in orthotopic liver transplantation]. | 2010 Jul |
|
| [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
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
WHO-ATC |
M03AC06
Created by
admin on Fri Dec 15 14:57:40 GMT 2023 , Edited by admin on Fri Dec 15 14:57:40 GMT 2023
|
||
|
WHO-VATC |
QM03AC06
Created by
admin on Fri Dec 15 14:57:40 GMT 2023 , Edited by admin on Fri Dec 15 14:57:40 GMT 2023
|
||
|
NCI_THESAURUS |
C29696
Created by
admin on Fri Dec 15 14:57:40 GMT 2023 , Edited by admin on Fri Dec 15 14:57:40 GMT 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
Pipecuronium bromide
Created by
admin on Fri Dec 15 14:57:40 GMT 2023 , Edited by admin on Fri Dec 15 14:57:40 GMT 2023
|
PRIMARY | |||
|
SUB14880MIG
Created by
admin on Fri Dec 15 14:57:40 GMT 2023 , Edited by admin on Fri Dec 15 14:57:40 GMT 2023
|
PRIMARY | |||
|
Y-86
Created by
admin on Fri Dec 15 14:57:40 GMT 2023 , Edited by admin on Fri Dec 15 14:57:40 GMT 2023
|
PRIMARY | |||
|
DTXSID8023478
Created by
admin on Fri Dec 15 14:57:40 GMT 2023 , Edited by admin on Fri Dec 15 14:57:40 GMT 2023
|
PRIMARY | |||
|
66983
Created by
admin on Fri Dec 15 14:57:40 GMT 2023 , Edited by admin on Fri Dec 15 14:57:40 GMT 2023
|
PRIMARY | RxNorm | ||
|
DBSALT000367
Created by
admin on Fri Dec 15 14:57:40 GMT 2023 , Edited by admin on Fri Dec 15 14:57:40 GMT 2023
|
PRIMARY | |||
|
R6ZTY81RE1
Created by
admin on Fri Dec 15 14:57:40 GMT 2023 , Edited by admin on Fri Dec 15 14:57:40 GMT 2023
|
PRIMARY | |||
|
4645
Created by
admin on Fri Dec 15 14:57:40 GMT 2023 , Edited by admin on Fri Dec 15 14:57:40 GMT 2023
|
PRIMARY | |||
|
65332
Created by
admin on Fri Dec 15 14:57:40 GMT 2023 , Edited by admin on Fri Dec 15 14:57:40 GMT 2023
|
PRIMARY | |||
|
C66393
Created by
admin on Fri Dec 15 14:57:40 GMT 2023 , Edited by admin on Fri Dec 15 14:57:40 GMT 2023
|
PRIMARY | |||
|
257-740-4
Created by
admin on Fri Dec 15 14:57:40 GMT 2023 , Edited by admin on Fri Dec 15 14:57:40 GMT 2023
|
PRIMARY | |||
|
m8841
Created by
admin on Fri Dec 15 14:57:40 GMT 2023 , Edited by admin on Fri Dec 15 14:57:40 GMT 2023
|
PRIMARY | Merck Index | ||
|
CHEMBL1201206
Created by
admin on Fri Dec 15 14:57:40 GMT 2023 , Edited by admin on Fri Dec 15 14:57:40 GMT 2023
|
PRIMARY | |||
|
100000079451
Created by
admin on Fri Dec 15 14:57:40 GMT 2023 , Edited by admin on Fri Dec 15 14:57:40 GMT 2023
|
PRIMARY | |||
|
52212-02-9
Created by
admin on Fri Dec 15 14:57:40 GMT 2023 , Edited by admin on Fri Dec 15 14:57:40 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD
