U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C35H62N4O4
Molecular Weight 602.8912
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 12
E/Z Centers 0
Charge 2

SHOW SMILES / InChI
Structure of PIPECURONIUM

SMILES

CC(=O)O[C@H]1[C@H](C[C@H]2[C@@H]3CC[C@H]4C[C@H](OC(C)=O)[C@H](C[C@]4(C)[C@H]3CC[C@]12C)N5CC[N+](C)(C)CC5)N6CC[N+](C)(C)CC6

InChI

InChIKey=OWWLUIWOFHMHOQ-XGHATYIMSA-N
InChI=1S/C35H62N4O4/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/q+2/t26-,27+,28-,29-,30-,31-,32-,33-,34-,35-/m0/s1

HIDE SMILES / InChI
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
ARDUAN

Approved Use

ARDUAN® (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 Date

1990
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.5 μg/mL
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
4.4 μg/mL
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
1.6 μg/mL
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
106.7 μg × min/mL
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
95.85 μg × min/mL
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
50.6 μg × min/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.5 min
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
2 min
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
5.8 min
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
PubMed

PubMed

TitleDatePubMed
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010-12
Reversal of profound vecuronium-induced neuromuscular block under sevoflurane anesthesia: sugammadex versus neostigmine.
2010-09-01
[Isoflurance-based intravenous and inhalation combined anesthesia versus low-dose-ketamine-based total intravenous anesthesia for valvuloplasty in minipigs].
2010-09
[Accuracy of perioperative cardiac preload monitoring by global end-diastolic volume and intrathoracic blood volume in orthotopic liver transplantation].
2010-07
Drug interaction: focusing on response surface models.
2010-05
Pre-hospital cooling of patients following cardiac arrest is effective using even low volumes of cold saline.
2010
[Remifentanil preconditioning lowers cardiac troponin I levels in patients undergoing off-pump coronary artery bypass graft surgery].
2009-08
Low-dose ketamine combined with pentobarbital in a miniature porcine model for a cardiopulmonary bypass procedure: a randomized controlled study.
2009-05
An overview of the articles published in the Indian Journal of Pharmacology during the year 2007.
2008-11
Determination of pipecuronium bromide and its impurities in pharmaceutical preparation by high-performance liquid chromatography with coulometric electrode array detection.
2008-08-08
Effect of magnesium sulphate on urinary catecholamine excretion in severe tetanus.
2008-07
Is time to peak effect of neuromuscular blocking agents dependent on dose? Testing the concept of buffered diffusion.
2008-07
[Use of nondepolarizing myorelaxants in neonates].
2008-03-29
Neuromuscular and cardiovascular effects of pipecuronium. A comparative study between different doses.
2008-01-22
Single transpulmonary thermodilution in off-pump coronary artery bypass grafting: haemodynamic changes and effects of different anaesthetic techniques.
2007-04
Influence of dextran-70 on systemic inflammatory response and myocardial ischaemia-reperfusion following cardiac operations.
2007
Magnesium sulphate for treatment of severe tetanus: a randomised controlled trial.
2006-10-21
Development of bronchoconstriction after administration of muscle relaxants in rabbits with normal or hyperreactive airways.
2006-07
A Markov computer simulation model of the economics of neuromuscular blockade in patients with acute respiratory distress syndrome.
2006-03-15
Acute effects of lobectomy on right ventricular ejection fraction and mixed venous oxygen saturation.
2006-01-28
Effect of priming in shortening onset of pipecuronium, a new nondepolarizing neuromuscular blocker.
2005-08
[New russian myorelaxant vero-pipecuronium (pipecuronium bromide) used for the anesthetic management of operations on the thorax and abdomen organs].
2004-12-03
[Effect of carboxyperitoneum on duration of the action of some non-depolarizing muscle relaxants].
2004-06-23
Chemical and analytical characterization of related organic impurities in drugs.
2003-11
[The first clinical experience with administration of new Russian myorelaxant aperomid (pipecuronium bromide)].
2003-08-28
[Carboxyperitoneum and clinical efficacy of nondepolarizing relaxants with different types of metabolism].
2003-03-04
[Acute normovolaemic haemodilution in children].
2003
Synthesis and neuromuscular blocking activity of 16beta-N-methylpiperazino steroidal derivatives.
2002-11
Synthesis and structure-activity relationships of neuromuscular blocking agents.
2002-08
[Magnesium sulfate usage for patients during cardiopulmonary bypass].
2002
[Investigation of neuromuscular blocking agents at Richter Ltd].
2002
[Correction of cardiorespiratory disorders in laparoscopic cholecystectomy].
2001-08-10
[Experience in administration of prolonged anesthesia in children].
2001-05-08
Interaction of neuromuscular blocking drugs with recombinant human m1-m5 muscarinic receptors expressed in Chinese hamster ovary cells.
1998-11
Patents

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
PIPECURONIUM
VANDF   WHO-DD  
Common Name English
PIPECURONIUM [VANDF]
Preferred Name English
Pipecuronium [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC M03AC06
Created by admin on Mon Mar 31 18:17:53 GMT 2025 , Edited by admin on Mon Mar 31 18:17:53 GMT 2025
NCI_THESAURUS C66886
Created by admin on Mon Mar 31 18:17:53 GMT 2025 , Edited by admin on Mon Mar 31 18:17:53 GMT 2025
Code System Code Type Description
SMS_ID
100000085287
Created by admin on Mon Mar 31 18:17:53 GMT 2025 , Edited by admin on Mon Mar 31 18:17:53 GMT 2025
PRIMARY
RXCUI
33742
Created by admin on Mon Mar 31 18:17:53 GMT 2025 , Edited by admin on Mon Mar 31 18:17:53 GMT 2025
PRIMARY RxNorm
PUBCHEM
50192
Created by admin on Mon Mar 31 18:17:53 GMT 2025 , Edited by admin on Mon Mar 31 18:17:53 GMT 2025
PRIMARY
NCI_THESAURUS
C77368
Created by admin on Mon Mar 31 18:17:53 GMT 2025 , Edited by admin on Mon Mar 31 18:17:53 GMT 2025
PRIMARY
EPA CompTox
DTXSID20860643
Created by admin on Mon Mar 31 18:17:53 GMT 2025 , Edited by admin on Mon Mar 31 18:17:53 GMT 2025
PRIMARY
CAS
68399-58-6
Created by admin on Mon Mar 31 18:17:53 GMT 2025 , Edited by admin on Mon Mar 31 18:17:53 GMT 2025
PRIMARY
DRUG CENTRAL
2183
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PRIMARY
WIKIPEDIA
Pipecuronium
Created by admin on Mon Mar 31 18:17:53 GMT 2025 , Edited by admin on Mon Mar 31 18:17:53 GMT 2025
PRIMARY
MESH
D017300
Created by admin on Mon Mar 31 18:17:53 GMT 2025 , Edited by admin on Mon Mar 31 18:17:53 GMT 2025
PRIMARY
FDA UNII
1N3O74HM92
Created by admin on Mon Mar 31 18:17:53 GMT 2025 , Edited by admin on Mon Mar 31 18:17:53 GMT 2025
PRIMARY
EVMPD
SUB03837MIG
Created by admin on Mon Mar 31 18:17:53 GMT 2025 , Edited by admin on Mon Mar 31 18:17:53 GMT 2025
PRIMARY
DRUG BANK
DB01338
Created by admin on Mon Mar 31 18:17:53 GMT 2025 , Edited by admin on Mon Mar 31 18:17:53 GMT 2025
PRIMARY