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

Details

Stereochemistry ABSOLUTE
Molecular Formula C35H62N4O4
Molecular Weight 602.8925
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 2

SHOW SMILES / InChI
Structure of PIPECURONIUM

SMILES

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

6.4635837E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
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
PubMed

PubMed

TitleDatePubMed
[Experience in administration of prolonged anesthesia in children].
2001 Jan-Feb
[Correction of cardiorespiratory disorders in laparoscopic cholecystectomy].
2001 Mar-Apr
[Carboxyperitoneum and clinical efficacy of nondepolarizing relaxants with different types of metabolism].
2002 Sep-Oct
[The first clinical experience with administration of new Russian myorelaxant aperomid (pipecuronium bromide)].
2003 Mar-Apr
[Effect of carboxyperitoneum on duration of the action of some non-depolarizing muscle relaxants].
2004 Mar-Apr
[New russian myorelaxant vero-pipecuronium (pipecuronium bromide) used for the anesthetic management of operations on the thorax and abdomen organs].
2004 Sep-Oct
Effect of priming in shortening onset of pipecuronium, a new nondepolarizing neuromuscular blocker.
2005 Aug
Influence of dextran-70 on systemic inflammatory response and myocardial ischaemia-reperfusion following cardiac operations.
2007
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
[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
Drug interaction: focusing on response surface models.
2010 May
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 [WHO-DD]
Common Name English
PIPECURONIUM [VANDF]
Common Name English
Classification Tree Code System Code
WHO-ATC M03AC06
Created by admin on Sat Jun 26 06:14:16 UTC 2021 , Edited by admin on Sat Jun 26 06:14:16 UTC 2021
NCI_THESAURUS C66886
Created by admin on Sat Jun 26 06:14:16 UTC 2021 , Edited by admin on Sat Jun 26 06:14:16 UTC 2021
Code System Code Type Description
RXCUI
33742
Created by admin on Sat Jun 26 06:14:16 UTC 2021 , Edited by admin on Sat Jun 26 06:14:16 UTC 2021
PRIMARY RxNorm
PUBCHEM
50192
Created by admin on Sat Jun 26 06:14:16 UTC 2021 , Edited by admin on Sat Jun 26 06:14:16 UTC 2021
PRIMARY
NCI_THESAURUS
C77368
Created by admin on Sat Jun 26 06:14:16 UTC 2021 , Edited by admin on Sat Jun 26 06:14:16 UTC 2021
PRIMARY
CAS
68399-58-6
Created by admin on Sat Jun 26 06:14:16 UTC 2021 , Edited by admin on Sat Jun 26 06:14:16 UTC 2021
PRIMARY
DRUG CENTRAL
2183
Created by admin on Sat Jun 26 06:14:16 UTC 2021 , Edited by admin on Sat Jun 26 06:14:16 UTC 2021
PRIMARY
WIKIPEDIA
Pipecuronium
Created by admin on Sat Jun 26 06:14:16 UTC 2021 , Edited by admin on Sat Jun 26 06:14:16 UTC 2021
PRIMARY
MESH
D017300
Created by admin on Sat Jun 26 06:14:16 UTC 2021 , Edited by admin on Sat Jun 26 06:14:16 UTC 2021
PRIMARY
FDA UNII
1N3O74HM92
Created by admin on Sat Jun 26 06:14:16 UTC 2021 , Edited by admin on Sat Jun 26 06:14:16 UTC 2021
PRIMARY
EVMPD
SUB03837MIG
Created by admin on Sat Jun 26 06:14:16 UTC 2021 , Edited by admin on Sat Jun 26 06:14:16 UTC 2021
PRIMARY
DRUG BANK
DB01338
Created by admin on Sat Jun 26 06:14:16 UTC 2021 , Edited by admin on Sat Jun 26 06:14:16 UTC 2021
PRIMARY