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

Details

Stereochemistry ABSOLUTE
Molecular Formula C35H62N4O4.2Br.2H2O
Molecular Weight 798.73
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIPECURONIUM BROMIDE DIHYDRATE

SMILES

O.O.[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=FOAWSDYIBDUHRY-MXXJCDGGSA-L
InChI=1S/C35H62N4O4.2BrH.2H2O/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;2*1H2/q+2;;;;/p-2/t26-,27+,28-,29-,30-,31-,32-,33-,34-,35-;;;;/m0..../s1

HIDE SMILES / InChI

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

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 HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
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
[Carboxyperitoneum and clinical efficacy of nondepolarizing relaxants with different types of metabolism].
2002 Sep-Oct
[Acute normovolaemic haemodilution in children].
2003
[The first clinical experience with administration of new Russian myorelaxant aperomid (pipecuronium bromide)].
2003 Mar-Apr
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
[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
Acute effects of lobectomy on right ventricular ejection fraction and mixed venous oxygen saturation.
2005 Nov-Dec
Development of bronchoconstriction after administration of muscle relaxants in rabbits with normal or hyperreactive airways.
2006 Jul
A Markov computer simulation model of the economics of neuromuscular blockade in patients with acute respiratory distress syndrome.
2006 Mar 15
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
Determination of pipecuronium bromide and its impurities in pharmaceutical preparation by high-performance liquid chromatography with coulometric electrode array detection.
2008 Aug 8
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

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 Sat Dec 16 08:43:20 GMT 2023
Edited
by admin
on Sat Dec 16 08:43:20 GMT 2023
Record UNII
W7B1R139K3
Record Status Validated (UNII)
Record Version
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Name Type Language
PIPECURONIUM BROMIDE DIHYDRATE
Common Name English
PIPECURONIUM BROMIDE HYDRATE
Common Name English
PIPERAZINIUM, 4,4'-((2.BETA.,3.ALPHA.,5.ALPHA.,16.BETA.,17.BETA.)-3,17-BIS(ACETYLOXY)ANDROSTANE-2,16-DIYL)BIS(1,1-DIMETHYL-, DIBROMIDE, DIHYDRATE
Systematic Name English
Pipecuronium bromide [WHO-DD]
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID60218528
Created by admin on Sat Dec 16 08:43:20 GMT 2023 , Edited by admin on Sat Dec 16 08:43:20 GMT 2023
PRIMARY
FDA UNII
W7B1R139K3
Created by admin on Sat Dec 16 08:43:20 GMT 2023 , Edited by admin on Sat Dec 16 08:43:20 GMT 2023
PRIMARY
CAS
68399-57-5
Created by admin on Sat Dec 16 08:43:20 GMT 2023 , Edited by admin on Sat Dec 16 08:43:20 GMT 2023
PRIMARY
PUBCHEM
6917835
Created by admin on Sat Dec 16 08:43:20 GMT 2023 , Edited by admin on Sat Dec 16 08:43:20 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
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ACTIVE MOIETY