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

Details

Stereochemistry ABSOLUTE
Molecular Formula C35H62N4O4.2Br
Molecular Weight 762.6996
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIPECURONIUM BROMIDE

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.[Br-].[Br-]

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

HIDE SMILES / InChI

Molecular Formula BrH
Molecular Weight 80.9115
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C35H62N4O4
Molecular Weight 602.8925
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.

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
Interaction of neuromuscular blocking drugs with recombinant human m1-m5 muscarinic receptors expressed in Chinese hamster ovary cells.
1998 Nov
[Correction of cardiorespiratory disorders in laparoscopic cholecystectomy].
2001 Mar-Apr
[Investigation of neuromuscular blocking agents at Richter Ltd].
2002
Synthesis and neuromuscular blocking activity of 16beta-N-methylpiperazino steroidal derivatives.
2002 Nov
Chemical and analytical characterization of related organic impurities in drugs.
2003 Nov
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
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
Neuromuscular and cardiovascular effects of pipecuronium. A comparative study between different doses.
2008 Nov-Dec
[Remifentanil preconditioning lowers cardiac troponin I levels in patients undergoing off-pump coronary artery bypass graft surgery].
2009 Aug
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
[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 Jun 26 02:45:47 UTC 2021
Edited
by admin
on Sat Jun 26 02:45:47 UTC 2021
Record UNII
R6ZTY81RE1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIPECURONIUM BROMIDE
INN   MART.   ORANGE BOOK   USAN   VANDF  
INN   USAN  
Official Name English
RGH-1106
Code English
ARDUAN
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
Common Name English
PIPECURIUM BROMIDE [MI]
Common Name English
PIPECURONIUM BROMIDE [INN]
Common Name English
PIPECURONIUM BROMIDE [ORANGE BOOK]
Common Name English
PIPECURONIUM BROMIDE [MART.]
Common Name English
PIPECURONIUM BROMIDE ANHYDROUS
Common Name English
PIPECURONIUM BROMIDE [VANDF]
Common Name English
PIPECURONIUM BROMIDE [USAN]
Common Name English
PIPECURONIUM BROMIDE [JAN]
Common Name English
RGH 1106
Code English
4,4'-(3.ALPHA.,17.BETA.-DIHYDROXY-5.ALPHA.-ANDROSTAN-2.BETA.,16.BETA.-YLENE)BIS(1,1-DIMETHYLPIPERAZINIUM)DIBROMIDE, DIACETATE (ESTER)
Common Name English
Classification Tree Code System Code
WHO-ATC M03AC06
Created by admin on Sat Jun 26 02:45:47 UTC 2021 , Edited by admin on Sat Jun 26 02:45:47 UTC 2021
WHO-VATC QM03AC06
Created by admin on Sat Jun 26 02:45:47 UTC 2021 , Edited by admin on Sat Jun 26 02:45:47 UTC 2021
NCI_THESAURUS C29696
Created by admin on Sat Jun 26 02:45:47 UTC 2021 , Edited by admin on Sat Jun 26 02:45:47 UTC 2021
Code System Code Type Description
EVMPD
SUB14880MIG
Created by admin on Sat Jun 26 02:45:47 UTC 2021 , Edited by admin on Sat Jun 26 02:45:47 UTC 2021
PRIMARY
EPA CompTox
52212-02-9
Created by admin on Sat Jun 26 02:45:47 UTC 2021 , Edited by admin on Sat Jun 26 02:45:47 UTC 2021
PRIMARY
RXCUI
66983
Created by admin on Sat Jun 26 02:45:47 UTC 2021 , Edited by admin on Sat Jun 26 02:45:47 UTC 2021
PRIMARY RxNorm
DRUG BANK
DBSALT000367
Created by admin on Sat Jun 26 02:45:47 UTC 2021 , Edited by admin on Sat Jun 26 02:45:47 UTC 2021
PRIMARY
FDA UNII
R6ZTY81RE1
Created by admin on Sat Jun 26 02:45:47 UTC 2021 , Edited by admin on Sat Jun 26 02:45:47 UTC 2021
PRIMARY
INN
4645
Created by admin on Sat Jun 26 02:45:47 UTC 2021 , Edited by admin on Sat Jun 26 02:45:47 UTC 2021
PRIMARY
PUBCHEM
65332
Created by admin on Sat Jun 26 02:45:47 UTC 2021 , Edited by admin on Sat Jun 26 02:45:47 UTC 2021
PRIMARY
NCI_THESAURUS
C66393
Created by admin on Sat Jun 26 02:45:47 UTC 2021 , Edited by admin on Sat Jun 26 02:45:47 UTC 2021
PRIMARY
ECHA (EC/EINECS)
257-740-4
Created by admin on Sat Jun 26 02:45:47 UTC 2021 , Edited by admin on Sat Jun 26 02:45:47 UTC 2021
PRIMARY
MERCK INDEX
M8841
Created by admin on Sat Jun 26 02:45:47 UTC 2021 , Edited by admin on Sat Jun 26 02:45:47 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL1201206
Created by admin on Sat Jun 26 02:45:47 UTC 2021 , Edited by admin on Sat Jun 26 02:45:47 UTC 2021
PRIMARY
CAS
52212-02-9
Created by admin on Sat Jun 26 02:45:47 UTC 2021 , Edited by admin on Sat Jun 26 02:45:47 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY