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 / 10
E/Z Centers 0
Charge 2

SHOW SMILES / InChI
Structure of PIPECURONIUM

SMILES

[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=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

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

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
[The first clinical experience with administration of new Russian myorelaxant aperomid (pipecuronium bromide)].
2003 Mar-Apr
Acute effects of lobectomy on right ventricular ejection fraction and mixed venous oxygen saturation.
2005 Nov-Dec
Determination of pipecuronium bromide and its impurities in pharmaceutical preparation by high-performance liquid chromatography with coulometric electrode array detection.
2008 Aug 8
An overview of the articles published in the Indian Journal of Pharmacology during the year 2007.
2008 Nov
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
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 Wed Jul 05 23:31:46 UTC 2023
Edited
by admin
on Wed Jul 05 23:31:46 UTC 2023
Record UNII
1N3O74HM92
Record Status Validated (UNII)
Record Version
  • Download
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 Wed Jul 05 23:31:46 UTC 2023 , Edited by admin on Wed Jul 05 23:31:46 UTC 2023
NCI_THESAURUS C66886
Created by admin on Wed Jul 05 23:31:46 UTC 2023 , Edited by admin on Wed Jul 05 23:31:46 UTC 2023
Code System Code Type Description
SMS_ID
100000085287
Created by admin on Wed Jul 05 23:31:46 UTC 2023 , Edited by admin on Wed Jul 05 23:31:46 UTC 2023
PRIMARY
RXCUI
33742
Created by admin on Wed Jul 05 23:31:46 UTC 2023 , Edited by admin on Wed Jul 05 23:31:46 UTC 2023
PRIMARY RxNorm
PUBCHEM
50192
Created by admin on Wed Jul 05 23:31:46 UTC 2023 , Edited by admin on Wed Jul 05 23:31:46 UTC 2023
PRIMARY
NCI_THESAURUS
C77368
Created by admin on Wed Jul 05 23:31:46 UTC 2023 , Edited by admin on Wed Jul 05 23:31:46 UTC 2023
PRIMARY
EPA CompTox
DTXSID20860643
Created by admin on Wed Jul 05 23:31:46 UTC 2023 , Edited by admin on Wed Jul 05 23:31:46 UTC 2023
PRIMARY
CAS
68399-58-6
Created by admin on Wed Jul 05 23:31:46 UTC 2023 , Edited by admin on Wed Jul 05 23:31:46 UTC 2023
PRIMARY
DRUG CENTRAL
2183
Created by admin on Wed Jul 05 23:31:46 UTC 2023 , Edited by admin on Wed Jul 05 23:31:46 UTC 2023
PRIMARY
WIKIPEDIA
Pipecuronium
Created by admin on Wed Jul 05 23:31:46 UTC 2023 , Edited by admin on Wed Jul 05 23:31:46 UTC 2023
PRIMARY
MESH
D017300
Created by admin on Wed Jul 05 23:31:46 UTC 2023 , Edited by admin on Wed Jul 05 23:31:46 UTC 2023
PRIMARY
FDA UNII
1N3O74HM92
Created by admin on Wed Jul 05 23:31:46 UTC 2023 , Edited by admin on Wed Jul 05 23:31:46 UTC 2023
PRIMARY
EVMPD
SUB03837MIG
Created by admin on Wed Jul 05 23:31:46 UTC 2023 , Edited by admin on Wed Jul 05 23:31:46 UTC 2023
PRIMARY
DRUG BANK
DB01338
Created by admin on Wed Jul 05 23:31:46 UTC 2023 , Edited by admin on Wed Jul 05 23:31:46 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY