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Details

Stereochemistry ABSOLUTE
Molecular Formula C35H62N4O4.2Br
Molecular Weight 762.699
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIPECURONIUM BROMIDE

SMILES

[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=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 80.912
Charge 0
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C35H62N4O4
Molecular Weight 602.8912
Charge 2
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
ARDUAN

Cmax

ValueDoseCo-administeredAnalytePopulation
1.6 μg/mL
120 μg/kg single, intravenous
PIPECURONIUM plasma
Homo sapiens
4.4 μg/mL
140 μg/kg single, intravenous
PIPECURONIUM plasma
Homo sapiens
3.5 μg/mL
100 μg/kg single, intravenous
PIPECURONIUM plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
50.6 μg × min/mL
120 μg/kg single, intravenous
PIPECURONIUM plasma
Homo sapiens
95.85 μg × min/mL
140 μg/kg single, intravenous
PIPECURONIUM plasma
Homo sapiens
106.7 μg × min/mL
100 μg/kg single, intravenous
PIPECURONIUM plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
5.8 min
120 μg/kg single, intravenous
PIPECURONIUM plasma
Homo sapiens
2 min
140 μg/kg single, intravenous
PIPECURONIUM plasma
Homo sapiens
2.5 min
100 μg/kg single, intravenous
PIPECURONIUM plasma
Homo sapiens

Sourcing

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
Unknown
Substance Class Chemical
Record UNII
R6ZTY81RE1
Record Status Validated (UNII)
Record Version