Page last updated: 2024-11-06

pipecuronium

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Description

Pipecuronium bromide is a non-depolarizing neuromuscular blocking agent used for skeletal muscle relaxation during anesthesia and surgery. It is a synthetic quaternary ammonium compound, derived from the natural alkaloid tubocurarine. Its chemical synthesis involves the reaction of the bis-quaternary ammonium compound, with a piperidine ring. Pipecuronium acts by competitively blocking the action of acetylcholine at the nicotinic receptors at the neuromuscular junction, preventing muscle contraction. It has a rapid onset of action and a moderate duration, making it suitable for both short and long surgical procedures. Pipecuronium is studied due to its clinical importance in providing muscle relaxation for various surgical procedures, its role in managing muscle spasms, and its potential application in the treatment of certain neurological disorders. The study of pipecuronium continues to explore its pharmacokinetic properties, drug interactions, and potential adverse effects, aiming to optimize its therapeutic use.'

Pipecuronium: A piperazinyl androstane derivative which is a non-depolarizing neuromuscular blocking agent (NEUROMUSCULAR NONDEPOLARIZING AGENTS). It is used as a muscle relaxant during ANESTHESIA and surgical procedures. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID50192
CHEMBL ID1201206
CHEBI ID8230
SCHEMBL ID359367
MeSH IDM0026260

Synonyms (16)

Synonym
C07554
68399-58-6
pipecuronium
DB01338
pipecurium
piperazinium, 4,4'-((2beta,3alpha,5alpha,16beta,17beta)-3,17-bis(acetyloxy)androstane-2,16-diyl)bis(1,1-dimethyl-
unii-1n3o74hm92
1n3o74hm92 ,
CHEMBL1201206
4-[(1s,2s,4s,5s,7s,10r,11s,13s,14r,15s)-5,14-bis(acetyloxy)-4-(4,4-dimethylpiperazin-4-ium-1-yl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl]-1,1-dimethylpiperazin-1-ium
pipecuronium [who-dd]
pipecuronium [vandf]
SCHEMBL359367
CHEBI:8230 ,
DTXSID20860643
Q20817188

Research Excerpts

Overview

Pipecuronium bromide is a non-depolarizing neuromuscular blocker with similar properties to pancuronium. We considered its haemodynamic effects during general anaesthesia.

ExcerptReferenceRelevance
"Pipecuronium is a steroidal neuromuscular blocking agent. "( Reversal of Pipecuronium-Induced Moderate Neuromuscular Block with Sugammadex in the Presence of a Sevoflurane Anesthetic: A Randomized Trial.
Asztalos, L; Fülesdi, B; Lengyel, S; Nemes, R; Pongrácz, A; Tassonyi, E, 2015
)
2.24
"Pipecuronium is a non-depolarizing neuromuscular blocker with similar properties to pancuronium, but without cardiovascular effects. "( Neuromuscular and cardiovascular effects of pipecuronium. A comparative study between different doses.
Braga, Ade F; Braga, FS; Frias, JA; Potério, GM; Rodrigues, Rde C; Yoshioka, L,
)
1.84
"Pipecuronium bromide is a new non depolarising muscle relaxant with a long duration of action; we considered its haemodynamic effects during general anaesthesia."( [Evaluation of the hemodynamic effects of pipecuronium bromide. Absence of adverse hemodynamic effects].
Amicucci, G; Ardigò, M; Candiani, A; Dicembrini, A; Latronico, N; Prandini, A; Venturini, M, 1995
)
2
"Pipecuronium bromide is a new steroidal non-depolarizing muscle relaxant currently under investigation. "( A dose-response evaluation of pipecuronium bromide in elderly patients under balanced anesthesia.
Azad, SS; Beach, CA; Goldberg, ME; Larijani, GE; Marr, AT; Seltzer, JL, 1989
)
2.01
"Pipecuronium bromide is a nondepolarising muscle relaxant which is an analogue of pancuronium. "( Observations on the neuromuscular blocking action of pipecuronium in the dog.
Jones, RS, 1987
)
1.97

Effects

Pipecuronium has a relatively rapid onset. It has no acetylcholine-like fragments in contrast with pancuronium.

ExcerptReferenceRelevance
"Pipecuronium has a relatively rapid onset. "( Intubating conditions after pipecuronium bromide: the influence of dose and time.
Azad, SS; Bartkowski, R; Goldberg, ME; Larijani, GE; Marr, A; Seltzer, JL; Weinberger, M,
)
1.87
"pipecuronium has no acetylcholine-like fragments in contrast with pancuronium and the interonium distance is also considerably larger than in pancuronium) may predict advantages."( [Pharmacologic effects of pipecuronium bromide (Arduan)].
Bíró, K; Kárpáti, E, 1992
)
1.31
"Pipecuronium has a relatively rapid onset. "( Intubating conditions after pipecuronium bromide: the influence of dose and time.
Azad, SS; Bartkowski, R; Goldberg, ME; Larijani, GE; Marr, A; Seltzer, JL; Weinberger, M,
)
1.87

Toxicity

ExcerptReferenceRelevance
" Apart from daily stress of paralysis preceding intubation no irreversible toxic changes were detected by laboratory and morphological tests."( Summary of safety tests with pipecurium bromide, a new neuromuscular blocking agent.
Cholnoky, E, 1980
)
0.26

Pharmacokinetics

Pipecuronium resembles pancuronium in its pharmacokinetic and neuromuscular blocking profile, but is devoid of cardiovascular effects.

ExcerptReferenceRelevance
" The pharmacokinetic variables were similar for the two groups, and pharmacodynamic analysis revealed a similar sensitivity at the neuromuscular junction."( Pharmacokinetics and pharmacodynamics of pipecuronium bromide (Arduan) in elderly surgical patients.
Diaz, J; Jamdar, SC; Matteo, RS; Ornstein, E; Schwartz, AE, 1992
)
0.55
" The elimination half-life in animals was found to be around 40 min, in humans between 44-137 min."( [Pharmacokinetics and metabolism of pipecuronium bromide (Arduan)].
Vereczkey, L, 1992
)
0.56
"To study the effects of succinylcholine on subsequent pharmacodynamics of nondepolarizing muscle relaxants, a comparative pharmacodynamic study was carried out in patients having balanced anesthesia (thiopental, fentanyl, nitrous oxide/oxygen) in whom equipotent doses of pipecuronium (80 micrograms/kg) and pancuronium (100 micrograms/kg) were given with or without prior administration of succinylcholine (1 mg/kg)."( Effects of succinylcholine on the pharmacodynamics of pipecuronium and pancuronium.
Dubois, MY; Fleming, NW; Lea, DE, 1991
)
0.71
" The pharmacokinetic parameters of pipecuronium were compared with those of pancuronium (0."( [Comparative pharmacokinetics of pipecuronium bromide, pancuronium bromide and vecuronium bromide in anesthetized man].
Hanaoka, K; Kushida, Y; Murakami, S; Numata, K; Sugai, N; Yajima, C; Yamamoto, K; Yamamura, H, 1990
)
0.84
" In connection with the pharmacodynamic evaluation, literature on the pipecuronium bromide and on the administration of the muscle relaxants in paediatric anaesthesiology is summarized."( [A pharmacodynamic study of pipecuronium bromide (Arduan) in newborn infants, infants and children].
Praefort, L, 1990
)
0.81
" The pharmacokinetic parameters derived by compartmental modelling were (normal vs."( The influence of renal failure on the pharmacokinetics and duration of action of pipecuronium bromide in patients anesthetized with halothane and nitrous oxide.
Caldwell, JE; Canfell, PC; Castagnoli, KP; Fahey, MR; Fisher, DM; Lynam, DP; Miller, RD, 1989
)
0.5
" Except for the volume of central compartment, all other pharmacokinetic variables differed significantly between the two experimental groups."( Pharmacokinetics and disposition of pipecuronium bromide in dogs with and without ligated renal pedicles.
Agoston, S; Caldwell, JE; Chung, K; Khuenl-Brady, KS; Miller, RD; Sharma, M, 1989
)
0.55
" Absence of renal function significantly altered the pharmacokinetic parameters and prolonged the time-course of the neuromuscular blocking effects of pipecuronium."( Pharmacokinetics and disposition of pipecuronium bromide in the cat.
Agoston, S; Houwertjes, MC; Kersten, UW; Vandenbrom, RH; Wierda, JM, 1988
)
0.75
" The pharmacokinetic parameters of pipecurium bromide were found as follows: apparent distribution volume V beta = 261 +/- 28 (n = 8) ml/kg, plasma clearance Cl = 320 +/- 55 (n = 8) ml/min."( Pharmacokinetics of pipecurium bromide, a new non-depolarizing neuromuscular blocking agent, in humans.
Szabó, G; Tassonyi, E; Vereczkey, L, 1981
)
0.26
" A two-compartment open model was used for pharmacokinetic analysis."( Pharmacokinetics and pharmacodynamics of pipecuronium in patients with cirrhosis.
D'Honneur, G; Dominique, C; Duvaldestin, P; Haberer, JP; Khalil, M; Kleef, UW, 1993
)
0.55
"We compared the pharmacodynamic effects and hospital costs of three long-acting neuromuscular blocking drugs in a prospective, randomized, double-blind manner."( Hemodynamic and pharmacodynamic comparison of doxacurium and pipecuronium with pancuronium during induction of cardiac anesthesia: does the benefit justify the cost?
Brooker, RF; Butterworth, JF; Gravlee, GP; Prielipp, RC; Rathmell, JP, 1993
)
0.53
" Pipecuronium resembles pancuronium in its pharmacokinetic and neuromuscular blocking profile, but is devoid of cardiovascular effects."( Clinical pharmacokinetics of the newer neuromuscular blocking drugs.
Atherton, DP; Hunter, JM, 1999
)
1.21

Dosage Studied

Pipecuronium effective doses 50,90,95 (ED50, ED90, ED95) have been obtained with the cumulative dosage method. Because of the low total plasma clearance in infants, pipe Curonium dosage should be carefully monitored.

ExcerptRelevanceReference
" The cumulative dose-response to pipecuronium was determined in both patients during nitrous oxide-oxygen-narcotic anaesthesia."( Myasthenia gravis and pipecuronium--report of two cases.
Ashour, M; Messahel, F; Naguib, M; Sari-Kouzel, A; Seraj, M, 1992
)
0.88
" Responses were defined in terms of percent depression in first-twitch height and train-of-four response, and the dose-response curves were constructed after probit transformation of the responses."( Pipecuronium-induced neuromuscular blockade during nitrous oxide-fentanyl, enflurane, isoflurane, and halothane anesthesia in surgical patients.
Abdulrazik, E; Naguib, M; Seraj, M, 1992
)
1.73
" In order to obtain a stable dosage form liophylized ampoules containing mannitol were prepared."( [Pharmaceutic development of injectable Arduan].
Deákné, RE; Guti, Z; Rádi, E, 1992
)
0.28
" Before its introduction into clinical practice in the USA, in the first phase of this study the neuromuscular potency of pipecuronium was determined under "balanced" and enflurance anaesthesia by the cumulative log dose-response method in 30 patients each."( Neuromuscular and cardiovascular effects of pipecuronium.
Duncalf, D; Foldes, FF; Goldiner, PL; Nagashima, H; Nguyen, HD, 1990
)
0.75
"The purpose of the study was to measure the neuromuscular effects of pipecuronium bromide (Arduan) and to determine its dosage in paediatric anaesthesiology by recording dose-effect curves in children, infants and newborn babies during diazepam, ketamine, fentanyl, nitrous oxide anaesthesia."( [A pharmacodynamic study of pipecuronium bromide (Arduan) in newborn infants, infants and children].
Praefort, L, 1990
)
0.81
"We determined the cumulative dose-response relations of pipecuronium in infants and children during nitrous oxidehalothane anesthesia."( Clinical pharmacology of pipecuronium in infants and children during halothane anesthesia.
Brandom, BW; Cook, DR; Dong, ML; Pickle, D; Sarner, JB; Weinberger, MJ, 1990
)
0.83
"The dose-response of pipecuronium bromide, the time course of its neuromuscular blocking effects, and the reversibility of the residual block by neostigmine and edrophonium have been investigated in patients undergoing various types of anesthesia."( Dose-response relation and time course of action of pipecuronium bromide in humans anesthetized with nitrous oxide and isoflurane, halothane, or droperidol and fentanyl.
Agoston, S; Richardson, FJ; Wierda, JM, 1989
)
0.85
" We examined the dose-response relation of pipecuronium in 27 patients, ages 66-79 years, utilizing the incremental dose method under balanced anesthesia."( A dose-response evaluation of pipecuronium bromide in elderly patients under balanced anesthesia.
Azad, SS; Beach, CA; Goldberg, ME; Larijani, GE; Marr, AT; Seltzer, JL, 1989
)
0.83
"Cumulative dose-response curves were constructed to determine the comparative potency of pipecuronium and pancuronium."( Comparative potency of pipecuronium bromide and pancuronium bromide.
Mirakhur, RK; Stanley, JC, 1989
)
0.81
" We conclude that there is no clinical indication that the dosage of atracurium and vecuronium during inhalation anesthesia should be reduced, but the doses of pipecuronium and pancuronium should be reduced when prolonged paralysis is not desired."( Interaction between nondepolarizing neuromuscular blocking agents and inhalational anesthetics.
Agoston, S; Hermans, J; Ket, JM; Koot, HW; Rashkovsky, OM; Swen, J, 1989
)
0.47
" Dosage was limited by prolonged paralysis time requiring artificial ventilation."( Summary of safety tests with pipecurium bromide, a new neuromuscular blocking agent.
Cholnoky, E, 1980
)
0.26
" We studied the dose-response relationships of each drug and their combination with rocuronium in 200 ASA I or II patients during propofol-fentanyl-nitrous oxide-oxygen anaesthesia."( Comparative potency of steroidal neuromuscular blocking drugs and isobolographic analysis of the interaction between rocuronium and other aminosteroids.
Bakhamees, HS; el-Bakry, AK; Magboul, MA; Naguib, M; Samarkandi, AH, 1995
)
0.29
" The duration of action and recovery time from 75% to 25% block were longer than those produced by twice the dosage of vecuronium (62."( [A comparison between neuromuscular blocking effects of pipecuronium and vecuronium; a double blind controlled study in collaboration with 5 departments of anesthesiology].
Amaki, Y; Hanaoka, K; Hashimoto, Y; Kobayashi, T; Suzuki, H; Yamamura, H, 1994
)
0.53
" The dose-response curves were determined by probit analysis."( Isobolographic and dose-response analysis of the interaction between pipecuronium and vecuronium.
Abdulatif, M; Naguib, M, 1993
)
0.52
"We have studied the dose-response relationships for neostigmine and edrophonium during antagonism of neuromuscular block induced by pipecuronium bromide."( Dose-response relationships for edrophonium and neostigmine antagonism of pipecuronium-induced neuromuscular block.
Abdulatif, M; Naguib, M, 1994
)
0.72
"The dose-response relationship and the variability of the time variables in pipercuronium neuromuscular blockade were studied in 29 patients (ASA physical status 3) during halothane anaesthesia."( Variability of pipecuronium neuromuscular blockade.
Buzello, W; Diefenbach, C; Mellinghoff, H, 1993
)
0.64
"Pipecuronium effective doses 50,90,95 (ED50, ED90, ED95) have been obtained with the cumulative dosage method studying the influences of two different anesthetic techniques (TIVA vs isoflurane), of the patients age, of two different monitoring techniques, force transduction vs accelerometry, both evaluated by T1/TC ratio, ratio between Ist muscular response following the muscle relaxant and the values obtained before its injection, and TOFR, ratio between 4th and Ist response of every train."( [A new instrument for neuromuscular transmission monitoring: the accelerometer Tofguard. Comparative study of isometric force transduction in the assessment of pipecuronium dose-response relationship].
Melloni, C, 1995
)
1.93
" Because of the low total plasma clearance in infants, pipecuronium dosage should be carefully monitored to avoid accumulation and prolonged paralysis."( Pharmacokinetics of pipecuronium in infants, children and adults.
Gemperle, G; Morel, DR; Pittet, JF; Rouge, JC; Schopfer, CN; Tassonyi, E; Wilder-Smith, OH,
)
0.7
"To compare dose-response relationship and maintenance requirement of pipecuronium in anesthetized infants, children, and adults."( Pipecuronium revisited: dose-response and maintenance requirement in infants, children, and adults.
Erkola, O; Meretoja, OA, 1997
)
1.97
" An individual cumulative log-probit dose-response curve was established and maintenance requirement of pipecuronium determined."( Pipecuronium revisited: dose-response and maintenance requirement in infants, children, and adults.
Erkola, O; Meretoja, OA, 1997
)
1.95
" Arduan dosage ought to be reduced because of it possible cumulation in blood due to hepatorenal disorders existing in this patients."( [Features of anesthesia in surgical removal of insulinoma].
Kostenko, AA, 1997
)
0.3
" The ED50 of each neuromuscular blocker was determined from cumulative log dose-response regression lines (n = 14)."( Adenosine potentiation of neuromuscular blocking agents in guinea-pigs.
Dan, K; Foldes, FF; Kornak, P; Nagashima, H; Nitahara, K; Vizi, ES, 2000
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
steroid ester
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (184)

TimeframeStudies, This Drug (%)All Drugs %
pre-199064 (34.78)18.7374
1990's106 (57.61)18.2507
2000's11 (5.98)29.6817
2010's3 (1.63)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 37.30

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index37.30 (24.57)
Research Supply Index5.60 (2.92)
Research Growth Index4.31 (4.65)
Search Engine Demand Index53.08 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (37.30)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials62 (29.81%)5.53%
Reviews15 (7.21%)6.00%
Case Studies8 (3.85%)4.05%
Observational0 (0.00%)0.25%
Other123 (59.13%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]