You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NamePancuronium
Accession NumberDB01337
TypeSmall Molecule
GroupsApproved
Description

A bis-quaternary steroid that is a competitive nicotinic antagonist. As a neuromuscular blocking agent it is more potent than curare but has less effect on the circulatory system and on histamine release.

Structure
Thumb
Synonyms
Bromure de pancuronium
Bromuro de pancuronio
Pancuronium
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Pancuronium Bromide - Liq IV 1mg/mlliquid1 mgintravenousSandoz Canada Incorporated1995-12-31Not applicableCanada
Pancuronium Bromide - Liq IV 2mg/mlliquid2 mgintravenousSandoz Canada Incorporated1996-12-31Not applicableCanada
Pancuronium Bromide 1mg/mlsolution1 mgintravenousHospira Healthcare Corporation1996-10-24Not applicableCanada
Pancuronium Bromide 2mg/mlsolution2 mgintravenousHospira Healthcare Corporation1995-12-31Not applicableCanada
Pavulon Inj 1mg/mlliquid1 mgintravenousOrganon Canada Ltd Ltee1979-12-311997-08-18Canada
Pavulon Inj 2mg/mlliquid2 mgintravenousOrganon Canada Ltd Ltee1973-12-311997-08-18Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Pancuronium Bromideinjection, solution1 mg/mLintravenousHospira, Inc.1989-01-19Not applicableUs
Pancuronium Bromideinjection, solution2 mg/mLintravenousTeva Parenteral Medicines, Inc.1990-08-01Not applicableUs
Pancuronium Bromideinjection, solution2 mg/mLintravenousTeva Parenteral Medicines, Inc.1990-08-01Not applicableUs
Pancuronium Bromideinjection, solution1 mg/mLintravenousTeva Parenteral Medicines, Inc.1990-08-01Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
MioblockNot Available
PavulonNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Pancuronium bromide
15500-66-0
Thumb
  • InChI Key: NPIJXCQZLFKBMV-YTGGZNJNSA-L
  • Monoisotopic Mass: 730.291983712
  • Average Mass: 732.67
DBSALT000368
Categories
UNIIJ76UF062FS
CAS numberNot Available
WeightAverage: 572.8619
Monoisotopic: 572.455308418
Chemical FormulaC35H60N2O4
InChI KeyInChIKey=GVEAYVLWDAFXET-XGHATYIMSA-N
InChI
InChI=1S/C35H60N2O4/c1-24(38)40-32-21-26-13-14-27-28(35(26,4)23-31(32)37(6)19-11-8-12-20-37)15-16-34(3)29(27)22-30(33(34)41-25(2)39)36(5)17-9-7-10-18-36/h26-33H,7-23H2,1-6H3/q+2/t26-,27+,28-,29-,30-,31-,32-,33-,34-,35-/m0/s1
IUPAC Name
1-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-5,14-bis(acetyloxy)-2,15-dimethyl-13-(1-methylpiperidin-1-ium-1-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-4-yl]-1-methylpiperidin-1-ium
SMILES
[H][C@@]12C[C@@H]([[email protected]](OC(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[[email protected]](OC(C)=O)[[email protected]](C[C@]12C)[N+]1(C)CCCCC1)[N+]1(C)CCCCC1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as steroid esters. These are compounds containing a steroid moiety which bears a carboxylic acid ester group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Androstane-skeleton
  • Cyclohexylamine
  • Piperidine
  • Acetate salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic cation
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationUsed as a muscle relaxant during anesthesia and surgical procedures.
PharmacodynamicsPancuronium is a typical non-depolarising curare-mimetic muscle relaxant. It acts as a competitive acetylcholine antagonist on neuromuscular junctions, displacing acetylcholine (hence competitive) from its post-synaptic nicotinic acetylcholine receptors. It is, unlike suxamethonium, a non-depolarising agent, which means, that it causes no spontaneous depolarisations upon association with the nicotinic receptor in neuromuscular junction, thus producing no muscle fasciculations upon administration. Pancuronium has no hormonal activity. It exerts slight vagolytic activity (i.e. diminishing activity of the vagus nerve) and no ganglioplegic (i.e., blocking ganglions) activity.
Mechanism of actionNondepolarizing neuromuscular blocking agents inhibit neuromuscular transmission by competing with acetylcholine for the cholinergic receptors of the motor end plate, thereby reducing the response of the end plate to acetylcholine. This type of neuromuscular block is usually antagonized by anticholinesterase agents.
Related Articles
AbsorptionNot Available
Volume of distribution
  • 241 to 280 mL/kg
Protein binding77 to 91%
Metabolism

Hepatic.

Route of eliminationNot Available
Half life1.5 to 2.7 hours.
Clearance
  • Plasma cl=1.1–1.9 mL/minute/kg
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8913
Blood Brain Barrier+0.878
Caco-2 permeable+0.5457
P-glycoprotein substrateSubstrate0.77
P-glycoprotein inhibitor IInhibitor0.6962
P-glycoprotein inhibitor IIInhibitor0.6508
Renal organic cation transporterNon-inhibitor0.6862
CYP450 2C9 substrateNon-substrate0.8382
CYP450 2D6 substrateNon-substrate0.7638
CYP450 3A4 substrateSubstrate0.742
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9229
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9368
Ames testNon AMES toxic0.7499
CarcinogenicityNon-carcinogens0.9265
BiodegradationNot ready biodegradable0.8557
Rat acute toxicity2.6653 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9021
hERG inhibition (predictor II)Non-inhibitor0.7784
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Injection, solutionintravenous1 mg/mL
Injection, solutionintravenous2 mg/mL
Liquidintravenous1 mg
Liquidintravenous2 mg
Solutionintravenous1 mg
Solutionintravenous2 mg
Prices
Unit descriptionCostUnit
Pancuronium 2 mg/ml vial2.59USD ml
Pancuronium 1 mg/ml vial0.13USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point215 °CPhysProp
water solubility5E+005 mg/LMERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility3.08e-06 mg/mLALOGPS
logP1.04ALOGPS
logP-3.3ChemAxon
logS-8.3ALOGPS
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity185.22 m3·mol-1ChemAxon
Polarizability69.44 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesM03AC01
AHFS Codes
  • 12:20.00
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AmikacinAmikacin may increase the activities of Pancuronium.
AminophyllineThe risk or severity of adverse effects can be increased when Aminophylline is combined with Pancuronium.
AmlodipineAmlodipine may increase the neuromuscular blocking activities of Pancuronium.
AmrinoneAmrinone may increase the neuromuscular blocking activities of Pancuronium.
ArbekacinArbekacin may increase the activities of Pancuronium.
BepridilBepridil may increase the neuromuscular blocking activities of Pancuronium.
Botulinum Toxin Type ABotulinum Toxin Type A may increase the neuromuscular blocking activities of Pancuronium.
Botulinum Toxin Type BPancuronium may increase the neuromuscular blocking activities of Botulinum Toxin Type B.
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Pancuronium.
ClindamycinClindamycin may increase the neuromuscular blocking activities of Pancuronium.
ColistimethateColistimethate may increase the neuromuscular blocking activities of Pancuronium.
CyclosporineCyclosporine may increase the neuromuscular blocking activities of Pancuronium.
DigoxinPancuronium may increase the arrhythmogenic activities of Digoxin.
DyphyllineThe risk or severity of adverse effects can be increased when Dyphylline is combined with Pancuronium.
FelodipineFelodipine may increase the neuromuscular blocking activities of Pancuronium.
FludrocortisonePancuronium may increase the adverse neuromuscular activities of Fludrocortisone.
FlunarizineFlunarizine may increase the neuromuscular blocking activities of Pancuronium.
FramycetinFramycetin may increase the activities of Pancuronium.
GabapentinGabapentin may increase the neuromuscular blocking activities of Pancuronium.
GentamicinGentamicin may increase the activities of Pancuronium.
IsofluraneIsoflurane may increase the neuromuscular blocking activities of Pancuronium.
IsradipineIsradipine may increase the neuromuscular blocking activities of Pancuronium.
KanamycinKanamycin may increase the activities of Pancuronium.
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with Pancuronium.
LamotrigineLamotrigine may increase the neuromuscular blocking activities of Pancuronium.
LercanidipineLercanidipine may increase the neuromuscular blocking activities of Pancuronium.
LincomycinLincomycin may increase the neuromuscular blocking activities of Pancuronium.
LithiumLithium may increase the neuromuscular blocking activities of Pancuronium.
Magnesium SulfateMagnesium Sulfate may increase the neuromuscular blocking activities of Pancuronium.
MinocyclineMinocycline may increase the neuromuscular blocking activities of Pancuronium.
NeomycinNeomycin may increase the activities of Pancuronium.
NetilmicinNetilmicin may increase the activities of Pancuronium.
NicardipineNicardipine may increase the neuromuscular blocking activities of Pancuronium.
NimodipineNimodipine may increase the neuromuscular blocking activities of Pancuronium.
NisoldipineNisoldipine may increase the neuromuscular blocking activities of Pancuronium.
NitrendipineNitrendipine may increase the neuromuscular blocking activities of Pancuronium.
OxytetracyclineOxytetracycline may increase the neuromuscular blocking activities of Pancuronium.
PerhexilinePerhexiline may increase the neuromuscular blocking activities of Pancuronium.
PhenytoinPhenytoin may decrease the neuromuscular blocking activities of Pancuronium.
Polymyxin B SulfatePolymyxin B Sulfate may increase the neuromuscular blocking activities of Pancuronium.
PrenylaminePrenylamine may increase the neuromuscular blocking activities of Pancuronium.
ProcainamideProcainamide may increase the neuromuscular blocking activities of Pancuronium.
QuinidineQuinidine may increase the neuromuscular blocking activities of Pancuronium.
QuinineQuinine may increase the neuromuscular blocking activities of Pancuronium.
RibostamycinRibostamycin may increase the activities of Pancuronium.
RisedronateRisedronate may increase the neuromuscular blocking activities of Pancuronium.
SpectinomycinSpectinomycin may increase the activities of Pancuronium.
SpironolactoneSpironolactone may increase the neuromuscular blocking activities of Pancuronium.
StreptomycinStreptomycin may increase the activities of Pancuronium.
TacrineTacrine may decrease the neuromuscular blocking activities of Pancuronium.
TheophyllineThe risk or severity of adverse effects can be increased when Theophylline is combined with Pancuronium.
TobramycinTobramycin may increase the activities of Pancuronium.
TorasemideTorasemide may decrease the neuromuscular blocking activities of Pancuronium.
VancomycinVancomycin may increase the neuromuscular blocking activities of Pancuronium.
VerapamilVerapamil may increase the neuromuscular blocking activities of Pancuronium.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Drug binding
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA2
Uniprot ID:
Q15822
Molecular Weight:
59764.82 Da
References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  2. Dilger JP, Vidal AM, Liu M, Mettewie C, Suzuki T, Pham A, Demazumder D: Roles of amino acids and subunits in determining the inhibition of nicotinic acetylcholine receptors by competitive antagonists. Anesthesiology. 2007 Jun;106(6):1186-95. [PubMed:17525594 ]
  3. Jonsson Fagerlund M, Dabrowski M, Eriksson LI: Pharmacological characteristics of the inhibition of nondepolarizing neuromuscular blocking agents at human adult muscle nicotinic acetylcholine receptor. Anesthesiology. 2009 Jun;110(6):1244-52. doi: 10.1097/ALN.0b013e31819fade3. [PubMed:19417616 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
G-protein coupled acetylcholine receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then trigge...
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular Weight:
51714.605 Da
References
  1. Milchert M, Spassov A, Meissner K, Nedeljkov V, Lehmann C, Wendt M, Loster BW, Mazurkiewicz-Janik M, Gedrange T, Pavlovic D: Skeletal muscle relaxants inhibit rat tracheal smooth muscle tone in vitro. J Physiol Pharmacol. 2009 Dec;60 Suppl 8:5-11. [PubMed:20400785 ]
  2. Cembala TM, Forde SC, Appadu BL, Lambert DG: Allosteric interaction of the neuromuscular blockers vecuronium and pancuronium with recombinant human muscarinic M2 receptors. Eur J Pharmacol. 2007 Aug 13;569(1-2):37-40. Epub 2007 May 22. [PubMed:17588565 ]
  3. Okanlami OA, Fryer AD, Hirshman C: Interaction of nondepolarizing muscle relaxants with M2 and M3 muscarinic receptors in guinea pig lung and heart. Anesthesiology. 1996 Jan;84(1):155-61. [PubMed:8572329 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM3
Uniprot ID:
P20309
Molecular Weight:
66127.445 Da
References
  1. Milchert M, Spassov A, Meissner K, Nedeljkov V, Lehmann C, Wendt M, Loster BW, Mazurkiewicz-Janik M, Gedrange T, Pavlovic D: Skeletal muscle relaxants inhibit rat tracheal smooth muscle tone in vitro. J Physiol Pharmacol. 2009 Dec;60 Suppl 8:5-11. [PubMed:20400785 ]
  2. Okanlami OA, Fryer AD, Hirshman C: Interaction of nondepolarizing muscle relaxants with M2 and M3 muscarinic receptors in guinea pig lung and heart. Anesthesiology. 1996 Jan;84(1):155-61. [PubMed:8572329 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
References
  1. Stovner J, Oftedal N, Holmboe J: The inhibition of cholinesterases by pancuronium. Br J Anaesth. 1975 Sep;47(9):949-54. [PubMed:1191483 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Secondary active organic cation transmembrane transporter activity
Specific Function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine...
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular Weight:
61153.345 Da
References
  1. Zhang L, Dresser MJ, Gray AT, Yost SC, Terashita S, Giacomini KM: Cloning and functional expression of a human liver organic cation transporter. Mol Pharmacol. 1997 Jun;51(6):913-21. [PubMed:9187257 ]
  2. Busch AE, Quester S, Ulzheimer JC, Waldegger S, Gorboulev V, Arndt P, Lang F, Koepsell H: Electrogenic properties and substrate specificity of the polyspecific rat cation transporter rOCT1. J Biol Chem. 1996 Dec 20;271(51):32599-604. [PubMed:8955087 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Quaternary ammonium group transmembrane transporter activity
Specific Function:
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridiniu...
Gene Name:
SLC22A2
Uniprot ID:
O15244
Molecular Weight:
62579.99 Da
References
  1. Gorboulev V, Ulzheimer JC, Akhoundova A, Ulzheimer-Teuber I, Karbach U, Quester S, Baumann C, Lang F, Busch AE, Koepsell H: Cloning and characterization of two human polyspecific organic cation transporters. DNA Cell Biol. 1997 Jul;16(7):871-81. [PubMed:9260930 ]
Comments
comments powered by Disqus
Drug created on June 30, 2007 12:07 / Updated on August 17, 2016 12:23