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Identification
NamePipecuronium
Accession NumberDB01338
TypeSmall Molecule
GroupsApproved
Description

Pipecuronium is a piperazinyl androstane derivative which is a non-depolarizing neuromuscular blocking agent.

Structure
Thumb
Synonyms
Pipecurium
Pipecuronium
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ArduanNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Pipecuronium bromide
Thumb
  • InChI Key: TXWBOBJCRVVBJF-YTGGZNJNSA-L
  • Monoisotopic Mass: 760.313781786
  • Average Mass: 762.699
DBSALT000367
Categories
UNII1N3O74HM92
CAS number68399-58-6
WeightAverage: 602.8912
Monoisotopic: 602.477106492
Chemical FormulaC35H62N4O4
InChI KeyInChIKey=OWWLUIWOFHMHOQ-XGHATYIMSA-N
InChI
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
IUPAC Name
4-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-5,14-bis(acetyloxy)-13-(4,4-dimethylpiperazin-4-ium-1-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-4-yl]-1,1-dimethylpiperazin-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)N1CC[N+](C)(C)CC1)N1CC[N+](C)(C)CC1
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
  • N-alkylpiperazine
  • N-methylpiperazine
  • Cyclohexylamine
  • Piperazine
  • 1,4-diazinane
  • Acetate salt
  • Quaternary ammonium salt
  • Tertiary aliphatic amine
  • Tertiary amine
  • 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 DescriptorsNot Available
Pharmacology
IndicationUsed as a muscle relaxant during anesthesia and surgical procedures.
PharmacodynamicsPipecuronium is a nondepolarizing neuromuscular blocking agent. Neuromuscular blocking agents produce skeletal muscle paralysis by blocking neural transmission at the myoneural junction. The paralysis is selective initially and usually appears in the following muscles consecutively: levator muscles of eyelids, muscles of mastication, limb muscles, abdominal muscles, muscles of the glottis, and finally, the intercostal muscles and the diaphragm. Neuromuscular blocking agents have no clinically significant effect on consciousness or the pain threshold.
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 distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeDistribution Normal renal function: 6.22 (range, 1.34 to 10.66) minutes. Renal function impairment: 4.33 (range, 1.69 to 6.17) minutes. Elimination Normal renal function: 1.7 (range, 0.9 to 2.7) hours. The elimination half-life is not altered by hypothermia and bypass. Renal function impairment: 4 (range, 2 to 8.2) hours. [PharmGKB]
ClearanceNot Available
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-0.8906
Blood Brain Barrier+0.6351
Caco-2 permeable+0.5
P-glycoprotein substrateSubstrate0.8501
P-glycoprotein inhibitor IInhibitor0.7487
P-glycoprotein inhibitor IIInhibitor0.5983
Renal organic cation transporterNon-inhibitor0.7112
CYP450 2C9 substrateNon-substrate0.8587
CYP450 2D6 substrateNon-substrate0.7823
CYP450 3A4 substrateSubstrate0.7542
CYP450 1A2 substrateNon-inhibitor0.9065
CYP450 2C9 inhibitorNon-inhibitor0.9152
CYP450 2D6 inhibitorNon-inhibitor0.9059
CYP450 2C19 inhibitorNon-inhibitor0.8819
CYP450 3A4 inhibitorNon-inhibitor0.8232
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9438
Ames testNon AMES toxic0.752
CarcinogenicityNon-carcinogens0.9083
BiodegradationNot ready biodegradable0.9272
Rat acute toxicity2.6004 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9193
hERG inhibition (predictor II)Non-inhibitor0.7647
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility9.5e-05 mg/mLALOGPS
logP-1.4ALOGPS
logP-5.3ChemAxon
logS-6.8ALOGPS
pKa (Strongest Basic)5.31ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area59.08 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity193.04 m3·mol-1ChemAxon
Polarizability72.22 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 CodesM03AC06
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
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. Karpati E, Biro K, Kukorelli T: [Investigation of neuromuscular blocking agents at Richter Ltd]. Acta Pharm Hung. 2002;72(1):37-48. [PubMed:12426786 ]
  3. Kiss JP, Windisch K, Balla A, Sershen H, Lajtha A: Dual effect of DMPP on the resting release of noradrenaline from rat hippocampal slices. Brain Res Bull. 1997;43(3):257-62. [PubMed:9227834 ]
  4. Torocsik A, Oberfrank F, Sershen H, Lajtha A, Nemesy K, Vizi ES: Characterization of somatodendritic neuronal nicotinic receptors located on the myenteric plexus. Eur J Pharmacol. 1991 Sep 24;202(3):297-302. [PubMed:1748153 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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. Karpati E, Biro K, Kukorelli T: [Investigation of neuromuscular blocking agents at Richter Ltd]. Acta Pharm Hung. 2002;72(1):37-48. [PubMed:12426786 ]
  2. Zappi L, Song P, Nicosia S, Nicosia F, Rehder K: Do pipecuronium and rocuronium affect human bronchial smooth muscle? Anesthesiology. 1999 Dec;91(6):1616-21. [PubMed:10598601 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
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. Karpati E, Biro K, Kukorelli T: [Investigation of neuromuscular blocking agents at Richter Ltd]. Acta Pharm Hung. 2002;72(1):37-48. [PubMed:12426786 ]

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. Simon G, Biro K, Karpati E, Tuba Z: The effect of the steroid muscle relaxant pipecurium bromide on the acetylcholinesterase activity of red blood cells in vitro. Arzneimittelforschung. 1980;30(2a):360-3. [PubMed:6248079 ]
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Drug created on June 30, 2007 12:08 / Updated on August 17, 2016 12:23