Identification
- Summary
Pipecuronium is a nondepolarizing neuromuscular blocking agent used to relax muscles during anesthesia and surgical procedures.
- Generic Name
- Pipecuronium
- DrugBank Accession Number
- DB01338
- Background
Pipecuronium is a piperazinyl androstane derivative which is a non-depolarizing neuromuscular blocking agent.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Pipecuronium (DB01338)
- Weight
- Average: 602.8912
Monoisotopic: 602.477106492 - Chemical Formula
- C35H62N4O4
- Synonyms
- Pipecurium
- Pipecuronium
Pharmacology
- Indication
Used as a muscle relaxant during anesthesia and surgical procedures.
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Pipecuronium 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 action
Nondepolarizing 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.
Target Actions Organism ANeuronal acetylcholine receptor subunit alpha-2 antagonistHumans UMuscarinic acetylcholine receptor M2 antagonistHumans UMuscarinic acetylcholine receptor M3 antagonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Distribution 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]
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Pipecuronium is combined with 1,2-Benzodiazepine. Acebutolol Pipecuronium may increase the bradycardic activities of Acebutolol. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Pipecuronium. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Pipecuronium. Acetylcholine The risk or severity of adverse effects can be increased when Pipecuronium is combined with Acetylcholine. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Pipecuronium bromide R6ZTY81RE1 52212-02-9 TXWBOBJCRVVBJF-YTGGZNJNSA-L - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Arduan Injection 10 mg/1 Intravenous Organon 1990-07-26 2001-09-27 US 
Categories
- ATC Codes
- M03AC06 — Pipecuronium bromide
- Drug Categories
- Agents producing tachycardia
- Anticholinergic Agents
- Central Nervous System Depressants
- Cholinergic Agents
- Cholinesterase Inhibitors
- Muscarinic Antagonists
- Muscle Relaxants
- Muscle Relaxants, Peripherally Acting Agents
- Musculo-Skeletal System
- Neuromuscular Agents
- Neuromuscular Blocking Agents
- Neuromuscular-Blocking Agents (Nondepolarizing)
- Neurotransmitter Agents
- Nicotinic Antagonists
- Peripheral Nervous System Agents
- Piperazines
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Steroid esters
- Direct Parent
- Steroid esters
- Alternative Parents
- Androstane steroids / N-methylpiperazines / Dicarboxylic acids and derivatives / Tetraalkylammonium salts / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic salts show 4 more
- Substituents
- 1,4-diazinane / Aliphatic heteropolycyclic compound / Amine / Amino acid or derivatives / Androstane-skeleton / Azacycle / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dicarboxylic acid or derivatives show 18 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- steroid ester (CHEBI:8230)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 1N3O74HM92
- CAS number
- 68399-58-6
- InChI Key
- 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-[(1R,2S,3aS,3bR,5aS,7S,8S,9aS,9bS,11aS)-1,7-bis(acetyloxy)-8-(4,4-dimethylpiperazin-4-ium-1-yl)-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-2-yl]-1,1-dimethylpiperazin-1-ium
- SMILES
- [H][C@@]12C[C@@H]([C@H](OC(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](OC(C)=O)[C@H](C[C@]12C)N1CC[N+](C)(C)CC1)N1CC[N+](C)(C)CC1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015431
- KEGG Compound
- C07554
- PubChem Compound
- 50192
- PubChem Substance
- 46508493
- ChemSpider
- 45517
- 33742
- ChEBI
- 8230
- ChEMBL
- CHEMBL1201206
- ZINC
- ZINC000003938681
- Therapeutic Targets Database
- DAP000353
- PharmGKB
- PA164764567
- Wikipedia
- Pipecuronium
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection Intravenous 10 mg/1 - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 9.5e-05 mg/mL ALOGPS logP -1.4 ALOGPS logP -5.3 Chemaxon logS -6.8 ALOGPS pKa (Strongest Basic) 5.31 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 59.08 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 193.04 m3·mol-1 Chemaxon Polarizability 72.35 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.8906 Blood Brain Barrier + 0.6351 Caco-2 permeable + 0.5 P-glycoprotein substrate Substrate 0.8501 P-glycoprotein inhibitor I Inhibitor 0.7487 P-glycoprotein inhibitor II Inhibitor 0.5983 Renal organic cation transporter Non-inhibitor 0.7112 CYP450 2C9 substrate Non-substrate 0.8587 CYP450 2D6 substrate Non-substrate 0.7823 CYP450 3A4 substrate Substrate 0.7542 CYP450 1A2 substrate Non-inhibitor 0.9065 CYP450 2C9 inhibitor Non-inhibitor 0.9152 CYP450 2D6 inhibitor Non-inhibitor 0.9059 CYP450 2C19 inhibitor Non-inhibitor 0.8819 CYP450 3A4 inhibitor Non-inhibitor 0.8232 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9438 Ames test Non AMES toxic 0.752 Carcinogenicity Non-carcinogens 0.9083 Biodegradation Not ready biodegradable 0.9272 Rat acute toxicity 2.6004 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9193 hERG inhibition (predictor II) Non-inhibitor 0.7647
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 257.1620282 predictedDarkChem Lite v0.1.0 [M-H]- 258.6351282 predictedDarkChem Lite v0.1.0 [M-H]- 223.60603 predictedDeepCCS 1.0 (2019) [M+H]+ 256.0164282 predictedDarkChem Lite v0.1.0 [M+H]+ 258.3683282 predictedDarkChem Lite v0.1.0 [M+H]+ 225.33516 predictedDeepCCS 1.0 (2019) [M+Na]+ 256.0653282 predictedDarkChem Lite v0.1.0 [M+Na]+ 258.1744282 predictedDarkChem Lite v0.1.0 [M+Na]+ 231.62733 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- Neuronal acetylcholine receptor subunit alpha-2
- Molecular Weight
- 59764.82 Da
References
- 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. [Article]
- Karpati E, Biro K, Kukorelli T: [Investigation of neuromuscular blocking agents at Richter Ltd]. Acta Pharm Hung. 2002;72(1):37-48. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- 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...
- Gene Name
- CHRM2
- Uniprot ID
- P08172
- Uniprot Name
- Muscarinic acetylcholine receptor M2
- Molecular Weight
- 51714.605 Da
References
- Karpati E, Biro K, Kukorelli T: [Investigation of neuromuscular blocking agents at Richter Ltd]. Acta Pharm Hung. 2002;72(1):37-48. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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...
- Gene Name
- CHRM3
- Uniprot ID
- P20309
- Uniprot Name
- Muscarinic acetylcholine receptor M3
- Molecular Weight
- 66127.445 Da
References
- Karpati E, Biro K, Kukorelli T: [Investigation of neuromuscular blocking agents at Richter Ltd]. Acta Pharm Hung. 2002;72(1):37-48. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- Cholinesterase
- Molecular Weight
- 68417.575 Da
References
- 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. [Article]
Drug created at June 30, 2007 18:08 / Updated at January 02, 2024 23:51