Identification
- Summary
Rapacuronium is a nondepolarizing neuromuscular blocking agent used as an adjunct to general anesthesia to facilitate tracheal intubation, and to provide skeletal muscle relaxation during surgical procedures.
- Generic Name
- Rapacuronium
- DrugBank Accession Number
- DB04834
- Background
Rapacuronium was withdrawn in 2001 in many countries due to risk of fatal bronchospasm.
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Structure
Structure for Rapacuronium (DB04834)
- Weight
- Average: 597.904
Monoisotopic: 597.462584872 - Chemical Formula
- C37H61N2O4
- Synonyms
- Not Available
Pharmacology
- Indication
Used in anaesthesia, to aid and enable endotracheal intubation.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Rapacuronium is a rapidly acting, non-depolarizing neuromuscular blocker.
- Mechanism of action
Target Actions Organism AMuscarinic acetylcholine receptor M2 antagonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Variable. Plasma protein binding of rapacuronium was studied in vitro for human plasma by equilibrium dialysis. The protein binding was variable and ranged between 50% and 88%, which was at least partly due to hydrolysis of rapacuronium bromide to its 3-hydroxy metabolite. The specific plasma protein to which rapacuronium binds is unknown. Plasma protein binding of the 3-hydroxy metabolite was not determined.
- Metabolism
Hydrolyzed to active metabolites (Cytochrome P450 system is not involved).
- Route of elimination
Not Available
- Half-life
141 minutes (mean)
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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 Rapacuronium is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Rapacuronium. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Rapacuronium. Acetyldigitoxin The risk or severity of Cardiac Arrhythmia can be increased when Rapacuronium is combined with Acetyldigitoxin. Aclidinium The risk or severity of adverse effects can be increased when Rapacuronium is combined with Aclidinium. Adenosine The risk or severity of Tachycardia can be increased when Adenosine is combined with Rapacuronium. Agomelatine The risk or severity of CNS depression can be increased when Rapacuronium is combined with Agomelatine. Alfentanil The risk or severity of adverse effects can be increased when Rapacuronium is combined with Alfentanil. Alimemazine The risk or severity of CNS depression can be increased when Alimemazine is combined with Rapacuronium. Alloin The therapeutic efficacy of Alloin can be decreased when used in combination with Rapacuronium. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - 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 Rapacuronium bromide 65Q4QDG4KC 156137-99-4 LVQTUXZKLGXYIU-GWSNJHLMSA-M - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Raplon Injection 200 mg/1 Intravenous Organon 1999-08-18 2001-03-30 US 
Raplon Injection 100 mg/1 Intravenous Organon 1999-08-18 2001-03-30 US
Categories
- Drug Categories
- 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 / Piperidines / Dicarboxylic acids and derivatives / Tetraalkylammonium salts / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic salts show 4 more
- Substituents
- Aliphatic heteropolycyclic compound / Amine / Amino acid or derivatives / Androstane-skeleton / Azacycle / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dicarboxylic acid or derivatives / Hydrocarbon derivative show 15 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- GG1LBM463S
- CAS number
- 465499-11-0
- InChI Key
- HTIKWNNIPGXLGM-YLINKJIISA-N
- InChI
- InChI=1S/C37H61N2O4/c1-6-20-39(21-12-9-13-22-39)32-24-30-28-15-14-27-23-33(42-26(3)40)31(38-18-10-8-11-19-38)25-37(27,5)29(28)16-17-36(30,4)35(32)43-34(41)7-2/h6,27-33,35H,1,7-25H2,2-5H3/q+1/t27-,28+,29-,30-,31-,32-,33-,35-,36-,37-/m0/s1
- IUPAC Name
- 1-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-5-(acetyloxy)-2,15-dimethyl-4-(piperidin-1-yl)-14-(propanoyloxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl]-1-(prop-2-en-1-yl)piperidin-1-ium
- SMILES
- [H][C@@]12C[C@@H]([C@H](OC(=O)CC)[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)N1CCCCC1)[N+]1(CC=C)CCCCC1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 5311399
- PubChem Substance
- 46506932
- ChemSpider
- 4470890
- 262100
- ChEBI
- 135845
- ChEMBL
- CHEMBL1201352
- ZINC
- ZINC000003943562
- PharmGKB
- PA451227
- RxList
- RxList Drug Page
- Wikipedia
- Rapacuronium
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection Intravenous 100 mg/1 Injection Intravenous 200 mg/1 - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5418226 No 1995-05-23 2013-04-14 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 4.64e-06 mg/mL ALOGPS logP 3.79 ALOGPS logP 2.32 Chemaxon logS -8.1 ALOGPS pKa (Strongest Basic) 9.65 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 55.84 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 183.1 m3·mol-1 Chemaxon Polarizability 72.25 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 - 0.5993 Blood Brain Barrier + 0.8937 Caco-2 permeable + 0.5 P-glycoprotein substrate Substrate 0.8064 P-glycoprotein inhibitor I Inhibitor 0.8735 P-glycoprotein inhibitor II Inhibitor 0.908 Renal organic cation transporter Non-inhibitor 0.7446 CYP450 2C9 substrate Non-substrate 0.85 CYP450 2D6 substrate Non-substrate 0.7966 CYP450 3A4 substrate Substrate 0.7018 CYP450 1A2 substrate Non-inhibitor 0.7843 CYP450 2C9 inhibitor Non-inhibitor 0.851 CYP450 2D6 inhibitor Non-inhibitor 0.8561 CYP450 2C19 inhibitor Non-inhibitor 0.7692 CYP450 3A4 inhibitor Non-inhibitor 0.6044 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7403 Ames test Non AMES toxic 0.6904 Carcinogenicity Non-carcinogens 0.8664 Biodegradation Not ready biodegradable 0.9886 Rat acute toxicity 2.6637 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8796 hERG inhibition (predictor II) Non-inhibitor 0.7349
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- 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
- Jooste E, Klafter F, Hirshman CA, Emala CW: A mechanism for rapacuronium-induced bronchospasm: M2 muscarinic receptor antagonism. Anesthesiology. 2003 Apr;98(4):906-11. [Article]
Drug created at September 11, 2007 21:43 / Updated at October 02, 2023 22:14