Cisatracurium
Identification
- Name
- Cisatracurium
- Accession Number
- DB00565
- Description
Cisatracurium is a nondepolarizing skeletal muscle relaxant for intravenous administration. Cisatracurium acts on cholinergic receptors, blocking neuromuscular transmission. This action is antagonized by acetylcholinesterase inhibitors such as neostigmine. The neuromuscular block produced by cisatracurium besylate is readily antagonized by anticholinesterase agents once recovery has started. As with other nondepolarizing neuromuscular blocking agents, the more profound the neuromuscular block at the time of reversal, the longer the time required for recovery of neuromuscular function. Compared to other neuromuscular blocking agents, it is intermediate in its onset and duration of action.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Cisatracurium (DB00565)
- Weight
- Average: 929.16
Monoisotopic: 928.507428607 - Chemical Formula
- C53H72N2O12
- Synonyms
- Cisatracurium cation
Pharmacology
- Indication
For inpatients and outpatients as an adjunct to general anesthesia, to facilitate tracheal intubation, and to provide skeletal muscle relaxation during surgery or mechanical ventilation in the ICU.
- Associated Therapies
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Cisatracurium Besylate is a nondepolarizing skeletal muscle relaxant for intravenous administration. Cisatracurium Besylate acts on cholinergic receptors, blocking neuromuscular transmission. This action is antagonized by acetylcholinesterase inhibitors such as neostigmine. The neuromuscular block produced by cisatracurium besylate is readily antagonized by anticholinesterase agents once recovery has started. As with other nondepolarizing neuromuscular blocking agents, the more profound the neuromuscular block at the time of reversal, the longer the time required for recovery of neuromuscular function. Compared to other neuromuscular blocking agents, it is intermediate in its onset and duration of action.
- Mechanism of action
Cisatracurium Besylate binds to the nicotinic acetycholine (cholinergic) receptors in the motor endplate and blocks access to the receptors. In the process of binding, the receptor is actually activated - causing a process known as depolarization. Since it is not degraded in the neuromuscular junction, the depolarized membrane remains depolarized and unresponsive to any other impulse, causing muscle paralysis.
Target Actions Organism ANeuronal acetylcholine receptor subunit alpha-2 antagonistHumans - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
The binding of cisatracurium to plasma proteins has not been successfully studied due to its rapid degradation at physiologic pH.
- Metabolism
The degradation of cisatracurium is largely independent of liver metabolism. Results from in vitro experiments suggest that cisatracurium undergoes Hofmann elimination (a pH and temperature-dependent chemical process) to form laudanosine and the monoquaternary acrylate metabolite. The monoquaternary acrylate undergoes hydrolysis by non-specific plasma esterases to form the monoquaternary alcohol metabolite. The monoquaternary alcohol metabolite can also undergo Hofmann elimination but at a much slower rate than cisatracurium. Laudanosine is further metabolized to desmethyl metabolites which are conjugated with glucuronic acid and excreted in the urine.
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- Route of elimination
Biliary and urinary excretion were the major routes of excretion of radioactivity (totaling >90% of the labeled dose within 7 hours of dosing), of which atracurium represented only a minor fraction.
- Half-life
Elimination half-life of 22 minutes.
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
Overdosage with neuromuscular blocking agents may result in neuromuscular block beyond the time needed for surgery and anesthesia.
- Affected organisms
- Humans and other mammals
- 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 Unlock Additional DataAcetazolamide The risk or severity of adverse effects can be increased when Cisatracurium is combined with Acetazolamide. Acetophenazine The risk or severity of adverse effects can be increased when Cisatracurium is combined with Acetophenazine. Acetyldigitoxin The risk or severity of Cardiac Arrhythmia can be increased when Cisatracurium is combined with Acetyldigitoxin. Aclidinium Cisatracurium may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Agomelatine The risk or severity of adverse effects can be increased when Cisatracurium is combined with Agomelatine. Alfentanil The risk or severity of adverse effects can be increased when Cisatracurium is combined with Alfentanil. Alimemazine The risk or severity of adverse effects can be increased when Cisatracurium is combined with Alimemazine. Alloin The therapeutic efficacy of Alloin can be decreased when used in combination with Cisatracurium. Almotriptan The risk or severity of adverse effects can be increased when Cisatracurium is combined with Almotriptan. Alosetron The risk or severity of adverse effects can be increased when Cisatracurium is combined with Alosetron. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Cisatracurium besylate 80YS8O1MBS 96946-42-8 XXZSQOVSEBAPGS-DONVQRBFSA-L - International/Other Brands
- Nimbex Forte (GlaxoSmithKline) / Nimbium (GlaxoSmithKline)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataCisatracurium Besylate Injection Solution Intravenous Mylan Pharmaceuticals Not applicable Not applicable Canada 
Cisatracurium Besylate Injection Solution Intravenous Accord Healthcare Inc Not applicable Not applicable Canada Cisatracurium Besylate Injection Solution Intravenous Pfizer Canada Ulc 2015-06-01 2019-03-28 Canada Cisatracurium Besylate Injection (preservative-free) Solution Intravenous Mylan Pharmaceuticals Not applicable Not applicable Canada Cisatracurium Besylate Injection Multi-dose Solution Intravenous Fresenius Kabi Not applicable Not applicable Canada Cisatracurium Besylate Injection Single Dose Solution Intravenous Fresenius Kabi Not applicable Not applicable Canada Cisatracurium Omega Multidose Solution Intravenous Omega Laboratories Ltd 2014-01-20 Not applicable Canada Cisatracurium Omega Single Dose Solution Intravenous Omega Laboratories Ltd 2014-01-28 Not applicable Canada Nimbex Injection 2 mg/1mL Intravenous AbbVie Inc. 2010-12-09 Not applicable US 
Nimbex Injection 10 mg/1mL Intravenous AbbVie Inc. 1995-12-15 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataAj-cisatracurium Solution Intravenous Agila Jamp Canada Inc Not applicable Not applicable Canada Aj-cisatracurium Solution Intravenous Agila Jamp Canada Inc Not applicable Not applicable Canada Cisatracurium Injection, solution 2 mg/1mL Intravenous Fresenius Kabi USA, LLC 2015-02-26 Not applicable US Cisatracurium Injection, solution 10 mg/1mL Intravenous Fresenius Kabi USA, LLC 2015-02-26 Not applicable US Cisatracurium Injection, solution 2 mg/1mL Intravenous Fresenius Kabi USA, LLC 2015-02-26 Not applicable US Cisatracurium Besylate Injection 10 mg/1mL Intravenous Jiangsu Hengrui Medicine Co., Ltd. 2017-09-19 Not applicable US Cisatracurium Besylate Injection 2 mg/1mL Intravenous Zydus Pharmaceuticals (USA) Inc. 2020-02-12 Not applicable US Cisatracurium Besylate Injection 2 mg/1mL Intravenous Somerset Therapeutics, Llc 2019-02-04 Not applicable US Cisatracurium Besylate Injection, solution 10 mg/5mL Intravenous Meitheal Pharmaceuticals Inc. 2019-10-31 Not applicable US Cisatracurium Besylate Injection 200 mg/20mL Intravenous Teva Parenteral Medicines, Inc. 2018-09-04 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- M03AC11 — Cisatracurium
- Drug Categories
- Alkaloids
- Anticholinergic Agents
- Benzylisoquinolines
- Central Nervous System Depressants
- Heterocyclic Compounds, Fused-Ring
- Isoquinolines
- Muscle Relaxants
- Muscle Relaxants, Peripherally Acting Agents
- Musculo-Skeletal System
- Neuromuscular Agents
- Neuromuscular Blocking Agents
- Neuromuscular Nondepolarizing Blockade
- Neuromuscular-Blocking Agents (Nondepolarizing)
- Nicotinic Antagonists
- Peripheral Nervous System Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Isoquinolines and derivatives
- Sub Class
- Benzylisoquinolines
- Direct Parent
- Benzylisoquinolines
- Alternative Parents
- Tetrahydroisoquinolines / Dimethoxybenzenes / Phenoxy compounds / Anisoles / Alkyl aryl ethers / Aralkylamines / Dicarboxylic acids and derivatives / Tetraalkylammonium salts / Carboxylic acid esters / Azacyclic compounds show 6 more
- Substituents
- Alkyl aryl ether / Amine / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzylisoquinoline / Carbonyl group / Carboxylic acid derivative show 21 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
Chemical Identifiers
- UNII
- QX62KLI41N
- CAS number
- 96946-41-7
- InChI Key
- YXSLJKQTIDHPOT-LJCJQEJUSA-N
- InChI
- InChI=1S/C53H72N2O12/c1-54(22-18-38-32-48(62-7)50(64-9)34-40(38)42(54)28-36-14-16-44(58-3)46(30-36)60-5)24-20-52(56)66-26-12-11-13-27-67-53(57)21-25-55(2)23-19-39-33-49(63-8)51(65-10)35-41(39)43(55)29-37-15-17-45(59-4)47(31-37)61-6/h14-17,30-35,42-43H,11-13,18-29H2,1-10H3/q+2/t42-,43-,54-,55-/m1/s1
- IUPAC Name
- (1R,2R)-1-[(3,4-dimethoxyphenyl)methyl]-2-(3-{[5-({3-[(1R,2R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-2-ium-2-yl]propanoyl}oxy)pentyl]oxy}-3-oxopropyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-2-ium
- SMILES
- COC1=CC2=C(C=C1OC)[[email protected]@H](CC1=CC(OC)=C(OC)C=C1)[[email protected]@+](C)(CCC(=O)OCCCCCOC(=O)CC[[email protected]@+]1(C)CCC3=C(C=C(OC)C(OC)=C3)[[email protected]]1CC1=CC(OC)=C(OC)C=C1)CC2
References
- General References
- GlaxoSmithKline: NIMBEX injection product information [Link]
- External Links
- Human Metabolome Database
- HMDB0240286
- PubChem Compound
- 62886
- PubChem Substance
- 46506666
- ChemSpider
- 56615
- 319864
- ChEBI
- 140621
- ChEMBL
- CHEMBL1201248
- ZINC
- ZINC000238809664
- Therapeutic Targets Database
- DAP000196
- PharmGKB
- PA164744925
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Cisatracurium_besilate
- AHFS Codes
- 12:20.20 — Neuromuscular Blocking Agents
- MSDS
- Download (25.2 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Not Available Neuromuscular Block 1 4 Completed Basic Science ARDS, Human / Illness, Critical / Neuromuscular Blockade / Paralysis / Respiratory Distress Syndrome, Adult / Respiratory Failure 1 4 Completed Prevention C.Delivery; Surgery (Previous), Gynecological 1 4 Completed Prevention Neuromuscular Blockade / Postoperative Complications 1 4 Completed Prevention Postoperative Residual Curarization / Residual Neuromuscular Block 1 4 Completed Treatment Acute Respiratory Distress Syndrome (ARDS) 1 4 Recruiting Treatment Intracranial Pressure Increase / Traumatic Brain Injury (TBI) 1 4 Unknown Status Prevention Anesthesia; Reaction 1 4 Unknown Status Treatment Acute Respiratory Distress Syndrome (ARDS) 1 4 Unknown Status Treatment Adrenal Suppression / Hemodynamics Instability 1
Pharmacoeconomics
- Manufacturers
- Baxter healthcare corp anesthesia and critical care
- Baxter healthcare corp anesthesia critical care
- Bedford laboratories div ben venue laboratories inc
- Hospira inc
- Marsam pharmaceuticals llc
- Teva parenteral medicines inc
- Abbott laboratories
- Packagers
- Abbott Laboratories Ltd.
- Baxter International Inc.
- Bedford Labs
- Ben Venue Laboratories Inc.
- GlaxoSmithKline Inc.
- Hospira Inc.
- Patheon Inc.
- Teva Pharmaceutical Industries Ltd.
- Dosage Forms
Form Route Strength Injection, solution 2 MG/ML Injection, solution 5 MG/ML Injection, solution Intravenous 10 mg/1mL Injection, solution Intravenous 2 mg/1mL Injection, solution Parenteral 2 mg/ml Injection, solution Parenteral 5 mg/ml Injection Intravenous 10 mg/1mL Injection Intravenous 10 mg/5mL Injection Intravenous 2 mg/1mL Injection Intravenous 20 mg/10mL Injection Intravenous 200 mg/20mL Injection, solution Intravenous 10 mg/5mL Injection, solution Intravenous 20 mg/10mL Injection, solution Intravenous 200 mg/20mL Solution Parenteral 2 mg/ml Solution Solution Intravenous Injection Intravenous 10 mg Solution Intravenous 10 mg Injection, solution 10 mg/5mL Injection, solution 150 mg/30mL Injection, solution Intravenous 10 mg Injection, solution Intravenous 150 mg Injection, solution Intravenous 20 mg Injection, solution Intravenous 5 mg Injection, solution Intravenous 50 mg Liquid Intravenous 2 mg Injection 10 mg/5ml Liquid Intravenous Injection 20 mg/10ml Injection 5 mg/2.5ml Injection 50 mg/25ml Injection - Prices
Unit description Cost Unit Nimbex 10 mg/ml vial 13.8USD ml Nimbex 2 mg/ml vial 2.91USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS5453510 No 1995-09-26 2012-09-26 US CA2087104 No 1998-08-18 2011-07-12 Canada Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 2.32e-05 mg/mL ALOGPS logP 3.41 ALOGPS logP -0.96 ChemAxon logS -7.6 ALOGPS pKa (Strongest Acidic) 19.02 ChemAxon pKa (Strongest Basic) -4.1 ChemAxon Physiological Charge 2 ChemAxon Hydrogen Acceptor Count 10 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 126.44 Å2 ChemAxon Rotatable Bond Count 26 ChemAxon Refractivity 280.68 m3·mol-1 ChemAxon Polarizability 104.19 Å3 ChemAxon Number of Rings 6 ChemAxon Bioavailability 0 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 - 0.9847 Blood Brain Barrier + 0.9291 Caco-2 permeable - 0.5966 P-glycoprotein substrate Substrate 0.6828 P-glycoprotein inhibitor I Inhibitor 0.7177 P-glycoprotein inhibitor II Inhibitor 0.5808 Renal organic cation transporter Non-inhibitor 0.5871 CYP450 2C9 substrate Non-substrate 0.7994 CYP450 2D6 substrate Non-substrate 0.7779 CYP450 3A4 substrate Substrate 0.6527 CYP450 1A2 substrate Non-inhibitor 0.8244 CYP450 2C9 inhibitor Non-inhibitor 0.7179 CYP450 2D6 inhibitor Non-inhibitor 0.791 CYP450 2C19 inhibitor Non-inhibitor 0.7048 CYP450 3A4 inhibitor Non-inhibitor 0.7338 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8547 Ames test Non AMES toxic 0.544 Carcinogenicity Non-carcinogens 0.5302 Biodegradation Ready biodegradable 0.8169 Rat acute toxicity 2.6124 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6043 hERG inhibition (predictor II) Inhibitor 0.6507
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Targets
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- 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]
- Tuba Z, Maho S, Vizi ES: Synthesis and structure-activity relationships of neuromuscular blocking agents. Curr Med Chem. 2002 Aug;9(16):1507-36. [PubMed:12171561]
Drug created on June 13, 2005 07:24 / Updated on October 19, 2020 07:46
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