Identification
- Summary
Mivacurium is a short-acting non-depolarizing neuromuscular blocking agent used to induce anesthesia during intubation and promote skeletal muscle relaxation during surgery or mechanical ventilation.
- Generic Name
- Mivacurium
- DrugBank Accession Number
- DB01226
- Background
Mivacurium is a bisbenzylisoquinolinium based neuromuscular blocker or muscle relaxant. It binds competitively to cholinergic receptors on the motor end-plate to antagonize the action of acetylcholine, resulting in a block of neuromuscular transmission.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Mivacurium (DB01226)
- Weight
- Average: 1029.2608
Monoisotopic: 1028.560955278 - Chemical Formula
- C58H80N2O14
- Synonyms
- Mivacurium
- External IDs
- BW B109OU
- BW-B109OU
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.
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- Contraindications & Blackbox Warnings
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Mivacurium is a short-acting, nondepolarizing skeletal neuromuscular blocking agent which is hydrolyzed by plasma cholinesterase. Mivacurium results in a blockade of neuromuscular transmission by binding competitively with cholinergic receptors on the motor end-plate to antagonize the action of acetylcholine. The neuromuscular block produced by mivacurium is readily antagonized by anticholinesterase agents. The deeper the level of neuromuscular block at reversal, the longer the time required for recovery of neuromuscular function and the greater the dose of anticholinesterase agent required. Because spontaneous recovery after mivacurium is rapid, routine reversal may not always result in a clinical benefit.
- Mechanism of action
Mivacurium binds competitively to cholinergic receptors on the motor end-plate to antagonize the action of acetylcholine, resulting in a block of neuromuscular transmission. This action is antagonized by acetylcholinesterase inhibitors, such as neostigmine.
Target Actions Organism ANeuronal acetylcholine receptor subunit alpha-2 antagonistHumans NMuscarinic acetylcholine receptor M2 antagonistpartial agonistHumans NMuscarinic acetylcholine receptor M3 antagonistHumans UCholinesterase Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
The protein binding of mivacurium has not been determined due to its rapid hydrolysis by plasma cholinesterase.
- Metabolism
Extensive and rapid via enzymatic hydrolysis catalyzed by plasma cholinesterase. Biotransformation may be significantly slowed in patients with abnormal or decreased plasma cholinesterase activity, especially individuals with a homozygous atypical cholinesterase gene abnormality.
- Route of elimination
Not Available
- Half-life
The mean elimination half-life ranges from 1.7 to 2.6 minutes in healthy, young adults administered 0.1 to 0.25 mg/kg mivacurium. In 9 patients with end-stage liver disease undergoing liver transplant surgery, plasma clearance was approximately 50% lower than that in 8 control patients with normal hepatic function, while the elimination half-life increased to 4.4 minutes from the 1.8 minute control value.
- Clearance
Not Available
- Adverse Effects
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Overdosage with neuromuscular blocking agents may result in neuromuscular block beyond the time needed for surgery and anesthesia.
- 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 Mivacurium is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Mivacurium. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Mivacurium. Acetyldigitoxin The risk or severity of Cardiac Arrhythmia can be increased when Mivacurium is combined with Acetyldigitoxin. Aclidinium The risk or severity of adverse effects can be increased when Mivacurium is combined with Aclidinium. - Food Interactions
- No interactions found.
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 Mivacurium chloride 600ZG213C3 106861-44-3 WMSYWJSZGVOIJW-ONUALHDOSA-L - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Mivacron Solution 2 mg/1mL Intravenous AbbVie Inc. 2015-01-30 2018-12-29 US 
Mivacron Injection, solution 2 mg/1mL Intravenous Hospira, Inc. 2010-12-13 2010-12-14 US Mivacron Liquid 2 mg / mL Intravenous Abbvie 1994-12-31 2012-11-03 Canada 
Mivacron Injection, solution 2 mg/1mL Intravenous Hospira, Inc. 2010-12-13 2010-12-14 US Mivacurium Chloride Injection, solution 2 mg/1mL Intravenous Sandoz 2009-04-30 2009-08-27 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Mivacurium Chloride Mivacurium chloride (2 mg/1mL) Injection, solution Intravenous Sandoz 2009-04-30 2009-08-27 US
Categories
- ATC Codes
- M03AC10 — Mivacurium chloride
- Drug Categories
- Agents producing tachycardia
- Anticholinergic Agents
- Central Nervous System Depressants
- Cholinergic Agents
- Cholinesterase substrates
- Heterocyclic Compounds, Fused-Ring
- Isoquinolines
- Muscarinic Antagonists
- Muscle Relaxants
- Muscle Relaxants, Peripherally Acting Agents
- Musculo-Skeletal System
- Neuromuscular Agents
- Neuromuscular Blocking Agents
- 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 / Phenoxy compounds / Anisoles / Methoxybenzenes / Alkyl aryl ethers / Aralkylamines / Fatty acid esters / Dicarboxylic acids and derivatives / Tetraalkylammonium salts / Carboxylic acid esters show 7 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
- isoquinolines (CHEBI:6958)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 77D66S9Q93
- CAS number
- 133814-19-4
- InChI Key
- ILVYCEVXHALBSC-OTBYEXOQSA-N
- InChI
- InChI=1S/C58H80N2O14/c1-59(25-21-41-35-47(63-3)49(65-5)37-43(41)45(59)29-39-31-51(67-7)57(71-11)52(32-39)68-8)23-17-27-73-55(61)19-15-13-14-16-20-56(62)74-28-18-24-60(2)26-22-42-36-48(64-4)50(66-6)38-44(42)46(60)30-40-33-53(69-9)58(72-12)54(34-40)70-10/h13-14,31-38,45-46H,15-30H2,1-12H3/q+2/b14-13+/t45-,46-,59?,60?/m1/s1
- IUPAC Name
- (1R)-2-(3-{[(4E)-8-{3-[(1R)-6,7-dimethoxy-2-methyl-1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-ium-2-yl]propoxy}-8-oxooct-4-enoyl]oxy}propyl)-6,7-dimethoxy-2-methyl-1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-ium
- SMILES
- COC1=CC(C[C@@H]2C3=CC(OC)=C(OC)C=C3CC[N+]2(C)CCCOC(=O)CC\C=C\CCC(=O)OCCC[N+]2(C)CCC3=CC(OC)=C(OC)C=C3[C@H]2CC2=CC(OC)=C(OC)C(OC)=C2)=CC(OC)=C1OC
References
- Synthesis Reference
Maurizio Francesco Velati, Andrea Busca, Cristina Manfrotto, Marco Nicolini, Claudio Gianluca Pozzoli, "Process for the preparation of mivacurium chloride." U.S. Patent US20070293534, issued December 20, 2007.
US20070293534- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015357
- KEGG Compound
- C07550
- PubChem Compound
- 5281042
- PubChem Substance
- 46505071
- ChemSpider
- 4444509
- 30077
- ChEBI
- 6958
- ChEMBL
- CHEMBL1182833
- ZINC
- ZINC000150338702
- Therapeutic Targets Database
- DAP000716
- PharmGKB
- PA450528
- RxList
- RxList Drug Page
- Wikipedia
- Mivacurium_chloride
- FDA label
- Download (1.5 MB)
- MSDS
- Download (25.3 KB)
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 4 Completed Prevention Kidney Diseases / Prostate Hypertrophy 1 4 Completed Treatment Efficacy and Safety of Mivacurium Chloride for Pediatric Patients 1 4 Completed Treatment Intubation / Newborns / Preterms 1 2 Unknown Status Treatment Hepatic dysfunction 1 1 Completed Treatment Muscle Relaxation / Sex 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Intravenous 2 mg/1mL Injection, solution Intravenous; Parenteral 2 MG/ML Liquid Intravenous 2 mg / mL Solution Intravenous 2 mg/1mL Injection, solution Intravenous 10 mg/5ml Injection, solution Parenteral 2 mg/ml Injection, solution Intravenous 20 mg/10ml Injection Intravenous 2 MG/ML Injection Intravenous 10 mg/5ml - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 3.26e-05 mg/mL ALOGPS logP 3.8 ALOGPS logP -0.76 Chemaxon logS -7.5 ALOGPS pKa (Strongest Acidic) 18.59 Chemaxon pKa (Strongest Basic) -4.1 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 12 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 144.9 Å2 Chemaxon Rotatable Bond Count 30 Chemaxon Refractivity 308.74 m3·mol-1 Chemaxon Polarizability 116.99 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 - 0.9832 Blood Brain Barrier + 0.9465 Caco-2 permeable + 0.629 P-glycoprotein substrate Substrate 0.8476 P-glycoprotein inhibitor I Non-inhibitor 0.5119 P-glycoprotein inhibitor II Inhibitor 0.7645 Renal organic cation transporter Non-inhibitor 0.5515 CYP450 2C9 substrate Non-substrate 0.8376 CYP450 2D6 substrate Non-substrate 0.7529 CYP450 3A4 substrate Substrate 0.6975 CYP450 1A2 substrate Non-inhibitor 0.8986 CYP450 2C9 inhibitor Non-inhibitor 0.9583 CYP450 2D6 inhibitor Non-inhibitor 0.8914 CYP450 2C19 inhibitor Non-inhibitor 0.9348 CYP450 3A4 inhibitor Non-inhibitor 0.8426 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.919 Ames test Non AMES toxic 0.7046 Carcinogenicity Non-carcinogens 0.9137 Biodegradation Not ready biodegradable 0.876 Rat acute toxicity 2.6607 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8134 hERG inhibition (predictor II) Non-inhibitor 0.6401
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 363.2461661 predictedDarkChem Lite v0.1.0 [M-H]- 310.8675 predictedDeepCCS 1.0 (2019) [M+H]+ 363.1690661 predictedDarkChem Lite v0.1.0 [M+H]+ 312.59122 predictedDeepCCS 1.0 (2019) [M+Na]+ 363.1234661 predictedDarkChem Lite v0.1.0 [M+Na]+ 318.92014 predictedDeepCCS 1.0 (2019)
Targets
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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
- Ihmsen H, Schmidt J, Schwilden H, Schmitt HJ, Muenster T: Influence of disease progression on the neuromuscular blocking effect of mivacurium in children and adolescents with Duchenne muscular dystrophy. Anesthesiology. 2009 May;110(5):1016-9. doi: 10.1097/ALN.0b013e31819daf31. [Article]
- 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. [Article]
- Jonsson M, Gurley D, Dabrowski M, Larsson O, Johnson EC, Eriksson LI: Distinct pharmacologic properties of neuromuscular blocking agents on human neuronal nicotinic acetylcholine receptors: a possible explanation for the train-of-four fade. Anesthesiology. 2006 Sep;105(3):521-33. [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
- No
- Actions
- AntagonistPartial agonist
- Curator comments
- Though Mivacurium has some inhibitory effects on this target, it is not a very potent inhibitor.
- 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
- Hou VY, Hirshman CA, Emala CW: Neuromuscular relaxants as antagonists for M2 and M3 muscarinic receptors. Anesthesiology. 1998 Mar;88(3):744-50. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- 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
- Habre W, Adamicza A, Lele E, Novak T, Sly PD, Petak F: The involvement of histaminic and muscarinic receptors in the bronchoconstriction induced by myorelaxant administration in sensitized rabbits. Anesth Analg. 2008 Dec;107(6):1899-906. doi: 10.1213/ane.0b013e318186587c. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- Kao YJ, Le ND: The reversal of profound mivacurium-induced neuromuscular blockade. Can J Anaesth. 1996 Nov;43(11):1128-33. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
- Ostergaard D, Rasmussen SN, Viby-Mogensen J, Pedersen NA, Boysen R: The influence of drug-induced low plasma cholinesterase activity on the pharmacokinetics and pharmacodynamics of mivacurium. Anesthesiology. 2000 Jun;92(6):1581-7. doi: 10.1097/00000542-200006000-00014. [Article]
- Kao YJ, Le ND: The reversal of profound mivacurium-induced neuromuscular blockade. Can J Anaesth. 1996 Nov;43(11):1128-33. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:53