Mivacurium

Identification

Name

Mivacurium

Accession Number

DB01226  (APRD01119)

Type

Small Molecule

Groups

Approved

Description

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.

Structure

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Mivacurium (DB01226)

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Synonyms

• Mivacurium

External IDs

BW B109OU / BW-B109OU

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Mivacurium chloride	600ZG213C3	106861-44-3	WMSYWJSZGVOIJW-ONUALHDOSA-L

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Unlock Additional Data
Mivacron	Injection, solution	2 mg/1mL	Intravenous	Hospira, Inc.	2010-12-13	2010-12-14
Mivacron	Liquid	2 mg	Intravenous	Abbvie	1994-12-31	2012-11-03
Mivacron	Solution	2 mg/1mL	Intravenous	AbbVie Inc.	2015-01-30	2018-12-29
Mivacron	Injection, solution	2 mg/1mL	Intravenous	Hospira, Inc.	2010-12-13	2010-12-14
Mivacurium Chloride	Injection, solution	2 mg/1mL	Intravenous	Sandoz	2009-04-30	2009-08-27

Additional Data Available

Application Number
Application Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
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Product Code
Product Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Mivacurium Chloride	Mivacurium chloride (2 mg/1mL)	Injection, solution	Intravenous	Sandoz	2009-04-30	2009-08-27

Categories

• Agents producing tachycardia
• Anticholinergic Agents
• Central Nervous System Depressants
• Cholinergic Agents
• 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

UNII

77D66S9Q93

CAS number

133814-19-4

Weight

Average: 1029.2608
Monoisotopic: 1028.560955278

Chemical Formula

C₅₈H₈₀N₂O₁₄

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

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.

Associated Therapies

• Curarization therapy
• Neuromuscular blocking therapy therapy
• Adjunct to general anesthesia therapy
• Facilitation of small bowel intubation therapy
• Smooth muscle relaxation prior to radiological procedures

Pharmacodynamics

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	antagonist	Humans
NMuscarinic acetylcholine receptor M2	antagonist partial agonist	Humans
NMuscarinic acetylcholine receptor M3	antagonist	Humans
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

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.

• All Drugs
• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental

Drug	Interaction
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1,10-Phenanthroline	1,10-Phenanthroline may decrease the neuromuscular blocking activities of Mivacurium.
2,5-Dimethoxy-4-ethylamphetamine	The risk or severity of Tachycardia can be increased when Mivacurium is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of adverse effects can be increased when Mivacurium is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamine	The risk or severity of adverse effects can be increased when Mivacurium is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-Methoxyamphetamine	The risk or severity of adverse effects can be increased when Mivacurium is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamine	The risk or severity of adverse effects can be increased when Mivacurium is combined with 5-methoxy-N,N-dimethyltryptamine.
7-Nitroindazole	The risk or severity of adverse effects can be increased when Mivacurium is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline	The risk or severity of adverse effects can be increased when Mivacurium is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
Abediterol	The risk or severity of Tachycardia can be increased when Mivacurium is combined with Abediterol.
Acepromazine	The risk or severity of adverse effects can be increased when Mivacurium is combined with Acepromazine.

Additional Data Available

Extended Description
Extended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
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Severity
Severity
A severity rating for each drug interaction, from minor to major.
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Evidence Level
Evidence Level
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Action
Action
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Food Interactions

Not Available

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

RxNav

30077

ChEBI

6958

ChEMBL

CHEMBL1182833

ZINC

ZINC000150338702

Therapeutic Targets Database

DAP000716

PharmGKB

PA450528

RxList

RxList Drug Page

Wikipedia

Mivacurium

ATC Codes

M03AC10 — Mivacurium chloride

• M03AC — Other quaternary ammonium compounds
• M03A — MUSCLE RELAXANTS, PERIPHERALLY ACTING AGENTS
• M03 — MUSCLE RELAXANTS
• M — MUSCULO-SKELETAL SYSTEM

FDA label

Download (1.5 MB)

MSDS

Download (25.3 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Treatment	Muscle Relaxation / Sex	1
2	Recruiting	Treatment	Liver Dysfunction	1
4	Completed	Prevention	Kidney Diseases / Prostate Hypertrophy	1
4	Completed	Treatment	Efficacy and Safety of Mivacurium Chloride for Pediatric Patients	1
4	Completed	Treatment	Intubations / Newborns / Preterms	1
Not Available	Completed	Not Available	Neuromuscular Blockade	1
Not Available	Completed	Treatment	Intubating Conditions / Performance With Respiratory Exercise Device / Postoperative Myalgia	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Form	Route	Strength
Injection, solution	Intravenous	2 mg/1mL
Liquid	Intravenous	2 mg
Solution	Intravenous	2 mg/1mL

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	116.68 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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Not Available

Taxonomy

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 estersAzacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives / Carbonyl compounds / Organic oxides / Organic salts / Organic cations

show 7 more

Substituents

Benzylisoquinoline / Tetrahydroisoquinoline / Phenoxy compound / Anisole / Phenol ether / Methoxybenzene / Alkyl aryl ether / Fatty acid ester / Aralkylamine / Monocyclic benzene moietyDicarboxylic acid or derivatives / Fatty acyl / Benzenoid / Tetraalkylammonium salt / Quaternary ammonium salt / Carboxylic acid ester / Azacycle / Ether / Carboxylic acid derivative / Amine / Organooxygen compound / Organonitrogen compound / Hydrocarbon derivative / Organic nitrogen compound / Carbonyl group / Organic oxide / Organopnictogen compound / Organic oxygen compound / Organic salt / Organic cation / Aromatic heteropolycyclic compound

show 21 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoquinolines (CHEBI:6958)

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Drug created on June 13, 2005 07:24 / Updated on June 12, 2020 10:51