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Mivacurium

PubChem CID
5281042
Structure
Mivacurium_small.png
Molecular Formula
Synonyms
  • Mivacurium
  • Mivacron
  • 133814-19-4
  • Mivacurium cation
  • MIVACURIUM CHLORIDE
Molecular Weight
1029.3 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-06-24
  • Modify:
    2024-12-28
Description
Mivacurium is a member of isoquinolines.
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.
MIVACURIUM is a small molecule drug with a maximum clinical trial phase of IV that was first approved in 1992 and has 1 investigational indication.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Mivacurium.png

1.2 3D Status

Conformer generation is disallowed since too many atoms, too flexible

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

bis[3-[(1R)-6,7-dimethoxy-2-methyl-1-[(3,4,5-trimethoxyphenyl)methyl]-3,4-dihydro-1H-isoquinolin-2-ium-2-yl]propyl] (E)-oct-4-enedioate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

ILVYCEVXHALBSC-OTBYEXOQSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C[N+]1(CCC2=CC(=C(C=C2[C@H]1CC3=CC(=C(C(=C3)OC)OC)OC)OC)OC)CCCOC(=O)CC/C=C/CCC(=O)OCCC[N+]4(CCC5=CC(=C(C=C5[C@H]4CC6=CC(=C(C(=C6)OC)OC)OC)OC)OC)C
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)

2.2 Molecular Formula

C58H80N2O14+2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

106791-40-6

2.3.2 ChEBI ID

2.3.3 ChEMBL ID

2.3.4 DrugBank ID

2.3.5 DSSTox Substance ID

2.3.6 HMDB ID

2.3.7 KEGG ID

2.3.8 Metabolomics Workbench ID

2.3.9 NCI Thesaurus Code

2.3.10 Nikkaji Number

2.3.11 PharmGKB ID

2.3.12 Pharos Ligand ID

2.3.13 Wikidata

2.3.14 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • BW B 1090U
  • BW B1090U
  • BW-B 1090U
  • BW-B-1090U
  • BW-B1090U
  • BWB 1090U
  • BWB1090U
  • Mivacron
  • mivacurium
  • mivacurium chloride

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
1029.3 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
8.7
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
14
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
30
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
1028.56095523 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
1028.56095523 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
145Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
74
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
2
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1550
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
2
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
2
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Liquid

3.2.2 Solubility

3.26e-05 g/L

3.3 Chemical Classes

3.3.1 Drugs

3.3.1.1 Human Drugs
Human drug -> Discontinued; Active ingredient (MIVACURIUM CHLORIDE)
Human drug -> Discontinued

5 Chemical Vendors

6 Drug and Medication Information

6.1 Drug 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.

6.2 FDA Approved Drugs

6.3 FDA Orange Book

6.4 Clinical Trials

6.4.1 ClinicalTrials.gov

6.4.2 EU Clinical Trials Register

7 Pharmacology and Biochemistry

7.1 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.

7.2 MeSH Pharmacological Classification

Neuromuscular Nondepolarizing Agents
Drugs that interrupt transmission at the skeletal neuromuscular junction without causing depolarization of the motor end plate. They prevent acetylcholine from triggering muscle contraction and are used as muscle relaxants during electroshock treatments, in convulsive states, and as anesthesia adjuvants. (See all compounds classified as Neuromuscular Nondepolarizing Agents.)

7.3 ATC Code

M - Musculo-skeletal system

M03 - Muscle relaxants

M03A - Muscle relaxants, peripherally acting agents

M03AC - Other quaternary ammonium compounds

M03AC10 - Mivacurium chloride

7.4 Metabolism / Metabolites

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.

7.5 Biological 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.

7.6 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.

7.7 Human Metabolite Information

7.7.1 Cellular Locations

  • Cytoplasm
  • Membrane

8 Use and Manufacturing

8.1 Uses

<b>Use (kg; approx.) in Germany (2009):</b> >10

<b>Consumption (g per capita; approx.) in Germany (2009):</b> 0.000122

<b>Calculated removal (%):</b> 99.7

8.1.1 Use Classification

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

9 Toxicity

9.1 Toxicological Information

9.1.1 Drug Induced Liver Injury

Compound
mivacurium
DILI Annotation
No-DILI-Concern
Label Section
No match
References

M Chen, V Vijay, Q Shi, Z Liu, H Fang, W Tong. FDA-Approved Drug Labeling for the Study of Drug-Induced Liver Injury, Drug Discovery Today, 16(15-16):697-703, 2011. PMID:21624500 DOI:10.1016/j.drudis.2011.05.007

M Chen, A Suzuki, S Thakkar, K Yu, C Hu, W Tong. DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans. Drug Discov Today 2016, 21(4): 648-653. PMID:26948801 DOI:10.1016/j.drudis.2016.02.015

9.1.2 Protein Binding

The protein binding of mivacurium has not been determined due to its rapid hydrolysis by plasma cholinesterase.

10 Associated Disorders and Diseases

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Chemical Co-Occurrences in Literature

11.4 Chemical-Gene Co-Occurrences in Literature

11.5 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Chemical-Target Interactions

13.2 Drug-Drug Interactions

14 Biological Test Results

14.1 BioAssay Results

15 Classification

15.1 MeSH Tree

15.2 NCI Thesaurus Tree

15.3 ChEBI Ontology

15.4 WHO ATC Classification System

15.5 ChemIDplus

15.6 ChEMBL Target Tree

15.7 NORMAN Suspect List Exchange Classification

15.8 EPA DSSTox Classification

15.9 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DrugBank
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    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. Human Metabolome Database (HMDB)
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    http://www.hmdb.ca/citing
  6. ChEBI
  7. Open Targets
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    https://platform-docs.opentargets.org/licence
  8. ChEMBL
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    http://www.ebi.ac.uk/Information/termsofuse.html
  9. ClinicalTrials.gov
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    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  10. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  11. Therapeutic Target Database (TTD)
  12. Drug Induced Liver Injury Rank (DILIrank) Dataset
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  13. Drugs@FDA
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    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  14. EU Clinical Trials Register
  15. FDA Orange Book
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  16. Japan Chemical Substance Dictionary (Nikkaji)
  17. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  18. Metabolomics Workbench
  19. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  20. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    MIVACURIUM CHLORIDE
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  21. PharmGKB
    LICENSE
    PharmGKB data are subject to the Creative Commons Attribution-ShareALike 4.0 license (https://creativecommons.org/licenses/by-sa/4.0/).
    https://www.pharmgkb.org/page/policies
  22. Pharos
    LICENSE
    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
    https://pharos.nih.gov/about
  23. WHO Anatomical Therapeutic Chemical (ATC) Classification
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    https://www.whocc.no/copyright_disclaimer/
  24. Wikidata
  25. Wikipedia
  26. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
    Neuromuscular Nondepolarizing Agents
    https://www.ncbi.nlm.nih.gov/mesh/68003473
  27. PubChem
  28. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  29. PATENTSCOPE (WIPO)
  30. NCBI
CONTENTS