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Clevidipine

PubChem CID
153994
Structure
Clevidipine_small.png
Clevidipine_3D_Structure.png
Molecular Formula
Synonyms
  • Clevidipine
  • 167221-71-8
  • Clevidipine butyrate
  • Cleviprex
  • Clevelox
Molecular Weight
456.3 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-01-11
Description
Clevidipine is a dihydropyridine.
Clevidipine is a dihydropyridine L-type calcium channel blocker that is selective for vascular smooth muscle and is indicated for blood pressure reduction when oral therapy is not an option.
Clevidipine is a Dihydropyridine Calcium Channel Blocker. The mechanism of action of clevidipine is as a Calcium Channel Antagonist.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Clevidipine.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-O-(butanoyloxymethyl) 3-O-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C21H23Cl2NO6/c1-5-7-15(25)29-10-30-21(27)17-12(3)24-11(2)16(20(26)28-4)18(17)13-8-6-9-14(22)19(13)23/h6,8-9,18,24H,5,7,10H2,1-4H3
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

KPBZROQVTHLCDU-UHFFFAOYSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

CCCC(=O)OCOC(=O)C1=C(NC(=C(C1C2=C(C(=CC=C2)Cl)Cl)C(=O)OC)C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C21H23Cl2NO6
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

166432-28-6

2.3.2 Deprecated CAS

166432-28-6

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DrugBank ID

2.3.8 DSSTox Substance ID

2.3.9 HMDB ID

2.3.10 KEGG ID

2.3.11 Metabolomics Workbench ID

2.3.12 NCI Thesaurus Code

2.3.13 Nikkaji Number

2.3.14 Pharos Ligand ID

2.3.15 RXCUI

2.3.16 Wikidata

2.3.17 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • butyroxymethyl methyl 4-(2',3'-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
  • clevidipine
  • Cleviprex

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
456.3 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3
Property Value
4.3
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
10
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
455.0902428 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
455.0902428 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
90.9 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
30
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
748
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
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 Chemical Classes

3.2.1 Drugs

3.2.1.1 Human Drugs
Human drug -> Prescription; Discontinued
Human drug -> Active ingredient (CLEVIDIPINE)
Paediatric drug

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 MS-MS

1 of 2
Spectra ID
Ionization Mode
positive
Top 5 Peaks

478.078644 100

480.07605 62.23

360.014923 30.64

479.081482 29.49

362.011383 19.83

Thumbnail
Thumbnail
Notes
instrument=qTof
2 of 2
Spectra ID
Ionization Mode
positive
Top 5 Peaks

338.03421 100

340.031372 62.81

339.038147 16.85

302.056549 9.70

341.03421 8.52

Thumbnail
Thumbnail
Notes
instrument=qTof

4.1.2 LC-MS

1 of 2
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+Na]+
Precursor m/z
478.079
Instrument
qTof
Ionization Mode
positive
Top 5 Peaks

478.078644 100

480.076050 62.23

360.014923 30.64

479.081482 29.49

362.011383 19.83

Thumbnail
Thumbnail
2 of 2
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
456.098
Instrument
qTof
Ionization Mode
positive
Top 5 Peaks

338.034210 100

340.031372 62.81

339.038147 16.85

302.056549 9.70

341.034210 8.52

Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

For the reduction of blood pressure when when oral antihypertensive therapy is not feasible or not desirable.
Treatment of hypertensive disease

7.2 FDA Approved Drugs

7.3 FDA Orange Book

7.4 FDA National Drug Code Directory

7.5 Drug Labels

Drug and label
Active ingredient and drug

7.6 Clinical Trials

7.6.1 ClinicalTrials.gov

7.6.2 EU Clinical Trials Register

7.7 EMA Drug Information

Type
Paediatric investigation
Active Substance
Therapeutic Area
Cardiovascular diseases
Drug Form
Emulsion for infusion
Administration Route
Intravenous use
Decision Type
PM: decision on the application for modification of an agreed PIP
Decision Date
2014-01-22

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

Clevidipine belongs to a well-known class of drugs called dihydropyridine calcium channel antagonists. Clevidpine is the first third generation intravenous dihydropyridine calcium channel blocker. In vitro studies demonstrated that clevidipine acts by selectively relaxing the smooth muscle cells that line small arteries, resulting in arterial dilation, widening of the artery opening, and without reducing central venous pressure or reducing cardiac output.

8.2 MeSH Pharmacological Classification

Calcium Channel Blockers
A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)

8.3 FDA Pharmacological Classification

1 of 3
FDA UNII
19O2GP3B7Q
Active Moiety
CLEVIDIPINE
Pharmacological Classes
Mechanisms of Action [MoA] - Calcium Channel Antagonists
Pharmacological Classes
Established Pharmacologic Class [EPC] - Dihydropyridine Calcium Channel Blocker
Pharmacological Classes
Chemical Structure [CS] - Dihydropyridines
FDA Pharmacology Summary
Clevidipine is a Dihydropyridine Calcium Channel Blocker. The mechanism of action of clevidipine is as a Calcium Channel Antagonist.
2 of 3
Non-Proprietary Name
CLEVIDIPINE
Pharmacological Classes
Dihydropyridines [CS]; Dihydropyridine Calcium Channel Blocker [EPC]; Calcium Channel Antagonists [MoA]
3 of 3
Non-Proprietary Name
CLEVIPIDINE
Pharmacological Classes
Calcium Channel Antagonists [MoA]; Dihydropyridine Calcium Channel Blocker [EPC]; Dihydropyridines [CS]

8.4 ATC Code

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

C - Cardiovascular system

C08 - Calcium channel blockers

C08C - Selective calcium channel blockers with mainly vascular effects

C08CA - Dihydropyridine derivatives

C08CA16 - Clevidipine

8.5 Absorption, Distribution and Excretion

Route of Elimination
urine 63-74%, feces 7-22%

8.6 Metabolism / Metabolites

Clevidipine is rapidly hydrolyzed to inactive metabolites by esterases in arterial blood.

8.7 Biological Half-Life

1 minute

8.8 Mechanism of Action

Possibly by deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum, clevidipine inhibits the influx of extracellular calcium across both the myocardial and vascular smooth muscle cell membranes. The resultant inhibition of the contractile processes of the myocardial smooth muscle cells leads to dilation of the coronary and systemic arteries and improved oxygen delivery to the myocardial tissue.

9 Use and Manufacturing

9.1 Uses

9.1.1 Use Classification

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

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

1 of 2
View All
Pictogram(s)
Health Hazard
Signal
Warning
GHS Hazard Statements

H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

H371 (50%): May cause damage to organs [Warning Specific target organ toxicity, single exposure]

Precautionary Statement Codes

P203, P260, P264, P270, P280, P308+P316, P318, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Repr. 2 (100%)

STOT SE 2 (50%)

Repr. 2 (100%)

11 Toxicity

11.1 Toxicological Information

11.1.1 Drug Induced Liver Injury

Compound
clevidipine
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

11.1.2 Protein Binding

>99.5%

12 Associated Disorders and Diseases

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Wiley References

13.6 Chemical Co-Occurrences in Literature

13.7 Chemical-Gene Co-Occurrences in Literature

13.8 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 FDA Orange Book Patents

14.4 Chemical Co-Occurrences in Patents

14.5 Chemical-Disease Co-Occurrences in Patents

14.6 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Chemical-Target Interactions

15.2 Drug-Drug Interactions

16 Biological Test Results

16.1 BioAssay Results

17 Classification

17.1 MeSH Tree

17.2 NCI Thesaurus Tree

17.3 ChEBI Ontology

17.4 KEGG: ATC

17.5 KEGG: Target-based Classification of Drugs

17.6 KEGG: Drug Groups

17.7 KEGG: Drug Classes

17.8 WHO ATC Classification System

17.9 FDA Pharm Classes

17.10 ChemIDplus

17.11 ChEMBL Target Tree

17.12 UN GHS Classification

17.13 NORMAN Suspect List Exchange Classification

17.14 EPA DSSTox Classification

17.15 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
    3,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, 3-methyl 5-[(1-oxobutoxy)methyl] ester
    https://commonchemistry.cas.org/detail?cas_rn=167221-71-8
  2. DrugBank
    LICENSE
    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
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    3-((butyryloxy)methyl)-5-methyl-4(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
    https://echa.europa.eu/substance-information/-/substanceinfo/100.208.117
    5-O-(butanoyloxymethyl) 3-O-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
    https://echa.europa.eu/substance-information/-/substanceinfo/100.246.076
    3-((butyryloxy)methyl)-5-methyl-4(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (EC: 682-702-2)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/213105
    5-O-(butanoyloxymethyl) 3-O-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (EC: 814-032-5)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/254111
  5. FDA Global Substance Registration System (GSRS)
    LICENSE
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  6. ChEBI
  7. FDA Pharm Classes
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  8. Open Targets
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  9. ChEMBL
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    http://www.ebi.ac.uk/Information/termsofuse.html
  10. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  11. ClinicalTrials.gov
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    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  12. Comparative Toxicogenomics Database (CTD)
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    http://ctdbase.org/about/legal.jsp
  13. Drug Gene Interaction database (DGIdb)
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    http://www.dgidb.org/downloads
  14. Therapeutic Target Database (TTD)
  15. DailyMed
  16. Drug Induced Liver Injury Rank (DILIrank) Dataset
    LICENSE
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    https://www.ema.europa.eu/en/about-us/legal-notice
  18. Drugs@FDA
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  19. EU Clinical Trials Register
  20. FDA Orange Book
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  21. National Drug Code (NDC) Directory
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  22. Human Metabolome Database (HMDB)
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    http://www.hmdb.ca/citing
  23. Japan Chemical Substance Dictionary (Nikkaji)
  24. KEGG
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    https://www.kegg.jp/kegg/legal.html
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
    Target-based classification of drugs
    http://www.genome.jp/kegg-bin/get_htext?br08310.keg
  25. MassBank of North America (MoNA)
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  26. Metabolomics Workbench
  27. NCI Thesaurus (NCIt)
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    https://www.cancer.gov/policies/copyright-reuse
  28. NLM RxNorm Terminology
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    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  29. 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/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  30. WHO Anatomical Therapeutic Chemical (ATC) Classification
    LICENSE
    Use of all or parts of the material requires reference to the WHO Collaborating Centre for Drug Statistics Methodology. Copying and distribution for commercial purposes is not allowed. Changing or manipulating the material is not allowed.
    https://www.whocc.no/copyright_disclaimer/
  31. Pharos
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    https://pharos.nih.gov/about
  32. Springer Nature
  33. Thieme Chemistry
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    https://creativecommons.org/licenses/by-nc-nd/4.0/
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  39. GHS Classification (UNECE)
  40. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  41. PATENTSCOPE (WIPO)
  42. NCBI
CONTENTS