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OPC-28326 free base

PubChem CID
219020
Structure
OPC-28326 free base_small.png
OPC-28326 free base_3D_Structure.png
Molecular Formula
Synonyms
  • OPC-28326
  • 167626-17-7
  • OPC-28326 free base
  • 77QB6Y63UM
  • UNII-77QB6Y63UM
Molecular Weight
421.6 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-08-09
  • Modify:
    2025-01-11
Description
At low doses, OPC 28326 selectively vasodilates the femoral arterial bed due to its inhibitory action at alpha-2-adrenoceptors while having minimal action on systemic blood pressure, heart rate and coronary, carotid, vertebral, renal, and mesenteric blood flows. It is the only clinical compound with this profile. It is currently being investigated in the treatment of peripheral vascular diseases and Raynaud's syndrome.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
OPC-28326 free base.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[2,6-dimethyl-4-[4-[methyl(2-phenylethyl)amino]piperidine-1-carbonyl]phenyl]propanamide
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C26H35N3O2/c1-5-24(30)27-25-19(2)17-22(18-20(25)3)26(31)29-15-12-23(13-16-29)28(4)14-11-21-9-7-6-8-10-21/h6-10,17-18,23H,5,11-16H2,1-4H3,(H,27,30)
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

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

2.1.4 SMILES

CCC(=O)NC1=C(C=C(C=C1C)C(=O)N2CCC(CC2)N(C)CCC3=CC=CC=C3)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C26H35N3O2
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

167626-17-7

2.3.2 UNII

2.3.3 ChEMBL ID

2.3.4 DrugBank ID

2.3.5 Metabolomics Workbench ID

2.3.6 Nikkaji Number

2.3.7 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 4-(N-methyl-2-phenylethylamino)-1-(3,5-dimethyl-4-propionylaminobenzoyl)piperidine
  • OPC 28326
  • OPC-28326

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
421.6 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
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
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
421.27292737 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
421.27292737 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
52.7 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
31
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
569
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
0
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

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749

5 Chemical Vendors

6 Drug and Medication Information

6.1 Drug Indication

Investigated for use/treatment in peripheral vascular disease and raynaud's disease.

7 Pharmacology and Biochemistry

7.1 Pharmacodynamics

At low doses, OPC 28326 selectively vasodilates the femoral arterial bed due to its inhibitory action at alpha-2-adrenoceptors while having minimal action on systemic blood pressure, heart rate and coronary, carotid, vertebral, renal, and mesenteric blood flows.

7.2 Mechanism of Action

At low doses, OPC 28326 selectively vasodilates the femoral arterial bed due to its inhibitory action at alpha-2C-adrenoceptors. Other studies have also reported selectivity for a-2B-adrenoceptors.

8 Associated Disorders and Diseases

9 Literature

9.1 Consolidated References

9.2 NLM Curated PubMed Citations

9.3 Chemical Co-Occurrences in Literature

9.4 Chemical-Gene Co-Occurrences in Literature

9.5 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

10.2 WIPO PATENTSCOPE

10.3 Chemical Co-Occurrences in Patents

10.4 Chemical-Disease Co-Occurrences in Patents

10.5 Chemical-Gene Co-Occurrences in Patents

11 Interactions and Pathways

11.1 Chemical-Target Interactions

12 Biological Test Results

12.1 BioAssay Results

13 Classification

13.1 MeSH Tree

13.2 ChemIDplus

13.3 NORMAN Suspect List Exchange Classification

13.4 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. FDA Global Substance Registration System (GSRS)
    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
  4. 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
  5. Therapeutic Target Database (TTD)
  6. Japan Chemical Substance Dictionary (Nikkaji)
  7. Metabolomics Workbench
  8. 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/
    Opc-28326
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  9. Wikidata
    N-[2,6-dimethyl-4-[4-[methyl(2-phenylethyl)amino]piperidine-1-carbonyl]phenyl]propanamide
    https://www.wikidata.org/wiki/Q126601013
  10. PubChem
  11. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  12. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  13. PATENTSCOPE (WIPO)
CONTENTS