Movatterモバイル変換

[0]ホーム
URL:

Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
Thehttps:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

NIH NLM Logo
Log inShow account info
Access keysNCBI HomepageMyNCBI HomepageMain ContentMain Navigation
pubmed logo
Advanced Clipboard
User Guide

Full text links

Atypon full text link Atypon Free PMC article
Full text links

Actions

Share

Review
.2014 Mar;6(4):385-412.
doi: 10.4155/fmc.13.215.

Fentanyl-related compounds and derivatives: current status and future prospects for pharmaceutical applications

Affiliations
Review

Fentanyl-related compounds and derivatives: current status and future prospects for pharmaceutical applications

Ruben S Vardanyan et al. Future Med Chem.2014 Mar.

Abstract

Fentanyl and its analogs have been mainstays for the treatment of severe to moderate pain for many years. In this review, we outline the structural and corresponding synthetic strategies that have been used to understand the structure-biological activity relationship in fentanyl-related compounds and derivatives and their biological activity profiles. We discuss how changes in the scaffold structure can change biological and pharmacological activities. Finally, recent efforts to design and synthesize novel multivalent ligands that act as mu and delta opioid receptors and NK-1 receptors are discussed.

PubMed Disclaimer

Conflict of interest statement

Financial & competing interests disclosure

The authors have no relevant affiliations or financial involvement with any organization or entity with a financial interest in or financial conflict with the subject matter or materials discussed in the manuscript. This includes employment, consultancies, honoraria, stock ownership or options, expert testimony, grants or patents received or pending, or royalties.

No writing assistance was utilized in the production of this manuscript.

Figures

Figure 1
Figure 1
Fentanyl and major fentanyl analogs.
Figure 2
Figure 2
Approaches to the synthesis of fentanyl.
Figure 3
Figure 3
Modifications of the structure of fentanyl.
Figure 4
Figure 4
Synthesis of perhydroazepine analogs of fentanyl.
Figure 5
Figure 5
Methyl-substituted fentanyls.
Figure 6
Figure 6
Synthesis of 4-aryl-fentanyl analogs.
Figure 7
Figure 7
Synthesis of carfentanyl, alfentanil sufentanil, R30490, and their analogs.
Figure 8
Figure 8
Alternative synthesis of 4-acyl- fentanyls from corresponding acids.
Figure 9
Figure 9
Synthesis of 4-acyloxymethyl- fentanyls.
Figure 10
Figure 10
Examples of ‘ring-closed’ analogs of fentanyl.
Figure 11
Figure 11
One more example of ‘ring-closed’ analogs of fentanyl – indolylpiperidines.
Figure 12
Figure 12
Synthesis of series of pyridoindoles a benzo[a]-quinolizidine derivatives of fentanyl.
Figure 13
Figure 13
Synthesis of isothiocyanate derivatives of fentanyl.
Figure 14
Figure 14
Replacement of 2-arylethylsubstituents at piperidine ring.
Figure 15
Figure 15
Bivalent ligands based on fentanyl.
Figure 16
Figure 16
Functionalized fentanyls for the synthesis of bivalent ligands.
Figure 17
Figure 17
Newly created bivalent ligands based on fentanyl.
Figure 18
Figure 18
Attempts to synthesize fentanyl/adjuvant bivalent compounds.
Figure 19
Figure 19
One other attempt to synthesize fentanyl/δ-agonist bivalent compounds.
Figure 20
Figure 20
Phenylethyl moiety present in all classes of opioids.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Woolf CJ, Borsook D, Koltzenburg M. Mechanism-based classifications of pain and analgesic drug discovery. In: Bountra C, Munglani R, Schmidt WK, editors. Pain: Current Understanding, Emerging Therapies and Novel Approaches to Drug Discovery. NY, USA: Marcel Dekker; 2003. pp. 1–8.
    1. Woodcock J, Witter J, Dionne RA. Stimulating the development of mechanism-based, individualized pain therapies. Nat. Rev. Drug Disc. 2007;6(9):703–710. - PubMed
    1. Kissin I. The Development of new analgesics over the past 50 years: a lack of real breakthrough drugs. Anesth. Analg. 2010;110(3):780–789. - PubMed
    1. Grape S, Schug SA, Lauer S, Schug BS. Formulations of fentanyl for the management of pain. Drugs. 2010;70(1):57–72. - PubMed
    1. Nelson L, Schwaner R. Transdermal fentanyl: pharmacology and toxicology. J. Med. Toxicol. 2009;5(4):230–241. - PMC - PubMed

Publication types

MeSH terms

Substances

Related information

Grants and funding

LinkOut - more resources

Full text links
Atypon full text link Atypon Free PMC article
Cite
Send To

NCBI Literature Resources

MeSHPMCBookshelfDisclaimer

The PubMed wordmark and PubMed logo are registered trademarks of the U.S. Department of Health and Human Services (HHS). Unauthorized use of these marks is strictly prohibited.

[8]ページ先頭
©2009-2025 Movatter.jp