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    Chemistry

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    Also known as: Fentanyl hcl, 1443-54-5, 59h156xy46, Fentanyl hydrochloride (jan), Fentanyl hydrochloride [jan], N-phenyl-n-[1-(2-phenylethyl)piperidin-4-yl]propanamide;hydrochloride
    Molecular Formula
    C22H29ClN2O
    Molecular Weight
    372.9  g/mol
    InChI Key
    LHCBOXPPRUIAQT-UHFFFAOYSA-N
    FDA UNII
    59H156XY46
    Fentanyl Hydrochloride
    Fentanyl Hydrochloride is the hydrochloride salt form of fentanyl, a synthetic, lipophilic phenylpiperidine opioid agonist with analgesic and anesthetic properties. Fentanyl selectively binds to the mu-receptor in the central nervous system (CNS) thereby mimicking the effects of endogenous opiates. Stimulation of the mu-subtype opioid receptor stimulates the exchange of GTP for GDP on the G-protein complex and subsequently inhibits adenylate cyclase. This results in a decrease in intracellular cAMP and leads to a reduction in the release of neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline. The analgesic effect of fentanyl is likely due to its metabolite morphine, which induces opening of G-protein-coupled inwardly rectifying potassium (GIRK) channels and blocks the opening of N-type voltage-gated calcium channels, thereby resulting in hyperpolarization and reduced neuronal excitability.
    1 2D Structure

    Fentanyl Hydrochloride

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide;hydrochloride
    2.1.2 InChI
    InChI=1S/C22H28N2O.ClH/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19;/h3-12,21H,2,13-18H2,1H3;1H
    2.1.3 InChI Key
    LHCBOXPPRUIAQT-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    59H156XY46
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. Fentanyl Hcl

    2. 1443-54-5

    3. 59h156xy46

    4. Fentanyl Hydrochloride (jan)

    5. Fentanyl Hydrochloride [jan]

    6. N-phenyl-n-[1-(2-phenylethyl)piperidin-4-yl]propanamide;hydrochloride

    7. Unii-59h156xy46

    8. Ionsys (tn)

    9. N-(1-phenethyl-4-piperidyl)propionanilide Hydrochloride

    10. Mls002320669

    11. Schembl242876

    12. Chembl1201159

    13. Dtxsid90162666

    14. Propionanilide, N-(1-phenethyl-4-piperidyl)-, Hydrochloride

    15. Fentanyl Hydrochloride [mart.]

    16. Fentanyl Hydrochloride [who-dd]

    17. Fentanyl Hydrochloride [ema Epar]

    18. Smr001338815

    19. Fentanyl Hydrochloride [orange Book]

    20. D10811

    21. Q27261701

    22. Propanamide, N-phenyl-n-(1-(2-phenylethyl)-4-piperidinyl)-, Monohydrochloride

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 372.9 g/mol
    Molecular Formula C22H29ClN2O
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count6
    Exact Mass372.1968412 g/mol
    Monoisotopic Mass372.1968412 g/mol
    Topological Polar Surface Area23.6 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity391
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Indication

    Ionsys is indicated for the management of acute moderate to severe post-operative pain in adult patients.

    Management of acute moderate to severe post-operative pain for use in a hospital setting only

    Treatment of acute pain

    5 Pharmacology and Biochemistry
    5.1 ATC Code

    N02AB03

    N02AB03

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