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    Loxicodegol

    DEVELOPMENTS

    PharmaCompass
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    2D Structure
    Also known as: Oxycodegol, Oxycodegol [usan], Nktr-181, J2wiv0jmml, Oxycodegol (usan), 1211231-76-3
    Molecular Formula
    C31H49NO10
    Molecular Weight
    595.7  g/mol
    InChI Key
    RQHILGKAOIGUHU-XPLSERNMSA-N
    FDA UNII
    J2WIV0JMML
    Loxicodegol was developed by Nektar Therapeutics as an opioid analgesic with low abuse potential for the treatment of chronic pain. The lack of abuse potential is believed to be due to the drug's slow rate of entry into brain, a unique characteristic compared to others in the opioid class. This is also thought to be the reason behind the reduced frequency of CNS-mediated adverse effects, like sedation, seen with Loxicodegol. Nektar Therapeutics has filed an application for FDA approval of Loxicodegol for use in the treatment of chronic lower back pain
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4R,4aS,7S,7aR,12bS)-9-methoxy-7-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]-3-methyl-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-ol
    2.1.2 InChI
    InChI=1S/C31H49NO10/c1-32-9-8-30-27-23-4-5-24(35-3)28(27)42-29(30)25(6-7-31(30,33)26(32)22-23)41-21-20-40-19-18-39-17-16-38-15-14-37-13-12-36-11-10-34-2/h4-5,25-26,29,33H,6-22H2,1-3H3/t25-,26+,29-,30-,31+/m0/s1
    2.1.3 InChI Key
    RQHILGKAOIGUHU-XPLSERNMSA-N
    2.1.4 Canonical SMILES
    CN1CCC23C4C(CCC2(C1CC5=C3C(=C(C=C5)OC)O4)O)OCCOCCOCCOCCOCCOCCOC
    2.1.5 Isomeric SMILES
    CN1CC[C@]23[C@@H]4[C@H](CC[C@]2([C@H]1CC5=C3C(=C(C=C5)OC)O4)O)OCCOCCOCCOCCOCCOCCOC
    2.2 Other Identifiers
    2.2.1 UNII
    J2WIV0JMML
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4,5-epoxy-6-(3,6,9,12,15,18-hexaoxanonadec-1-yloxy)-3-methoxy-17-methylmorphinan-14-ol

    2. Nktr-181

    2.3.2 Depositor-Supplied Synonyms

    1. Oxycodegol

    2. Oxycodegol [usan]

    3. Nktr-181

    4. J2wiv0jmml

    5. Oxycodegol (usan)

    6. 1211231-76-3

    7. Oxicodegol

    8. Loxicodegol [inn]

    9. Unii-j2wiv0jmml

    10. Oxycodegol [inn]

    11. Loxicodegol (deleted Inn)

    12. Loxicodegol [who-dd]

    13. Nktr181

    14. Gtpl10652

    15. Who 9971

    16. Db14146

    17. Cs-0033429

    18. D11424

    19. (4r,4as,7s,7ar,12bs)-9-methoxy-7-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]-3-methyl-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-ol

    20. 4,5.alpha.-epoxy-6.alpha.-((2,5,8,11,14,17-hexaoxanonadecan-19-yl)oxy)-3-methoxy-17-methylmorphinan-14-ol

    21. 4,5alpha-epoxy-6alpha-((2,5,8,11,14,17-hexaoxanonadecan-19-yl)oxy)-3-methoxy-17-methylmorphinan-14-ol

    22. Morphinan-14-ol, 4,5-epoxy-6-(3,6,9,12,15,18-hexaoxanonadec-1-yloxy)-3-methoxy-17-methyl-, (5.alpha.,6.alpha.)-

    2.4 Create Date
    2014-05-19
    3 Chemical and Physical Properties
    Molecular Weight 595.7 g/mol
    Molecular Formula C31H49NO10
    XLogP3-1.1
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count20
    Exact Mass595.33564676 g/mol
    Monoisotopic Mass595.33564676 g/mol
    Topological Polar Surface Area107 Ų
    Heavy Atom Count42
    Formal Charge0
    Complexity808
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Loxicodegol was developed as an opioid analgesic with low abuse potential for use in treating chronic pain. An application has been filed for FDA approval of Loxicodegol for use in treating chronic lower back pain.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Loxicodegol displays full analgesic activity comparable to that of oxycodone, producing similar acetone-writhing test responses in mice and hot-plate test maximal latencies in rats. The safety profile of Loxicodegol is much improved from that of other opioid analgesics. The incidence of respiratory depression and sedation is reduced compared to oxycodone and morphine. Generalized pruritus occurred in 7.3% and 4.9% of subjects at 200mg and 400mg of Loxicodegol compared to 41.5% with 40mg oxycodone. Nausea occurred in 2.5%, 2.4%, and 7.3% with 100mg, 200mg, and 400mg of Loxecodegol compared to 29.3% with 40mg oxycodone. Lastly, vomiting occurred in 2.4% with both 200mg and 400mg Loxicodegol compared to 24.4% with 40mg oxycodone. Loxicodegol is much less addictive than other opioid analgesics. It produces a only a slight high at dosages of 400mg, peaking at scores only 25% that of oxycodone, with no difference compared to placebo at lower dosages. No differences have been noted between Loxicodegol and saline in self-administration or behavior reinforcement in monkeys or rats

    5.2 Absorption, Distribution and Excretion

    Absorption

    Loxicodegol has a Tmax of 1.8h and a bioavailability of 34% with oral administration. It enters the brain about 17-70 times more slowly than oxycodone. Loxicodegol is also a p-glycoprotein substrate further reducing its transport into the brain.

    Volume of Distribution

    Loxicodegol has a steady-state Vd of 4.19 L/kg.

    Clearance

    Loxicodegol has a clearance rate of 59.3 mL/min/kg.

    5.3 Biological Half-Life

    Loxicodegol has a half-life of 4.53 h allowing for a longer duration of action.

    5.4 Mechanism of Action

    Loxicodegol is a full agonist at the -opioid receptor. It also displays selectivity towards this subtype with an affinity of 237 nM compared to 4150 nM and >100000 nM for the - and -opioid receptors. The -opioid receptor is activated with an EC of 12.5 M. Activation of this receptor produces an inhibitory effect on neurotransmission through Gi/Go coupling. Opioid medications like Loxicodegol inhibit voltage gated Ca channel opening presynaptically on C fibres and activate inward-rectifying K channels post-synaptically on 2nd order neurons, leading to hyperpolarization. Together, these prevent the nociceptive signal from traveling up the spinal cord to the brain. In the brain, opioids work through a mechanism of inhibition of inhibition to allow regulatory neurons to suppress nociception.