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Opioid Analgesics - PDF

VIEWS: 4 PAGES: 14

  • pg 1
									                 8
           H H            7            PHAR 752                            Opioid Analgesics
       N         14               OH
                                       Wilson + Gisvold, Ch. 22, pp. 731-752.
H 3C                          6


                      O


             3
                 OH


(-)-Morphine




                                                         1
           H H
       N
                            OH
 H3C


                        O



(-)-Codeine        OCH3




           H   H
       N
                            O
 H3C


                        O



                   OH
(-)-Hydromorphone HCl (Dilaudid®)




                                    2
            H    H
                                                     Opioid Analgesics
        N                     O
  H3C


                          O



                     OCH3

(-)-Hydrocodone bitartrate (Lortab®, Vicodin®)




                HO
            H
        N                     O
  H3C


                          O



                     OH
 (-)-Oxymorphone (Numorphan®)




                                                 3
                                               Opioid Analgesics
            HO
           H
       N                    O
 H3C


                      O



                 OCH3

(-)-Oxycodone HCl (Percocet®, Percodan®)




                      H3C       OH

                                C3H7
           H                H
       N
                            OCH3
 H3C


                      O



                 OH

 Etorphine




                                           4
            H H                           Opioid Analgesics
        N
H 3C




                      OH
(-)-Levorphanol (Levo-Dromoran®)




        H
  Cl-
        N+
H 3C


                  O        O

Meperidine hydrochloride (Demarol®)




                                      5
        H
 H 3C
        N+
 H 3C
             CH3
                         O


(±)-Methadone HCl (Dolophine® HCl)




        Metabolism of Methadone


                               [Major route]
                     CH3                                  CH3
                     N
                         CH3
                                 Cyp3A4                   N
                                                          ..   H
                                                                                       CH3
                   CH3                                  CH3          HO          N
        O                                       O
                                                                                 CH3
                                                                           CH3
    Methadone                                  Normethadone

                                                                                     Rapid
                                                                   - H2O
                                                                                 Non-enzymatic




                                                                                       CH3
                                                                                 N
                                                                                 CH3
                                                                           CH3
                                                                    Inactive pyrrolidine




                                                    6
                                         Opioid Agonists


       H         CH3
 H3C
       N+
 H3C
       Cl-
             O       O




 Propoxyphene HCl (Darvon®)




                 N
                             N

                         H       O

Fentanyl citrate (Sublimaze®)




                                     7
                                               Opioid Agonists


    S               N
                                   N

                                       O
                        H3CO
         Sufentanil citrate (Sufenta®)




O               N
                               N

        OCH3
                                   O
                    H3CO       O

    Remifentanil (Ultiva®)




                                           8
(H3C)2N   H

          HO




               OCH3
 Tramadol (Ultram®)




                      9
            HO                             Opioid Antagonists
           H
       N
                                  O


                          O



                     OH
Naloxone (Narcan®)




                HO
            H
        N                         O


                             O



                        OH
  Naltrexone (ReVia®)




                   HO
               H
           N



                              O



                        OH
  Nalmefene (Revex®)
                                      10
                    HO                      Opioid Mixed or Partial Agonists
                H
            N




                         OH

(-)-Butorphanol tartrate (Stadol®)




                    HO
                H
            N
                                  OH


                              O



                         OH
(-)-Nalbuphine (Nubain®)




                                       11
                                                     Opioid Mixed or Partial Agonists
                    H H   CH3
                N

                               CH3




                          OH
(-)-Pentazocine HCl (Talwin®)




                          H 3C       OH
                                          CH3

                                 H    CH3
            H                      CH3
        N                        OCH3


                          O



                     OH
 Buprenorpine (Buprenex®)




                                                12
                                               Antidiarrheal Agents
                  H
            Cl-
                  N+
   NC

                            O   O


  Diphenoxylate HCl
  (with Atropine = Lomotil®)




        O              H             Cl
               Cl-
                       N+
H3C N

 H 3C                           OH


 Loperamide HCl (Immodium®)




                                          13
                                        O




                                        H


                    O                   O
                        H           H
H 3C        O
                                            O
                              CH3
       O


                        CH3


                O       OCH3




           Salvinorin A -

           From Salvia divinorum
           (Diviner's sage, Mexican mint)

A kappa opioid agonist lacking a basic nitrogen. Salvia divinorum was traditionally
used by shamanic healers in the Mexican state of Oaxaca. Salvinorin A has been
reported to be the psychoactive principle of this hallucinogenic plant. It is likely that
this compound acts at other sites in addition to the kappa opioid receptor, but it is
known to be a potent kappa agonist.

In August, 2005, the states of Louisiana and Missouri passed laws criminalizing
possession, sale, and use of S. divinorum/salvinorin A. In Missouri, salvinorin A is
now considered a Schedule I drug. Other states, including Oregon, are considering
regulation of this plant/drug.




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