Dihydrocodeine: Difference between revisions

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'''Dihydrocodeine''' is a semi-synthetic [[opioid]] [[analgesic]] prescribed for pain or severe ~~dyspnea~~, or as an [[antitussive]], either alone or compounded with paracetamol (as in co-dydramol) or aspirin. It was developed in Germany in 1908 and first marketed in 1911.<ref>http://books.google.co.uk/books?id=qoyYobgX0uwC&pg=PA404&lpg=PA404&dq=dihydrocodeine+1908+1911&source=bl&ots=Y7ALb1Yqjo&sig=FIkb3K4UwiXhn8LeO2EzXgxOGQk&hl=en&sa=X&ei=-mq9UsT5J4a10QXT0ID4CQ&ved=0CEQQ6AEwAzgK#v=onepage&q=dihydrocodeine%201908%201911&f=false</ref>

'''Dihydrocodeine''' is a semi-synthetic [[opioid]] [[analgesic]] prescribed for pain, severe shortness of breath, or as an [[antitussive]], either alone or compounded with paracetamol (as in co-dydramol) or aspirin. It was developed in Germany in 1908 and first marketed in 1911.<ref>http://books.google.co.uk/books?id=qoyYobgX0uwC&pg=PA404&lpg=PA404&dq=dihydrocodeine+1908+1911&source=bl&ots=Y7ALb1Yqjo&sig=FIkb3K4UwiXhn8LeO2EzXgxOGQk&hl=en&sa=X&ei=-mq9UsT5J4a10QXT0ID4CQ&ved=0CEQQ6AEwAzgK#v=onepage&q=dihydrocodeine%201908%201911&f=false</ref>

Dihydrocodeine is also known as ''Drocode, Paracodeine and Parzone. Its many brand names include Synalgos DC, Panlor DC, Panlor SS, Contugesic, New Bron Solution-ACE, Huscode, Drocode, Paracodin, Codidol, Dehace, Didor Continus, Dicogesic, Codhydrine, Dekacodin, DH-Codeine, Didrate, Dihydrin, Hydrocodin, Nadeine, Novicodin, Rapacodin, Fortuss, Paramol, Remedeine, Dico and DF-118''.

~~Commonly~~ available as tablets, solutions, elixirs, and other oral forms, ~~dihydrocodeine~~ is ~~also~~ available ~~in some countries~~ as an injectable solution for deep subcutaneous and intra-muscular administration. As with codeine, intravenous administration should be avoided, as it could result in anaphylaxis and dangerous pulmonary edema. ~~In past times, dihydrocodeine suppositories were used; however, dihydrocodeine~~ is available in suppository form on prescription.

Dihydrocodeine is available as tablets, solutions, elixirs, and other oral forms. In some countries, the drug is available as an injectable solution for deep subcutaneous and intra-muscular administration. As with codeine, intravenous administration should be avoided as it could result in anaphylaxis and dangerous pulmonary edema. Dihydrocodeine is available in suppository form on prescription.

Dihydrocodeine is used as an alternative or adjunct to [[codeine]] and is similar in chemical structure. Depending on individual metabolism, dihydrocodeine is 100 to 150 percent as strong as codeine. Although dihydrocodeine does have extremely active metabolites, in the form of dihydromorphine and dihydromorphine-6-glucuronide (one hundred times more potent), these metabolites are produced in such small amount that they do not have clinically important effects.<ref>The role of active metabolites in dihydrocodeine effects | http://www.ncbi.nlm.nih.gov/pubmed/12665158</ref>

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Dihydrocodeine is also the original member and chemical base of a number of similar semi-synthetic opiates such as [[acetyldihydrocodeine]], [[dihydrocodeine enol acetate]], [[dihydroisocodeine]], [[nicocodeine]], and [[nicodicodeine]].

==Chemistry==

Dihydrocodeine shares similar chemical structure to codeine, but lacks the double bond. This results in a much more stable chemical structure and also affects its metabolism. Dihydrocodeine can be synthesised from morphine by reduction of the 7,8-double bond. It readily converts to dihydromorphine with high yields (>95%).

Dihydrocodeine shares similar chemical structure to codeine, but lacks the double bond. This results in a much more stable chemical structure and also affects its metabolism. Dihydrocodeine can be synthesised from morphine by reduction of the 7,8-double bond. It readily converts to [[dihydromorphine]] with high yields (>95%).

==Pharmacology==

Dihydrocodeine produces effects that are typical of μ-opioid agonists which suggests that it is pharmacologically similar to more traditional opioids such as codiene and morphine. These all appear to mimic endogenous endorphins. Endorphins are responsible for analgesia (reducing pain), causing sleepiness, and feelings of pleasure. They can be released in response to pain, strenuous exercise, orgasm, or excitement. This mimicking of natural endorphins results in the drug's [[euphoric]], [[analgesic]] (pain relief), and [[anxiolytic]] (anti-anxiety) effects. Dihydrocodeine is metabolized via CYP2D6 to the active metabolite, dihydromorphine, which has a potency similar to morphine. Other weakly active metabolites include nordihydrocodeine, which is formed via CYP3A4, and dihydrocodeine-6-glucuronide. <ref>Kirkwood LC, Nation RL, Somogyi AA. Characterization of the human cytochrome P450 enzymes involved in the metabolism of dihydrocodeine. Br J Clin Pharmacol. 1997;44:549-55.</ref>

Dihydrocodeine produces effects that are typical of μ-opioid agonists which suggests that it is pharmacologically similar to more traditional opioids such as [[codiene]] and [[morphine. These all appear to mimic endogenous endorphins. Endorphins are responsible for analgesia (reducing pain), causing sleepiness, and feelings of pleasure. They can be released in response to pain, strenuous exercise, orgasm, or excitement. This mimicking of natural endorphins results in the drug's [[euphoric]], [[analgesic]] (pain relief), and [[anxiolytic]] (anti-anxiety) effects. Dihydrocodeine is metabolized via CYP2D6 to the active metabolite, dihydromorphine, which has a potency similar to morphine. Other weakly active metabolites include nordihydrocodeine, which is formed via CYP3A4, and dihydrocodeine-6-glucuronide. <ref>Kirkwood LC, Nation RL, Somogyi AA. Characterization of the human cytochrome P450 enzymes involved in the metabolism of dihydrocodeine. Br J Clin Pharmacol. 1997;44:549-55.</ref>

==Subjective effects==

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 {{SubstanceBox/Dihydrocodeine}}
 {{Proofread}}
-'''Dihydrocodeine''' is a semi-synthetic [[opioid]] [[analgesic]] prescribed for pain or severe dyspnea, or as an [[antitussive]], either alone or compounded with paracetamol (as in co-dydramol) or aspirin. It was developed in Germany in 1908 and first marketed in 1911.<ref>http://books.google.co.uk/books?id=qoyYobgX0uwC&pg=PA404&lpg=PA404&dq=dihydrocodeine+1908+1911&source=bl&ots=Y7ALb1Yqjo&sig=FIkb3K4UwiXhn8LeO2EzXgxOGQk&hl=en&sa=X&ei=-mq9UsT5J4a10QXT0ID4CQ&ved=0CEQQ6AEwAzgK#v=onepage&q=dihydrocodeine%201908%201911&f=false</ref>
+'''Dihydrocodeine''' is a semi-synthetic [[opioid]] [[analgesic]] prescribed for pain, severe shortness of breath, or as an [[antitussive]], either alone or compounded with paracetamol (as in co-dydramol) or aspirin. It was developed in Germany in 1908 and first marketed in 1911.<ref>http://books.google.co.uk/books?id=qoyYobgX0uwC&pg=PA404&lpg=PA404&dq=dihydrocodeine+1908+1911&source=bl&ots=Y7ALb1Yqjo&sig=FIkb3K4UwiXhn8LeO2EzXgxOGQk&hl=en&sa=X&ei=-mq9UsT5J4a10QXT0ID4CQ&ved=0CEQQ6AEwAzgK#v=onepage&q=dihydrocodeine%201908%201911&f=false</ref>
 Dihydrocodeine is also known as ''Drocode, Paracodeine and Parzone. Its many brand names include Synalgos DC, Panlor DC, Panlor SS, Contugesic, New Bron Solution-ACE, Huscode, Drocode, Paracodin, Codidol, Dehace, Didor Continus, Dicogesic, Codhydrine, Dekacodin, DH-Codeine, Didrate, Dihydrin, Hydrocodin, Nadeine, Novicodin, Rapacodin, Fortuss, Paramol, Remedeine, Dico and DF-118''.
-Commonly available as tablets, solutions, elixirs, and other oral forms, dihydrocodeine is also available in some countries as an injectable solution for deep subcutaneous and intra-muscular administration. As with codeine, intravenous administration should be avoided, as it could result in anaphylaxis and dangerous pulmonary edema. In past times, dihydrocodeine suppositories were used; however, dihydrocodeine is available in suppository form on prescription.
+Dihydrocodeine is available as tablets, solutions, elixirs, and other oral forms. In some countries, the drug is available as an injectable solution for deep subcutaneous and intra-muscular administration. As with codeine, intravenous administration should be avoided as it could result in anaphylaxis and dangerous pulmonary edema. Dihydrocodeine is available in suppository form on prescription.
 Dihydrocodeine is used as an alternative or adjunct to [[codeine]] and is similar in chemical structure. Depending on individual metabolism, dihydrocodeine is 100 to 150 percent as strong as codeine. Although dihydrocodeine does have extremely active metabolites, in the form of dihydromorphine and dihydromorphine-6-glucuronide (one hundred times more potent), these metabolites are produced in such small amount that they do not have clinically important effects.<ref>The role of active metabolites in dihydrocodeine effects | http://www.ncbi.nlm.nih.gov/pubmed/12665158</ref>
@@ Line 11: / Line 11: @@
 Dihydrocodeine is also the original member and chemical base of a number of similar semi-synthetic opiates such as [[acetyldihydrocodeine]], [[dihydrocodeine enol acetate]], [[dihydroisocodeine]], [[nicocodeine]], and [[nicodicodeine]].
 ==Chemistry==
-Dihydrocodeine shares similar chemical structure to codeine, but lacks the double bond. This results in a much more stable chemical structure and also affects its metabolism. Dihydrocodeine can be synthesised from morphine by reduction of the 7,8-double bond. It readily converts to dihydromorphine with high yields (>95%).
+Dihydrocodeine shares similar chemical structure to codeine, but lacks the double bond. This results in a much more stable chemical structure and also affects its metabolism. Dihydrocodeine can be synthesised from morphine by reduction of the 7,8-double bond. It readily converts to [[dihydromorphine]] with high yields (>95%).
 ==Pharmacology==
-Dihydrocodeine produces effects that are typical of μ-opioid agonists which suggests that it is pharmacologically similar to more traditional opioids such as codiene and morphine. These all appear to mimic endogenous endorphins. Endorphins are responsible for analgesia (reducing pain), causing sleepiness, and feelings of pleasure. They can be released in response to pain, strenuous exercise, orgasm, or excitement. This mimicking of natural endorphins results in the drug's [[euphoric]], [[analgesic]] (pain relief), and [[anxiolytic]] (anti-anxiety) effects. Dihydrocodeine is metabolized via CYP2D6 to the active metabolite, dihydromorphine, which has a potency similar to morphine. Other weakly active metabolites include nordihydrocodeine, which is formed via CYP3A4, and dihydrocodeine-6-glucuronide. <ref>Kirkwood LC, Nation RL, Somogyi AA. Characterization of the human cytochrome P450 enzymes involved in the metabolism of dihydrocodeine. Br J Clin Pharmacol. 1997;44:549-55.</ref>
+Dihydrocodeine produces effects that are typical of μ-opioid agonists which suggests that it is pharmacologically similar to more traditional opioids such as [[codiene]] and [[morphine. These all appear to mimic endogenous endorphins. Endorphins are responsible for analgesia (reducing pain), causing sleepiness, and feelings of pleasure. They can be released in response to pain, strenuous exercise, orgasm, or excitement. This mimicking of natural endorphins results in the drug's [[euphoric]], [[analgesic]] (pain relief), and [[anxiolytic]] (anti-anxiety) effects. Dihydrocodeine is metabolized via CYP2D6 to the active metabolite, dihydromorphine, which has a potency similar to morphine. Other weakly active metabolites include nordihydrocodeine, which is formed via CYP3A4, and dihydrocodeine-6-glucuronide. <ref>Kirkwood LC, Nation RL, Somogyi AA. Characterization of the human cytochrome P450 enzymes involved in the metabolism of dihydrocodeine. Br J Clin Pharmacol. 1997;44:549-55.</ref>
 ==Subjective effects==