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Dihydrocodeine
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Dihydrocodeine : ウィキペディア英語版
Dihydrocodeine


| bioavailability = 20%
| metabolism =
| elimination_half-life = 4 hours〔
| excretion =

| IUPHAR_ligand = 7594
| CAS_number_Ref =
| CAS_number = 125-28-0
| ATC_prefix = N02
| ATC_suffix = AA08
| PubChem = 5284543
| DrugBank_Ref =
| DrugBank = DB01551
| ChemSpiderID_Ref =
| ChemSpiderID = 4447600
| UNII_Ref =
| UNII = N9I9HDB855
| KEGG_Ref =
| KEGG = D07831
| ChEMBL_Ref =
| ChEMBL = 1595

| C=18 | H=23 | N=1 | O=3
| molecular_weight = 301.38 g/mol
| smiles = O()1()2OC3=C(OC)C=CC4=C3()2(()5CC1)CCN(C)()5C4
| InChI = 1/C18H23NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
| InChIKey = RBOXVHNMENFORY-DNJOTXNNBM
| StdInChI_Ref =
| StdInChI = 1S/C18H23NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
| StdInChIKey_Ref =
| StdInChIKey = RBOXVHNMENFORY-DNJOTXNNSA-N
}}
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.〔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〕
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 life-threatening pulmonary edema. In the past, dihydrocodeine suppositories were used. Dihydrocodeine is available in suppository form on prescription.
Dihydrocodeine is used as an alternative or adjunct to codeine for the aforementioned indications. It is available as the following salts, in approximate descending order of frequency of use: bitartrate, phosphate, hydrochloride, tartrate, hydroiodide, methyliodide, hydrobromide, sulfate, and thiocyanate. The salt to free base conversion factors are 0.67 for the bitartrate, 0.73 for the phosphate, and 0.89 for the hydrochloride.
Dihydrocodeine was developed during the intense international search for more effective antitussives, especially to help reduce the airborne spread of tuberculosis, pertussis, pneumonia, and similar diseases, in the years from c.a. 1895 to 1915. It is similar in chemical structure to codeine. Depending on individual metabolism, dihydrocodeine is 100 to 150% 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 amounts that they do not have clinically important effects.
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.
== Indications ==

Approved indication for dihydrocodeine is the management of moderate to moderately severe pain as well as coughing and shortness of breath. As is the case with other drugs in this group, the antitussive dose tends to be less than the analgesic dose, and dihydrocodeine is a powerful cough suppressant like all other members of the immediate codeine family (see below) and their cousins hydrocodone, oxycodone and ethylmorphine, whole opium preparations, and the strong opioid hydromorphone.
For use against pain, dihydrocodeine is usually formulated as tablets or capsules containing a quarter grain (15 or 16 mg) or a half grain (30 or 32 mg) with or without other active ingredients such as aspirin, paracetamol (acetaminophen), ibuprofen, or others.
Controlled-release dihydrocodeine is available for both pain and coughing, as indicated below, as waxy tablets containing 60 to 120 mg of the drug. Some formulations, intended for use against coughing and the like, have other active ingredients such as antihistamines, decongestants and others.

Other oral formulations, such as packets of effervescent powder, sublingual drops, elixirs and the like are also available in many locations.
Injectable dihydrocodeine is most often given as a deep subcutaneous shot.

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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