Dihydrocodeine

Structural formula
General
Non-proprietary name	Dihydrocodeine
other names	DHC (4 R , 7 S , 7a R , 12b S ) -9-methoxy-3-methyl-2,4,4a, 5,6,7,7a, 13-octahydro-1 H -4.12-methanobenzofuro [3 , 2- e ] isoquinolin-7-ol ( IUPAC ) 3-methoxy-17-methyl-4,5 α -epoxymorphinan-6-ol
Molecular formula	C 18 H 23 NO 3
Brief description	white crystals (free base) colorless and odorless powder (tartrate)
External identifiers / databases
CAS number 125-28-0 5965-13-9 [( R , R ) -hydrogen tartrate] EC number 204-732-3 ECHA InfoCard 100.004.303 PubChem 5284543 ChemSpider 4447600 DrugBank DB01551 Wikidata Q377270
Drug information
ATC code	N02 AA08
Drug class	Antitussive , analgesic
Mechanism of action	Opioid
properties
Molar mass	301.37 g · mol -1
Physical state	firmly
Melting point	112-113 ° C (free base) 88-89 ° C (monohydrate) 193 ° C (tartrate)
boiling point	248 ° C (free base)
pK s value	8.68
solubility	soluble in water (tartrate, 200 g l −1 at 20 ° C)
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances Tartrate Caution H and P phrases H: 302 P: 301-313-280
Toxicological data	80 mg kg −1 ( LD 50 ,  mouse ,  iv ) 357 µg kg −1 ( TD Lo ,  human ,  iv ) 359 mg kg −1 ( LD 50 ,  rat ,  oral ) 252 mg kg −1 ( LD 50 ,  mouse ,  ip ) 350 mg kg −1 ( LD 50 ,  mouse ,  sc ) 142 mg kg −1 ( LD 50 ,  rabbit ,  sc )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dihydrocodeine (DHC) or dihydrocodeine is a semi-synthetic derivative of opium - alkaloid morphine that as, pain medication is applied, and as a cough suppressant. Chemically it is related to the codeine , from which it is produced by reduction . Dihydrocodeine was a commonly used drug for the treatment of opiate dependent patients from the late 1970s to around 2001 . It is administered orally, for example as a sustained-release tablet (containing 60, 90 or 120 mg of the active ingredient).

application

The analgesic potency of dihydrocodeine is about twice as high as that of codeine and corresponds to one sixth to one fifth of the potency of morphine. The analgesic effect of a prolonged-release tablet with, for example, 60 mg DHC lasts for about 12 hours. Dihydrocodeine is mainly used as a cough suppressant ( antitussive ) for short-term use in the symptomatic treatment of irritable cough (unproductive cough), but also for the treatment of moderate pain and for heroin substitution.

Use in substitution programs for opiate addicts may only take place under medical supervision. Since 2001, dihydrocodeine, like codeine, has only been permitted for substitution treatment in justified exceptional cases and has been replaced by methadone or levomethadone . Dihydrocodeine is subject to international narcotics regulations.

In Germany, it is listed in Appendix III of the Narcotics Act and must be prescribed on official narcotics prescriptions; This does not apply, however, to preparations with a concentration of up to 2.5% or, depending on the divided form, up to 100 mg of dihydrocodeine (calculated as base ). These can be prescribed in Germany and Austria without a prescription for narcotics.

Side effects

Dihydrocodeine causes sedation , euphoria , constriction of the pupils , lowering of blood pressure and orthostatic hypotension. You may feel sick or even vomit. The contraction of the smooth muscles can lead to constipation ( constipation ), contraction of the ureter and inhibition of the micturition reflex . Allergic reactions with itching and reddening of the skin are rare.

Trade names

Monopreparations : Codidol (A), Codicontin (CH), DHC Mundipharma (D), Dehace (A), Dicodin (F), Paracodin (D, A, CH), Tiamon (D)

Combination preparations: Escotussin (CH), Makatussin comp. (CH)

Web links

Commons : Dihydrocodeine  - Collection of Images

Individual evidence

1. ↑ ^{a b c d e} Entry on dihydrocodeine. In: Römpp Online . Georg Thieme Verlag, accessed on June 30, 2019.
2. ↑ ^{a b c d e f g h i j} Caelo: Dihydrocodeine Hydrogen Tartrate (PDF; 98 kB), accessed on December 27, 2019.
3. ^ Entry on dihydrocodeine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
4. ↑ ^{a b c} Herman H. Waldvogel: Analgesics Antinociceptives Adjuvants Manual for Pain Practice . Springer-Verlag, 2013, ISBN 978-3-642-56710-0 , pp. 277 ( limited preview in Google Book search).
5. ^ Hermann Hager, G. Frerichs, G. Arends, H. Zörnig (eds.): Hager's handbook of pharmaceutical practice for pharmacists, drug manufacturers, chemists, doctors and medical officials. Second volume, Springer-Verlag, Berlin, Heidelberg 1949, ISBN 978-3-642-49767-4 , p. 348.
6. ^ ^{A b} Michael Krausz, Christian Haasen, Dieter Naber: Pharmacotherapy of addiction . Karger Medical and Scientific Publishers, 2003, ISBN 978-3-8055-7482-2 , pp. 105 ff . ( limited preview in Google Book search).
7. ↑ Eberhard Klaschik : Pain therapy and symptom control in palliative medicine. In: Stein Husebø , Eberhard Klaschik (ed.): Palliative medicine. 5th edition, Springer, Heidelberg 2009, ISBN 3-642-01548-4 , pp. 207-313, here: p. 232.
8. ↑ Eberhard Klaschik : Pain therapy and symptom control in palliative medicine. 2009, p. 232.
9. ↑ Thomas Geschwinde: Drugs market forms and modes of action . Springer-Verlag, 2013, ISBN 978-3-642-30163-6 , pp. 752 ( limited preview in Google Book search).
10. ↑ International Narcotics Control Board: List of Narcotic Drugs under International Control Annex to Forms A, B and C 54th edition, December 2015.
11. ↑ Appendix III to the German Narcotics Act
12. ↑ Ordinance of the Federal Minister for Labor, Health and Social Affairs on traffic and dealing with drugs (Suchtgiftverordnung - SV)

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