Hydrocodone

from Wikipedia, the free encyclopedia
Structural formula
Hydrocodone structural formula
General
Non-proprietary name Hydrocodone
other names
  • (5 R , 9 R , 13 S , 14 R ) -3-Methoxy-17-methyl-4,5-epoxymorphinan-6-one ( IUPAC )
  • Hydrocodonum ( Latin )
  • Dihydrocodeinone
Molecular formula C 18 H 21 NO 3
External identifiers / databases
CAS number
  • 125-29-1 (hydrocodone)
  • 143-71-5 (hydrocodone bitartrate)
  • 25968-91-6 (hydrocodone hydrochloride )
  • 34195-34-1 (hydrocodone hydrogen tartrate 2.5 hydrate )
EC number 204-733-9
ECHA InfoCard 100.004.304
PubChem 5284569
ChemSpider 4447623
DrugBank DB00956
Wikidata Q411441
Drug information
ATC code

R05 DA03

Drug class

Antitussive

Mechanism of action

Opioid

properties
Molar mass 299.36 g · mol -1
Melting point
  • 198 ° C
  • 185–186 ° C (hydrocodone hydrochloride)
  • 118-128 ° C (hydrocodone · hydrogen tartrate · 2,5 hydrate)
solubility
  • poor in water (6.9 g l −1 at 25 ° C)
  • soluble in ethanol and dilute acids
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

150 mg kg −1 ( LD 50 ,  rat ,  sc )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Hydrocodone or dihydrocodeinone is an opioid that is structurally related to codeine and, like this, belongs to the derivatives of morphine . As a single preparation (such as Dicodid ) it acts as an analgesic (pain reliever) and as an antitussive (cough suppressant). In the US, the drug is mainly sold in combination preparations with paracetamol (such as Vicodin ) or ibuprofen .

effect

Hydrocodone or dihydrocodeinone (not to be confused with dihydrocodeine ) is chemically related to codeine and has a stronger (approximately 2 to 8-fold) antitussive effect than codeine. Antitussive effectiveness is already achieved when there is practically no respiratory depression. In this concentration, hydrocodone has a weak analgesic effect and is not euphoric. The literature contains divergent data on analgesic potency , which are 15% or 59% of the analgesic potency of morphine (according to other sources, the analgesic potency is 100% that of morphine). However, an analgesic effect lasting four to eight hours is possibly not only caused by hydrocodone itself, but also by its metabolite hydromorphone, which is formed by O-demethylation .

The inhibition of the cough reflex is based not only on a central inhibition in the medulla oblongata , but probably also on a blockage of sensitive receptors ("cough receptors") in the bronchial tract. The active ingredient can be addictive (“may be habit-forming”).

Side effects

The side effects of hydrocodone include:

application areas

  • Analgesic (pain reliever)
  • Antitussive (cough suppressant)

In patients with an otherwise treatment-resistant obsessive-compulsive disorder , observational studies showed a spontaneous reduction in symptoms when taking hydrocodone.

Legal status

In Germany, hydrocodone is subject to the Narcotics Act Appendix III and the Narcotics Prescription Ordinance , in the United Kingdom to the Misuse of Drugs Act, in which it is classified in class A (highest level of danger). In Switzerland it is subject to the federal law on narcotics and psychotropic substances .

Trivia

In the doctor series Dr. House consumes the protagonist Dr. Gregory House ( Hugh Laurie ) used hydrocodone ( Vicodin ) to numb his pain.

See also

Web links

Individual evidence

  1. ↑ a b c Entry on hydrocodone in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  2. ↑ a b c Entry on hydrocodone. In: Römpp Online . Georg Thieme Verlag, accessed on June 1, 2014.
  3. ↑ Data sheet Hydrocodone (+) - bitartrate salt from Sigma-Aldrich , accessed on April 4, 2011 ( PDF ).
  4. ↑ ABDA active ingredient dossier : Hydrocodone , retrieved from dimdi.de
  5. ↑ Technical information Hydrocodone Streuli 5 mg / 10 mg , as of September 2012.
  6. ↑ Mellar P. Davis: Opioids in Cancer Pain. OUP Oxford, 2009, ISBN 978-0-19-923664-0 ( limited preview in Google book search), p. 89 ff.
  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. 233.
  8. ↑ Eberhard Klaschik : Pain therapy and symptom control in palliative medicine. 2009, p. 233.
  9. ↑ Vicodin , drugs.com, accessed June 3, 2013.
  10. ↑ Joyce Davidson, Throstur Bjorgvinsson: Current and potential pharmacological treatments for obsessive-compulsive disorder . In: Expert Opinion on Investigational Drugs . tape 12 , no. 6 , June 2003, p. 993-1001 , doi : 10.1517 / 13543784.12.6.993 , PMID 12783603 .
  11. ^ Misuse of Drugs Act 1971: Schedule 2: Controlled Drugs, Part I: Class A Drugs , accessed June 3, 2013.
  12. ↑ Quoted from the Swiss Medicines Compendium .