Apomorphine

Structural formula
General
Surname	Apomorphine
other names	( R ) -6-methyl-5,6,6a, 7-tetrahydro-4 H -dibenzo [ de, g ] quinoline-10,11-diol (6a R ) -6-methyl-5,6,6a, 7-tetrahydro-4 H -dibenzo [ de, g ] quinoline-10,11-diol
Molecular formula	C 17 H 17 NO 2 (apomorphine) C 17 H 17 NO 2 HCl (apomorphine hydrochloride)
External identifiers / databases
CAS number 58-00-4 (apomorphine) 314-19-2 (apomorphine hydrochloride ) 41372-20-7 ( R - (-) - apomorphine hydrochloride hemihydrate) EC number 200-360-0 ECHA InfoCard 100,000,327 PubChem 6005 ChemSpider 5783 DrugBank DB00714 Wikidata Q269111
Drug information
ATC code	G04 BE07 N04 BC07
Drug class	Parkinson’s drug , emetic
Mechanism of action	Dopamine D 2 receptor - agonist
properties
Molar mass	267.32 g · mol -1 (Apomorphine) 303.78 g · mol -1 (· apomorphine hydrochloride)
Physical state	firmly
Melting point	195 ° C (apomorphine)
pK s value	8.92 (apomorphine)
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances Hydrochloride danger H and P phrases H: 301 P: 301 + 310
Toxicological data	300 mg kg −1 ( LD 50 ,  mouse ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Apomorphine is a representative (and the namesake) of the so-called aporphine alkaloids and is produced by heating morphine with concentrated hydrochloric acid. It is a dopamine D ₂ receptor - agonist and was as strong emetic (emetic) at poisoning used. Today apomorphine is mainly used in Parkinson's therapy. Despite its name, apomorphine has no narcotic effects and is not addictive.

Pharmacokinetics

Subcutaneously injected / infused apomorphine has a distribution half-life of 5 ± 1.1 minutes and an elimination half-life of 33 ± 3.9 minutes. Apomorphine is rapidly and completely absorbed from the subcutaneous tissue. This correlates with the rapid onset of clinical effects (4-12 minutes) and the short duration of clinical effects (about 1 hour).

Therapeutic use

Parkinson's

Apomorphine pen

Apomorphine is used in the diagnosis (apomorphine test) and treatment of Parkinson's disease . Due to its strong anti-Parkinson's effect, apomorphine is mainly used in patients in the late phase as a subcutaneous injection or continuous infusion. Apomorphine is mainly used when the fluctuations in the effect of oral Parkinson drugs can no longer be treated satisfactorily, because z. B. increased dyskinesia or "wearing-off" occur. In Germany apomorphine is sold under the trade names Dacepton ^® , Apomorphin-Archimedes ^® and APO-go ^® , in Austria under the trade names Dacepton ^® and APO-go ^® .

Due to the subcutaneous infusion / injection, the effect of apomorphine usually sets in very quickly, on average within about 8 minutes. In particular, patients who suffer from slow gastric emptying can benefit from parenteral drug administration . The clinical effect of subcutaneous administration of apomorphine lasts for about an hour. Therefore, the therapy can be adjusted within a short time in the event of possible side effects.

Apomorphine pump with catheter for Parkinson's therapy

There are various apomorphine pens for intermittent therapy (single injections). To continuously administer apomorphine subcutaneously, you can switch to a mini pump / syringe pump. The constant supply of the active ingredient stimulates dopamine receptors evenly, which can reduce the incidence of motor fluctuations and dyskinesia.

In order to reduce the emetic effects of apomorphine, pre-treatment with domperidone is usually carried out before the primary dose .

Alternative options for treating Parkinson's disease, which cannot be adequately treated with oral drugs, are deep brain stimulation and the duodopa pump, both of which, however, involve surgery.

drug withdrawal

In addition, apomorphine is occasionally given during drug withdrawal in connection with the dopamine antagonist metoclopramide .

Erection problems

Apomorphine also has an erection-stimulating effect at lower doses . This was discovered by accident in the treatment of Parkinson's patients. Apomorphine develops the potency-increasing effect especially when absorbed through the oral mucosa . The mechanism of action differs from that of PDE-5 inhibitors , such as B. Sildenafil ( Viagra ): Apomorphine has a stimulating effect on the regions of the central nervous system responsible for erection . Apomorphine was approved in Germany as a prescription drug for the treatment of erectile dysfunction (ED) since June 2001 . It was sold as a lozenge under the trade names Ixense ^® and Uprima ^® . The tablet was placed under the tongue , where it completely dissolved in about 10 minutes; the desired potency-increasing effect occurred after about 20 minutes. However, Ixense ^® and Uprima ^® were withdrawn from the market at the end of 2004 and beginning of 2005 due to insufficient sales. However, research continues with apomorphine in ED. So that has been in trials inhalation than the sublingual shown superior response.

Emetic

In veterinary medicine , apomorphine is still the drug of choice for inducing nausea.

Individual evidence

1. ↑ ^{a b} The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 121, ISBN 978-0-911910-00-1 .
2. ↑ ^{a b c} Data sheet R - (-) - Apomorphine hydrochloride hemihydrate, calcined, ≥98.5% from Sigma-Aldrich , accessed on December 21, 2019 ( PDF ).
3. ↑ Entry on apomorphine. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.
4. ↑ ^{a b} Rote Liste Service GmbH (Ed.): SPECIALIST INFORMATION . July 2016 ( gelb-liste.de [accessed on October 27, 2016]).
5. ↑ K. Eggert, W. Oertel: Apomorphintest . In: Current Neurology . tape 38 , S 01, February 1, 2011, p. S7-S10 , doi : 10.1055 / s-0030-1265946 .
6. ↑ ^{a b} M. Südmeyer: pump therapy in the treatment of Parkinson's disease. (PDF) Retrieved October 27, 2016 . 
7. ^ W. Poewe, B. Kleedorfer, F. Gerstenbrand, WH Oertel: The treatment of Parkinson's patients with L-Dopa - effect fluctuation by means of subcutaneous apomorphine administration . In: Current Neurology . tape 16 , no. 03 , June 1, 1989, pp. 73-77 , doi : 10.1055 / s-2007-1020585 .
8. ↑ Manson AJ, Hanagasi H, Turner K, et al. : Intravenous apomorphine therapy in Parkinson's disease: clinical and pharmacokinetic observations . In: Brain: a Journal of Neurology . 124, No. Pt 2, February 2001, pp. 331-340. PMID 11157560 .
9. ↑ ^{a b} Merello M et al .: Comparison of subcutaneous apomorphine versus dispersible Madopar latency and effect duration in Parkinson's disease patients: . Ed .: Clinical Neuropharmacology. 1997, p. 165-167 .
10. ↑ Ameri, Abdol A .: Individualized Parkinson's Therapy - Gastrointestinal symptoms come into focus . Ed .: Thieme. 2015.
11. ↑ M. Gerlach, P. Riederer: Current preclinical findings on anti-Parkinson agents . In: The neurologist . tape 74 , no. 1 , p. s2-s6 , doi : 10.1007 / s00115-003-1481-x .

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !